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$3,000,000
3 Beds ⋅ 3 Baths ⋅ 620907 MLS
Welcome to your Venetian Shores retreat, where relaxed coastal living meets effortless waterfront luxury. This completely updated pool home is designed for easy living and unforgettable entertaining, with an open floor plan, beautiful finishes, and seamless indoor-outdoor flow. The heart of the home is a spacious kitchen with a generous island, opening to the living area and a wall of sliding glass doors. Step outside to a covered terrace overlooking the resort-style pool and waterfront, with plenty of pool deck for soaking up the sun and a shaded poolside area for lingering over long lunches or evening cocktails. Boaters will love the 70 feet of dockage, complete with a 24,000-pound boat lift. Venetian Shores is known for its 100-foot-wide canals and exceptional boating access, with a quick route to the ocean or bay through Snake Creek. Built with CBS construction and a concrete roof, the home offers an elevator plus both interior and exterior stair access between floors. Upstairs, you'll find the main living area and two bedrooms and two baths, while the downstairs offers an additional bedroom and bath. A bonus room, ample storage, and cabana bath add flexibility and convenience. With its resort-style pool, generous waterfront, easy boating access, and beautifully updated interiors, this is the kind of home that makes everyday life feel like a vacation, casual, polished, and unmistakably coastal.

121 Severino Dr, Islamorada
$3,850,000
4 Beds ⋅ 4 Baths ⋅ 620893 MLS
Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing property is being sold fully furnished, allowing the new owner to seamlessly continue operating it as a successful vacation rental from day one or immediately begin enjoying it as a private island retreat. Designed with flexibility in mind, this two-story home features a total of 4 bedrooms, 4 bathrooms, and two full kitchens. The upper level offers 3 bedrooms, 2 bathrooms, a full kitchen, and a private balcony, while the lower level includes 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen, making it ideal for guests, multi-generational living, or maximizing short term rental income.Step outside to your private pool, then take just a few steps to your own private beach, creating the ultimate island experience. A new A/C system and metal roof also adds comfort and peace of mind. Conveniently located just minutes from Robbie's Marina and Theater of the Sea, you'll enjoy world class fishing, boating, snorkeling, waterfront dining, and everything that makes Islamorada one of the premier destinations in the Florida Keys.

74049 Overseas Hwy, Islamorada
$439,000
1 Beds ⋅ 1 Baths ⋅ 620845 MLS
Charming concrete bungalow in the heart of Islamorada! Move right into this beautifully updated 1BR/1BA retreat featuring fabulous ocean views from your private rooftop deck. Blending timeless Florida Keys charm with modern finishes, this home offers durable concrete construction with beautiful interior finishes, impact windows, an updated electrical panel, and parking for two vehicles. Relax under the covered Chickee Hut while enjoying spectacular Atlantic sunrises and unforgettable sunset skies. Community amenities include dock privileges, the Atlantic Ocean Jetty Area, a community Chickee Hut, and a low HOA fee of just $149/month, all conveniently located near Snake Creek Marina. Looking for a weekend getaway, vacation rental, or full-time island escape, this is your opportunity to experience the best of Florida Keys living.

84961 Old Hwy Unit A1, Islamorada
$3,999,000
4 Beds ⋅ 4 Baths ⋅ 620828 MLS
Welcome to your own private slice of Atlantic Ocean Paradise!. an Oversized Oceanfront Lot! Over 1/2 acre (23,500 sqf) Estate boasting 100 feet of absolute astonishing direct shoreline with ever changing crystal clear turquoise Atlantic Ocean waters plus an additional 100'x200' (20,000 sqf) of submerged Ocean Land. Arrive to expansive grounds, your own Private dock and what many consider exceptional,rare and extraordinary among Oceanfront homes/estates in all Islamorada is your own Private concrete boat ramp! Ideal for launching your pontoon, bay boat or jet skis with ease plus a generous parking for RVs, boats, trailers, and guests. Inside the main residence, discover three beautiful bedrooms and three full baths, with Spectacular Ocean view from most every room, complemented by a charming separate cottage with its own bedroom, bathroom, and full kitchen ideal for guest!Step outside to a sparkling chill/heated swimming pool where you can sip your morning coffee or evening cocktail while overlooking endless ocean views and the natural coastal wildlife. It's exclusive , it's unique and it's a true gem!. It's The Kind Of Oceanfront setting with a True Resort-Like Feel Everyday!.

