Refine Search
Map
Sort by
$2,500,000
3 Beds ⋅ 3 Baths ⋅ 621119 MLS
OCEAN ACCESS WATERFRONT OPPORTUNITY IN VENETIAN SHORES! Immaculate 2-story CBS concrete home offering the ultimate Florida Keys lifestyle! Situated on a 100' wide deep-water canal with NO FIXED BRIDGES and direct access to both the Atlantic Ocean and Florida Bay via Snake Creek, this is a boater's dream. Minutes to open water with a private dock featuring power and davits, perfect for large boats. This spacious home features 3 bedrooms, 2.5 baths with a flexible floor plan. The first floor offers 2 bedrooms, 1 full bath, family room, and bar area, while the second floor features the primary suite, oversized kitchen, dining room, laundry room, and half bath to maximize the spectacular waterfront views. Enjoy breathtaking sunsets and tropical breezes from the expansive wraparound covered porch. Additional features include beautiful hardwood floors, an oversized kitchen ideal for entertaining, brand-new saltwater pool (2026), three large exterior storage rooms, circular driveway, and fresh exterior paint (2025). Lovingly maintained and in immaculate condition, this home is ready for your personal updates to create the ultimate Keys retreat. Located in the highly desirable Venetian Shores community, known for its deep, wide canals, outstanding boating access, and optional homeowners association. Whether you're looking for a full-time residence, weekend getaway, or luxury waterfront escape, this is a rare opportunity to own in one of Islamorada's premier boating communities.

107 Valencia Dr, Islamorada
$3,952,000
5 Beds ⋅ 3 Baths ⋅ 621117 MLS
THIS UPDATED BEAUTY LOCATED IN RENOWNED VENETIAN SHORES IS A TRUE MUST SEE!! LOCATED IN ONE OF VENETIAN SHORES MOST EXCLUSIVE LOCATIONS GIARDINO DRIVE. UPSTAIRS: THREE BEDROOMS AND TWO SPACIOUS BATHROOMS !! COMFORTABLE LIVING ROOM AND DINING ROOM AREA WITH ACCESS TO A LARGE SCREENED IN PORCH WITH BEAUTIFUL WATERFRONT VIEWS !! LARGE KITCHEN WITH BEAUTIFUL CONNECTED ISLAND AND STATE OF THE ART COUNTERTOPS; MODERN APPLIANCES !! WET BAR AND WINE CELLAR CABINET !! INDEPENDENT INDOOR LAUNDRY ROOM WITH PLENTY OF STORAGE !! CUSTOM CLOSETS THROUGHOUT. HIGH END CEILING FANS THROUGHOUT THE ENTIRE HOME !! NEW EFFICIENT A/C !! INDEPENDENT DOWNSTAIRS: TWO SPACIOUS BEDROOMS AND ONE BATHROOM, CUSTOM CLOSETS !! KITCHENETTE WITH MICROWAVE, REFRIGERATOR, SINK AND FILTERED WATER WITH LOTS OF STORAGE SPACE !! LARGE SCREENED IN PORCH WITH GREAT WATERFRONT VIEWS !! OUTDOOR FEATURES: 100 FEET OF WATERFRONT WITH TWO BOAT LIFTS !! UPDATED FLOOR DECK AND LIGHTING. THREE DOORS DOWN FROM SNAKE CREEK WITH EASY ACCESS TO BAYSIDE AND ATLANTIC !! (2) BOAT LIFTS 14,000 LB. AND 10000 LB. FISH CLEANING STATION WITH WATER AND POWER ACCESS WITH LOTS OF STORAGE. LARGE HEATED POOL ( NEW POOL PUMP ) WITH FIRE WATERFALL AND FIREPIT. OUTDOOR POOL SHOWER. GAS TIKI TORCHES AROUND THE POOL AREA !! LARGE TIKI HUT WITH TV AND FAN AND WITH POWER ACCESS. LARGE AREA OF ARTIFICIAL GRASS WITH A FIVE HOLE PUTTING GREEN !! ROOF TOP DECK WITH BEAUTIFUL VIEWS !! LUSH LANDSCAPING THROUGHOUT !! SAFETY,CONVENIENCE, ENERGY FEATURES: CONCRETE ROOF. IMPACT WINDOWS AND DOORS THROUGHOUT THE ENTIRE HOME !! ELECTRIC ROLLER SHUTTERS ON BOTH PORCHES !! SOLAR PANELS THAT POWER THE ENTIRE HOME ( CURRENT CREDIT WITH POWER CO-OP ). TWO TESLA BATTERIES FOR POWER STORAGE, ELECTRIC CAR CHARGER !! TOTALLY FENCED FRONT/BACK; ELEVATOR, ONE CAR GARAGE AND A CARPORT. 2 LARGE STORAGE AREAS. NEAR FOUNDERS PARK AND GREAT RESTAURANTS IN ISLAMORADA. RUN DON'T WALK, THIS A TRUE MUST SEE FOR ANY ISLAMORADA BUYER!!!

