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$1,750,000
620523 MLS
Waterfront commercial building with boat slips for sale in Tavernier. Located near Tavernier Creek on the oceanside, this newer CBS building was constructed in 2016 and offers 1,584 square feet of commercial space on a 7,920 square foot lot with approximately 72 feet of waterfront. Zoned Village Center (VC). The building is divided into four commercial units and includes four separate electric meters and four mini-split A/C units. Two tenants are currently in place with leases. One tenant occupies Units 1-3, representing approximately 75% of the building, along with one restroom and one boat slip. The second tenant occupies three boat slips, the outdoor tiki area, and one parking space. Unit #4, representing approximately 25% of the building, and one boat slip are currently vacant, offering the opportunity for increased income. Excellent Tavernier location with direct ocean access without bridges, off-street parking for 7+ vehicles, and high visibility. Real estate only; businesses do not convey. Showings by appointment only. Please do not disturb tenants.

90515 Old Hwy, Tavernier
$2,350,000
3 Beds ⋅ 3 Baths ⋅ 620442 MLS
Welcome to your slice of paradise in the village of Islamorada! This solid concrete waterfront home was completely updated in 2007 including seawall, all plumbing and electrical and new concrete roof engineered to add another floor. The home has 3 bedrooms, 3 bathrooms and 75 feet of deep water dockage in one of the most desirable boating locations in the Florida Keys. Built with impact windows and doors, this home provides peace of mind while embracing the relaxed island lifestyle. Situated just one house in from Florida Bay, you'll enjoy breathtaking sunset views nearly every evening. Located just moments from Tavernier Creek, you'll have quick and convenient access to the Atlantic Ocean, making it the perfect location for anglers, boaters, and water enthusiasts alike. Inside the home offers comfortable living with 2/2 upstairs with walk in closets, high ceilings and crown molding and a large screen porch to watch sunsets. A spiral staircase leads to a 1/1 downstairs with kitchen and open living area. Plenty of storage and work area downstairs and a garage. Convenience is unmatched with a prime location close to schools, grocery stores, movie theaters, restaurants, shopping, and all the amenities that make island living so enjoyable. Whether you're searching for a full-time residence, a vacation home, or an investment in one of the Keys' most sought-after communities, this waterfront gem offers the perfect combination of location, boating access, quality construction, and endless potential.

239 Plantation Ave, Tavernier
$5,950,000
4 Beds ⋅ 4 Baths ⋅ 620455 MLS
Introducing an extraordinary, newly constructed waterfront estate that must be experienced in person. Perfectly positioned on a generous 13,200 sq ft double lot with 120 linear feet of water frontage, this one-of-a-kind residence showcases sweeping bay views, refined custom finishes, 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 bay vistas. 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 2,400 sq ft of balcony space. Outdoors, the property is equally impressive. The concrete dock and cut-in boat slip have been fully reinforced and rebuilt, providing excellent accommodations for your boat and all your waterfront toys. A beautiful swimming pool and charming gazebo create an ideal setting for entertaining family and friends. Plans are approved by the Army Corps for a new 20K lb boat lift, and final landscaping is scheduled for completion by July 2026. Additional features include ample space for a trailer or RV on the left side of the property and a spacious 278 sq ft storage area, perfect for fishing gear and water-sport accessories. Tucked away on a quiet dead-end street adjacent to a tranquil nature preserve, this home offers exceptional privacy and a peaceful, natural backdrop. Located within the highly coveted Indian Waterways community in the Village of Islamorada, you'll enjoy close proximity to world-class fishing, renowned waterfront dining, boutique shopping, and the unparalleled natural beauty of the Florida Keys. Owner/Agent.

195 Ojibway Ave, Tavernier
$3,995,000
5 Beds ⋅ 4 Baths ⋅ 620430 MLS
Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege. With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership. A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout. Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout. Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.