75433 Overseas Hwy, Islamorada
$4,650,000
5 Beds ⋅ 6 Baths ⋅ 620757 MLS
Experience the best of the Florida Keys in this exceptional pool home, ideally situated in Venetian Shores--one of Islamorada's most coveted waterfront communities. Offering 70 feet of protected dockage, this property is a premier boating opportunity with quick access to the bay and ocean via Snake Creek Bridge. Designed to accommodate family and guests with ease, the oversized home features five spacious bedrooms, four-and-a-half baths, a garage, and an upstairs flex space with a private balcony overlooking the pool and wide canal. Timeless finishes include a charming foyer, rich hardwood flooring throughout, a dedicated office, game room complete with a custom built-in bar, and abundant natural light that enhances every level of the home. Built for both comfort and peace of mind, the residence is equipped with impact-rated doors and windows, a whole-home generator, and a propane tank, providing year-round reliability and resilience. Whether you're entertaining poolside, hosting extended family, or setting out for a day on the water, this exceptional waterfront residence embodies the relaxed luxury and boating lifestyle that define Islamorada.

109 Valencia Dr, Islamorada
$2,890,000
3 Beds ⋅ 3 Baths ⋅ 620743 MLS
Welcome to your coastal retreat in the highly sought-after Port Antigua neighborhood--where relaxed Keys living meets exceptional boating access and resort-style amenities. Residents enjoy a private homeowner's beach and boat ramp, enhancing the ease of life on the water. This solid CBS construction home offers approximately 75 feet of dockage, a 12,000 lb boat lift, and a convenient fish cleaning station--perfect for avid boaters and anglers alike. After a day on the water, unwind by the beautifully designed pool where a spa cascades into the water, complete with a swim jet, heater, and chiller for year-round enjoyment. Upstairs, the open floor plan is bright and inviting, anchored by a well-appointed kitchen featuring stainless steel appliances, quartz countertops, and a generous island ideal for gathering. Two spacious bedrooms and baths provide comfort and privacy, while a versatile Florida room serves perfectly as a home office and gym. Built for durability and peace of mind, the home includes a concrete roof, impact windows and doors, and an Arlo security system. A rooftop deck offers additional space to relax and take in the coastal surroundings. Downstairs, an expansive covered entertaining area flows seamlessly to the pool and tiki hut--thoughtfully equipped with lighting, ceiling fan, grill, side burner, sink, and refrigerator--creating the ultimate setting for outdoor living. Elevated above flood, the guest quarters feature a private living area, bedroom, and bath with access from both the pool and interior, making it ideal for visitors. A perfect blend of comfort, function, and island charm--this is Port Antigua living at its finest.

101 Madeira Ct, Islamorada
$2,485,000
3 Beds ⋅ 3 Baths ⋅ 620704 MLS
Refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket. This three-story home offers a thoughtful layout and spectacular bay views throughout. The ground floor features covered parking, a versatile multi-purpose room, and access through a gracious foyer entry. Upstairs, the main living level boasts an open-concept kitchen and dining area with panoramic bay vistas, two bedrooms, two bathrooms, and a tranquil porch ideal for enjoying sunset skies. The top floor is reserved for the expansive master suite, complete with a private balcony and sweeping waterfront views. Tarpon Flats offers an amenity-rich lifestyle tailored to the discerning buyer. Enjoy a waterfront pool and gazebo, private beachfront access, generous dockage for your skiff, a charming greenhouse, and a tennis court with shaded seating for guests. Adding to the ease of ownership, the community provides a full-time concierge service and an on-site handyman, ensuring both comfort and convenience year-round. Sophistication, privacy, and natural beauty converge in this exceptional Islamorada retreat--come discover what makes Tarpon Flats truly one of a kind.

