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Featured Properties

$2,300,000
4 Beds 3 Baths 614697 MLS
Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows and doors, durable metal roof, stainless steel appliances, quartz countertops, open-concept living areas, screened porch, private in-ground pool, and covered parking below. Built with modern coastal construction in mind, the CBS structure, impact openings, elevated design, and metal roof provide lasting durability, low-maintenance appeal, and insurance-friendly features for coastal living. The waterfront setting is enhanced by allocated dockage with an approximately 45' access walk leading to a 91' platform, creating a great setup for enjoying boating, kayaking, paddleboarding, and the surrounding water views. Situated on a generous 14,680-square-foot lot with approximately 75' of waterfront frontage, the property captures panoramic Bay/Gulf-front water views and beautiful sunrise exposure. Enjoy boating access via Bogie Channel, with easy access to the backcountry and fast open-water routes to both the Atlantic Ocean and the Gulf. Nearby Looe Key Reef is a favorite destination for snorkeling and scuba diving, with excellent fishing opportunities nearby. Located on the Big Pine Key side of the Bogie Channel Bridge to No Name Key, this setting offers peaceful water views and a unique sense of island privacy. The property can be used as an investment property for vacation rental use, adding flexibility and income appeal. Located near the iconic No Name Pub and surrounded by the natural beauty of Big Pine Key, where Key Deer are a beloved and frequent part of everyday island life. Unlike smaller, more remote keys, Big Pine Key serves as a convenient Lower Keys hub with everyday necessities nearby while still offering the quiet waterfront lifestyle people come to the Keys to enjoy. Construction is complete and ready for immediate occupancy.

30995 Watson Blvd, Big Pine

$2,300,000
4 Beds 3 Baths 617283 MLS
Welcome to 16 Azalea Drive, a completely reimagined home that embodies sophisticated coastal living, blending modern elegance with meticulous attention to detail at every turn. Thoughtfully redesigned from the ground up, this 4-bedroom, 3-bath property spans nearly 2,400 sq ft of refined living space. The open layout creates a seamless flow between the living, dining & kitchen areas, each curated to maximize light, function & aesthetic appeal. Impact-rated windows & sliding glass doors frame lush tropical views & invite in the natural beauty of the Florida Keys, while the soft coastal palette & high-end finishes create a serene, contemporary atmosphere. The custom kitchen is both striking & functional, featuring quartz countertops, shaker-style cabinetry, a farmhouse sink & top-of-the-line stainless steel appliances. Bathrooms are masterfully finished with designer vanities, custom glass shower enclosures & LED-lit mirrors, creating a spa-like retreat. Throughout the interior, new tile flooring laid in a herringbone pattern adds visual interest & luxury underfoot, complemented by modern black fixtures & ceiling fans that bring a clean architectural touch. This property underwent a comprehensive renovation, including full replacement of plumbing & electrical components, a seamless V-Crimp metal roof, exterior stucco, & interior/exterior painting. The landscape was redesigned with artificial turf, tropical palms & decorative shell features, creating a refined, low-maintenance aesthetic. Expansive deck & patio areas are ideal for outdoor living, with paver walkways leading to a pool & hot tub beside a private canal-front setting. Situated on a wide canal with excellent boating access, this residence offers the ultimate Keys lifestyle for those who appreciate fine craftsmanship, privacy & quick access to open water. A new wood privacy fence, polished detailing & smart LED lighting complete this exceptional home where craftsmanship, comfort & design excellence converge.

16 Azalea Dr, Key Haven

$2,299,000
4 Beds 2 Baths 621230 MLS
Set along the water in sought-after Key Colony Beach, this 4-bedroom, 2-bath home captures everything buyers love about the Florida Keys--boating, a private pool, generous outdoor living space, and a strong history as a successful vacation rental. Inside, the layout is comfortable and inviting, with an open kitchen featuring abundant cabinetry, expansive countertops, and bar seating that flows naturally into the dining and living areas. Four bedrooms provide plenty of room for family and guests, while the primary suite enjoys its own bath and access to a covered outdoor deck. A dedicated laundry area adds everyday convenience. The outdoor spaces are the real highlight. The waterfront backyard is designed for the Keys lifestyle, with a private swimming pool, spacious pool deck, covered entertaining area, outdoor shower, tropical landscaping, and plenty of room to relax after a day on the water. The property also offers substantial canal frontage with a seawall, dockage, and a boat lift, creating an easy setup for boaters. From here, enjoy convenient access toward both the Gulf and Atlantic for fishing, diving, snorkeling, and days on the water. Back at home, cool off in the pool, lounge along the canal, or gather beneath the covered lower-level entertaining space. Additional features include a metal roof, covered parking and storage areas, mature tropical landscaping, and multiple outdoor spaces that make the home especially well suited for full-time living, a family getaway, or continued vacation rental use. With its 4-bedroom layout, private pool, dockage, boat lift, outdoor shower, and established rental history, this waterfront home offers a wonderful opportunity to enjoy the best of Key Colony Beach.