87445 Old Hwy, Islamorada
$3,875,000
4 Beds ⋅ 3 Baths ⋅ 620412 MLS
Coastal elegance meets the ultimate boating lifestyle in this beautifully updated Venetian Shores home. Designed for effortless Keys living, the open floor plan is filled with natural light, highlighted by a dramatic floor-to-ceiling wall of windows in the living area that brings the outdoors in. An inviting entrance foyer welcomes you inside, with interior stairs to the main living level. The spacious kitchen is the heart of the home, featuring stainless steel appliances, a large island for gathering, and a separate laundry room and pantry for added convenience. The main living level offers two guest bedrooms and two full baths, including one bedroom with a private en-suite bath. Direct access from the second-floor living area to the pool deck creates a seamless connection between indoor and outdoor living. The open floor plan offers plenty of room for dining, watching TV, conversation and even some ping pong. Upstairs, the expansive primary suite provides a peaceful retreat with a walk-in closet and luxurious en-suite bath. A fourth bedroom on the third floor offers flexibility for guests, family, or a home office. Separate air-conditioning systems for each floor ensure year-round comfort. Outside, 70 feet of dockage and a 27,000-pound boat lift make this property a dream for boating enthusiasts, with quick access to both the Atlantic Ocean and Florida Bay. The resort-style backyard is ready for endless summer fun, featuring a sparkling pool, expansive sun deck, shady lounging area, and abundant storage for all your fishing, diving, and water sports gear. Whether you're entertaining friends, heading out for a day on the water, or simply relaxing poolside, this exceptional Venetian Shores home offers the perfect blend of coastal sophistication and waterfront adventure.

109 Giardino Dr, Islamorada
$2,999,000
3 Beds ⋅ 4 Baths ⋅ 620411 MLS
Updated canal front pool home located in a desirable neighborhood with quick and easy access to the bay or ocean via Tavernier Creek, a boaters dream. It features a 3 bedrooms, 3.5 bath, a ground level entry with beautifully designed foyer, a large entertainment room with bar, a laundry room and a half bath. The second level has a spacious bedroom with an en-suite bath and an additional room for bedroom or office space with easy access to the pool/outdoor entertainment area. The main living area has an open-concept design with balcony, dining area and updated kitchen along with a guest bedroom and guest full bath. The spacious private master suite is located on the upper level with an en-suite bath, balcony and easy access to roof-top entertaining, which includes beautiful bay views, sunrises and sunsets. Additional interior features include new recessed lighting throughout the house along with interior stair lighting, updated bathrooms and new tile throughout the house, including outdoor balconies. Outdoor features include a beautifully designed entertainment area that includes a new pool with heater/cooler, outdoor shower, a fire pit and brand new outdoor kitchen with tiki, which makes it a great area to relax with friends and family after a long day of fishing. A new 70 ft dock with new pilings, Trex Decking and a newly installed 20,000# lift for your boat. Solid concrete construction with a new metal roof, newly waterproof coated/sealed flat roof top, impact windows and doors, new driveway pavers, new privacy fence, low voltage lighting and low maintenance landscaping. An attached air-controlled garage with new hurricane rated garage door and side doors, has plenty of storage for all your toys. This home checks all the boxes whether it's a primary residence, a weekend getaway or luxury vacation rental, it's move in ready. Great location near shopping, schools & restaurants.

111 Spoonbill Rd, Tavernier
$599,000
2 Beds ⋅ 2 Baths ⋅ 620393 MLS
Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. The main level features an open-concept floor plan with a spacious living area and kitchen, plus full bath, creating an inviting space for entertaining and everyday living. Upstairs, you'll find an expansive primary suite, a generously sized guest bedroom and full bathroom, and a thoughtfully finished loft accessed from the hallway that serves as an ideal bonus sleeping area or home office. Step outside and enjoy the exceptional amenities that make Executive Bay Club one of Islamorada's most sought-after waterfront communities. Residents have access to the newly expanded first-come, first-serve dockage, a bayfront beach area, unforgettable sunsets, and a new heated swimming pool complete with an updated pool deck, clubhouse and bath facilities, pickleball and tennis courts, kayak storage and 24/7 staffed gated entry. Whether you're searching for a full-time residence, vacation retreat, or investment opportunity, this welcoming townhouse offers the ideal blend of island charm to enjoy the Florida Keys lifestyle.