81250 Overseas Highway Unit 2, Islamorada
$11,700,000
6 Beds ⋅ 8 Baths ⋅ 620680 MLS
Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom suites, media room, an elevator, and a custom kitchen showcasing mahogany cabinetry and Thermador appliances. Expansive balconies extend the living spaces into the natural surroundings. The third-level Sunset Lounge elevates entertaining with a full bar, wine storage, generous seating, a mega-TV, and views toward Florida Bay. Outdoors, the property features a saltwater pool and spa, covered dining and entertaining areas, a private pickleball court, and a dock with boat lift. A detached guest house provides comfortable accommodations with added separation from the main residence. This distinctive Islamorada estate brings together natural beauty, recreation, boating access, and elevated island living.

77350 Overseas Hwy, Islamorada
$649,000
1 Beds ⋅ 1 Baths ⋅ 620677 MLS
Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries. The resort encompasses 27 acres with 1,200' of beach frontage and a 525' fishing pier. This beautiful one-bedroom King suite, with additional sleeper sofa in the living room and private screened balcony, overlooks the garden and waterfall. This is a luxury, income-producing property. Nightly rentals are allowed, with onsite management, an owner's closet, and owner's use of up to 28 days. The resort offers a 24-hour shuttle, valet parking, concierge service, 5-star fine dining, ballroom, conference room, a spa, fitness center, beach, pools, dock, tiki bars, 9-hole par 3 golf course, Pickle Ball courts, lighted tennis courts, lush gardens, bike path, fishing, diving, snorkeling, water sports and Camp Cheeca for children.

81801 Old Hwy Unit 754, Islamorada
$8,500,000
620668 MLS
BUSINESS INCLUDED: Very Profitable Marina & Unique Resort in Islamorada, FL. 2025 NET Income reported over $800,000/yr. !! Offered at over 9.5% Cap rate at Asking Price. Manager on site handles responsibilities with oversight from the absentee owner. Rare 1+ Acre Oceanside Lot with many uses possible. Deep water protected harbor with 18 large boat slips that can accommodate 50+ ft. yachts. Approach depth approximately 6 ft.+ at high tide with a clearly marked channel. Successful Boat Rental Business with 17 boats included in the sale. Lucrative Vacation Rental Business with (10) Aqua Lodges and 1 houseboat also included. Features include water, new 30 Amp and 50 Amp electric at each slip, fuel dock, concrete building with office, ship store, workshop, and garage/storage. 2 outdoor showers, 2 bath houses with indoor showers, stalls, and dressing area. New waste/pump-out station and fuel station. An additional separate concrete building used for storage on the North side of the property. New Concrete In-ground Pool, Deck and Fence just completed. Brand new floating docks. Private marina, must call for an appointment and sign an NDA/CA for more information.

200 Treasure Harbor Dr, Islamorada
$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
$549,500
1 Beds ⋅ 1 Baths ⋅ 620633 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This king bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 715, Islamorada
$549,500
1 Beds ⋅ 1 Baths ⋅ 620629 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This double queen bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 716, Islamorada
$315,000
620621 MLS
50' X 22' boat slip at the World famous Lor E Lei marina. Excellent in-town location, you know you're going to boat over here anyway so you might as well tie up for the night! Enjoy the sunsets, unwind, Uber home, or use for your fishing business, so many possibilities. A rare find.

96 Madeira Rd Unit # 10, Islamorada
$2,500,000
3 Beds ⋅ 2 Baths ⋅ 620603 MLS
Welcome to 154 Biscayne Boulevard in the heart of Islamorada. This beautifully maintained 3 bedroom, 2 bathroom concrete home is designed for those who want to enjoy life on the water. Located in the highly sought after Port Antigua neighborhood, this home offers the perfect balance of comfort, durability, and island living. Whether you are searching for a full time residence, a weekend retreat, or an investment opportunity in the Florida Keys, this is your chance to own a piece of paradise and experience everything Islamorada has to offer. Built for lasting peace of mind, the home features a concrete roof, full impact windows and doors, and an inviting open concept floor plan that seamlessly connects the kitchen, dining, and living areas. Natural light fills the space, creating a bright and welcoming atmosphere that is perfect for everyday living or entertaining family and friends. Step outside to the spacious screened balcony overlooking the canal, the perfect place to enjoy your morning coffee or unwind in the evening while taking in the tropical breeze. Downstairs, the covered outdoor living area offers exceptional space for entertaining, relaxing after a day on the water, or storing everything you need for the Florida Keys lifestyle. For boating enthusiasts, this property features a concrete dock with two boat lifts, and quick access to some of the best fishing and boating waters in the world. A large enclosed storage area provides plenty of room for fishing gear, paddleboards, diving equipment, and all of your essentials.

