Feature Properties

Discover an extraordinary oceanfront retreat in the Florida Keys, where 1.38 acres of lush tropical grounds, 150 feet of private sandy beachfront, and sweeping Atlantic Ocean views create an exceptional setting for island living. Designed to embrace its spectacular surroundings, this 4,770-square-foot estate offers five bedrooms and five-and-a-half baths, including separate guest quarters for added privacy. Soaring 30-foot ceilings and expansive windows fill the interiors with natural light while showcasing breathtaking ocean views. Elegant furnishings and thoughtfully appointed living spaces complement the home's sophisticated yet relaxed coastal atmosphere. Offered fully furnished and turnkey, the property is ready for immediate enjoyment. Outdoors, a resort-style infinity-edge pool and spa overlook the turquoise Atlantic waters, creating a seamless connection between luxury living and the natural beauty of the Keys. The expansive private beach invites endless days of kayaking, fishing, swimming, or simply relaxing beneath the palms. A spacious two-car garage adds convenience to this exceptional property. With zoning that permits weekly rentals, the estate also presents an attractive opportunity for those seeking a luxury vacation retreat with income-producing potential. Whether envisioned as a private family compound, an unforgettable vacation escape, or a full-time residence, this remarkable estate captures the essence of Florida Keys living--privacy, natural beauty, and effortless oceanfront luxury.

75931 Overseas Hwy, Islamorada

$7,295,000

4 Beds ⋅ 4 Baths ⋅ 621778 MLS

A rare opportunity to own one of the most extraordinary oceanfront properties in the Florida Keys, offering the exceptional combination of expansive Atlantic Ocean frontage and over 110 feet of protected canal dockage. Situated on a spectacular private peninsula extending into the Atlantic, this remarkable estate encompasses approximately 1.6 acres of upland and an additional 0.7 acres of submerged land. Beyond the gated entrance, a long, winding driveway introduces a property defined by privacy, exclusivity, and breathtaking panoramic ocean views. What truly sets this property apart is the ability to enjoy unobstructed oceanfront living while having over 110 feet of protected dockage along a concrete seawall, providing convenient boating access without sacrificing the beauty and tranquility of the open Atlantic. The existing executive residence features soaring ceilings, a dramatic curved staircase, spacious entertaining areas, and spectacular water views. The main living levels offer four bedrooms and three-and-a-half bathrooms, with additional ground-level space below base flood elevation. Outside, a swimming pool overlooks the Atlantic, while a private tiki hut at the end of the peninsula offers an unforgettable setting surrounded by tropical waters. Whether you envision restoring and enhancing the existing residence or creating a magnificent new oceanfront estate, the possibilities are extraordinary, subject to applicable approvals. Properties combining substantial upland acreage, panoramic Atlantic views, exceptional privacy, and protected dockage are exceedingly rare in the Florida Keys. This is more than an oceanfront home; it is an opportunity to create a lasting waterfront legacy.

80 Ocean Front Dr, Key Largo

$7,199,000

7 Beds ⋅ 6 Baths ⋅ 616613 MLS

Experience refined oceanfront living on sought-after Duck Key. This double lot estate offers 138 feet of protected deepwater dockage, complete with a solid concrete seawall designed to accommodate a sportfishing yacht, multiple center consoles, and all of your waterfront lifestyle needs. A true boater's paradise, this property offers both privacy and exceptional access to the Atlantic Ocean. The fully remodeled residence is constructed of concrete with a new roof. Inside, seven spacious bedrooms and six bathrooms provide ample accommodations for family and guests. Coastal-inspired interiors feature wood-look tile flooring throughout, woven statement light fixtures, and soaring ceilings with exposed beams and pecky cypress accents. Expansive impact windows and doors frame sweeping ocean views, bringing natural light into nearly every room. The gourmet kitchen anchors the main living space as the heart of the home, with a striking 12' island that creates the perfect setting for gatherings. Outfitted with top-of-the-line appliances, this space is equally suited for everyday living with family or hosting unforgettable evenings of entertaining. Spa-like marble bathrooms further elevate the home, blending comfort with luxury. Designed for both style and function, the property also offers a rare 4+ car garage and abundant storage. Outdoors, a sparkling pool invites afternoons in the sun, while the expansive double lot offers unmatched opportunities for expansion. Whether envisioning a private guest house, a tennis or pickleball court, or exploring the option to build and sell, this rare property provides endless possibilities for both personal enjoyment and investment potential—an uncommon luxury in the Florida Keys. Balancing modern sophistication with coastal simplicity, this sanctuary captures the essence of waterfront living from sunrise over the Atlantic to evenings by the water, in one of the most desirable neighborhoods in the Florida Keys.

308 Sabal St, Duck Key

$6,895,000

6 Beds ⋅ 7 Baths ⋅ 621466 MLS

The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

317 Whitehead St, Key West

$6,750,000

5 Beds ⋅ 5 Baths ⋅ 621141 MLS

Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment. This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. ft. of living space on an 8,227 sq. ft.oversized lot, providing rare space and privacy in one of the island's most desirable neighborhoods. Enter through the white picket fence and tropical courtyard to your grand Key West estate, where every detail has been thoughtfully designed. The first floor is set for entertaining, featuring a spacious living area and a chef's kitchen with stone countertops, an oversized island, custom cabinetry, and premium Sub-Zero, Viking, and Wolf appliances. A generous walk-in pantry adds extra storage convenience. The primary suite, also on the ground level, overlooks the pool and boasts a spa-inspired bath with dual showers, a freestanding soaking tub (with air bubble massage) and a large walk-in closet with one of two laundry areas. Outdoors, enjoy your private resort-style backyard with an oversized pool, covered lounge, and outdoor kitchen complete with gas grill, ice maker, and mini-fridge, perfect to grill up those fresh catches or hotdogs for the kids. Sonos speakers throughout set the tone to enjoy a relaxed Key West lifestyle. A floating living room staircase leads to two inviting guest rooms and a full bath. Two additional bedrooms currently serve as offices, each with en suite baths and private entrances, ideal for guest suites, studios, or remote workspaces (one includes a kitchenette). A climate-controlled standalone workshop offers a perfect space for projects, hobbies, or extra storage. Designed for both resilience and comfort, the home includes impact-rated doors and windows, a 30 KW Cummins diesel generator with 500-gallon fuel tank, smart home automation for lighting and shades, and off-street parking for two vehicles.

411 Louisa St, Key West

$6,500,000

10 Beds ⋅ 9 Baths ⋅ 620838 MLS

Embrace the essence of coastal living at this extraordinary bayfront estate, where privacy, comfort, and natural beauty come together on two sun-drenched acres along Florida Bay. Graced with year-round sunsets and endless opportunities for waterfront adventures, this property offers a rare sanctuary for extended families or groups of friends seeking their own slice of paradise. Three charming dwellings rest on two separate parcels--complete with deeded baybottom--creating a truly unparalleled retreat. Beyond the gated entrance, a winding drive leads first to the Coral House, a spacious 4-bedroom, 3-bath residence currently enjoyed as a licensed vacation rental. Continue toward the shoreline and you'll find the Cottage and the Florida Bay House tucked amid mature tropical landscaping, each offering its own unique character and comfort. The Florida Bay House, originally built in 1961 and thoughtfully expanded in the early 1970s, features 3 bedrooms and 3 baths, including an upstairs primary suite with sweeping views. The Cottage, built in 1956, provides a quaint and welcoming guest retreat. The Coral House, constructed in 1992 and situated in the desirable X flood zone, adds yet another layer of versatility to this exceptional estate. Step outside to where Florida Bay stretches before you--complete with a private jetty ideal for sunning, stargazing, or simply soaking in the peaceful coastal atmosphere. A convenient boat ramp beside the jetty makes it easy to launch kayaks and paddleboards for hours of exploration on the shimmering bay. This is a rare opportunity to own a remarkable coastal haven unlike any other. Contact us today to schedule your private tour and experience the magic of this timeless bayfront escape.