87200 Overseas Hwy Unit D3, Islamorada
$2,899,000
4 Beds ⋅ 4 Baths ⋅ 620278 MLS
Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily lot, giving you both immediate rental income and room to grow. In the Village of Islamorada, it is rare to find side-by-side multifamily parcels in such a convenient, desirable Upper Keys neighborhood. 127 Monroe Drive is a concrete triplex of roughly 2,400 sq ft on a 7,500 sq ft lot, with 3 rental units (1/1, 1/1, 2/2), full kitchens and baths, abundant on-site parking, and comfortable outdoor living areas. Units 1 and 3 were renovated with fresh finishes and updated interiors that attract solid tenants and keep maintenance in check. In 2025, the dock electric was upgraded with a dedicated meter for the dock power, one on each property. Next door, 121 Monroe Drive is an additional multifamily parcel of about 7,500 sq ft, now vacant and ready for your next phase of development. Consider adding more units, a pool, covered parking with storage, or enhanced outdoor spaces to create a cohesive compound and boost rental revenue. Multifamily waterfront land in Islamorada is limited, and demand for quality rentals remains strong. With recent upgrades already completed and easy access to the mainland, this combined offering is a great opportunity for investors, 1031 buyers, or owner-operators who want a flexible Keys property with income today and room for future build-out and long-term appreciation. Free access to Founders Park, with sandy beach, swimming pool, boat ramp, playground, tennis, pickleball, walking paths, sports fields, dog park and daily fun activities and regular events.

127 & 121 Monroe Dr Unit 1-3, Tavernier
$609,900
2 Beds ⋅ 2 Baths ⋅ 620243 MLS
Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situated next to Founders Park, this gated bayfront community offers an unbeatable combination of location, lifestyle, and investment potential. One of the standout features of this residence is the rare open kitchen layout, creating a more spacious and inviting main living area ideal for everyday living or entertaining. EBC is highly desirable for boaters and investors alike, with first-come, first-served dockage available for boats, immediate bay access, and quick ocean access via Snake Creek and Tavernier Creek. Residents and guests enjoy a private sandy beach with beautiful sunset views, plus community amenities that include a renovated pool and clubhouse, tennis courts, pickleball courts, BBQ area, kayak launch, kayak storage, trailer parking, and secure gated entry. Short-term rentals are allowed with a 28-day minimum, making this an excellent opportunity for full-time living, a vacation getaway, or an income-producing property. Located in the heart of Islamorada and within walking distance to Founders Park events, recreation, and nearby dining, this property offers the ideal blend of waterfront enjoyment, boating convenience, and rental flexibility in one of the Florida Keys' most desirable communities.

87200 Overseas Hwy Unit APT A 7, Islamorada
$2,550,000
5 Beds ⋅ 3 Baths ⋅ 620127 MLS
Welcome to one of Islamorada's finest homes! Located in Venetian Shores the premier boating community of Islamorada. One of only two streets in the neighborhood with curbs and street drainage system. 70ft of deep water dockage and 100ft wide canal. Direct Ocean and Bay access via Snake Creek. Draw bridge to ocean for yachts and tower boats. This home is a must see! Extremely clean and well maintained home. Fantastic layout. Upstairs you have a little over 1,900 sq ft of living space all on one floor - which includes your kitchen, living room, dining room, 3 large bedrooms and 2 bathrooms. Downstairs you have your rec room with 2 bedrooms, cabana bath and tackle room/workshop. Solid concrete construction designed to offer peace of mind during hurricane season. Conveniently located close to restaurants, shopping, Publix, schools, and hospital. Buyer to verify all information.