581 12th St, Key Colony

$2,299,000
2 Beds 3 Baths 620384 MLS
Enjoy endless ocean views from this charming Florida Keys waterfront retreat. Sitting on the edge of the Atlantic just one house in from open water, this stilted 2-bedroom, 2.5-bath CBS home also offers possible 3-bedroom flexibility and is a true boater's dream with 85 feet of waterfront frontage, concrete seawall, a 13,500 lb boat lift, deep-water dockage, and instant access to the Atlantic. The channel is slightly right as soon as you come out of the canal, placing you just minutes from Sombrero Light and some of the best boating, fishing, and diving the Keys have to offer. The home features a spacious, light-filled layout with a large living area, generous waterside windows, and sliding glass doors that frame the ocean views and open to east-facing covered porches on two levels. Inside, you'll find a comfortable eat-in kitchen with stainless steel appliances, abundant natural light, generous storage, walk-in closets, and impact windows and doors for added peace of mind. Outdoor living is the highlight, with a new waterfront pool and hot tub, expansive deck, large waterside porch, fenced yard, tropical landscaping, and multiple spaces to relax, dine, entertain, or simply take in the ocean breeze. Additional features include a garage, CBS construction, metal roof, travertine-paved driveway, inviting covered patio areas, and a large front yard offering flexibility for additional parking, boat/RV storage, or future use. The home is also available furnished, offering added convenience for those ready to start enjoying the Keys lifestyle right away. With open water just moments away, this Marathon property offers the perfect blend of boating, ocean views, poolside relaxation, and laid-back Keys living. This one is a must-see to truly appreciate.

1400 W 63rd St, Marathon

$2,299,000
3 Beds 3 Baths 614782 MLS
OWNER FINANCING. Lowest priced waterfront in Port Largo. INVEST, redesign, or rebuild in one of the Upper Keys' most coveted boating enclaves, Port Largo. Just a few lots in from the open ocean, this CBS residence is positioned on a wide, protected waterway with 75 feet of concrete dockage, capable of accommodating large center consoles, express boats, or sport fishing vessels. Generous canal widths and turning basins, a defining feature of Port Largo, provide ease of navigation and a level of boating infrastructure rarely found in the Keys. The existing two-story home offers a flexible foundation for transformation, including a substantial lower level with approximately 1,000 square feet of finished space suitable for future living areas, gym, media lounge, guest quarters, or private office. The upper level captures natural light and water views with soaring ceilings and the open concept layout. Modernize the interior or serve as a temporary residence while plans for a custom new build are decided. The lot allows room to add a pool and outdoor entertaining areas, creating the potential for a fully realized waterfront estate that maximizes indoor-outdoor living and long-term appreciation. An optional homeowners park located one street away provides access to a private boat ramp and additional waterfront amenities, further enhancing the value and convenience for boaters. Port Largo is prized not only for its direct ocean access but for its lifestyle. Golf cart connectivity allows residents to reach neighborhood restaurants, bars, and even convenience stores without ever accessing US-1. A state-of-the-art community park nearby features pickleball and tennis courts, recreational fields, walking trails, exercise equipment, and a playground, elevating daily living beyond the waterfront. Whether envisioned as a high-end redevelopment, a custom luxury build, or a strategic long-term investment, the opportunity is now to secure a lot with enduring market appeal in Key Largo

184 Bahama Ave, Key Largo

$2,295,000
3 Beds 2 Baths 621228 MLS
Ocean's Edge Cottage -- a rare oceanfront opportunity in Key Largo, offering expansive open-water views, protected dockage and immediate direct access to the Atlantic. Situated on an oversized 60' x 90' peninsula-style corner lot, this unique property offers approximately 150 feet of shoreline with water on two sides, providing exceptional views from both inside and out. For the boating enthusiast, Ocean's Edge Cottage offers the best of both worlds: approximately 60 feet of concrete dockage in a protected area with a 17,000-lb boat lift, while still providing direct and immediate ocean access with no bridges. A natural coral breakwater provides additional protection while allowing water to flow freely along the north side, creating a clear swimming area where fish and marine life are frequent visitors. A private homeowners' oceanfront boat ramp provides additional convenience. The 3-bedroom, 2-bath home was designed to embrace its waterfront setting, with walls of glass capturing incredible water views from multiple sides of the main living and kitchen areas. The renovated kitchen features sparkling white cabinetry, granite countertops and stainless-steel appliances, complemented by an open-concept floor plan ideal for relaxed Keys living and entertaining. Additional features include impact-resistant windows and doors, an en-suite primary bedroom, interior laundry, outdoor shower and fenced yard. With open ocean in front, protected dockage for your boat and the Atlantic just moments away, Ocean's Edge Cottage delivers a combination increasingly difficult to find in Key Largo -- true oceanfront living without sacrificing protected boating.

