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$27,000,000
5 Beds ⋅ 8 Baths ⋅ 619825 MLS
Set on over 2 acres along prestigious Millionaire's Row in Tavernier, this newly constructed oceanfront estate represents a rare convergence of scale, design, and functionality in the Upper Florida Keys. Encompassing 8,200 square feet of interior living space and over 16,000 square feet total, the residence is thoughtfully designed to accommodate both elevated everyday living and large-scale entertaining.The home features 5 bedrooms, 6 full baths, and 2 half baths, with all bedrooms offering en suite accommodations, custom closet build-outs, and refined finishes throughout. Additional interior spaces include a dedicated office, control room, mud room, and laundry room, providing both comfort and operational efficiency. A private elevator, whole-home sound system, and advanced mechanical infrastructure--including 600-amp service, multiple electrical panels, and five independent AC zones--underscore the property's level of detail and performance. Interior finishes are curated with a modern coastal aesthetic, highlighted by white diamond marble and teak wood flooring & a custom steel roof. The chef's kitchen is outfitted with top-tier Wolf, SubZero, and Cove appliances, including a 60-inch range, dual dishwashers, farmhouse sinks, and custom mahogany countertops--designed to seamlessly blend form and function. Outdoor living is equally exceptional, with 240 feet of oceanfront, anchored by a 120-foot resort-style pool, complete with multiple heating and chilling systems, a gas-heated spa, and full smart control. A fully equipped summer kitchen, cabana bath, and multiple covered entertaining areas create a true indoor-outdoor lifestyle experience. Additional highlights include a 3-car garage and fully equipped workshop with air conditioning, utilities, security systems, and custom lighting. The property is also zoned for weekly rentals, presenting a compelling opportunity for both personal enjoyment and income potential.

88845 Old Hwy, Tavernier
$15,000,000
3 Beds ⋅ 3 Baths ⋅ 619824 MLS
An exceptional opportunity on coveted Millionaire's Row in Tavernier, 88835 Old Highway offers over 3 acres of oceanfront property paired with a rare additional acre featuring a protected boat basin--delivering a unique blend of privacy, usability, and future potential in the Upper Keys. Completed in 2022, the existing 3-bedroom, 3 bath residence spans approximately 1,500 square feet and is thoughtfully designed with impact windows and doors, hardwood flooring, a steel metal roof, and a well-appointed kitchen featuring Viking appliances. Outdoor living is enhanced by shell stone porch flooring, covered parking, and professionally designed landscaping with turf for low-maintenance coastal living. The property is comprised of three distinct parcels, including a buildable lot (Lot 2A), the current homesite (Lot 2), and a natural hammock parcel (Lot 3A) that serves as a permanent privacy buffer from the road, preserving the integrity and seclusion of the estate. A highly valuable feature of this offering is the inclusion & rare opportunity to create a custom waterfront compound tailored to your vision, while maintaining immediate livability. With direct access to a private boat basin and expansive acreage rarely found in the Keys, 88835 Old Highway represents a compelling combination of current enjoyment, future development flexibility, and long-term value in one of the area's most desirable waterfront corridors.

88835 Old Hwy, Tavernier
$8,000,000
3 Beds ⋅ 3 Baths ⋅ 619592 MLS
Discover your dream retreat in this beautiful oceanfront home, set on 1.5 acres of prime beachfront property with 150 feet of pristine white sandy beach, this is the ultimate getaway for relaxation and adventure. Unwind in the oversized heated pool or customized hot tub after a day of sun and fun. The Tiki Hut provides convenient storage for all your water toys, making your boating and beach days effortless. Enjoy practicing your swing on the private putting golf course, all while surrounded by breathtaking ocean scenery. With a lucrative 7-day rental option and an easily obtainable license, this gem is perfect for both personal enjoyment and investment. Don't miss your chance to own this slice of paradise--schedule a viewing today!