95480 & 90 Overseas Hwy, Key Largo

$6,500,000

4 Beds ⋅ 4 Baths ⋅ 620228 MLS

Presenting an extraordinary pre-construction opportunity to own a luxury oceanfront masterpiece, designed and newly constructed in the prestigious enclave of Shipman Point. Thoughtfully designed to embrace the beauty of the Florida Keys, this sophisticated residence will showcase refined coastal architecture, elevated finishes, and seamless indoor-outdoor living, all set against a backdrop of breathtaking Gulf views. Construction is scheduled to begin soon, offering a limited window for the discerning buyer to collaborate with the builder and personalize select finishes and design elements to create a truly bespoke waterfront retreat. The carefully curated floor plan features expansive living and entertaining spaces, a dramatic open-to-below architectural design, private elevator access, a temperature-controlled wine cellar, and a private guest casita designed for comfort and privacy. Floor-to-ceiling glass invites natural light and panoramic ocean vistas throughout the home, while the gourmet kitchen and elegant gathering spaces flow effortlessly to outdoor terraces overlooking a private resort-style pool, includes a 70-foot private dock with a new boat lift installed. Whether as a primary residence, seasonal retreat, weekly vacation rental or legacy waterfront estate, this is a rare opportunity to secure a brand-new luxury home and influence its final design before completion. Experience the pinnacle of oceanfront living at Shipman Point--where timeless design, exceptional craftsmanship, and the natural beauty of the Florida Keys converge.

4800 Overseas Highway Unit 54, Marathon

$6,500,000

4 Beds ⋅ 5 Baths ⋅ 618703 MLS

Very few things in life live up to the hype--but living on ''The Creek'' exceeds it. The location is world-class, the people-watching and boating scene never gets old, and the level of construction top-notch. What makes this property even more extraordinary is that the home itself now matches the setting. Following a meticulous two-year, top-to-bottom renovation, this residence was completely reimagined--from structural improvements to the finest design details--resulting in a flawless, move-in-ready showpiece. The main living level commands attention the moment you walk in, with dramatic vaulted ceilings, exposed wood beams, and an open-concept living and kitchen area designed for unforgettable entertaining. Two bedrooms and 1.5 bathrooms complete this floor with style and comfort. The entire third level is dedicated to a private primary suite that feels like a retreat in the sky. Wake up to elevated views over the Creek from your own private porch, admire the craftsmanship of the tongue-and-groove ceilings, and enjoy a stunning spa-style bathroom featuring a soaking tub within the shower and--finally--a large walk-in closet rarely found in Keys homes. The ground level offers a fully independent guest quarters with its own bedroom, bathroom, and full kitchen. Two functional garages with durable coated floors and bright LED lighting, plus a cabana bath accessible from both inside and outside for pool days. And then there's the backyard--where this home shifts from impressive to unforgettable. A full outdoor kitchen, heated pool, and hot tub set the stage, but the dock steals the show: deep-water dockage with two boat lifts (22,000 lb and 18,000 lb) and plenty of space for visiting boats, because friends will come. Tropical landscaping, an exterior elevator, and thoughtful details throughout complete a property that simply refuses to compromise. If you're looking for ordinary, keep scrolling. If you want a home you'll never get tired of walking into, this is it.

228 Tide Ave, Tavernier

$6,500,000

4 Beds ⋅ 3 Baths ⋅ 610778 MLS

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires' Row... Islamorada's premier address. New dock with two boat lifts (16,000 lb. and 10,000 lb.) to enjoy one of the best boating locations in the Keys, plus a 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for great income potential. The sandy backyard is shaded by palms and the large pool is fenced for privacy. The winding drive from the gate to the home is dotted with seating spots for enjoying the wildlife and tropical foliage. There is also a separate storage room and workshop downstairs, a gardening shed and landscape lighting along the driveway. Call today!

88547 Old Hwy, Tavernier

$6,450,000

7 Beds ⋅ 9 Baths ⋅ 621458 MLS

A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural character of historic Key West with the comfort, quality and convenience of newly constructed living. Thoughtfully designed to retain the home's traditional aesthetic, the property offers remarkable flexibility as a private compound, multigenerational residence or sophisticated investment property, with beautifully finished interiors, resort-style outdoor spaces and exceptional parking for the neighborhood. The main residence is a legal triplex, with each home offering its own privacy and character and 3 off street parking spaces. At the front of the property, a charming 1-bedroom, 1-bath residence occupies the first floor and opens to a generous covered porch and private yard. A separate side entrance leads to a distinctive three-story, 2-bedroom, 2.5-bath residence with its own side porch and upper levels overlooking the front of the property. Occupying the rear portion of the main house is the largest residence, a spacious 3-bedroom, 3.5-bath home arranged entirely on the main living level. Beautifully finished interiors open to a lush tropical retreat with a private pool, fountains, expansive patios, outdoor dining and multiple lounging areas. An unfinished basement offers exceptional potential for a wine cellar, tasting room or collection space. A landscaped walkway leads to a separate 1-bedroom, 1-bath cottage fronting Peacon Lane, with a private rear deck, outdoor dining area and two-car off-street parking. Importantly, the Peacon Lane residence sits on its own separate legal parcel, providing the rare flexibility for it to be owned or sold independently from the main property should a future owner ever choose to do so. Just beyond the gates, the waterfront, restaurants, galleries, shops and historic sites are all within an easy walk in one of Old Town Key West's most desirable neighborhoods.

723 Eaton St, Key West

$6,449,000

7 Beds ⋅ 8 Baths ⋅ 621544 MLS

Some Key West homes are historic because they are old. 1311 Truman Avenue is historic because of who built it, who gathered within its walls, and who saved it. Its front door came from the Old Southernmost House. Past it, Dade County pine flows through every room, chandeliers light high ceilings on both floors, and the original staircase still rises where it has stood for more than a century. A second staircase toward the rear, also original to the house, recalls the scale on which it was built. Outside, sweeping double-story porches wrap the Victorian-influenced home, set on a third of an acre. The house was built at the turn of the twentieth century by Benjamin Douglas Trevor and his wife, Mary Fogarty Trevor. Mr. Trevor founded Key West's first Steam Laundry and in 1903 became Mayor of Key West. In the decades that followed, the house became home to the Key West Woman's Club and later served as a church. In 1975 two prominent local antique dealers purchased it and returned it to its original glory, and their work received the first award for an excellent restoration given by the Old Island Restoration Foundation. That restoration still defines the house. The original windows remain, along with the moldings and trim, and verandas open to the grounds from both floors. A large covered porch offers room for both dining and living, with views over the refinished pool and the guest cottage. Over the past decade, the current owners have carried that stewardship forward. A magnificent tropical garden and a stunning pool now grace the 14,490-square-foot lot. Every bathroom has been updated and finished in a fine selection of marble, granite, and quartz, and the kitchen and appliances have been updated, bringing modern comfort to a house whose history remains its defining feature. Built by a mayor, gathered in by the Woman's Club, and saved by the restoration that set the standard for Old Town, 1311 Truman Avenue is ready for the next chapter of its story.