301 Little Miss Muffett Ln, Key Largo

$2,250,000
3 Beds 3 Baths 621121 MLS
Welcome to your private island home retreat, The Belle House. Highlighted on the Netflix series Bloodline as the home of Kevin & Belle Rayburn. Set on an expansive half-acre double lot enveloped by lush, tropical native plantings, this beautifully updated home offers a rare combination of privacy, tranquility, & effortless Keys living. This home offers room to breathe, unwind & genuinely enjoy your surroundings. Mature landscaping creates a secluded, garden-like setting that feels more like a private resort than a traditional residential property. Featured on the Upper Keys 40th Anniversary Garden Walk, this concrete home with metal roof, Anderson impact windows & doors throughout, & lovely, relaxing wraparound porch is situated in an X flood zone. The neighborhood boasts one of Islamorada's nicest homeowners' parks offering a boat ramp, temporary dockage, a beach & wade in swimming area. Depart from your driveway, launch your boat, & be in Florida Bay in under 10 minutes! Located walking distance to Islamorada's Founder's Park. The interior provides casual, timeless elegance with vaulted ceilings & hand sculpted walnut flooring. The main level consists of free-flowing living & dining, chef's kitchen featuring Wolf, Sub Zero & Meile appliances with honed granite countertops, large pantry/laundry area, very spacious primary suite, as well as guest bedroom, bath and under stair storage. The second level provides privacy for your guests or older children, offering a second guest bedroom and bath as well as a sitting room with mini fridge and breakfast bar. This area could easily transition into a 4th bedroom. There is a detached, all concrete garage on the second lot w/ ample space for parking a flats boat and RV ready with 30-amp service. Two driveways provide plenty of parking for multiple vehicles. This unique home is move in ready. It has been beautifully maintained and cared for and is ready for you and your family to make new memories on Palm Lane!

130 Palm Ln, Islamorada

$2,250,000
5 Beds 3 Baths 620153 MLS
Welcome to luxury waterfront living in sought-after Key Haven. Completely reimagined by Affiliated Builders, this stunning residence offers the perfect blend of sophisticated design, modern functionality, and island lifestyle. This home has been thoughtfully renovated with gorgeous designer finishes and meticulous attention to detail, creating a truly turnkey coastal retreat. The spacious floor plan features 2086 sq foot, 4 bedrooms plus a flexible office/living space that can easily serve as a 5th bedroom, along with a dedicated laundry room, mudroom, and 1-car garage. At the heart of the home is a spectacular gourmet kitchen and dining complete with premium Bosch & Bertazzoni appliances, quartz countertops, and custom cabinetry designed for both everyday living and entertaining. Custom built-in closets throughout the home add both style and functionality. Step outside to your private waterfront oasis featuring a heated and chilled custom saltwater pool surrounded by elegant limestone decking, creating the ultimate setting for relaxing or entertaining year-round. Boaters will appreciate the 10,000-pound boat lift accommodating up to a 25-foot boat, offering quick access to the beautiful waters of the Florida Keys. Additional upgrades include a whole-house Generac generator, irrigation system, and countless high-end improvements throughout. Furniture is negotiable, making this exceptional Key Haven property ready to enjoy immediately.

1 Bougainvillea Ave, Key Haven

$2,249,000
4 Beds 3 Baths 619793 MLS
Over 3400 sqft of Luxury Living is featured with this 2007 custom built CBS in the gated community of Stirrup Key Sub in Marathon. Elevated water views, a deeded boat slip, protected community marina, multiple outdoor living areas and a private pool. Designed for both everyday comfort and entertaining, this multi-level home offers generous interior space, flexible living areas, and a thoughtful indoor-outdoor layout. The ground level features a three-car garage, ample storage, and direct access to the pool area, creating an easy flow for relaxing, hosting, and enjoying the Keys lifestyle. The second floor serves as the main living level with two bedrooms, two full baths, a full kitchen, and open living and dining areas that extend onto a large screened lanai. This level is ideal for casual gatherings, quiet mornings, and evening breezes. The third floor offers a private primary suite, sitting area or fourth bedroom, bar/kitchenette, fireplace, spa-style bath, and an expansive lanai with peaceful elevated views. A spiral staircase leads to the fourth-floor widow's walk, finished with travertine flooring and a water hookup. From this vantage point, panoramic views stretch across Marathon and toward the Gulf, creating a quiet setting for sunrise, sunset, and open-air relaxation. A private nature path winds through preserved surroundings and leads to a Gulf-front observation dock, ideal for wildlife viewing and enjoying the surrounding natural setting. Additional features include a lift to the second floor for added convenience. Centrally located in Marathon, the home offers convenient access to shopping, dining, & daily necessities. With a deeded marina slip, elevated water views, pool, garage space, storage, multiple lanais, and a flexible custom layout, this property offers a rare combination of privacy, space, and boating access in Marathon. Schedule a private showing to experience this custom home and deeded marina slip in person.

