Refine Search
Map
Sort by
$374,000
2 Beds ⋅ 2 Baths ⋅ 620635 MLS
Turn key furnished condo in Islamorada! This beautifully appointed 2 bedroom, 2 bath condo features an open floor plan, abundant natural light and a rare balcony. Remodeled unit which includes impact windows and doors, crown molding, wood engineered laminate flooring, and a full size washer and dryer. The open-chef's kitchen boasts a spacious breakfast bar, extra tall hardwood cabinets, granite counter tops and backsplash, under-cabinet and recessed lighting, a dishwasher, and a newer refrigerator in 2022. The primary ensuite offers a walk-in closet with custom shelving. AC was replaced in 2023, Metal roof installed in 2024. The complex offers a heated swimming pool, and clubhouse. Founder's Park, Islamorada's Community Park, is on the same island. Admission into the park is free for Islamorada residents. The park offers an Olympic size swimming pool, tennis courts, pickleball courts, ball fields, marina, beach and boat ramp. Plantation Villas is close to Plantation Key Elementary School and Coral Shores High School, grocery store, shopping, restaurants and movie theater.

40 High Point Rd Unit 703, Islamorada
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 620649 MLS
Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan with an open kitchen, dining room and living area, impact windows and doors, new a/c and water heater along with an enclosed air-conditioned porch, all overlooking breathtaking views of the Atlantic Ocean. Enjoy the convenience of a private rear entry staircase leading directly to your 50' boat slip (#27), nestled in the expansive marina. Additional perks include storage room and covered parking. Set on 12 acres of lush tropical grounds, Ocean Harbour offers endless amenities including a heated swimming pool, hot tub, sandy beach, boat ramp, trailer storage, tennis and pickleball courts, clubhouse, and a fitness center with ocean views. Enjoy nearby Florida Bay access through Snake Creek offering offshore or backcountry fishing and numerous delicious waterfront restaurants. This property truly offers the best of Keys living!

87851 Old Hwy Unit P3, Islamorada
$1,049,500
3 Beds ⋅ 2 Baths ⋅ 620610 MLS
Gorgeous 3 bedroom 2 bathroom home on a spacious corner lot, with plenty of room for boats and RVs. Updated and remodeled bathrooms, open concept kitchen, laundry room and stainless steel appliances . This property is situated in one of the highest elevations in the area, Property is surrounded by beautiful mature trees and it has an in-ground heated pool, lots of space to enjoy the open air, just a block away from the community park and boat ramp. Enjoy ramp access for boat launching, fishing, kayaking or to just take in a spectacular sunset on the water! You can either walk, bike, or take a ride on a golf cart to the park/ramp area. You also have nearby, Founder's Park, with excellent recreation, boat ramp access, public beach, a huge pool as well as several local festivals throughout the year, FREE for local residents. Property features a VOLUNTARY HOA, $250 annually. Seller offering $10K in contributions towards buyer's closing costs!

157 Navajo St, Tavernier
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 620538 MLS
Waterfront 3/3 Canal Home located in the Best Islamorada Plantation key Location. Great Vacation Rental is being sold furnished . Turnkey with 5 star reviews ! Large bedrooms with King Beds. Metal Roof , Smart TVs, Quartz countertops , Split level living layout which works great as in law quarters ,open kitchen , Modern bathrooms, Great living room with open kitchen, Washer & Dryer, Screened in wrap around porch overlooking the water. 60 ' of Canal Frontage. 2 car garage, New AC, New appliances, large yard area plenty of parking , 60' Private Dock , Beautifully remodeled. Member of Founders Park with access to pickleball. swimming Pool , Beach, tennis and more. Own your own slice of paradise

135 Tequesta St, Tavernier
$3,600,000
620556 MLS
RARE WATERFRONT OPPORTUNITY! With BPAS allocations becoming increasingly limited, this is your chance to build the waterfront home of your dreams in the prestigious Venetian Shores, one of islamorada's most desirable boating communities. This oversized 8,700+ sq ft. waterfront lot offers significant advantages with house permits APPROVED and ready for pickup and the dock permit close to approval, allowing you to build almost immediately. Boaters will appreciate the exceptional access to both the Atlantic Ocean and Florida Bay, making it easy to spend your days offshore fishing, diving, snorkeling, or exploring the renowned backcountry waters of the Florida Keys. Whether you're envisioning a luxury full-time residence of the ultimate island getaway, this is a rare opportunity to build in one of the Keys' premiere waterfront neighborhoods.