154 Biscayne Blvd, Islamorada
$3,100,000
5 Beds ⋅ 3 Baths ⋅ 620602 MLS
Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathrooms with an open living floor plan. The main living level features three bedrooms and two bathrooms, complemented by a spacious living, dining, and kitchen area--ideal for entertaining and relaxed Keys living. The lower level includes two additional bedrooms and one bathroom, all above flood, perfect guest quarters with a full kitchen. Brand new exterior paint! Enjoy 75 feet of deep-water concrete dockage equipped with a 15,000 lb boat lift, providing excellent boating access. The home is solid concrete construction with a metal roof, fenced yard, and plenty of room for a pool. Port Antigua is known for its exceptional amenities, including one of the best private beaches in the Keys and a community boat ramp. With immediate access to Florida Bay and quick proximity to the Atlantic Ocean, this property offers the ultimate Florida Keys lifestyle--boating, water access, and island living at its finest. If you are seeking a waterfront property that has great rental history, this is the one!

117 El Capitan Dr, Islamorada
$13,750,000
5 Beds ⋅ 7 Baths ⋅ 620590 MLS
Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architects Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.

19 Avacado St, Islamorada
$1,680,000
3 Beds ⋅ 2 Baths ⋅ 620534 MLS
Prime Islamorada Mixed-Use Investment | Ocean Views | Overseas Highway Frontage Exceptional mixed-use investment opportunity in the heart of Islamorada. Positioned directly on the Overseas Highway at Mile Marker 74.5, this highly visible Neighborhood Commercial (NC) property offers outstanding exposure, excellent accessibility, and panoramic Atlantic Ocean views. Originally permitted as a three-unit apartment building, the property is currently configured with two primary residential/commercial spaces, presenting an opportunity for a future owner to explore the potential for a third apartment or additional income-producing space, subject to local approvals. The flexible layout lends itself to owner-occupancy, employee housing, professional offices, retail, vacation accommodations (where permitted), or a variety of commercial uses allowed under NC zoning. An increasingly rare feature in the Upper Keys, this property combines valuable highway frontage with parking, exceptional visibility, and an oceanfront setting. Investors, business owners, and developers will appreciate the property's versatility, while end users may envision transforming it into a distinctive single-family residence with sweeping Atlantic views. Located in one of the Florida Keys' most desirable markets, the property is surrounded by established businesses, restaurants, marinas, resorts, and world-endless fishing and diving destinations. Its strategic location offers convenient access for both locals and visitors traveling throughout the Keys. Whether you're seeking a long-term investment, owner-user opportunity, redevelopment potential, or a signature live-work property, this unique Islamorada offering delivers location, flexibility, visibility, and exceptional upside in one of Florida's most sought-after commercial corridors.

74450 Overseas Hwy, Islamorada
$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
$629,900
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
$1,100,000
2 Beds ⋅ 2 Baths ⋅ 620551 MLS
A unique opportunity to enjoy the Florida Keys boating lifestyle without the cost of waterfront ownership. This well-maintained dry lot home in desirable Tollgate Shores includes a deeded boat slip directly across the street, complete with a new dock, 20k boat lift, water, power, and a fish cleaning station. Enjoy the convenience of direct sight lines to your boat from the living room and front porch, with peekaboo views of Florida Bay and the iconic Channel 5 Bridge beyond. Upstairs, the home features two generously sized bedroom suites, each with its own ensuite bathroom. A pantry and laundry room are conveniently set off of the well-appointed, modern kitchen. The open-concept living area is highlighted by vaulted ceilings with exposed wood trusses and bamboo flooring. A clean interior offers a comfortable, move-in-ready space, with furnishings negotiable. The lower level includes covered parking, an air conditioned garage, a spacious bonus room, and a dedicated tackle storage closet, providing ample space for boating gear, hobbies, and everyday storage. A metal roof, high quality insulation and impact windows and doors add to the integrity and efficiency of this home. Located adjacent to the neighborhood park, the property benefits from additional open green space. The voluntary HOA is $250 annually. With quick boating access to both Florida Bay and the Atlantic Ocean via Channel 5, this property is well suited as a full-time residence, weekend retreat, or investment opportunity. Whether your priority is boating, fishing, or embracing the relaxed Florida Keys lifestyle, 321 Tollgate Shores offers a distinctive combination of convenience, functionality, and value with a niche setup.