88747 Old Hwy, Islamorada
$1,550,000
5 Beds ⋅ 3 Baths ⋅ 619545 MLS
Experience Coastal Luxury and privacy with this exceptional 5 bedroom, 3 bath home on two lots!! Over 2900 sq. ft. of thoughtfully designed living space. Constructed of concrete with impact windows and doors and recently painted inside and out, this home blends style, safety, and comfort. The property's coastal architectural charm is highlighted by a beautiful wrap-around porch and a curved pavered driveway leading to the air-conditioned garage. the main floor includes three bedrooms and 2 baths, featuring a master suite at the end of the home with private access to the backyard and heated pool. Upstairs two large bedrooms share a Jack-and-Jill bath, ideal for family or guests. The chef's kitchen boasts stainless steel appliances, an eat-in area, and a full walk-in pantry, flowing seamlessly into the sun-room and open living/dining area with a canal view. The outdoor living spaces are designed for entertaining and relaxation, including a heated pool with Jacuzzi, torch-lit ambiance around the pool, a fire pit and beautifully landscaped grounds. An air-conditioned shed - currently used as a potting shed - can easily serve as a playroom, art studio, or man cave. Boating enthusiasts will love the boat storage with in-and-out service less than 5 minutes away, offering reduced maintenance and added protection. Convenient access nearby to boat ramps at Founders Park, which also offers a sandy beach, pool, dog park, and sports field. Many community events held here - and you can just walk over to them. This home is set in a private, desirable neighborhood near upscale dining and amenities. Luxury, versatility, and lifestyle in one perfect package. Please schedule your private showing today to experience 169 Venetian Way!!

169 Venetian Way, Islamorada
$1,095,000
5 Beds ⋅ 3 Baths ⋅ 619499 MLS
Live the Florida Keys Lifestyle in Your Dream Home Experience the perfect blend of elegance, functionality, and laid-back tropical living in this beautifully designed Florida Keys-style home. The open-concept floor plan creates a seamless flow between the living, dining, kitchen, and loft areas--ideal for both everyday living and entertaining. The spacious primary suite offers a private retreat, complete with a custom ensuite bathroom featuring a luxurious rain shower--perfect for your own spa-like escape. Generously sized guest bedrooms and three full bathrooms ensure comfort and convenience for family and visitors alike. At the heart of the home, the expansive kitchen provides abundant workspace for everything from quick meals to gourmet cooking, all while staying connected to guests in the open living space. Above, a versatile loft adds architectural charm and flexibility--ideal for a home office, media room, or creative studio. Additional highlights include: Separate laundry room for added organization Detached garage with attic storage--perfect for a vehicle, boat, or potential guest conversion Attached storage shed for tools, toys, or future expansion Street-to-street access for easy parking and convenience Plenty of room to design your own private pool and outdoor oasis Enjoy cost savings with insulated glass windows and French doors that fill the home with natural light while enhancing energy efficiency. Step outside and unwind in your private tropical setting--perfect for entertaining, relaxing under the stars, or enjoying quiet moments with friends and family. Ideally located near shopping, dining, schools, and medical facilities, with convenient access to both the bay and ocean via Tavernier Creek. Welcome to your slice of paradise.

106 Gardenia Ave, Tavernier
$635,000
3 Beds ⋅ 3 Baths ⋅ 619364 MLS
Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setting. This nicely updated 3-bedroom plus loft townhouse offers a spacious and versatile layout designed for easy everyday living and entertaining. Upstairs, you'll find three inviting bedrooms, two full baths, and a charming loft--perfect for additional guests, a home office, or a cozy retreat. Downstairs, thoughtful updates create a seamless flow, with a level floor plan that connects the living and dining areas--no step-down interruptions--enhancing both function and openness. The expanded kitchen is a standout feature, showcasing stainless steel appliances, generous counter space, and a peninsula with double-sided storage, ideal for both cooking and gathering with friends and family. A full bath on the main level adds convenience for guests. Beyond your front door, Executive Bay Club offers an array of amenities to complement the coastal lifestyle. Enjoy two tennis and pickleball courts, newly expanded first-come, first-serve dockage for your boating adventures, and a beautifully renovated pool area complete with updated pool deck and bath facilities. The refreshed clubhouse provides an inviting space to relax and connect with neighbors. Whether you're seeking a full-time residence or a weekend escape, this welcoming townhouse delivers the perfect blend of elegance, comfort, and laid-back island living.