1311 Truman Ave, Key West

$6,400,000

5 Beds ⋅ 5 Baths ⋅ 621741 MLS

Stunning coastal architecture. Exceptional craftsmanship. Effortless waterfront luxury. This BRAND new home pairs classic Keys architecture with modern coastal elegance and quality concrete construction in sought-after Sugarloaf Key, just 20 mins from Key West. Set on a 12,500-square-foot lot with 100 feet of waterfrontage, this turnkey five-bedroom, five-bath home (ALL SUITES) overlooks a wide canal with beautiful turquoise water and abundant marine life. Thoughtfully curated architectural details and exquisite finishes reflect a commitment to quality throughout. A soaring 14FT vaulted entry welcomes you to European French oak floors and 8FT solid doors. Open-concept living, dining, kitchen and bar spaces flow through stacking Euro-Wall glass doors to the home's spectacular centerpiece: an expansive covered waterfront balcony with 14FT vaulted cypress ceilings. The chef's kitchen features Thermador appliances, wine & beverage centers, ice machine, handcrafted hammered stainless steel hood, Kohler water filtration & ambient lighting. All five bedrooms are ensuite; the primary bath offers ambient lighting, a soaking tub and separate water closet. Lush landscaping surrounds an enormous 1900 SFT outdoor entertaining area with travertine terraces, a spectacular pool, sun shelf & an elevated eight-person spa. A handcrafted live-edge monkeypod bar has electric roll-down hurricane shutters for quick, secure lockup and storm protection. An 80FT concrete dock, seawall, 15,000 LB boat lift & dockside utilities invite world-class fishing and diving adventures just minutes away. The enormous garage features hurricane-rated doors with LiftMaster side-mount openers; parking areas are provisioned for EV charging. A security system, two LG washer-dryer sets, solar panels to the grid, electric bedroom shades, hurricane-rated windows & doors complete this exceptional home. Meticulous attention to detail defines this stunning home, close to local dining & the magic of Key West!

17162 W Starfish Ln, Sugarloaf

$6,295,000

3 Beds ⋅ 3 Baths ⋅ 621587 MLS

Welcome to your private bayfront retreat at 62 Sunset Road, where beautifully remodeled interiors, lush tropical landscaping, and your own private beach capture the appeal of Florida Keys living. This property sits on almost half an acre of land. Offered fully furnished, this exceptional 3 bedroom, 3 full bath home combines high end upgrades with inviting spaces to relax, entertain, and enjoy life by the water. The thoughtfully appointed interiors offer a comfortable balance of style and spaciousness. Two bedrooms are located upstairs, including a generous primary suite with an adjoining area ideal for an office or peaceful sitting room. Downstairs, a third bedroom and expansive living space offer additional room to gather, host guests, or unwind after a day on the bay. Carefully selected finishes and upgrades throughout lend the home a polished, cohesive feel. Outside, several generous outdoor living areas create an inviting setting for everything from quiet morning coffee to leisurely meals and evenings with friends. Beautiful landscaping enhances the sense of privacy and surrounds the home with tropical character. The stunning pool features both a heater and chiller, allowing you to adjust the water temperature to your preference. Along the shoreline, your private beach offers a place to settle into a chair, enjoy the bay breeze, and take in the waterfront surroundings with the most beautiful view for sunsets For boating enthusiasts, the private dock features two boat lifts; one suited for a smaller boat and another for your larger vessel, making time on the water an integral part of this lifestyle. A sought after two car garage adds valuable convenience and complements the property's impressive amenities. Whether you envision peaceful days at home or memorable gatherings beside the bay, 62 Sunset Road offers a distinctive combination of waterfront living, privacy, beautifully upgraded interiors, and exceptional outdoor space where luxury is seen thro

62 Sunset Rd, Key Largo

$6,200,000

5 Beds ⋅ 6 Baths ⋅ 621235 MLS

Experience Mediterranean elegance and open-water living at this private oceanfront estate, featuring a pool, all set on a gated 10,545 sq. ft. lot in prestigious Key Colony Beach. Spanning 4,401 sq. ft., the 5 Bedroom, 4 Full and 2 Half Bath residence features impact glass and a private sandy beach offering privacy along the open water. Built for the ultimate boating lifestyle, the estate boasts deep-water dockage, 2 Boat Lifts, and direct access to both the Atlantic Ocean and Gulf of Mexico. The waterfront unfolds into a resort-style escape, where a heated and chilled pool with raised Hot Tub overlooks the ocean and a poolside Gazebo invites you to relax beneath the palms and enjoy sunsets. A sweeping circular driveway centered by an elegant fountain introduces the Mediterranean façade, while expansive rear balconies and twin sweeping staircases descend to the Pool deck, providing a dramatic backdrop for waterfront entertaining. Inside, a breathtaking Foyer makes an unforgettable impression with a sweeping split staircase, marble flooring, crystal chandeliers, classic archways, and an open upper gallery. The adjoining Great Room showcases a custom sunset mural by local artist Nancy Gagliardini. French doors open to an oceanfront balcony with water views and a Cabana Half Bath. Designed around the view, the Kitchen features stainless-steel appliances, black granite surfaces, and windows opening toward the ocean for inspiring sunset views. The Primary Suite offers a walk-in closet, soaking tub, and ocean-view balcony access. Ensuite Guest Bedrooms, a Media Room, and Office provide privacy and versatility, while 2 attached Garages and a whole-house Generator add convenience. Owners also enjoy access to a private beach club, golf course, tennis and pickleball courts, shopping, dining, and a waterfront sunset park, all within walking distance. With 7-day rental zoning, this estate offers outstanding vacation-investment.

1285 Coury Dr, Key Colony

$6,200,000

5 Beds ⋅ 5 Baths ⋅ 620499 MLS

Don't miss this rare and exceptional opportunity to have your dream waterfront masterpiece begin construction in 2026! Located in the prestigious, gated community of Shark Key, 36 Cannon Royal is an extraordinary west-facing lot that spans nearly 14,500 square feet and boasts approximately 130 feet of waterfront, delivering breathtaking sunset views over the Gulf waters. The sale of this property includes the completed construction of a 4,624 square-foot single family residence in accordance with the approved architectural plans and all associated permits. This thoughtfully designed 5-bedroom, 4.5-bath home features an elevator, a high-end chef's kitchen, loft, outdoor shower, fire pit, outdoor kitchen, and multiple porches/balconies that set the tone for a seamless indoor-outdoor lifestyle. The expansive fifty foot resort-style pool with sun ledge completes the vision of perfectly tailored island life. Additional conveniences include a two car garage, ample storage, and large covered patio located on the ground level. 36 Cannon Royal is a fully realized, ready-to-build waterfront estate offering luxurious coastal living, impact-rated construction, and peace of mind without compromising comfort or design. Shark Key residents enjoy exclusive amenities including a clubhouse, private beach, swimming lagoon, and pickleball/tennis courts- just minutes away from the world-class dining, arts, and entertainment of iconic Key West. Current architectural plans of 36 Cannon Royal are pending review by Shark Key ARB.