205 Stirrup, Marathon

$2,249,000
3 Beds 4 Baths 619404 MLS
On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces. The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that encourages gathering, while the outdoor covered patio is perfect for dining or lounging creating a natural extension for everything from slow mornings to late evenings. Step outside and the pace shifts. Sitting on a large L shaped lot, the pool becomes the centerpiece, surrounded by deck space, greenery, and just enough privacy to make it feel like your own little corner of the island. The inviting primary suite is a peaceful retreat, featuring vaulted ceilings and French doors that open directly to the pool. Upstairs, two additional bedrooms and a shared bath provide comfortable separation, while the detached poolside cottage, with its own bath and outdoor shower offers flexible space for guests, a workspace, or added privacy. A convenient powder room is also located just off the kitchen. Dade County pine walls, wood floors, and tall ceilings bring warmth and authenticity, giving the home a sense of history without ever feeling heavy. It is comfortable, inviting, and easy to live in, the kind of home that makes everyday moments feel just a little more special. Quiet, central, and layered with history, 1109 Stump Lane stands as one of Old Town's most compelling hidden opportunities, a rare chance to own a truly private retreat in the heart of Key West.

1109 Stump Ln, Key West

$2,246,000
3 Beds 2 Baths 620177 MLS
Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about. Completely renovated from top to bottom, the property sits on a deep water canal with 60 feet of brand new concrete dockage and quick direct access to open water, making it ideal for larger center consoles, sportfish boats, and offshore cruising. Inside, the home was designed for relaxed Keys living with vaulted ceilings, impact windows and doors, quartz countertops, custom wood cabinetry, stainless steel appliances, and an open layout filled with natural light and canal views. The spacious primary suite is privately situated on the second floor, offering a peaceful retreat with elevated views and added separation from the guest accommodations below. The outdoor living experience is what truly sets this property apart. The waterfront pool features all brand-new equipment, including a heater and chiller, allowing for year-round enjoyment in every season. A portion of the pool area is partially covered, creating the perfect shaded outdoor lounge space after a day on the water. Covered balconies, spacious patios, and tropical landscaping give the property a true private resort feel. The custom putting green and mini golf area adds a unique touch rarely found in the Keys, creating an incredible space for entertaining guests while enjoying the waterfront setting. Whether you're heading offshore for tuna and swordfish, running to the reef, or enjoying sunset cruises through the Lower Keys, this location puts you minutes from some of the best boating and fishing in the Florida Keys. Built with durable Hardie board construction, a metal roof, impact windows and doors, covered parking, and more than 1,000 square feet of enclosed storage space underneath the home, this turnkey waterfront retreat offers the perfect balance of luxury, functionality, and the authentic Florida Keys boating lifestyle.

848 E Caribbean Dr, Summerland

$2,200,000
3 Beds 2 Baths 620645 MLS
Welcome to 273 W Seaview Dr, a private retreat in the heart of Duck Key, home to Hawks Cay Resort and some of the best boating and fishing waters in the Florida Keys. Built in 2020 on a 15,247 SF lot, this concrete home is elevated on concrete pilings and engineered to withstand hurricane force winds, with impact windows and doors throughout for lasting peace of mind and favorable insurance considerations. The main living level is reached by two separate entries, a front stairway and a rear balcony, and offers 3 bedrooms, 2 full bathrooms, and an in unit washer and dryer across a bright, thoughtfully finished floor plan with custom exterior finishes, drywall interiors, a flat clay tile roof, and forced air cooling. Below, the ground level provides extensive covered parking and storage space, along with a shaded open porch, ideal for boat gear or beach equipment. Outdoors, the property has been extensively upgraded. The owner just completed a brand new 288 SF pool with a paver deck, and recently added a paver brick driveway and multiple brick and tile patio areas for entertaining. The yard is enclosed with wrought iron fencing and gates for added privacy. A standout feature is the detached 2,046 SF garage on the south side of the property, built in 2023 with room for up to nine vehicles, a rare find for boat owners, car collectors, or anyone in need of serious storage space in the Keys. This property suits a vacation home or full time residence equally well. Duck Key offers a welcoming, close knit island community along with excellent public, private, and charter schools nearby. Enjoy the Florida Keys lifestyle: no state income tax, roughly 230 sunny days a year, and some of the most stunning beaches, fishing, and boating waters in the country. Live securely, comfortably, and luxuriously in paradise, and schedule your private showing today.