87200 Overseas Hwy Unit S3, Islamorada
$745,000
4 Beds ⋅ 3 Baths ⋅ 619243 MLS
Stunning 4-bedroom, 3-bathroom home, recently renovated to perfection. This modern masterpiece is located in the highly desirable X flood zone, offering peace of mind and lower insurance costs. Step inside to a bright, airy floor plan that blends classic design with the relaxed Keys lifestyle. Soaring ceilings and abundant natural light create an open, welcoming feel throughout the living areas, beautifully complemented by custom LED lighting.The open-concept gourmet kitchen features stylish finishes, stainless steel appliances, quartz countertops, and a large island that's perfect for entertaining. The luxurious primary suite includes a spacious en-suite bathroom with a walk-in shower. Three additional bedrooms provide plenty of flexible space for family, guests, or a home office. New flooring and contemporary fixtures complete the fresh, move-in-ready interior. Outside, enjoy a large screened-in porch ideal for relaxing or hosting gatherings, plus an expansive backyard with room to add a pool and beautiful views of swaying palms and endless blue skies. Residents of Edenaire enjoy exclusive access to the community park, which includes a fenced picnic area, grill, trailer parking, boat ramp, and 72-hour dockage--giving you direct access to Tavernier Creek, the ocean, and the bay for boating, fishing, paddleboarding, and more. You will not find a 4 Bed 3 Bath home fort this price and in this neighborhood. X Flood, 2021 Roof. This property is currently rented and requires at least 24 hours' notice for all showings. Contact agent for lease details.

178 Coral Ave, Tavernier
$2,750,000
3 Beds ⋅ 2 Baths ⋅ 619095 MLS
Don't let the address fool you, this home has easy bay access! Welcome to relaxed waterfront living in the Village of Islamorada, where open water views and nightly sunsets set the tone for an effortless Keys lifestyle. This inviting three-story home is designed to capture light, breezes, and the beauty of its surroundings. Inside, vaulted tongue-and-groove ceilings and an airy open floor plan create a warm coastal ambiance, while expansive impact windows and doors frame sweeping water views. The main living spaces flow seamlessly together, making it easy to entertain or simply unwind after a day on the water. Three comfortable bedrooms and two baths provide plenty of room for family and guests. Step outside to enjoy open terraces on both levels--perfect for morning coffee, sunset cocktails, or watching boats glide by on their way to Florida Bay just minutes away. Boaters will appreciate the concrete dock and quick access to some of the Keys' most spectacular waters. Thoughtfully equipped with impact windows and doors and a whole-house generator for peace of mind, this waterfront retreat blends comfort, practicality, and the timeless charm of Islamorada living--where every evening ends with a sunset over the bay.

149 Lake Rd, Tavernier
$4,445,000
8 Beds ⋅ 4 Baths ⋅ 619083 MLS
Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique and valuable than others, we offer 100 linear feet of dockage. There is a 30,000 pound lift for your large boats and a 10,000 lift for your smaller boats. And there is still room for another vessel or personal water crafts. This home offers three levels, the main level has three bedrooms a full bath a kitchenette and living area with great views of the water. The second level, large living area with soaring ceilings, a massive kitchen, 2 bedrooms and a full bath. The third level offers 3 bedrooms and 2 full baths. There is an abundant pool and bar area for entertaining family and friends. Looking for a home to accommodate the large extended family, this is it or put it out in the Airbnb world, it would make a great income property.

136 San Remo Dr, Islamorada
$2,400,000
3 Baths ⋅ 618987 MLS
Commercial opportunity for investors and owner-operators! 1,957 sq. ft. solid concrete professionally designed and built commercial building with impact windows and doors on an oversized 12,000 sq. ft. lot. Exceptional visibility from U.S. 1, access from Old Highway with ample parking, and prominent signage. 1st Floor: Spacious reception and work areas with custom-built-ins, one full and one-half bath, kitchenette, attic, sizable storage room, workshop/garage, and fenced parking area. Sale includes office seating and filing cabinets. 2nd Floor: Open layout with breakroom featuring kitchenette, washer/dryer, full bath, and interior design showroom (featuring two luxury sample closets and custom product display shelves). One of the most desirable areas of the Florida Keys located in the Village of Islamorada! Don't miss out on this investment with many zoning opportunities for businesses!

88701 Overseas Hwy, Tavernier
$14,990,000
6 Beds ⋅ 9 Baths ⋅ 618911 MLS
Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival. Set on over 2 usable acres with 210 feet of private sandy beachfront and a protected cove, the residence spans 7,590 square feet of interior living space & 1,736 square feet of exterior living, with an expansive 230-foot dock. Designed for seamless indoor-outdoor living, the home features a dramatic great room with 23-foot ceilings, panoramic Atlantic exposure, and expansive covered terraces with summer kitchen and outdoor dining areas. A 65-foot heated lagoon-style pool with swim-up bar and fire-pit lounge creates a resort-caliber setting. The chef's kitchen is appointed with Sub-Zero, Wolf, and Thermador appliances. Additional highlights include dual primary suites, private orchid garden, lounge & recreation room, elevator, Sonos surround sound, impact windows and doors, metal roof, double-height garage, water-sports storage room and a full home generator. The essence of beachfront living in Islamorada, combining impressive scale and ultimate privacy. ***A contiguous 0.7-acre lot with development rights for an ancillary building with upstairs storage is available separately.