101 Stromboli Dr, Islamorada
$619,995
2 Beds ⋅ 2 Baths ⋅ 620555 MLS
Welcome to Futura Yacht Club! Your island getaway awaits in this highly desirable Plantation Key community. Unit 304 is a 2 bed, 2 bath, beautifully maintained condo. Florida Bay views make this third floor perch heavenly. A hideaway murphy bed is an additional feature adding to the desirability of this coastal condo as an ideal second home or rental. Owners and renters benefit from extensive community amenities, including a boat ramp, on-site boat and trailer storage, a large pool with adjacent club area, kayak storage, paddleball and basketball courts, and well-maintained grounds with shaded picnic spots. The on-site management team maintains the serenity of this community. This immaculate condo is being sold fully furnished. Futura is the place to be for boating, with short run times to the Ocean and Florida Bay. Easy boating and spectacular Florida Bay sunsets make for a beautiful investment in island living.

88540 Overseas Hwy Unit APT 304, Islamorada
$4,600,000
5 Beds ⋅ 6 Baths ⋅ 620549 MLS
Located in sought-after Venetian Shores subdivision in Islamorada, this canal-front home was renovated in 2022. Sought after location - just one lot in from Snake Creek, offering exceptional boating access, 100' of deep water dockage with a 20k boat lift. With approximately 4,600sf of living space, 5 bedrooms and 5.5 bathrooms, the home is situated above base flood elevation and offers an impressive amount of space for the Florida Keys lifestyle. The east-facing orientation captures the morning sun and prevailing breezes while providing welcome afternoon shade. The main residence features 4 bedrooms and 4.5 bathrooms, an open living area with soaring ceilings, a spacious kitchen, pool table area, and a private office with incredible views stretching from the ocean to the bay. An expansive screened waterfront porch serves as an extension of the living area, offering a comfortable setting to relax, entertain, and enjoy the canal views and prevailing breezes. The lower level offers a separate 1 bedroom, 1 bath guest space with views of the pool and its own screened porch. With nearly 1,200sf of covered porches, the home was designed to fully embrace indoor-outdoor Keys living. A new pool was added in 2023, offering privacy and complemented by tropical landscaping, outdoor lighting, artificial turf, and white fencing. Situated on a 9,500sf lot, the property also offers an impressive 1,188sf four-car garage plus an additional dedicated storage room - an exceptional amount of storage rarely found in a Keys home. Additional features include impact windows and doors throughout, metal roof, a paver driveway, and a cul-de-sac location. With expansive living and outdoor spaces, panoramic water views, 100' of deep water dockage, and Snake Creek just seconds away for convenient ocean-to-bay access, this Venetian Shores home offers a rare combination of space, storage, location, and boating convenience in the heart of Islamorada.

157 Valencia Dr, Islamorada
$3,750,000
4 Beds ⋅ 5 Baths ⋅ 620543 MLS
Experience the ultimate Florida Keys waterfront lifestyle in this exceptional BayFront retreat located in the prestigious Sunshine Estates community on Plantation Key. Situated on a private 12,565 sq. ft. lot with 100 feet of pristine bay frontage and 50 feet of deep-water dockage, this contemporary CBS home offers breathtaking open bay views and quick ocean access via Tavernier Creek. Thoughtfully designed in a distinctive V-shaped layout to maximize privacy and showcase water views from nearly every room, the home features 4 bedrooms and 4 bathrooms, including 3 en-suite bedrooms. The spacious open-concept living area boasts soaring vaulted ceilings with exposed wood beams, recessed lighting, rich oakwood flooring, and elegant marble finishes throughout the bedrooms and bathrooms. Built-in shelving adds both style and functionality, while the oversized laundry room and pantry include a convenient dumbwaiter. The ground level is designed for entertaining, offering parking for up to four vehicles, a spacious recreation room, cabana bath, and summer kitchen that seamlessly blend indoor and outdoor living. Enjoy world-class boating, fishing, lobstering, paddleboarding, and water sports right from your backyard. Ideally located just minutes from restaurants, shopping, and schools, this home is approximately 40 minutes from the Florida Turnpike and perfectly positioned at Mile Marker 91. Whether you're seeking a full-time residence or a luxury Keys getaway, this remarkable waterfront property delivers the best of island living.

154 Redwing Rd, Tavernier
$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
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 620396 MLS
Welcome to stunning Florida Bay views and breathtaking sunsets in the heart of Plantation Key! This beautifully remodeled and fully furnished modular home offers the perfect blend of comfort, style, and waterfront living. Featuring two spacious bedrooms, two bathrooms and an open-concept living area and kitchen, the home is thoughtfully designed with a light and airy coastal flair throughout. You will appreciate the huge amount of storage downstairs. Step outside to your inviting waterfront patio, where you can relax and take in beautiful open water views. Boaters will appreciate the 45' of concrete dockage and new 16K lb. boat lift, providing effortless access to Florida Bay and nearby Atlantic Ocean access through Snake Creek. Spend your days exploring the Keys by boat, enjoying waterfront dining, world-class fishing and diving. Founder's Park nearby for boat ramp, beach, pool and ball fields. Whether you're looking for a full-time residence, vacation retreat, or investment opportunity, this turnkey waterfront property represents the laid-back Florida Keys lifestyle. Come experience the beauty, boating, and unforgettable sunsets that make Plantation Key one of the most desirable locations in the Florida Keys.