36 Cannon Royal Dr, Shark Key

$6,200,000

5 Beds ⋅ 5 Baths ⋅ 619886 MLS

You can renovate a house. You can't recreate the land. At the end of Sunrise Lane, on a 28,500 SF peninsula with water on three sides, sits one of the most compelling residential sites in Key West. 3750 Sunrise Lane combines land, privacy, waterfront, and scale in a way that simply does not come to market. This is not just a residence. It is the chance to build a significant Key West waterfront estate around the one thing that cannot be improved upon: the setting. Originally built in the 1950s and extensively expanded and rebuilt in 1999, the 5,378 SF residence offers five bedrooms and four and a half baths with heart pine floors, French doors, abundant natural light, and wide waterfront terraces. Three bedrooms and a spacious primary suite are on the first floor, while two upstairs guest bedrooms open to a covered balcony and rare widow's walk with sweeping water and protected land views. An expansive family-style kitchen and breakfast room anchors the home, complemented by a den with built-in wet bar and a separate studio and flex room offering multiple possibilities. Outside, the true scale of the property reveals itself. More than 3,200 SF of brick patios surround the large pool and tropical landscaping. Over 500 linear feet of seawall provides protected dockage, two boat lifts, and immediate deep-water access to the Atlantic and Gulf. A finished 828 SF, four-door garage completes this exceptional waterfront property. The residence is offered as a restoration and reimagination opportunity. It carries deferred maintenance, and with it the freedom to shape the property's next chapter rather than inherit someone else's. Restore its character. Rethink its spaces. Create a waterfront compound worthy of the site. 28,500 SF of land. Water on three sides. More than 500 feet of seawall. Protected dockage. Direct access to the Atlantic and Gulf. Homes can be transformed. Land like this cannot be recreated.

3750 Sunrise Ln, Key West

$6,195,000

4 Beds ⋅ 5 Baths ⋅ 620986 MLS

Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

144 N Rolling Hill Rd, Islamorada

$6,150,000

6 Beds ⋅ 7 Baths ⋅ 620190 MLS

Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the home's exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the property's thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. Not included in the listed square footage is a 488 SF garage and over a thousand square feet of covered patio. This home is perfect for the indoor/outdoor entertainer. A true statement of coastal luxury—this is Florida Keys living at its finest.

194 Buttonwood Ln, Islamorada

$5,999,999

5 Beds ⋅ 6 Baths ⋅ 618481 MLS

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

137 Sapodilla Dr, Islamorada

$5,999,000

8 Beds ⋅ 6 Baths ⋅ 619673 MLS

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct access to both the Florida Bay and Atlantic Ocean. The main residence features 7 spacious bedrooms and 5 beautifully appointed bathrooms designed with both elegance and comfort in mind--perfect for entertaining or hosting large gatherings. A dramatic third-floor Birds Nest Sky Lounge features 360-degree glass walls and a walkout rooftop deck, capturing breathtaking vistas in every direction. Expansive living areas and thoughtfully designed spaces capture stunning water views from every angle. A Whole House Generator for peace of mind. A private 1-bedroom, 1-bathroom guesthouse provides the ideal retreat for visitors, accommodating extended family, or potential rental income or creating a secluded retreat. For boating enthusiasts, the estate includes an impressive 85+ foot deep-water yacht slip and four boat lifts, offering seamless access to both the Bay and Ocean--an unparalleled fishing advantage in the Florida Keys. Step outside to your own waterfront oasis, where a gorgeous heated bayfront pool invites relaxation while you take in breathtaking sunset views and the tranquil surroundings. Blending luxury, comfort, and premier waterfront access, this remarkable estate presents a rare mixed-use opportunity in one of Islamorada's most coveted locations. Seller will consider all reasonable offers.

1101 Mastic St, Islamorada

$5,999,000

3 Beds ⋅ 3 Baths ⋅ 608546 MLS

Beautiful 200' of oceanfront property on Lower Matecumbe Key. This offering consists of one 100' lot, vacant with TDR & contiguously, a 100' lot with a triplex apartment building (3 TDRs),.This gives you endless possibilities for redevelopment of the property. The vacant lot has an additional 200' of bay bottom. Fantastic 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Recap: 200' of oceanfront made up of 1 vacant lot with TDR, 1 lot with 3 apartments, bay bottom on the vacant lot, for a total of 4 TDRs on the property Note: One of the owners is a State of Florida Real Estate Licensee

75131 Overseas Hwy, Islamorada

$5,995,000

5 Beds ⋅ 4 Baths ⋅ 621057 MLS

Welcome to CASA MARE, where contemporary luxury meets the open Atlantic. Built in 2023 by Dellanos Construction of the Keys, this spectacular direct-oceanfront residence offers approximately 3,000 sq. ft. of living space with 5 bedrooms, 4 baths and breathtaking panoramic open-water views from virtually every level. Designed to embrace its extraordinary setting, expansive glass and generous covered terraces create a seamless connection between indoor and outdoor living, with the Atlantic Ocean providing an ever-changing backdrop. Contemporary architectural details include clean modern finishes, warm wood accents and a dramatic floating-style staircase with glass railings. Step outside into your own private oceanfront resort. An impressive infinity-edge pool with in-water seating seemingly blends into the horizon, while a private putting green and low-maintenance outdoor areas provide the perfect setting for entertaining, relaxing and enjoying the Florida Keys lifestyle. Boaters will appreciate the deed-cut boat slip with 17,000-lb. boat lift, offering the rare combination of protected boat storage and immediate access to the open water. Multiple covered outdoor living areas capture panoramic ocean views and tropical breezes, creating exceptional spaces for morning coffee, entertaining friends or simply watching the horizon. With 5 bedrooms, extensive outdoor amenities and an extraordinary direct-oceanfront setting, Casa Mare also offers excellent potential for seasonal rental use. Casa Mare is more than a home--it is a contemporary oceanfront retreat where architecture, boating and the beauty of the Florida Keys come together.

239 Tavernier Dr, Tavernier

$5,975,000

3 Beds ⋅ 4 Baths ⋅ 620553 MLS

Welcome to your private oceanfront retreat, ideally situated on a quiet cul-de-sac in the heart of Tavernier. Set on an expansive 28,705-square-foot lot, this beautifully renovated estate in 2024 offers breathtaking Atlantic Ocean views and seamless indoor-outdoor living. The open-concept floor plan is designed to showcase the spectacular water views from nearly every room, elevated ABOVE FLOOD for added peace of mind. The property features a 2-bedroom, 2.5-bath main residence and a private 1-bedroom guest suite above the garage, thoughtfully redesigned with interiors curated by acclaimed designer Kevin Gray. Top of the line finishes throughout. Outside, enjoy a stunning resort-style pool and spa, an expansive oceanfront veranda, tropical landscaping, and an exterior lift providing convenient access from the covered carport to the main entrance. For boating enthusiasts, the private dock is equipped with an elevator boat lift and a charming tiki hut, creating the ultimate Florida Keys waterfront lifestyle. Whether you're enjoying sunrise coffee overlooking the Atlantic or heading offshore for a day on the water, this exceptional estate offers luxury, comfort, and timeless coastal elegance.

197 Lowe St, Tavernier

$5,950,000

4 Beds ⋅ 4 Baths ⋅ 621338 MLS

Welcome to The Oasis on Ojibway! Introducing an extraordinary newly constructed waterfront estate that must be experienced in person. Perfectly positioned on a generous 13,200-square-foot double lot with 120 linear feet of waterfrontage, this one-of-a-kind residence showcases sweeping bay views, refined custom finishes, lush tropical landscaping, and effortless indoor-outdoor living. Designed with an inverted floor plan to maximize the panorama, the main living and entertaining spaces are located on the third floor, where walls of glass frame jaw-dropping views toward the world-famous Toilet Seat Cut. The spectacular gourmet chef's kitchen is equipped with Thermador appliances, a large center island, and a discreet hidden pantry. A private elevator services every level. The second floor hosts a family room and three bedrooms, including a serene primary suite, while the fourth bedroom is located on the third floor. Every bedroom captures breathtaking water views and offers access to the home's 2,400 square feet of balcony space. Outdoors, the property is equally impressive, featuring lush tropical landscaping, a private putting green, a beautiful swimming pool, and a charming gazebo--creating the perfect setting for entertaining family and friends. The concrete dock and cut-in boat slip have been fully reinforced and rebuilt, providing excellent accommodations for your boat and waterfront toys. Plans have also been approved by the Army Corps for a new 20,000-pound boat lift. Additional features include space for a trailer or RV and a 278-square-foot storage area. Situated on a quiet dead-end street beside a nature preserve, the home offers exceptional privacy within Islamorada's coveted Indian Waterways community, close to world-class fishing, waterfront dining, and boutique shopping. Owner/Agent. Call today!