88351 Old Hwy, Islamorada
$3,800,000
5 Beds ⋅ 3 Baths ⋅ 618165 MLS
Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Café, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and a rare tiki hut at the end of the dock—your new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living area—ideal for guests or extended family. Whether you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

87950 Overseas Hwy, Islamorada
$1,895,000
3 Beds ⋅ 2 Baths ⋅ 618096 MLS
Bay views with a canal front price! This beautifully coastal modern renovated property is located on the main free flowing canal in the desirable community of Indian Waterways. Designed with entertaining in mind, the open-concept floor plan features a stunning kitchen with a pass-through to the expansive deck, creating seamless indoor-outdoor living. Wake up to Florida Bay views from all of the bedrooms and living area with the primary bedroom being located on either the main level or second levels. Perfect for boating enthusiasts with deep water dockage for a large boat, this property provides direct access to Florida Bay and the Atlantic via Tavernier Creek or Snake Creek. There's plenty of room for a pool, while the versatile enclosed flex area downstairs invites endless possibilities for entertaining, storage, workshop and parking. Tucked away on a peaceful dead-end street in the sought-after Indian Waterways community, this home is the perfect sanctuary—whether for raising a family or enjoying a tranquil weekend escape in the Keys.

185 Ojibway Ave, Tavernier
$399,000
2 Beds ⋅ 1 Baths ⋅ 618336 MLS
This two bedroom, one bathroom home within the Village of Islamorada is perfectly situated with close proximity to the Florida Bay and breathtaking bay and sunset views! Property is on a 3,600 SF parcel. A large screened porch is attached for lovely outdoor living. Separate laundry facility and storage building on site. Also included is a Keys style concrete guest cottage behind the home. This property has an immediate building right should you choose to demo and rebuild. A quote is available to demo and re-build a 1,169 SF, three bedroom, three bathroom new modular residence. The home is conveniently located near Founders Park, restaurants, schools and shopping. This is a fantastic opportunity to find your place in the Florida Keys!

135 Airstream Ln, Tavernier
$4,799,000
3 Beds ⋅ 3 Baths ⋅ 618338 MLS
An exceptional and increasingly rare opportunity to own a coveted stretch of waterfront on Tavernier Creek, one of the Florida Keys' most treasured waterways. Set along protected open water in the heart of Plantation Key, this refined residence offers immediate access to both the Atlantic Ocean and Florida Bay, a privilege few properties can claim in the Upper Keys. Thoughtfully reimagined with interiors designed by a notable Ocean Reef Club designer, the home blends classic island architecture with sophisticated modern coastal updates. Solid concrete construction, a new roof and multiple new air-conditioning systems within the last five years, and a full mosquito control system provide comfort and peace of mind. The three-bedroom, three-bath interior is filled with natural light, featuring floor-to-ceiling windows and French doors that frame creek views. The gourmet kitchen features a six-burner gas range, premium stainless steel appliances, and seamless flow into the living and dining areas, ideal for entertaining and everyday living. Hardwired electric shutters provide storm readiness without compromising design. Ample room for thoughtful expansion provides the opportunity to further customize. Outdoors, the property unfolds as a private resort-style retreat with a custom inground pool and tanning ledge, summer kitchen with wet bar, beverage refrigerator and ice maker, gas fire pit, and a covered rooftop terrace offering elevated sunset views over the water. For boating enthusiasts, the T-dock with boat lift offers protected deepwater dockage. A Chicago brick driveway, professional landscaping, and a rare enclosed garage enhance curb appeal and functionality. Centrally located between Tavernier and Islamorada and offered as one of the lowest price-per-square-foot opportunities on the creek, this exceptional residence presents a premier opportunity to own a designer-finished waterfront home with outstanding boating, privacy, and long-term investment potential.