148 Giardino Dr, Islamorada
$999,999
3 Beds ⋅ 3 Baths ⋅ 621101 MLS
This waterfront home offers 36 feet of dockage and a beautifully renovated interior designed for effortless Keys living. Thoughtfully updated and tastefully decorated, the home is move-in ready and ideal for full time living or weekend getaway. The layout is exceptionally well-suited for hosting and entertaining, with two bedrooms and two bathrooms on the main living level, and a large separate guest suite and bonus area on the lower level providing privacy and flexibility. Enjoy peaceful views from the screened-in porch, perfectly positioned to capture a straight, open view down the canal, while the spacious backyard offers plenty of room to relax, entertain, and a blank canvas to further enhance your outdoor living experience to your liking. Boaters will appreciate quick access to the ocean, with a beautiful sandbar/beach nearby, perfect for anchoring up for a day of sun, as well as convenient routes to the bay via Channel 2 or Channel 5 bridges. Additional features include a rare garage space, ideal for storing a golf cart, jet skis, and gear while keeping everything protected from the elements.Located on Lower Matecumbe Key, this property provides a walkable Keys lifestyle. Stroll down to the fishing pier to catch dinner and take in a sunset view or hop in the golf cart and ride down to the locals favorite, Habanos restaurant and their new tapas bar right on the ocean for dining and drinks. This is a must-see waterfront opportunity combining comfort, functionality, and the best of island living.

100 Iroquois Dr Unit Unit 5, Islamorada
$2,000,000
3 Beds ⋅ 3 Baths ⋅ 620970 MLS
Canal front living, right where you want it. Set along one of Islamorada's most popular canals, this turnkey 3-bedroom, 3-bath home offers a waterfront setup that makes living easy. With 50 feet of deepwater dockage, a 10,000-lb. boat lift, and direct access to the Florida Bay, this one is hard to beat. Inside, the main level is bright and open, with vaulted ceilings, 2 spacious bedrooms, 2 baths and a beautiful kitchen with top-of-the-line appliances. A large screened-in porch off the living room and primary suite extends the living space and takes full advantage of the canal views. The lower level offers a private 1-bedroom, 1-bath en-suite apartment, ideal for guests or family. Outside, the backyard blends tropical landscaping with a spacious pavered area, creating an easy-to-maintain and welcoming spot to relax. The double-sided garage provides flexible space for storage, parking or recreation. Open both garage doors to extend the backyard or easily bring fishing gear to and from the boat. The cargo lift, filet table, storage shed and generous parking make this home as practical as it is inviting. Add in solid construction with a concrete roof, a great Plantation Key location and easy access to everything you need (both on and off the water), and you've got a home built for enjoying everything the Keys are about.

155 Plantation Ave, Islamorada
$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 20,000-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
$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
$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
$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.

117 El Capitan Dr, 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
$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
$3,900,000
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
$4,500,000
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
$3,875,000
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
$1,890,000
5 Beds ⋅ 3 Baths ⋅ 620271 MLS
Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly sought-after Lower Matecumbe. This exceptional 5-bedroom, 3-bath residence combines contemporary design with breathtaking water views, creating a truly unique island retreat. The thoughtfully designed layout features three spacious bedrooms on the lower level and two additional bedrooms upstairs, connected by a spectacular modern staircase that serves as a striking architectural centerpiece. Soaring ceilings and expansive windows fill the home with natural light, while the open-concept floor plan seamlessly connects the living, dining, and entertaining spaces. The sleek, modern kitchen is perfectly positioned to serve both everyday living and waterfront gatherings. Generously sized bedrooms and beautifully appointed bathrooms provide comfort and privacy for family and guests alike. Step outside to an impressive 667-square-foot waterfront screened deck overlooking the tranquil lagoon, offering the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Boaters will appreciate the deep-water dockage featuring a large boat slip and 16k boat lift, with convenient access to both the Atlantic Ocean and Florida Bay. Enjoy stunning views of the bayside lagoon and the ocean, along with world-class fishing, diving, and boating right from your backyard. Additional amenities include covered parking and ample storage space for all your water toys. Offering the perfect blend of modern elegance, waterfront living, and premier boating access, this remarkable Lower Matecumbe property is a rare opportunity to own a piece of paradise in one of Islamorada's most desirable locations. Onsite property management for true peace of mind.

74980 Overseas Highway Unit 3, Islamorada
$6,150,000
6 Beds ⋅ 7 Baths ⋅ 620190 MLS
Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the home's exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the property's thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. Not included in the listed square footage is a 488 SF garage and over a thousand square feet of covered patio. This home is perfect for the indoor/outdoor entertainer. A true statement of coastal luxury—this is Florida Keys living at its finest.