113 Villa Bella Dr, Islamorada
$13,900,000
6 Beds ⋅ 9 Baths ⋅ 620077 MLS
Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full residences, a separate garage/media house and a move-in ready package of extras unlike any other property in the Keys. This remarkable compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through a private gate to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, the new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. The welcome package also includes a newer 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The 100 ft. long resort-style pool with large spa create the centerpiece of the property, surrounded by multiple lounging areas, outdoor kitchen with covered bar, shady terraces and intimate gathering spaces. The estate's flexible layout includes two full homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes offer chef kitchens with high-end appliances including SubZero and La Cornue. Not only is this estate ready for fun, it's also ready to enjoy with furniture, decor, kitchenware and even linens included! This remarkable property encompasses 2 acres of upland, 1.2 acres of baybottom, a separate buildable lot, plus valuable development rights. It is also conveniently located next to Islamorada's crown jewel Founder's Park for near instant access to seasonal festivals, sports fields, dog park, playground, tennis and pickleball courts and much more. All of these features elevate the property into a true legacy holding--ideal as a luxury residence, family compound, or private retreat.

139 Gimpy Gulch Dr, Islamorada
$13,500,000
8 Beds ⋅ 8 Baths ⋅ 620067 MLS
Private Helicopter Estate in the Florida Keys. Behind private gates on prestigious Million Air Row, this exceptional oceanfront estate spans nearly 2.5 acres and offers a rare blend of luxury, privacy, and future potential. The recently renovated residence features 8 bedrooms, 7.5 bathrooms, double-height ceilings, spacious bedroom suites, abundant storage throughout, solid CBS construction, impact windows and doors, and a new concrete roof. Designed for the ultimate Florida Keys lifestyle, the property boasts protected basin dockage with a 24,000 lb boat lift, a private helicopter pad, hot yoga studio, resort-style pool with waterslides, waterfall, and spa, plus two covered carports and a large garage. Expansive grounds provide endless opportunities to add additional amenities such as pickleball, volleyball, guest accommodations, or a private beach retreat. A truly unique waterfront compound offering the space and exclusivity rarely found in the Florida Keys.

89401 Old Hwy, Tavernier
$26,400,000
7 Beds ⋅ 10 Baths ⋅ 620022 MLS
Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind gates on Plantation Key, this secluded retreat combines lush tropical landscaping with unmatched privacy for the ultimate island escape. The 8,988-square-foot main residence showcases exceptional craftsmanship and thoughtful design. One wing features a dramatic two-story primary suite with a private office, while the opposite wing includes four additional bedrooms and four bathrooms across two levels. A separate two-bedroom guest house provides extra space for visitors, and a whole-house generator adds convenience and peace of mind. Inside, custom woodwork, coffered ceilings, built-ins, and high-end finishes create a warm yet refined atmosphere. Amenities include a chef's kitchen, wine cellar, private gym, elevator, and seamless indoor-outdoor living spaces ideal for entertaining or relaxing by the water. Resort-style outdoor features include a custom pool, tiki bar, outdoor kitchen, beachside fire pit, putting green, observation pier, and a lighted tennis court with cabana. Convenient access by seaplane, helicopter, or a 90-minute drive from Miami makes travel effortless. Perfect for boating enthusiasts, the estate is near dockage and concierge dry storage options. Located in the heart of Islamorada, Palm Paradise offers easy access to world-class fishing, boating, dining, and the laid-back luxury of the Florida Keys. Offered at $26.4M, Palm Paradise is a rare opportunity to own a private waterfront compound ideal for luxury living, family retreats, or executive escapes.

89505 Old Hwy, Tavernier
$369,000
2 Beds ⋅ 2 Baths ⋅ 620020 MLS
Located in Plantation by the Sea, this Islamorada townhouse offers 2 bedrooms, 1.5 bathrooms, covered parking, and a storage unit in a gated oceanfront complex. Inside, the unit has been updated with renovated kitchen, bathrooms, and flooring. Both upstairs bedrooms feature open balconies, along with an additional balcony off the living room for added outdoor space. The upstairs layout includes 2 bedrooms and 1 full bathroom, while the half bath is conveniently located downstairs. Community amenities include a covered parking space, plenty of guest parking, storage unit, workout room, sauna, kayak and paddleboard storage, bicycle storage, clubhouse, and gated entry. Conveniently located near Founders Park, Islamorada's community park offering a beach, Olympic-size swimming pool, tennis courts, pickleball courts, ball fields, and an amphitheater.