273 W Seaview Dr, Duck Key

$2,200,000
3 Beds 2 Baths 620145 MLS
Welcome to your waterfront retreat on Ramrod Key, where beautiful open water views, quick ocean access, and exceptional outdoor living create the ultimate Florida Keys lifestyle. Built by renowned Tom Ryan in 2007, this well-maintained 3-bedroom, 2-bath home is designed for both relaxation and adventure. Step inside to a bright, open-concept living area featuring a spacious kitchen with ample storage and seamless flow between the living, dining, and outdoor spaces. A split floor plan offers privacy for owners and guests alike, while the primary suite enjoys its own porch overlooking your private salt pool, creating the perfect place to greet the sunrise with a cup of coffee. Outside, the property truly shines. Boaters will appreciate the 40-foot dock with a 60-foot walkway and quick access to the Atlantic Ocean. Spend your days fishing, diving, or exploring the backcountry before returning home to unwind beneath the tiki hut or take a dip in the heated and chilled saltwater pool, recently recoated and tiled and offering up to 6 feet of depth. A small sandy beach adds to the island charm and provides a unique waterfront setting rarely found in the Keys. Additional features include impact windows and doors, metal roof, a dedicated laundry room and garage with ample storage for all your gear, making this property an ideal full-time residence, vacation home, or investment opportunity. Experience the best of waterfront living in the Lower Florida Keys.

27348 Dominica Ln, Ramrod

$2,200,000
3 Beds 2 Baths 619483 MLS
Experience the pinnacle of Florida Keys waterfront living in this newly constructed (2023) open water home on Big Pine Key. Perfectly positioned to capture breathtaking sunrise views, this CBS-built residence offers a seamless blend of modern coastal design, durability, and effortless indoor-outdoor living. Spanning 1,834 square feet, the home features 3 Bedrooms and 2 Bathrooms, thoughtfully designed with soaring 10-foot ceilings, 8-foot doors, and expansive impact-rated windows and doors that invite in natural light while framing panoramic water views throughout the living spaces and Primary Suite. The heart of the home is the stunning chef's Kitchen, appointed with white quartz countertops, stainless steel appliances, custom cabinetry, and an oversized dining bar--ideal for entertaining guests or enjoying casual waterfront dining. The Primary Suite serves as a tranquil retreat, complete with sweeping water views, a spacious custom walk-in closet, and a beautifully finished modern Bathroom. Outdoors, the property transforms into a private resort. A large waterfront Pool overlooks the open water, while the 75-foot Concrete Dock with a protected cut-in Boat Slip provides exceptional boating convenience with deep water access to both the Gulf and Atlantic via Bogie Channel, renowned for its excellent fishing. Offered fully Turn-Key and rental ready, this property is perfectly suited for a luxury second home or income-producing investment. As a newer construction, it also benefits from lower insurance costs, an increasingly valuable advantage in the Keys. Located in Big Pine Key, home to serene nature preserves, the famous Key Deer, and convenient shopping and dining, you are also just minutes from the pristine beaches of Bahia Honda State Park.

1631 Sunrise Dr, Big Pine

$2,199,000
4 Beds 4 Baths 620883 MLS
Getting out on the water is simple from this beautifully remodeled 4-bedroom, 4-bath home, and coming home feels just as inviting. Set along a wide canal, the property offers quick access to open water with no fixed bridges. A private pool and inviting indoor-outdoor living spaces make being at home just as enjoyable as a day on the water. Inside, the open layout feels bright, spacious, and thoughtfully designed, with impact-rated windows and doors throughout. The kitchen is finished with KraftMaid cabinetry, quartz countertops, and stainless steel appliances, creating a clean space that connects naturally with the main living area. Impact-rated folding sliders open fully to a 450 sq. ft. covered lanai, making the home ideal for entertaining or unwinding. The spacious primary suite includes a walk-in closet and an updated bathroom with a rainfall shower head. One of the guest bedrooms also features a walk-in closet, adding valuable storage and comfort. Porcelain tile flooring runs throughout the main home, while arched architectural details inside and out give the property a distinctive sense of character. The outdoor area offers the kind of setting that makes it easy to lose track of time, with 1.25' Shellstone pavers, covered patio space, privacy fencing, and a full bathroom conveniently located off the pool deck. Along the canal, the concrete seawall offers excellent dockage and room for a future boat lift. Additional features include two-zone air conditioning, two on-demand water heaters, brand new PVC plumbing throughout, upgraded electrical, a detached poolside cabana with electricity. Located in Key Haven, just minutes from Key West, this home brings together privacy, thoughtful updates, excellent boating access, and the easy indoor-outdoor lifestyle that makes the Florida Keys so special.