195 Ojibway Ave, Tavernier

$5,850,000

5 Beds ⋅ 4 Baths ⋅ 620179 MLS

Completely transformed down to the studs and scheduled for completion in late 2026, this extraordinary bay front estate represents the pinnacle of modern Florida Keys luxury. Meticulously rebuilt with elevated design, superior craftsmanship, and today's most coveted finishes, every detail has been thoughtfully curated to deliver an unparalleled waterfront lifestyle. Experience the ultimate Florida Keys lifestyle in this stunning bay front retreat in highly sought-after Tavernier. Perfectly positioned to capture endless turquoise water views and breathtaking sunsets. This exceptional residence features a raised metal roof, impact windows and doors, designer finishes, and sophisticated modern touches throughout. Designed for the boating enthusiast, the property features a private dock equipped with a 15,000-pound boat lift, providing effortless access to the Florida Bay and Atlantic Ocean. Enjoy a resort-style outdoor oasis with a pool, expansive waterfront entertaining areas, private dockage all overlooking the bay. Just minutes from Islamorada's renowned dining, marinas, sandbars, and offshore adventures. A rare opportunity to own a newly reimagined masterpiece in the heart of the Upper Keys.

233 Aberdeen Ct, Tavernier

$5,800,000

4 Beds ⋅ 3 Baths ⋅ 621690 MLS

Think the Florida Keys can't accommodate a true yacht? Think again. Opportunities like this are exceptionally rare, this Port Largo waterfront home is one of the few properties in the Keys where a serious yacht owner can dock with confidence. Set on an over 200-foot-wide canal with protected, deep-water dockage, the property offers a brand-new 106' concrete dock with the depth and turning radius that most Keys homes simply cannot provide. Add in open ocean views and immediate access to world-class fishing and diving, and you have a location that checks boxes most buyers assume don't exist here. Designed for both lifestyle and entertaining, this 4-bedroom, 3-bath home delivers the ultimate Keys experience. The updated kitchen opens into comfortable living spaces, while the outdoor area is built for hosting, complete with a pool and expansive dockage that naturally becomes the focal point of every gathering. This is a true ''boat and entertain'' property. Tucked at the end of a quiet street, the home offers privacy while still capturing the energy of the waterway, perfect for enjoying the steady flow of boats passing through the channel. It's a setting that blends relaxation with just the right amount of activity. Located in the desirable Port Largo community, you're just minutes from some of the best fishing and diving in Key Largo, along with easy access to nearby restaurants and local favorites. The neighborhood also features a park with pickleball and tennis courts, an Olympic-sized pool, beach volleyball, and a convenient boat ramp. For buyers who thought the Keys couldn't support their boating lifestyle, this property changes that conversation. If you've been overlooking the Keys because of dockage limitations, this is the one that proves otherwise.

308 Atlantic Blvd, Key Largo

$5,750,000

4 Beds ⋅ 5 Baths ⋅ 612702 MLS

Located in the prestigious gated community of Shark Key, 30 Cannon Royal Drive is a distinctive waterfront residence inspired by classic Mediterranean design. Architectural details such as soft arches, warm finishes, and elegant lines create a sense of timeless character rarely found in the Lower Keys. Thoughtfully designed to embrace indoor-outdoor living, the home offers spacious interiors filled with natural light and serene water views throughout. Two expansive porches overlook breathtaking sunset vistas, perfectly positioned on a generous 20,438 sq ft lot. The outdoor living experience is equally compelling, featuring a dedicated entertainment area complete with an outdoor fireplace and a private beach--ideal for both relaxed evenings and elevated gatherings. Additional highlights include two garages, an integrated indoor/outdoor speaker system throughout the home, and a dedicated space for a future elevator--offering both comfort and long-term flexibility. Whether enjoyed in its current form or reimagined to reflect a more modern vision, the property presents a rare opportunity to own a home with architectural presence and creative potential just minutes from Key West. Sold furnished with exclusions.

30 Cannon Royal Dr, Shark Key

$5,700,000

4 Beds ⋅ 6 Baths ⋅ 621851 MLS

Where Ocean Views Meet the Ultimate Boating Lifestyle. Discover an exceptional waterfront estate on Plantation Key, where sweeping Atlantic views, 140 feet of protected dockage, and refined coastal living come together in one remarkable setting. Privately situated on a quiet cul-de-sac in Islamorada, this four-bedroom residence offers an extraordinary combination of luxury, comfort, and effortless access to the water. Designed to embrace its spectacular surroundings, the home features expansive windows, soaring ceilings, and beautifully connected living spaces that open to generous covered terraces overlooking the ocean. A chef-inspired kitchen anchors the main living area with premium appliances, dual ovens, two dishwashers, and an oversized island ideal for entertaining. Four full baths, two half baths, a private elevator, and a luxurious primary suite with separate walk-in closets complete the thoughtfully designed interior. Outdoors, a tropical waterfront retreat awaits. The resort-style saltwater pool and spa are surrounded by lush landscaping, while expansive covered entertaining areas, an outdoor kitchen, and multiple balconies create inviting spaces to gather, unwind, and enjoy the ocean breezes. For the boating enthusiast, 140 feet of protected dockage, a 15,000-pound boat lift, five garages, and direct Atlantic access deliver exceptional convenience. From early morning fishing excursions to afternoons cruising the Keys, the water is always just moments away. A flexible secondary living area offers possibilities for a fitness studio, media room, or private retreat, adding to the home's versatility. A rare opportunity to enjoy the best of both worlds: protected waterfront living with the Atlantic Ocean as your backdrop.

202 Plantation Shores Dr, Tavernier

$5,650,000

3 Beds ⋅ 4 Baths ⋅ 621891 MLS

Discover timeless design and effortless indoor-outdoor living in this custom-built 4-bedroom, 3.5-bath residence in Key West's coveted Casa Marina neighborhood. Completed in 2017, the home blends architectural elegance with comfortable everyday living, surrounded by lush landscaping and lighting throughout. At the heart of the home, a grand living room features soaring ceilings, cove lighting, and expansive NanaWall impact glass doors that open on both sides to both the pool and backyard patio. Designed for entertaining, the outdoor space features a substantial dining area and built-in kitchen. Inside, the kitchen and dining room are thoughtfully separated from the living room by a wall, with two connecting passages providing an easy flow between the spaces. The chef's kitchen showcases semi-precious dumortierite quartz countertops and premium Thermador appliances. A striking powder room features crushed Capiz shell wallpaper, an illuminated onyx sink, and a bronze waterfall faucet. The first-floor primary suite opens to an orchid potting garden on one side and an oversized outdoor shower on the other. Its bath features a private water closet and a six-foot window welcoming natural light. Upstairs, a bedroom or office offers a private terrace overlooking the pools, while two additional ensuite bedrooms share a den complete with a wet bar, and a full-size laundry room From the coral stone entry pathways over interconnected pools to the glass-railed staircase, and espresso Acacia wood flooring, thoughtful details distinguish this home. Additional amenities include a covered carport with a motorized door and EV charging, a whole-house generator, and a heated and chilled pool.