321 Tollgate Shores Dr, 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
$1,680,000
3 Beds ⋅ 2 Baths ⋅ 620533 MLS
Rare Mixed-Use Opportunity with Spectacular Ocean Views in Islamorada MM 74.5. Endless possibilities await at this highly visible, commercially zoned property located directly on the Overseas Highway at Mile Marker 74.5. Offering breathtaking open Atlantic Ocean views and exceptional highway frontage, this unique property is ideal for investors, entrepreneurs, or anyone seeking the perfect live-work lifestyle in the Florida Keys. Originally permitted as a three-unit apartment building, the property is currently configured with two primary living/work spaces, creating the opportunity for a buyer to explore the potential for a third apartment or reconfigure the property to suit their vision, subject to local approvals. Whether you're looking to maximize rental income, establish a business with residential accommodations, or create a one-of-a-kind family compound, the flexibility here is exceptional. The Neighborhood Commercial (NC) zoning opens the door to a wide variety of commercial uses while the existing residential layout also lends itself beautifully to conversion into a spacious single-family residence with incredible ocean views. Imagine waking each morning to the sunrise over the Atlantic while operating your business from one of Islamorada's most recognizable and accessible locations. The property offers generous parking, excellent visibility, fenced outdoor space, and a location surrounded by restaurants, shopping, marinas, and the best of the Florida Keys lifestyle. Opportunities with this combination of commercial frontage, residential flexibility, income potential, and unobstructed ocean views are exceptionally rare. Whether your vision is investment, business, residential living, or a combination of all three, this is a property where imagination truly becomes opportunity.

74450 Overseas Hwy, Islamorada
$485,900
2 Beds ⋅ 2 Baths ⋅ 620524 MLS
This is the exceptional deal you've been waiting for! Opportunity knocks on this 2 story townhouse in Islamorada's gated bayfront community, Executive Bay Club. These spacious units are highly desired for their well laid out floor plan, perfect for full time residence, a vacation home or as a seasonal rental (30 day minimum) Amenities include a Bayfront sandy beach, newly renovated marina with first come first serve dockage, a newly renovated pool lined with cabana chickee huts and a gorgeous clubhouse. Tennis and pickleball courts, a 24 hour gated security guard and 2 pets are allowed per townhouse. This unit is mostly original inside. Perfect for those looking to transform a unit to their desired style and preference. Townhouse B6 is in a great location within the community with a tastefully done back patio, it is ready for back yard summer time BBQ's! The sale is subject to Monroe County Probate court approval. Don't hesitate to call for a showing. This is priced to sell and won't last long. Easy to show. Must have an appointment to get into the community. All information to be verified by buyers.

87200 Overseas Hwy Unit APT B 6, Islamorada
$5,999,000
5 Beds ⋅ 7 Baths ⋅ 620457 MLS
Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf of thoughtfully designed living space, set just 2 lots from the bay and across from a tranquil mangrove preserve that enhances both privacy and natural beauty. Boaters will love the setup - 100' of dockage with 2 elevator boat lifts (20,000lb and 15,000lb), plus easy access to Everglades National Park and the Atlantic Ocean through the 65' Channel 5 Bridge. Inside, the home feels open, bright, and refined. There are 5 ensuite bedrooms and 2 half baths, each bedroom featuring its own ductless A/C along with the central system. The primary suite includes a cozy sitting area, his-and-hers closets, and partial bay views. A secondary primary suite opens directly to the pool deck, offering privacy for guests or family. The top level centers around a stunning great room with vaulted ceilings, fireplace, and a chef's kitchen with high-end appliances - the perfect setting for entertaining. On the lower level, a relaxed family room with fireplace and wet bar creates another comfortable gathering space. Additional features include laundry on both floors, an elevator, 2-car garage, and gated circular drive. Out back, the saltwater pool, outdoor kitchen, and sound system create a true resort-style atmosphere. The east-facing orientation means warm morning sunshine, shady afternoons, and gentle ocean breezes. With CBS construction, metal roof, whole house generator and impact windows and doors, this home blends luxury, comfort, and peace of mind. This is waterfront living for those who value both elegance and ease - the Keys lifestyle at its finest.