52 Key Haven, Key Haven

$2,199,000
4 Beds 4 Baths 613691 MLS
INVESTORS will appreciate and experience waterfront living at its finest in this beautiful 2 story residence with a ground level elevated entry that has been renovated to achieve the perfect blend of coastal living with upscale entertaining in mind. Thoughtfully designed with an open and airy interior space, and grand entrance that flows effortlessly onto two outdoor balconies makes this residence perfect for entertaining or relaxing and enjoying the bay and sunset views. Features include a beautiful granite kitchen, custom and private bar area, open concept great room and neutral tiled flooring. The spacious chef's kitchen with granite counter tops and stainless steel appliances, a second level master suite with walk in closet, en suite bathroom with jetted tub and separate shower, three well appointed guest bedrooms, 3 bathrooms and office space off the main living area. Windowed porches allow for more living space outside of air-conditioned space as well as more entertaining room. Enjoy fishing off the dock or boating in and out of the area. The nearby community park boasts a small beach, and boat ramp which can be used to launch your boat. Restricted rentals makes this community even more desirable due to less vacation rentals and more serenity. This open water bay front home is located near Marathon Airport and the property can be purchased on one lot or can be combined with two parcels for potentially more living space, a cabana accessory structure, pool, putting green, or pickle ball court. West of Marathon Airport in a gated bay side community. Buy both for future potential living space or simply enjoy the green space overlooking the Florida Bay. Additional lot can be purchase separately and is contiguous to this home on 120 Pirates Cove Drive in exclusive and gated Stirrup Key.

120 Pirates Cove Dr, Marathon

$2,199,000
6 Beds 5 Baths 617882 MLS
This versatile 3-family property offers a rare blend of privacy & income potential. Designed as 3 distinct residences, each with a private entrance and it's own kitchen and w/d, the property is ideal for an owner-occupant seeking rental income or an investment for long term, vacation rentals or family compound. Main Level - Primary Residence: The spacious downstairs layout features a 2 bed, 2 bath, open-concept living area & updated kitchen w/ quartz countertops, wine cooler, & pantry overlooking the pool. The master suite has a built-in office, a custom walk-in closet system, & updated bath w/walk in shower. Main Level - Guest Suite is freshly painted w/private entrance, full kitchen, dedicated laundry, & full bathroom. Upper Level -3 beds & 2 baths, w/d, private entrance, French doors & balconies overlook the backyard foliage & pool. The 2nd remodeled bathroom services the 2 bedrooms, 1 of which is used as a media room. The open Living room/Kitchen has built-in wall shelves, The secluded backyard features a heated/chilled saltwater pool w/custom water feature by renowned master potter Jay Gogin. The grounds are secured by unique bamboo fencing and include a refreshing outdoor shower. Whole-house Generac generator and a large Rheem on-demand gas tankless water heater. Front of the house features an elevated patio overlooking the street. metal roof, accordion/panel storm shutters, & 2 driveways as well as 3 off-street parking . Need 24 hour notice to show!

1609 United St, Key West

$2,195,000
5 Beds 3 Baths 620325 MLS
TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven income, privacy, and future potential like this. Situated on nearly two acres spanning four lots, this unique compound offers a coveted transient license allowing nightly rentals and a well-established vacation rental business with a strong history of performance. Historically generating over $200,000 annually, with recent projections ranging from $250,000 to $300,000, this is an outstanding opportunity for investors, vacation rental operators, or buyers seeking a premier 1031 Exchange replacement property. More than just a rental property, this is a proven income-producing asset with an established guest base, and delivering the authentic Florida Keys experience that visitors seek. Rather than starting from scratch, a new owner can step into a property with a successful operating history and demonstrated demand. The property features a 4-bedroom, 2-bath main residence, relaxing pool, expansive outdoor living areas, and a separate concrete guest structure complete with bedroom, bath, and kitchenette. Fully fenced with two private entrances, the grounds offer exceptional privacy, abundant tropical landscaping, fruit trees, palms, and ample space for RVs, boat trailers, and recreational equipment. Over 100 Palm trees Future upside may exist through additional development opportunities, expansion of the existing compound, or further enhancement of the guest experience, subject to buyer verification and applicable regulations. Properties offering a transient license, multiple lots, substantial acreage, proven income, and future potential are increasingly rare in today's Florida Keys market. Whether you're seeking a high-performing vacation rental, a strategic 1031 Exchange acquisition, or a private Florida Keys retreat, this property is positioned to deliver value and Solid ROI from day one.