87455 Old Hwy Unit 244, Islamorada
$2,375,000
4 Beds ⋅ 4 Baths ⋅ 620004 MLS
Welcome to your own private slice of Islamorada paradise! This canal-front home offers easy access to Florida Bay along with stunning lake views and unforgettable sunsets. This home features CBS construction, a metal roof, accordion shutters, living areas above base flood elevation, and plenty of parking. The upstairs main living area offers over 2,000 square feet of living space with 3 bedrooms and 2.5 bathrooms. Vaulted ceilings and an open, spacious layout are designed to capture natural light and water views. The large kitchen flows seamlessly into the living and dining areas, making it ideal for entertaining or simply enjoying the relaxed Keys lifestyle. The bedrooms are located down the hallway, creating a nice separation from the main living spaces. The primary suite features a walk-in closet and a beautifully appointed spa-like bathroom with marble finishes, dual vanities, granite countertops, soaking tub, and a glass-enclosed steam shower with multiple shower heads. All bedrooms are generously sized with ample closet space. The downstairs living space offers over 770 square feet and is separate from the upstairs, creating a great private area for guests to enjoy, complete with sliding glass doors that open directly to the pool area. Outside, enjoy lush tropical landscaping, a canal-front pool with heater, 60' of dockage with a 15,000 lb boat lift, and quick boating access to Florida Bay. The outdoor living space is ideal for entertaining with plenty of room under the carport along with an outdoor kitchen. Whether you are heading out for a sunset cruise, fishing trip, or waterfront dining, this location puts the best of the Florida Keys lifestyle right at your fingertips.

316 Woods Ave, Islamorada
$2,900,000
2 Beds ⋅ 2 Baths ⋅ 619931 MLS
What does everyone want? The smallest house in a great neighborhood! THIS IS THE ONE! Tucked away in the sought-after Venetian Shores neighborhood of Islamorada, this solid CBS waterfront home is perfectly positioned for enjoying the effortless boating lifestyle the Keys are known for. With 100 feet of dockage, a 15,000 lb. boat lift, and a fish cleaning station, this home is just one lot from Snake Creek which offers immediate access to both the Atlantic Ocean and Florida Bay. Enjoy peaceful Snake Creek views and the constant reminder that the water is always just moments away. Upstairs, the open floor plan is designed to capture natural light and Snake Creek views, with vaulted ceilings creating an airy coastal feel throughout the living, dining, and kitchen areas that span the width of the home. Three sets of sliding glass doors invite the outdoors in, opening the space to breezes and waterfront scenery. Two bedrooms and one full bath complete the upper level, while downstairs offers valuable storage space, a permitted full bath, and covered carport parking. The cleared lot provides exceptional flexibility with ample room for boats on trailers, additional vehicles, or the opportunity to expand the existing home and create an even larger waterfront retreat. Don't miss out on this exceptional value!

154 Milano Dr, Islamorada
$645,000
2 Beds ⋅ 2 Baths ⋅ 619878 MLS
Welcome to Summer Sea Condominium Apt 424, a beautifully remodeled and fully furnished bayfront residence in the heart of Islamorada. This turnkey, 2-bedroom, 2-full bath condominium offers 1,148 square feet of light-filled living space with open water bay views from an oversized double-width balcony perched among the treetops on the top floor. Designed for both comfort and entertaining, the open-concept floor plan features a spacious living area, modern kitchen, generous storage throughout, and a custom wet bar with a second refrigerator -- ideal for boating and fishing enthusiasts. Both bedrooms are well-appointed and offer comfortable accommodations for owners and guests alike. Summer Sea is a gated waterfront community known for its beautifully maintained grounds, welcoming residential atmosphere, and outstanding amenities. Residents enjoy two swimming pools including a large heated pool, sandy beach area, fitness center, game rooms, community gathering spaces, elevator access, and breathtaking sunset views over Florida Bay. This community has successfully completed its milestone inspection and continues to reflect exceptional pride of ownership with numerous recent improvements, including 2 new elevators, composite dock, remodeled poolside bathrooms, and storm-rated windows and more-- all completed with no special assessments. Whether you are seeking a full-time residence, weekend retreat, or investment opportunity, this exceptional bayfront condominium captures the very best of the Islamorada lifestyle.