171 Kahiki Dr, Tavernier
$999,999
2 Baths ⋅ 616512 MLS
Looking to purchase your own office space while also generating rental income? This property delivers both. Located in Islamorada, this two-story Key West/Conch-inspired building is zoned for mixed-use highway commercial. 50 feet of frontage along the Overseas Highway, providing strong visibility and signage potential. The exterior is accented by mature landscaping, with parking that includes four spaces in front of the building (per survey, now landscaped) and nine more spaces in the rear with direct access from Old Highway. Inside, the building offers a bright reception area and functional layout. The second floor features 5 one-room offices with a shared kitchenette and half bath, providing the potential of consistent income from annual or month to month tenants. On the ground level, the owner's suite includes a private office, a small meeting room, and a larger executive-style conference room, along with its own kitchenette and half bath. There is one additional office and locked storage room down another set of stairs bringing the total to 7 private offices and two conference rooms. Positioned in a central Upper Keys location, the property is just minutes from local courthouse, downtown Islamorada and Tavernier, with convenient access to local restaurants, shopping, and Founder's Park. With the space for an owner's own office and conference room this property presents an excellent investment in one of the most desirable areas of the Florida Keys.

88101 Old Hwy, Islamorada
$630,000
2 Beds ⋅ 2 Baths ⋅ 617971 MLS
Private location for your pleasure at this roomy townhouse offering an abundance of space to enjoy. Spiral stairs leading to the primary suites with an additional loft for your quests. Soft carpet on the living area floors with tile in the remodeled kitchen and beautiful bathrooms. Two pets allowed, with first come first serve the waterfront area. Pool and club house for your recreation along with a nice, landscaped community for your pleasure. 28-day rentals permitted. Garden setting from you extended living room to enjoy the outdoors at your back yard.

87200 N Overseas Hwy Unit N2, Islamorada
$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
$750,000
3 Beds ⋅ 2 Baths ⋅ 613083 MLS
All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms plus oversized loft with additional queen and three twin beds. This Townhouse has ALL NEW kitchen, new bar, new built-ins, new custom fishing closet & storage, brand new 4 ton AC unit, 2 brand new Bathrooms with showers, new extended loft area, new full size Washer/Dryer, new BBQ area with new patio chicago brick pavers plus private patio shaded area with beautiful palms trees, serena & lily furniture inside, new electric panel, new electric water heater, new 80' smart OLED TV, new area just for refreshments, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. New Electric car charging electric panel exclusive to this unit. Best area in the community next to pool and marina with two pickleball courts and basketball court in the rear. Sleeps easily over 10 people. King bed in the master bedroom, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for over $6,500 a month! Call today! This community features a new private beach, marina, dock and clubhouse. Being SOLD fully furnished and fully equipped with high end appliances (FRIGIDAIRE), high end furniture (SERENA & LILY) and furnishings. See 3 Videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

87200 Overseas Hwy Unit V9, Islamorada
$18,999,000
6 Beds ⋅ 8 Baths ⋅ 615643 MLS
The Oasis Islamorada is a waterfront estate of exceptional scale, conceived as a private Florida Keys compound where architecture, land and water come together spanning nearly 3 meticulously landscaped acres. More than 400' of shoreline, sweeping ocean views and a protected deepwater basin create a marine setting rarely available within a single residential offering. Beyond the grand porte-cochère, the single-level main residence unfolds with soaring ceilings, white oak floors and 12-foot retractable glass walls that dissolve the boundary between interior and oceanfront living. At its center, a chef's kitchen pairs a cascading Calacatta marble island with Thermador appliances and a walk-in pantry, opening seamlessly to expansive living and dining spaces. The main residence includes four bedrooms and six full baths, with an impressive primary suite featuring a fireplace, dual walk-in closets, safe room and spa bath with steam shower. Additional suites offer en suite baths, private balconies and ocean views. A detached two-bedroom, two-bath guest residence brings the estate to six bedrooms while preserving privacy between owners and guests, with substantial grounds offering extraordinary flexibility for the future. Outside, the property assumes the scale of a private resort. Two resort-style pools with spas and sun decks are joined by a summer kitchen, alfresco dining and multiple waterfront terraces. A fitness center with sauna, soundproof theater and golf simulator complete the lifestyle offering. For the yachtsman, the protected deepwater basin accommodates substantial vessels with convenient direct Atlantic access. Built with an uncompromising focus on quality, security and enduring construction, The Oasis is more than an oceanfront residence. It is a legacy-scale Florida Keys estate offering the increasingly rare combination of acreage, significant shoreline, protected deepwater dockage, multiple residences and complete privacy within one extraordinary property