125 Colson Dr, Cudjoe

$2,195,000
3 Beds 4 Baths 619577 MLS
Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort-style living awaits in this Key West-inspired residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined by serenity and sophistication. A palm-lined entrance leads to a vibrant exterior with wraparound porches and sun-filled interiors framed by lush garden views. The spacious three-bedroom layout is designed for effortless indoor-outdoor living, with multiple gathering spaces opening to expansive patios ideal for entertaining, unwinding, or savoring golden sunsets. Mature palms, bougainvillea, and the scent of salt air create a secluded sanctuary that feels worlds away. Residents enjoy exclusive access to a resort-style pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to world-class sport fishing and boating, while full-time on-site property management ensures peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. Whether you're seeking a seasonal escape or a long-term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.

33 Pen Ky, Islamorada

$2,195,000
4 Beds 4 Baths 618256 MLS
This fully renovated canal front home at 1724 Bahama Drive offers modern waterfront living in a highly convenient location in Key West. The property features four bedrooms and four bathrooms and includes a separate mother in law unit, making it well suited for guests, extended family, or flexible use. The home has been completely updated with a new kitchen featuring quartz countertops, custom cabinetry, and stainless steel Thermador appliances. New tile flooring, updated lighting, and fully renovated bathrooms with clean modern finishes create a bright and comfortable interior throughout. The home also includes a new central air conditioning system and discreet security cameras that blend seamlessly into the design. A new roof adds peace of mind and makes this a true move in ready property. Outside, the home offers 56 feet of concrete seawall along a calm canal, providing excellent dockage potential and easy access for boating and paddleboarding. The outdoor space includes a bar and grilling area that is ideal for entertaining, along with a fully fenced yard finished with low maintenance turf for privacy and ease of care. The location is one of the home's strongest features. It is close to schools and the local high school and is within five minutes of grocery stores, restaurants, and beaches. Downtown Key West is approximately ten minutes away, offering quick access to Old Town, shopping, dining, and entertainment. This is a rare opportunity to own a fully renovated canal front home with flexible living space, boat ready frontage, and a central Key West location. One of the owners is a Licensed Florida Realtor.

1724 Bahama Dr, Key West

$2,149,000
3 Beds 3 Baths 620284 MLS
The Boater's Dream. Navigate the Marathon waters with ease right from your backyard. This property features a 55-foot, new composite dock situated on a deep canal, paired with a 20,000 lb boat lift. Embrace the sunshine in your private, fenced-in backyard. The grounds feature a heated in-ground pool, a screened patio, and a custom outdoor kitchen with a built-in outdoor kitchen--the perfect setup for hosting post-fishing dinners. The property is solid concrete construction and also boasts a brand-new metal roof for ultimate peace of mind. Massive storage, workshop, and garage. The stunning main living area is perched on the second floor, maximizing the beautiful canal views. The open-concept design seamlessly connects the living room to a gourmet kitchen outfitted with granite countertops, stainless steel appliances, a wine cooler, and custom cabinetry. The second floor also hosts two bedrooms and two bathrooms, including the spacious master suite. Fully furnished and fortified with impact-resistant doors and windows (plus accordion and Bahama shutters), this home is move-in ready. An interior staircase leads down to a highly desirable feature: a legal, above-flood ground-floor bedroom and full bathroom. An additional bonus room could easily be the fourth bedroom. The lower level is incredibly practical, offering a fully equipped garage, a dedicated storage room, and a workshop for all your maritime gear and tackle. This home is eligible for seven night rentals and would make a tremendous vacation rental investment.

969 Ocotillo Ln, Marathon

$2,099,000
4 Beds 4 Baths 621161 MLS
Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the surrounding water views and tropical air into everyday life. The main level is designed for both privacy and gathering, offering 3 guest bedrooms, 2 full baths and a laundry room alongside a second living area that opens onto a spacious covered balcony. One bedroom enjoys its own ensuite, while the remaining two share a well-appointed Jack and Jill bath. Ascend to the main living level and the home opens into a bright and airy Great room where kitchen, dining and living areas unfold together. Anchored by a substantial island and dining bar, the kitchen is finished with Silestone countertops, a sea glass tile backsplash and abundant custom cabinetry. Beyond, another expansive balcony extends the living space into the open air, ideal for evening entertaining or a quiet morning coffee. The primary suite occupies its own private wing upstairs, offering generous closets and a spa inspired ensuite with a jetted tub and separate walk-in shower. Outside, a heated and chilled concrete pool sets the stage for effortless indoor-outdoor living, while a 30-foot concrete dock with lighting and bubblers provides canal access for boating, paddling or an evening line in the water, with the open water just minutes beyond. Located just minutes from local restaurants, shopping and coffee shops, this a rare balance of quality, privacy and island sophistication, backed by a proven rental history that makes it as compelling an investment as it is a home.