88500 Overseas Hwy Unit APT 424, Tavernier
$40,000,000
8 Beds ⋅ 11 Baths ⋅ 619826 MLS
A rare dual-offering on coveted Millionaire's Row in Tavernier, this extraordinary oceanfront compound spans over multiple acres across two parcels-delivering an unmatched combination of scale, privacy, and future development flexibility in the Florida Keys. At 88845, a newly constructed 8,200SF estate sets a new standard for modern coastal luxury. Thoughtfully designed for both grand entertaining and private retreat, the residence offers 5 bedrooms, 6 full baths & 2 half baths, complemented by a dedicated office, control room, mudroom, and expansive 3-car garage with climate-controlled workshop. Interior finishes are curated at the highest level, including white diamond marble, teak wood flooring, custom millwork & a vapor fireplace, while a full-home sound system, elevator & advanced mechanical infrastructure provide seamless functionality. The chef's kitchen is equipped with top-tier Wolf, SubZero, & Cove appliances, dual dishwashers, farmhouse sinks, refrigerated drawers, wine storage & custom mahogany countertops-designed to accommodate both everyday living and large-scale entertaining. Outdoor living is equally impressive, anchored by a 120-foot resort-style pool with integrated spa, heating & chilling systems, & full smart control. A fully equipped summer kitchen, cabana bath, & multiple covered terraces create a true waterfront lifestyle experience. With 480 feet of water frontage, the protected basin offers exceptional boating capabilities, including 90 feet of dockage & room to expand, a 20,000lb lift, boat ramp & deep-water access. The adjacent parcel at 88835 provides over 3 acres of additional opportunity featuring a renovated 3-bedroom residence completed in 2022, with a transferable TDR allowing for the development of a substantially larger primary home. The property also includes a buildable lot & natural hammock buffer for added privacy. Together, these two properties present a generational opportunity to own a one of a kind waterfront compound.

88835 & 88845 Old Hwy, Tavernier
$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
$999,000
4 Beds ⋅ 3 Baths ⋅ 619796 MLS
Spacious 4 bed, 3 bath home in the desirable Indian Mound neighborhood on Plantation Key. Sitting on two lots totaling about 11,000 sq ft, there's plenty of privacy and extra space to enjoy. As you enter, you're welcomed by a large, open floor plan with high ceilings, giving the home a bright and airy feel. The kitchen features granite countertops, upgraded stainless steel appliances, and high-output tankless water heater with instant hot water. Tile flooring runs throughout the main level, with carpet upstairs. Just off the living room, there's a large screened-in outdoor space that's perfect for relaxing or entertaining. This ground-level, above-flood CBS home was built in 2010 and includes a metal roof, impact windows and doors, split-zone A/C, and ceiling fans throughout. It offers 2,361 sq ft of living space, along with exterior lighting and a fenced backyard. Located at 148 Iroquois St and close to local schools, it's a great option for anyone needing both space and convenience. The oversized lot gives you room for kids, pets, or even future additions, while the fenced yard adds an extra layer of privacy. The neighborhood also offers a boat ramp, making it easy to enjoy everything the Keys lifestyle has to offer.