182 Airstream Ln, 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
$1,595,000
620208 MLS
DIRECT OCEANFRONT LOT IN ISLAMORADA WITH ACTIVE BUILDING PERMIT! A rare opportunity to own a beautifully situated direct oceanfront parcel in the heart of Islamorada, offering breathtaking panoramic views of the Atlantic Ocean. An active building permit is already in place, allowing you to begin construction of your dream waterfront estate immediately, or take advantage of the Village of Islamorada's available two-year permit extension. This spacious homesite includes a mangrove height reduction permit, allowing the mangroves to be trimmed to six feet. Upon completion, the property will enjoy unobstructed ocean views at ground level, creating an exceptional setting for luxury coastal living. Enjoy direct ocean access with convenient nearby Florida Bay access via Snake Creek, as well as close proximity to dry-dock marina facilities. Potential exists for an observation deck and/or dock, further enhancing the property's appeal and maximizing the spectacular waterfront setting. The elevation rendering is conceptual and provided for illustrative purposes. Utilize the approved plans currently in place or modify them to create a custom residence tailored to your vision. Opportunities like this are increasingly rare--build your dream home and experience the unparalleled beauty, boating, fishing, and island lifestyle that make the Florida Keys so desirable.

229 Coral Rd, Islamorada
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 620148 MLS
Futura Yacht Club Rare 3 Bed/2 Bath Condo with 39 ft. Deeded Boat Slip AND 24,000 lb. Boat Lift in desirable Futura Yacht Club! Located in the heart of Plantation Key in Islamorada, this is one of the most coveted boating locations in the Florida Keys with crystal clear water, spectacular nightly sunsets and easy boating access to both the bay and the ocean! This spacious condo is nicely updated inside and offers a private balcony overlooking the sports courts, grounds and gardens. Owners and renters alike enjoy the abundant community amenities, including an easy boat ramp, onsite boat/trailer storage, a huge pool with poolside club area, kayak storage, tennis and basketball courts and spacious grounds with shady picnic areas. After a day on the water, grab a cocktail and stroll over to the sandy beach area with sunset seating and shaded hammocks to enjoy spectacular Florida Keys sunsets! This first level condo allows for easy access via a single flight of nearby stairs or take the elevator to the lobby. Don't miss this opportunity and make sure you see the property video and 3D tour. Call today to arrange a private showing.

88540 Overseas Hwy Unit 101 & Boat Slip 22, 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
$949,000
3 Beds ⋅ 2 Baths ⋅ 620010 MLS
Rare opportunity to own a half-acre corner parcel in the heart of Plantation Key. With an existing structure already in place, the property offers the flexibility for an extensive renovation or full redevelopment into a custom home with room for a pool, garage, outdoor entertaining areas, boat and RV storage, and additional parking. The bayside homeowner's park and boat ramp provide direct and easy access to some of the best boating and fishing in the Florida Keys, including nearby backcountry waters, sandbars, and sunset cruises. Centrally located near restaurants, shopping, marinas, and everyday conveniences, this property not only offers an ideal Plantation Key location, but also a rare opportunity to own a large parcel with redevelopment potential in the Upper Keys.

156 Monroe Dr, Tavernier
$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
$347,500
619950 MLS
1 Wet TDR - for Village of Islamorada ONLY transferable building right to use as market rate residential construction. Buyer to verify that their lot will be approved by the Village of Islamorada. Buyer to pay all costs associated with applying for the transfer to the Buyer's lot and all costs associated with the closing of transaction. OWNER FINANCING Available. This sale does not include any real property Seller is License Real Estate Broke in State of Florida

Not Provided
$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
$999,000
619899 MLS
Begin building now. Lowest priced Canal Front Lot with Building Allocation letter in hand in the Village and more specifically, highly sought after Plantation Key.This beautiful build ready waterfront Lot located in the desirable Indian Waterways Subdivision. Why settle for inferior older construction and design choices when you can build your own dream home to you personal specifications. Provides excellent dockage and direct access to the Florida Bay and also to Tavernier or Snake Creek cut for Ocean access. The current house plans for a 3/2 , CBS 2183 Square foot home are included. You can revise the plans to meet your own design preferences. 60' Engineered dock & dredging plans are available for review. Contact agent to view plans. Easy commute to Miami. Close to schools, shopping, watersports activities. Free entrance to nearby Founders Park , the jewel of Islamorada with sandy beach, pickleball, tennis, bayfront, dogpark, vida course, basketball, Olympic pool (small entry fee), concerts and more.. Voluntary Neighborhood Community Homeowners park with boat ramp & sunsets available for small annual fee ($175.00). Permit application PRSFC202101049

148 Tequesta St, Tavernier