87429 Old Hwy, Islamorada
$1,390,000
2 Beds ⋅ 2 Baths ⋅ 616971 MLS
Located on a tranquil canal-front setting in the desirable Plantation Key Colony, this impeccably updated, turnkey ground-level residence offers two bedrooms, two baths, 50 ft of coveted dockage, and boat slip with immediate bay access. Meticulously maintained and ready for carefree island living. The home's concrete, ground-level construction enhances both durability and ease of maintenance, while a fresh, clean aesthetic unfolds inside and out. Recent upgrades and improvements include brand new metal roof, impact windows and doors, new interior and exterior paint, new interior doors, energy efficient appliances, new sewer line, and re-thatched tiki hut. Updates to the attached pull through garage includes new door rollers, lock hardware, and upgraded flooring and wall finishes, all designed to keep the property in turnkey condition. This home is for those who embrace water-based recreation with easy bay and ocean access via Tavernier Creek, a boat slip with ramp through the garage, and new fish cleaning station with electric and water hookup. The voluntary homeowners association offers a bayfront HOA park with a new boat ramp, beach, and picnic area. With its ideal location and exceptional features, this canal home presents a unique opportunity to embrace the vibrant lifestyle of the Upper Keys.

251 Azalea St, 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
$2,200,000
3 Beds ⋅ 2 Baths ⋅ 618660 MLS
First time on the market, this beautiful oceanside Key West/Bahama style home features 3 bedrooms/2 bathrooms, split floorplan for privacy, open living & entertaining area highlighted by soaring vaulted ceilings and abundant natural light. Spacious living area flows effortlessly onto an expansive lanai creating the perfect setting for outdoor dining, relaxing evenings, and enjoying the waterfront surroundings. The ground level features an impressive 2,376 square foot garage space (rarely found in the Keys) ideal for vehicles, boats, storage & workshop. Coveted corner lot with 215 feet of concrete dockage with davits. The canal provides direct ocean access to Tavernier Creek offering convenient & efficient passage to both the ocean and the bay, making this location especially desirable for anglers and cruisers alike. This is an opportunity to own a special waterfront home with exceptional dockage, oversized 10,000 square foot lot, tropical landscaping, and a paver driveway. This home is located near schools, shopping, restaurants, marinas (to fuel your boat). movie theater, and hospital.

216 Sonny Rd, Tavernier
$1,849,000
4 Beds ⋅ 2 Baths ⋅ 617994 MLS
Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp & Boat lift, . Step outside to your Private Oasis complete with a Private Tiki hut - Gorgeous secluded in-ground Pool and Cabana Hut Bungalow - The open-concept kitchen features Granite countertops and stainless steel appliances, ideal for effortless entertaining--Perfect for Boaters and outdoor enthusiasts. Tucked away in a quiet neighborhood, yet just minutes from restaurants, shopping, and top-rated schools, this home truly offers the best of island living. Seller will consider all reasonable offers.

150 Azalea St, Tavernier
$3,250,000
4 Beds ⋅ 3 Baths ⋅ 616450 MLS
Venetian Shores Has It All! Welcome to your slice of paradise in the heart of Islamorada's most sought-after boating community. This beautiful 4 bedroom, 3 bath coastal retreat is designed for both relaxation and entertainment, featuring 70 feet of deep-water dockage along a 100-foot wide canal - just seconds from open water via Snake Creek. Step inside the front door to access the elevator and interior stairs. Upstairs, the main living area offers 2 bedrooms and 2 baths, a wide open floor plan, and a gourmet kitchen with a large center island, granite countertops, stainless steel appliances, and a dedicated workstation. Enjoy sunset cocktails from the screened canal-side terrace, accessed via impact-rated sliding glass doors. Downstairs, the ground level is a haven for guests and fun - featuring a pool table, a comfortable tv area, 2 more bedrooms and a full bath, laundry room, and garage for all your gear. The backyard is pure Keys magic - complete with a heated pool, tiki hut, hot tub and an expansive deck for sunbathing or relaxing in the shade. Boaters will love the 70 ft concrete dock with a 15,000 lb boat lift, 50 amp shore power and fish cleaning station. This home checks every box for the ultimate island lifestyle - whether you're heading east to the Atlantic or west to Florida Bay's backcountry to enjoy fishing and breathtaking sunsets. Live the dream in Venetian Shores - where the boating is easy and the living is even better.

136 Giardino Dr, Islamorada