148 Iroquois St, Tavernier
$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
$875,000
2 Beds ⋅ 2 Baths ⋅ 619533 MLS
Islamorada luxury condo and boat slip for boats to 44' - the perfect combination for serious boaters! Located within a 14-acre, resort-style ocean front community of just eight buildings, this home sits in a peaceful low-rise building with only three units. As an end unit with no one above or below, it feels very much like a single-family home. Windows on three sides bring in natural light and a comfortable, airy feel throughout. The kitchen and baths are up-to-date and beautiful. The layout includes 2 bedrooms and 2 baths, plus a screened porch and an expansive 650+/- sq ft open patio overlooking a peaceful swimming lagoon, surrounded by mature trees. You'll want to dine outdoors every night! It's a quiet, private setting that still keeps you close to everything. Impact windows and doors throughout - and - electric roll down shutters for the screen porch. For boaters, the marina is a standout. There's a ramp, shore power, ice, and a private fuel dock exclusively for owners which is an uncommon and valuable feature. It's not just more convenient to gas up at home... it's less expensive than local marinas too! This unit comes with a slip that can accommodate up to a 44' boat and is in a prime location, close to shore and just a short distance from the unit. It's also near a popular gathering spot where owners tend to unwind and connect at the end of the day. Community amenities include an oceanfront pool, clubhouse, a lighted tennis court, and an additional court for tennis or pickleball. The grounds are lush, green, well-kept and spread out, giving the entire property a relaxed, uncrowded feel. Pet-friendly with no size restrictions. If you're looking for a low-maintenance Keys home with excellent dockage and a true Keys boating lifestyle, this one checks the boxes. Offered beautifully furnished. An absolute must-see! Slip #24. Using exterior measurements, total footprint is 2,650 sf +/-.

88181 Old Hwy Unit B3, Islamorada
$700,000
2 Beds ⋅ 2 Baths ⋅ 619480 MLS
TOP FLOOR oceanfront living awaits in this beautifully updated 2-bedroom, 2-bath condo located in desirable Sea Gulls development in Plantation Key. Enjoy breathtaking Atlantic Ocean views from the main living area, primary suite, and an expansive private balcony, perfect for soaking in stunning sunrises and refreshing ocean breezes. The tastefully renovated interior is offered turnkey, fully furnished, allowing for immediate enjoyment as a full-time residence or the ideal vacation retreat. Sea Gulls is a gated, resort-style oceanside community offering exceptional amenities, including an oceanfront pool, sandy beach, kayak and paddleboard storage with launch access, chickee huts, outdoor grilling areas, and a fully equipped renovated oceanfront fitness center and a spacious clubhouse featuring a kitchen and game room. Residents and guests are welcomed through an interior foyer with elevator access and beautiful oceanviews. Experience the best of the Florida Keys lifestyle in this exceptional oceanfront offering.

200 Wrenn St Unit 606, Tavernier
$840,000
2 Beds ⋅ 2 Baths ⋅ 619413 MLS
Welcome to your Keys get-a-away! Snuggled in the heart of Plantation Key colony, right at the entrance of the village of Islamorada: your island dreams, weekend oasis, or real estate investment is waiting! This 2/2 1793 sq.ft CBS home and 7455 sq.ft. lot, recently renovated in 2025 with new plumbing/pipes, kitchen/cabinetry, and a movable island, homeowners put love and sweat into making this their Keys castle. This home includes 2 storage sheds and circular driveway. Located within seconds/minutes to 2 Upper-Keys schools--PK-8 & 9-12, if you are making the move to become a full time resident or to offer potential tenants the convenience of a closer school, this home offers it! Also, this community offers a homeowners park with ramp, exclusively for the residents. $250 yearly access with a voluntary HOA for the access. Why pay the prices for docks/ramp? Why wait those long lines to put your watercraft in our beautiful waters? Waters that are world class in fishing, diving, snorkeling, or just casually cruising on some of the clearest waters in North America! You can have it here within 5 minutes of your home!