1119 Johnson St, Key West

$5,650,000

3 Beds ⋅ 4 Baths ⋅ 614935 MLS

Discover unparalleled privacy and tranquility in this one-of-a-kind oceanfront estate, a true sanctuary nestled amidst the untouched beauty of the Florida Keys. Tucked behind a private gate, the estate begins with a scenic drive through acres of pristine, preserved nature, leading to your own private island. This secluded haven, like no other in the Florida Keys, was once a source of inspiration for Budd Post—the visionary engineer behind the legendary Card Sound Road. It offers an extraordinary blend of history, natural beauty, and modern luxury. Surrounded by breathtaking 360-degree views, the property's expansive decks and waterfront tiki hut provide unmatched solitude and serenity. Here, you can reflect on days spent exploring the unspoiled waters of the Florida Keys, far removed from the bustle of everyday life. Crafted to perfection, the estate's concrete construction ensures strength and resilience while maintaining an air of timeless elegance. Inside, cathedral ceilings and a grand limestone fireplace create a warm and sophisticated ambiance. The dining room, framed by panoramic ocean views, offers an intimate setting for unforgettable gatherings. Three en-suite bedrooms promise unmatched comfort and privacy, making the home as functional as it is exquisite. This listing includes an additional lot offering even more possibilities and potential. Boasting over 200 feet of concrete dockage, and a private boat ramp, the estate is a boater's dream, offering the perfect gateway to explore the azure waters that surround you. Whether pursuing nautical adventures or savoring the peace of waterfront living, this property delivers an exceptional experience. This private haven is truly like no other in the Florida Keys—a rare gem where luxury, seclusion, and nature converge. Every corner of this secluded retreat invites you to embrace the unparalleled charm of coastal living in an enchanting and one-of-a-kind setting.

10987 County Road 905, Key Largo

$5,500,000

3 Beds ⋅ 3 Baths ⋅ 621388 MLS

Exceptional Investment Opportunity in the Lower Florida Keys! Owner and private financing are available. This is one of the very few vacation rental properties licensed for daily, weekly, or monthly rentals. Boasting an impressive occupancy rate and generating up to $400,000 annually, this property offers stress-free, passive income in Summerland Key, a premier location. Discover a rare gem in the heart of the Lower Keys! Recently remodeled to perfection, this luxurious three-bedroom beach house includes a sunroom with a palatial ocean view, currently used as a fourth bedroom. Just 20 miles from vibrant Key West, this coastal retreat features a private natural beach, breathtaking ocean views, and access to a private airport for island residents less than two blocks from the property. Don't miss this unparalleled investment opportunity!

481 E Shore Dr, Summerland

$5,500,000

13 Beds ⋅ 7 Baths ⋅ 620213 MLS

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe

$5,500,000

6 Beds ⋅ 8 Baths ⋅ 617840 MLS

Stunning brand-new waterfront estate offering 6 bedrooms and 8 bathrooms with modern designs and luxury finishes throughout. The gourmet kitchen features premium Sub-Zero appliances and flows seamlessly into spacious living and entertaining areas. Built for long-term durability with a metal roof, solar panels, and a water cistern system. Enjoy resort-style outdoor living with a custom pool, covered lounge areas, and a 65-foot private dock with a garage and tackle room, perfect for boaters and fishing enthusiasts. Experience the best of modern waterfront living in Key Largo.

258 Caribbean Dr, Key Largo

$5,500,000

6 Beds ⋅ 6 Baths ⋅ 618573 MLS

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12' ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chef's dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views and the island's best spot to view the spectacular 4th of July firework show. Two charming detached guest cottages tucked amongst the gardens offer secluded retreats each with full baths and one offering a living room and kitchenette. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill; the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear Atlantic, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Don't miss the opportunity to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent. Seller is a licensed real estate broker and related to the listing agent.

906 Johnson St, Key West

$5,499,000

6 Beds ⋅ 6 Baths ⋅ 621304 MLS

Experience exceptional waterfront living in this impressive Spanish-inspired concrete residence, built in 2019 and offering approximately 8,107 square feet of construction and 16,500 square feet lot size. Thoughtfully elevated and designed with an emphasis on space, quality, and comfort, this remarkable home showcases a highly customized interior with refined finishes throughout. Solid wood interior doors, generous room proportions, and carefully designed living spaces reflect the attention to detail found throughout the residence. Expansive recreational and entertainment areas on both the first and second floors provide exceptional flexibility for hosting, relaxing, and enjoying everyday family living. The home's substantial concrete construction and elevated design complement its commanding presence, while the spacious interior offers an ideal combination of elegance and functionality. Positioned along an exceptionally Deepwater, wide-canal home with direct ocean access, the property provides an impressive waterfront setting and a sense of privacy and tranquility. A distinctive luxury residence offering exceptional scale, generous entertainment spaces, and outstanding waterfront appeal. Ideally located near the airport and surrounded by a variety of restaurants, dining options, and everyday conveniences, the home offers an excellent balance of privacy, accessibility, and lifestyle.

108 Ave D, Marathon

$5,499,000

5 Beds ⋅ 5 Baths ⋅ 621212 MLS

At the very tip of a private peninsula in the heart of the Florida Keys, this stunning Gulffront property delivers the ultimate waterfront lifestyle. Built in 2022, this 4,146 sq. ft. Coastal Modern residence was crafted by one of Marathon's premier builders with meticulous attention to detail, blending clean architectural lines with the relaxed elegance of island living. From the moment you arrive, the Gulf is your constant backdrop. Expansive walls of glass flood the interiors with natural light and frame endless turquoise waters. Every living area, from the two spacious lounges to the gourmet kitchen, was designed to maximize the view and the connection to the outdoors. The chef's kitchen is both beautiful and functional, featuring waterfall-edge quartz counters, premium stainless appliances, and abundant prep space. Whether hosting a casual brunch or an elegant dinner, this open-concept space flows seamlessly to indoor and outdoor gathering areas. Five ensuite bedrooms provide private sanctuaries for family and guests. The primary suite is a haven unto itself, offering a sitting area, spa-inspired bath, and a private porch where morning coffee comes with dolphin sightings and golden sunrises. Step outside to a personal resort: a shimmering pool with sun shelf, expansive patios for lounging, and a palm-lined peninsula with a fire pit at its tip. A deep-water dock, private boat basin, and 4-post lift make boating effortless, with 5' control depth ensuring smooth access to open water. This home offers the convenience of an elevator, an oversized 2-car garage, and low-maintenance construction designed for coastal living. Located 5 minutes from Marathon Jet Center, you can go from tarmac to tiki torch in record time. Whether it's a weekend escape, seasonal retreat, or full-time residence, this Gulf Front estate offers something truly rare: privacy, luxury, and the beauty of the Keys wrapped into one extraordinary address. Fantastic Rental History. Offer Turnkey.

875 50th St, Marathon

$5,499,000

5 Beds ⋅ 5 Baths ⋅ 619946 MLS

Welcome to 142 Guilford Court, a stunning bayfront home located in the highly desirable and sought out neighborhood of Hammer Point. Built in 2021 with solid concrete construction and a concrete roof, this luxury waterfront home was designed for effortless Florida Keys living with panoramic bay views from both the the living spaces and primary bedroom, exceptional outdoor spaces, and high-end finishes throughout. Offered completely turnkey furnished and professionally decorated, this 5-bedroom, 5.5-bathroom residence features approximately 3,500 square feet of interior living space spread across three levels with elevator access to all floors. Every bedroom offers its own private en-suite bathroom, creating the perfect layout for hosting family and guests in comfort and privacy. The open-concept main living area is filled with natural light and framed by expansive impact glass doors overlooking the bay. The chef's kitchen includes premium appliances, quartz countertops, a large butler's closet/pantry, warming drawer, and generous entertaining space that flows seamlessly into indoor and outdoor living areas. Outside, enjoy a resort-style bayfront setting with a concrete dock, sparkling in-ground pool, multiple balconies and patios, fenced yard, covered parking, and breathtaking sunset views over the water. Whether you are looking for a full-time residence, luxury vacation home, or premier Florida Keys waterfront retreat, this property delivers the best of island living. Located in the Tavernier, minutes from Tavernier Creek and many dining venues, 142 Guilford Court is a rare opportunity to own a newer construction bayfront home in the Florida Keys with direct water access and timeless coastal design.