1106 Thatch Ln, Cudjoe

$2,099,000
3 Beds 2 Baths 620226 MLS
Enjoy sweeping ocean views from this beautifully designed Coastal Modern waterfront home in the heart of Marathon. Built with both style and durability in mind, this 3 Bedroom, 2 Bath CBS residence features concrete walls, floors, and roof, along with impact windows and doors for added peace of mind. Inside, oversized tile flooring and a bright open-concept layout create a clean, contemporary feel filled with natural light. The main living area flows comfortably to outdoor spaces, making the home ideal for relaxed Keys living and effortless entertaining. Two spacious guest bedrooms and a well-appointed guest bath provide inviting accommodations, while the private top-floor primary suite offers a peaceful retreat with access to the rooftop deck. An additional bonus space on the main level adds valuable flexibility and could serve as a possible 4th bedroom, office, pool cabana/dressing room or convenient guest overflow area. The rooftop deck is a true highlight, showcasing panoramic views of the turquoise Atlantic waters. Whether enjoying sunrise coffee, afternoon breezes, or evening cocktails under the stars, this elevated outdoor space captures the best of coastal living. After a day on the water, return to your concrete dock and unwind beside the canal-front pool with jets, or gather with guests on the expansive pavered patio overlooking the water. With multiple outdoor living areas, dockage, pool, and ocean views, the property is perfectly suited for boating, entertaining, and enjoying the laid-back island lifestyle. Conveniently located just minutes from restaurants, shopping, and the Marathon Airport, this property offers an exceptional blend of modern construction, coastal style, and Florida Keys waterfront living. With a proven rental history, this property also presents an outstanding investment opportunity for those seeking personal enjoyment and income potential in one of the Keys' most desirable destinations.

1040 81st Street Ocean St, Marathon

$2,075,000
2 Beds 2 Baths 618666 MLS
What does everyone dream of? The smallest house in the best neighborhood -- and this one delivers. Welcome to easy, breezy living in Port Antigua, where charm, quality, and location come together beautifully. This thoughtfully updated home is being offered fully furnished -- from stylish pieces down to kitchen wares, dishes, and linens -- making your transition to the Keys seamless. Just bring your flip-flops. Impact windows and doors are installed throughout, including three skylights set into the concrete roof, so you can relax knowing your investment is well protected while natural light pours in from above. Upstairs, the open-concept living space feels airy and inviting, perfectly suited for gathering with friends and family. Triple sliding glass doors lead to a spacious second-floor terrace, creating that effortless indoor-outdoor flow we all love about coastal living. A separate laundry room just off the kitchen adds everyday convenience without sacrificing style. Both bedrooms feature their own sliding glass doors to the terrace, welcoming in sunshine and soft island breezes -- a gentle reminder that you're living somewhere special. Downstairs, you'll find abundant storage space and a 70-foot concrete dock complete with a fish-cleaning station and boat lift -- ready for offshore adventures or sunset cruises at a moment's notice. The yard is designed for low-maintenance enjoyment, with river rock and a clean concrete driveway in front, and artificial turf in the back for a lush look without the upkeep. This is the one you've been waiting for -- refined yet relaxed, polished yet playful. A perfectly sized slice of paradise in one of the Keys' most desirable neighborhoods.

121 Lisbon Ct, Islamorada

$2,060,000
5 Beds 3 Baths 620686 MLS
Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat. Featuring an adjacent oceanfront parcel with a private beach, kayaks, and a floating dock for fishing or docking boats up to 24 feet, this property provides everything needed for fun and relaxation. Outdoors, enjoy a sparkling swimming pool, soothing hot tub, tropical landscaping with coconut palms and banana trees, and a screened-in porch for al fresco dining. Inside, the open floor plan includes four king bedrooms and a fifth bedroom with a queen and single bed, smart TVs, and updated appliances. Centrally located at MM21.5, Fandango is just 20 minutes from Key West, 10 minutes from Big Pine Key, and 15 minutes from Bahia Honda State Park, with dining options nearby, including a 5-star restaurant within a mile. This property is offered fully furnished and equipped, including bookings into 2027 and 10-years' average income of $160+k. Professional property management is in place, ensuring both secure investment returns and worry-free family vacations. This low-maintenance, turn-key home offers the rare opportunity to own one of the few legally licensed short-term rentals in the Lower Keys. Owning a vacation rental property means you're not just paying for vacations--you're building equity and unlocking financial benefits, all while eliminating the scramble for accommodations every trip. Show up, relax, and let your investment work for you.

94 Sacarma Dr, Cudjoe

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