179 Hibiscus St, Tavernier
$3,499,000
5 Beds ⋅ 6 Baths ⋅ 619367 MLS
Stunning Plantation Key canal front pool home! This exceptional all-concrete residence boasts a rare layout with five bedrooms, five full baths, and one-half bathroom, perfect for family living and entertaining. The chef's kitchen is a true standout, featuring a sprawling granite island, top of the line appliances, and abundant cabinet space, making it a culinary dream. A gorgeous exotic wood staircase leads you through the home's three magnificent levels, starting from the welcoming entryway and ascending to the stunning primary suite on the third floor. The suite is an oasis of tranquility, with ample space and stunning views of the surrounding beauty.Enjoy the marble floors as you make your way to the private concrete rooftop deck, where you can soak in breathtaking panoramic ocean views. On the first level, enjoy the cozy theater room for movie nights, a legal one bedroom, one bathroom guest suite offering privacy and comfort, and a tackle room ideal for storing fishing gear and outdoor equipment. The home is designed for peace of mind, elevated above potential flooding, and offers ample storage space throughout. Adventure awaits just minutes away in Tavernier Creek, providing quick access to both the Atlantic Ocean and Florida Bay for fishing enthusiasts or anyone who loves water. The exterior features a heated and chilled swimming pool, outdoor entertainment area, and a 24,000-pound boat lift, making this home the ultimate in luxury coastal living.

141 Canal St, Islamorada
$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
$625,000
2 Beds ⋅ 2 Baths ⋅ 619284 MLS
Elevated direct oceanfront living from a 5th-floor 2 bedroom 2 bath residence in Sea Gulls on Plantation Key in Islamorada. This all concrete building offers peace of mind and stunning Atlantic Ocean views from a full-length private balcony that spans the entire unit, providing water views from every room. The renovated interior is offered turnkey and ready for immediate enjoyment, ideal as a full-time residence or vacation retreat. Sea Gulls is a gated oceanside community featuring a resort-style oceanfront pool, lounging area overlooking Atlantic & sandy beach, kayak/paddleboard storage & launch area, chickee huts, outdoor grilling areas, oceanfront fitness center w/dedicated yoga room, clubhouse w/kitchenette & game room. Owners and guests are welcomed through an interior foyer with elevator access w/scenic water views, enhancing both convenience and arrival experience. Enjoy the best of the Florida Keys lifestyle with breathtaking sunrises, refreshing ocean breezes, and exceptional amenities all within a beautifully maintained waterfront setting.

200 Wrenn St Unit APT 510, Tavernier
$1,075,000
2 Beds ⋅ 2 Baths ⋅ 619193 MLS
Experience the relaxed lifestyle of Islamorada at its finest, at Ocean Harbor Condominiums. This first-floor unit sits directly above its assigned covered parking space and is conveniently closest to the elevator for easy access. A private backyard staircase leads you straight to the pool, and the beach is just steps from your door. This home can serve as a personal retreat or monthly vacation rental, and offers the perfect mix of comfort, convenience, and coastal charm. Inside, the spacious 2 bed/ 2-bath split floor plan offers 1,536 square feet of thoughtfully designed living space, providing privacy for guests, family, or friends. The primary suite features unobstructed ocean views, allowing you to wake up to the beauty of the sea each morning. The living room shares these sweeping vistas, perfect for tranquil sunrises. Enjoy your morning coffee on the porch or take a short walk to the Tiki Hut at the point, which offers ample entertainment space complete with barbecue grills and ice makers ideal for gatherings. Ocean Harbor is a gated community known for its extremely well maintained grounds, with meticulously raked beaches, freshly cut grass, and lush tropical landscaping. Resort style amenities include a large pool and jacuzzi, tennis courts, and a jetty with a Tiki Hut offering breathtaking, unobstructed ocean views. The beautifully appointed clubhouse features a gym, co-working space, and lounge areas. Outdoor grills are located throughout the beach area and near the clubhouse for casual entertaining. For boating enthusiasts, there's a boat launch for trailers, on-site boat storage, and slips available for rent for long term, which just might be cheaper than owning one and paying property taxes on the slip you own. Additional conveniences include electric vehicle charging stations, a pet-friendly policy allowing up to two pets of any size, and one assigned covered parking space. Call today for your private showing!

87851 Old Hwy Unit M3, Islamorada
$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