430 Palm Dr, Islamorada
$3,900,000
620460 MLS
A truly once in a generation opportunity to build your dream estate in the heart of Islamorada's coveted Lower Matecumbe. This exceptional vacant homesite is one of the few remaining parcels of its size available in all of Islamorada, offering an incredibly rare combination of breathtaking ocean views and expansive wide canal views. Encompassing over 32,000 square feet, this extraordinary property provides the perfect canvas for a custom waterfront residence designed to capture spectacular sunrises, refreshing ocean breezes, and the unmatched beauty of the Florida Keys. Its unique setting offers the best of both worlds--open water vistas in the front and a wide canal in the rear, creating an unparalleled lifestyle for boating enthusiasts and those seeking privacy, space, and unforgettable scenery. Opportunities to acquire a property of this caliber have become increasingly scarce in Islamorada, where large vacant parcels are exceptionally limited. Whether you're envisioning a private family compound or a legacy waterfront estate, this one-of-a-kind offering represents a chance to create something truly extraordinary in one of the Florida Keys' most desirable destinations.

74900 Overseas Hwy, Islamorada
$1,295,000
6 Beds ⋅ 3 Baths ⋅ 620458 MLS
3 plex ( 3 separate units) in the heart of downtown Islamorada. A total of 6 bedrooms and 3 baths. Two of the units are remodeled. Walk to Shopping, Boutiques, Bars, Restaurants, World Wide Sportsman/Bas Pro Shops, Florida Keys Brewery. Or take your street legal golf cart. Currently fully rented on annual leases. Would make great 30 days rentals or really great employee housing. Do not miss this opportunity. Two separate electric meters and one water meter.

81160 Old Hwy, Islamorada
$4,900,000
3 Beds ⋅ 5 Baths ⋅ 620441 MLS
An Unfinished Masterpiece Awaits in the prestigious **Venetian Shores**, one of Islamorada's most desirable waterfront communities, known for its deep-water canals and quick access to both the Florida Bay and the Atlantic Ocean via Snake Creek. This extraordinary opportunity allows you to complete what was envisioned as one of the Florida Keys' most premier luxury estates. Elevated above flood on **100 feet of canal frontage**, this solid concrete home features a striking concrete roofline and nearly all impact-rated windows and doors already installed, providing an exceptional foundation for your dream home. Designed with **5,559 square feet of air-conditioned living space**, the residence offers an ideal blend of luxury and boating lifestyle. The first level includes **1,467 square feet** of living space, an oversized **897-square-foot garage**, and plans for an expansive entertainment area, fishing gear room, and direct waterfront access. The second level features **2,361 square feet** of living space plus over **1,100 square feet of covered porches**, with plans for three spacious guest suites, each with a private bath, a half bath, laundry room, chef's kitchen, and open-concept living area. The entire third floor is dedicated to the **1,731-square-foot primary retreat**, designed with ocean views, a spa-inspired bath, oversized custom closet, executive office, and private covered porch. An elevator shaft is already in place for easy access to every level. Plans also include a canal-front pool and cabana overlooking Snake Creek Bridge. With a concrete dock, 100 feet of waterfront, deep-water boating, and one of the Keys' finest locations, this property offers the rare opportunity to complete a truly remarkable custom estate while selecting every finish to reflect your own vision. Property is being sold as is. Some images are AI computer generated to show future potential.

155 Palo De Oro Dr, Islamorada
$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