142 Guilford Ct, Tavernier

$5,400,000

6 Beds ⋅ 7 Baths ⋅ 621215 MLS

Step back into timeless Key West soul, where leaf-stamped garden paths, sun-dappled outdoor showers, and the gentle trickle of private pool waterfalls create an unforgettable Old Town sanctuary. Hidden behind a classic wooden gate just moments from the Historic Seaport and Duval Street, this compound offers two private, fully equipped homes on a lush 7,796-sq. ft lot, providing the ultimate luxury island retreat or multi-generational estate. Verdant foliage frames the wrap-around front porch of the front cottage, inviting you to sit back and enjoy quintessential island living. Inside, sky-lit vaulted ceilings with exposed wooden beams pour warm sunshine across white-painted walls and rich wood floors. The light-filled layout centers around an enchanting cottage kitchen filled with warmth and timeless charm that flows seamlessly into the living space and guest half bath. Three bedrooms-each featuring its own private ensuite bath-offer exceptional comfort. Floor-to-ceiling glass draws you out to an outdoor dining area and a sparkling heated pool nestled among vibrant gardens. Wander through the botanical grounds to the rear house, a custom-crafted two-story sanctuary built in 2016. Showcasing exquisite Hickory hardwood floors, whitewashed Cypress interior walls, and slate-tiled baths, this home balances coastal elegance with high-end luxury. The chef's kitchen boasts an elite ILVE range and custom cabinetry, flowing into open living quarters that slide open to the backyard oasis. The main floor offers versatile living with a guest suite that double-functions as a private home office with a built-in Murphy bed. Upstairs, a Craftsman staircase leads to a secondary guest suite with an ensuite bath and a sprawling primary retreat, complete with an oversized spa bath and a private balcony overlooking the second heated waterfall pool. Do not miss this rare chance to own one of Old Town's premier dual-home properties, complete with dedicated off-street parking for two cars.

613 Margaret St, Key West

$5,399,000

5 Beds ⋅ 6 Baths ⋅ 621590 MLS

WEST-FACING BAYFRONT HOME | 5 Bedrooms | 5.5 Bathrooms | 3,208 SF | 180 Feet of Dockage | CBS Construction | Built Above Flood Zone Imagine ending every day with a breathtaking Florida Keys sunset right outside your door. Perfectly positioned to capture the spectacular west-facing views over Buttonwood Sound, this exceptional bayfront residence offers a front-row seat to nature's nightly masterpiece. Watch the sky transform into brilliant shades of gold, coral, pink, and crimson as the sun melts into the horizon, creating unforgettable evenings right in your own backyard. Offering 5 bedrooms, 5.5 bathrooms, and 3,208 square feet of living space, this impressive home blends relaxed Keys elegance with exceptional indoor-outdoor living. Beautiful travertine flooring, an open-concept Keys-style kitchen, and spacious living areas create an ideal setting for entertaining family and friends. Impact-resistant doors and windows and a durable metal roof add to the home's appeal. Designed for flexibility, the home features a ground-floor primary suite or private mother-in-law quarters with additional living space, ideal for multigenerational living or hosting guests. Upstairs, the primary suite offers a private retreat with captivating views of Buttonwood Sound. Outside, enjoy your own tropical oasis with a swimming pool on the main living level, surrounded by elegant travertine decking and lush tropical landscaping. Boating enthusiasts will appreciate 180 feet of dockage, two boat lifts (35K lb and 7K lb), composite dock construction, and a sandy beach area with kayak storage. Additional features include a private gated entrance, a one-car garage with storage, and automatic remote-controlled roll-down sunshades. This remarkable waterfront property offers an exceptional combination of boating amenities, versatile living spaces, tropical privacy, and unforgettable west-facing sunsets. Your Florida Keys waterfront dream awaits.

126 Point Pleasant Dr, Key Largo

$5,399,000

8 Beds ⋅ 8 Baths ⋅ 621248 MLS

Looking for a truly unique opportunity in the Florida Keys? Check out these 2 Custom Luxury CBS Pool Homes that are side by side! Live in one, and rent the other, corporate retreats, weddings, vacation rentals, tons of options! Can be sold furnished and turn key too. Experience luxury waterfront living in these custom-built, new construction two-story concrete homes featuring 4 bedrooms and 4 private en-suite baths. Designed for entertaining, the open-concept layouts seamlessly blends indoor and outdoor living. The chef's kitchens boasts top-of-the-line stainless steel appliances including double convection ovens, Smart refrigerator, dishwasher, vented range hood, prep sink, wine chiller, quartz countertops, custom cabinetry, and a large island. Porcelain tile flooring, custom fixtures, LED lighting, and abundant natural light enhance every space. A first-floor en-suite bedroom offers balcony access overlooking the pool, dock, and water. The dramatic floating staircase with custom LED chandelier leads to three additional en-suite bedrooms upstairs. The primary suite features a floating soaking tub, double vanity, custom porcelain tile shower, and MOEN programmable multi-head shower system with smartphone controls. Additional features include impact windows and doors, web-enabled security camera system, 4K Smart TVs in every room, 8-foot interior doors, two 3-ton 16 SEER A/C units, standing seam metal roof, aluminum railings, and expansive balconies on both levels. Located in the desirable Flamingo Island neighborhood of Marathon, just minutes from Sombrero Beach, dining, shopping, and entertainment. Enjoy quick access to open water, world-class fishing, boating, diving, and the crystal-clear turquoise waters of the Florida Keys. Built to impress and built to last, these exceptional waterfront retreats offer the ultimate Florida Keys lifestyle. Set up your preview today!

835 & 837 Copa D Oro, Marathon

$5,375,000

4 Beds ⋅ 5 Baths ⋅ 621589 MLS

Experience exceptional Florida Keys living in this stunning waterfront estate, featuring custom craftsmanship, luxurious finishes, and exceptional indoor-outdoor entertaining. The chef's kitchen boasts custom cabinetry, a built-in coffee bar, a 60-inch Wolf gas range, Sub-Zero refrigerator, and a 166-bottle wine cooler. The home offers four spacious bedrooms, each with its own private en-suite bathroom. The luxurious top-floor primary suite features a private office, custom walk-in closet, a dedicated coffee bar with a mini refrigerator, and an expansive waterfront terrace. A rooftop deck offers breathtaking sunset views. Designed for entertaining, the outdoor oasis features a beautiful pool, putting green, fire pit, and outdoor kitchen with a built-in grill connected to a gas line, all surrounded by lush landscaping and ambient lighting. Modern conveniences include an elevator, a whole-home Sonos sound system, a tankless water heater, and Lutron smart lighting that can be controlled right from your smartphone. Thoughtful craftsmanship shines throughout, with features such as a concrete roof, custom baseboards, and 8-foot louvered doors. Boating enthusiasts will appreciate 122 feet of concrete dockage with deep-water access, shore power, a boat lift, jet ski lift, and fish-cleaning station--creating the ultimate waterfront retreat. From sunset views on the rooftop to poolside gatherings, evenings around the fire pit, and days spent on the water, this exceptional property captures the very best of the Florida Keys lifestyle. A home this special must be experienced in person. Schedule your private showing today!

328 S Coconut Palm Blvd, Tavernier

$5,300,000

7 Beds ⋅ 6 Baths ⋅ 621882 MLS

A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.

923 Fleming St, Key West

$5,200,000

6 Beds ⋅ 8 Baths ⋅ 621737 MLS

Stunning brand-new waterfront estate offering 6 bedrooms and 8 bathrooms with modern designs and luxury finishes throughout. The gourmet kitchen features premium Sub-Zero appliances and flows seamlessly into spacious living and entertaining areas. Built for long-term durability with a metal roof, solar panels, and a water cistern system. Enjoy resort-style outdoor living with a custom pool, covered lounge areas, and a 55-foot private dock with a garage and tackle room, perfect for boaters and fishing enthusiasts. Experience the best of modern waterfront living in Key Largo. House is completely fenced not shown on pictures because all fencing is new.

259 Saint Thomas Ave, Key Largo

$5,200,000

4 Beds ⋅ 4 Baths ⋅ 618184 MLS

Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound. Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT impact windows/doors, and Hardi board siding. Inside, enjoy a sunlit open-concept floor plan with soaring ceilings, a gourmet kitchen with quartz counters, premium stainless appliances, gas stove, a hidden butler's pantry, and a waterfront Bedroom wing, all oriented to frame the water from every room. Step outside and immerse yourself in resort-style living with a heated and chilled waterfront pool, soothing spa, hot tub, invigorating cold plunge, and a fire pit encircled by flickering tiki torches to gather with friends and family while sipping cocktails as the sun melts into the horizon. Lounge on the expansive covered porch while enjoying views of the peaceful nature preserve for incredible bird watching, and a setting that offers total privacy and serenity. Boaters will love the protected canal access with 2 boat lifts (8K & 12K lbs), just minutes from open water. Additional features include a 4-car garage with EV charger, covered RV Tiki with 50 amp service, whole-house 35kW generator (750-gal tank), whole house water softening system and Sonos throughout, including garage and outdoor zones. Whether you're seeking a private sanctuary, a trophy lot, or the ultimate Florida Keys lifestyle, Blue Sky Pointe delivers. This is the most premiere lot on Sugarloaf Key — a once-in-a-lifetime opportunity.

17013 Coral Dr, Sugarloaf

$5,195,000

5 Beds ⋅ 6 Baths ⋅ 621709 MLS

Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75' by 300' bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living room's custom hand built beamed wood cathedral ceiling and a majestic staircase. The sunroom features French doors that open to views of the pool and harbor. The expansive backyard includes a covered dining area, a 45' waterfront deck overlooking the dock and boat lift. The chef's kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to a rear private deck and dock. Completing the first floor is the laundry room, half-bath, full bath, and a charming guest bedroom. The sunroom with wet bar and bathroom provides access to the one car garage, and second staircase leading to the second floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. The property must be seen to truly appreciate it. https://show.tours/v/2qnvjWF

18 Hilton Haven Road, Key West

$5,100,000

5 Beds ⋅ 4 Baths ⋅ 621368 MLS

OWNER FINANCING AVAILABLE AT 6% Experience luxury waterfront living in the Florida Keys with this exceptional 5 bedroom, 4 bath estate, ideally positioned at the end of a quiet street with 173 feet of deep-water dockage and an expansive turning basin offering easy maneuverability for large boats, performance boats, and large sportfishing vessels. Offered fully furnished and completely move-in ready, this home is designed for effortless Keys living from day one. Furnishings, décor, and thoughtfully selected finishes complement the home's sophisticated design, while the chef's kitchen features a complete suite of premium Thermador appliances. Built for both luxury and durability, the smart home showcases high-end interior finishes and premium composite exterior materials designed for the coastal environment. Features include a private elevator, programmable smart-home hubs throughout, whole-house surround sound extending to the pool and rooftop, and two laundry rooms, one on each living level. Expansive indoor living areas transition seamlessly outdoors to a private resort-style pool with sun shelf and gazebo. Oversized balconies off the primary suite and kitchen overlook the water, capturing spectacular bay sunsets and views of boats passing through iconic Toilet Seat Cut. The nearly 2,000-square-foot rooftop terrace is a true showpiece, complete with turf, bar, BBQ area, immersive audio, and panoramic views. With direct bay access and a short ride to Tavernier Creek for convenient Atlantic Ocean access, this fully furnished waterfront estate delivers boating, entertaining, luxury, and the Florida Keys lifestyle in one extraordinary package.

265 Pueblo St, Tavernier

$4,999,999

5 Beds ⋅ 5 Baths ⋅ 621022 MLS

Looking for one of the most unique Bayfront Estates in the Florida keys, well you just found it. Just over 3 acres located on the Gulf of America. What makes the property so unique first and foremost is the privacy it offers. Upon entering the double gate, you are surrounded by huge trees, heavy foliage and vegetation which provides you with complete privacy. There are walking trails all through the entire property, including out to the Bayfront to enjoy some of the most spectacular year round sunsets you will ever see. The property directly to the North is a preserve called, Crane Point Hammock and Museum & Nature Trails. The subject property boasts its own huge boat basin with new custom Ipe wooden dock to accommodate large vessels and/or multiple vessels with two 50 AMP services, all the power you may need. There is a separate dock and slip tucked inside the private boat basin the owner had custom built for his 52 foot Viking Express. There is also a 20,000 pound boat lift and a small boat ramp for your flats skiff. The main home has that Old Florida Charm, three bedrooms, two baths and great room with exposed beams and tongue and groove ceilings. Take the stairs up you your private master retreat with spectacular views overlooking your private basin and the bay. The home also offers three screened lanais with water views. Attached to the main home is a private, separate entrance apartment with bedroom, bathroom and kitchen for complete privacy from the main living quarters. Across the pavered driveway is the detached three car garage and above offers a 1 bedroom, 1 bath, living room and kitchenette. The property is located 1.5 miles South of Marathon International Airport to make it easy for pilots and chartered jets and prop planes to come and go from this one of a kind Estate. Easy access to the Atlantic Ocean. Looking for peace, privacy and serene relaxing Florida Bay and sunsets views? You just found it!!

1590 Pelican, Marathon

$4,995,000

4 Beds ⋅ 3 Baths ⋅ 621521 MLS

Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

1100 Johnson St, Key West

$4,972,500

3 Beds ⋅ 3 Baths ⋅ 621314 MLS

Welcome to Your Private Oasis in the Heart of the Florida Keys! Discover this hidden gem, a secluded gated estate nestled amidst the stunning landscape of the Florida Keys. Located directly on the sparkling waters of the Atlantic Ocean with 120' of protected deep-water dockage on canal, this property is perfect for boating enthusiasts. This half-acre estate exudes charm and casual elegance, with wide, sweeping porches at both the front and back, providing the perfect setting for outdoor relaxation and entertaining. Inside, you'll find three spacious bedrooms, three luxurious baths, and a cozy den that offers versatile living space. Beautifully landscaped with mature tropical plants, this home features a stunning pool set amidst lush gardens, creating your own slice of paradise. Plus, you're just a short walk from the Millionaire FBO Jet Center, making travel to and from this exquisite location a breeze. Don't miss the opportunity to own this exceptional estate in the Florida Keys! Schedule your private showing today!

851 104th St, Marathon

$4,950,000

4 Beds ⋅ 4 Baths ⋅ 621632 MLS

DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.

720d Simonton St, Key West

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