194 Buttonwood Ln, 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
$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
$4,750,000
4 Beds ⋅ 5 Baths ⋅ 619714 MLS
Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating infrastructure meets the crystalline waters of the Florida Keys. Port Antigua residents enjoy exclusive access to a private beach and boat ramp amenities known only to a select few. Where unmatched dockage and island luxury converge in one of Islamorada's most coveted addresses.

44 W Plaza Del Lago, Islamorada
$995,000
619655 MLS
Potential Short sale!!!Waterfront commercial investment opportunity with 100 feet of dockage on a 13,500 sq ft lot, offering both canal frontage and open ocean views--an increasingly scarce combination in the Upper Keys. Ideally located just outside Port Antigua and White Marlin Beach, the property benefits from strong visibility and proximity to established boating and residential communities. The site features convenient eastbound ingress and egress, supporting efficient operations and customer access. Zoned Commercial Fishing, it allows for a diverse range of income-producing uses, including charter services, boat rentals, marine repair, seafood distribution, restaurant or other waterfront commercial ventures. With direct water access, substantial dockage, and flexible zoning, this parcel is well-positioned for long-term appreciation and immediate revenue potential in a supply-constrained coastal market.

74520 Overseas Hwy, Islamorada
$1,550,000
5 Beds ⋅ 3 Baths ⋅ 619545 MLS
Experience Coastal Luxury and privacy with this exceptional 5 bedroom, 3 bath home on two lots!! Over 2900 sq. ft. of thoughtfully designed living space. Constructed of concrete with impact windows and doors and recently painted inside and out, this home blends style, safety, and comfort. The property's coastal architectural charm is highlighted by a beautiful wrap-around porch and a curved pavered driveway leading to the air-conditioned garage. the main floor includes three bedrooms and 2 baths, featuring a master suite at the end of the home with private access to the backyard and heated pool. Upstairs two large bedrooms share a Jack-and-Jill bath, ideal for family or guests. The chef's kitchen boasts stainless steel appliances, an eat-in area, and a full walk-in pantry, flowing seamlessly into the sun-room and open living/dining area with a canal view. The outdoor living spaces are designed for entertaining and relaxation, including a heated pool with Jacuzzi, torch-lit ambiance around the pool, a fire pit and beautifully landscaped grounds. An air-conditioned shed - currently used as a potting shed - can easily serve as a playroom, art studio, or man cave. Boating enthusiasts will love the boat storage with in-and-out service less than 5 minutes away, offering reduced maintenance and added protection. Convenient access nearby to boat ramps at Founders Park, which also offers a sandy beach, pool, dog park, and sports field. Many community events held here - and you can just walk over to them. This home is set in a private, desirable neighborhood near upscale dining and amenities. Luxury, versatility, and lifestyle in one perfect package. Please schedule your private showing today to experience 169 Venetian Way!!

169 Venetian Way, Islamorada
$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
$649,000
2 Beds ⋅ 2 Baths ⋅ 619328 MLS
This island resort style unit offers stations for dockage up to 25-foot boats, trailer storage and boat ramp. There is a pool for the development, pickle ball and tennis courts. The unit has hurricane impact windows as well as updated balcony area. It offers a large garage area with plenty of storage space.

118 Cortez Dr Unit B2, Islamorada
$400,000
619203 MLS
This is for the sale of 1 (one) Waterfront Transferable Development Right (TDR aka TBR) for use in The Village only. Buyer to pay ALL closing costs associated with the transaction and the transfer fee to The Village. The sale DOES NOT include any real property. Buyer must have an eligible property to which the rights can be transferred.

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

136 San Remo Dr, Islamorada
$3,999,999
2 Beds ⋅ 2 Baths ⋅ 619064 MLS
Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. An existing legal nonconforming home with a waterfront swimming pool currently sits on the property and may be used as a residence or rental while architectural plans and permits are finalized, offering flexibility during the planning process. For buyers who understand the value of land in the Florida Keys, this offering represents something increasingly difficult to find: the opportunity to create a custom waterfront estate tailored entirely to your vision, rather than inheriting someone else's. A remarkable parcel for a remarkable build.

77340 Overseas Hwy, Islamorada
$3,995,000
5 Beds ⋅ 3 Baths ⋅ 618653 MLS
Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling approximately 1,500 square feet, and 2 bedrooms and 1 bathroom downstairs totaling approximately 1,140 square feet. The private resort-style backyard features a heated pool with sun shelf, hot tub, expansive patio, hammock lounge, and mature palms creating a true tropical setting. Enjoy deep-water canal frontage with 70 feet of dockage and two boat lifts rated at approximately 15,000 pounds and 20,000 pounds, providing exceptional boating capacity. Located on one of Venetian Shores' desirable 100-foot-wide canals, the property offers generous maneuvering space and convenient access to both the Atlantic Ocean and Florida Bay through nearby Snake Creek, making offshore fishing and backcountry boating easily accessible within minutes. The custom tiki pavilion includes a full outdoor kitchen with built-in grill, refrigeration, sink, bar seating, mounted TV, and generous space for hosting gatherings year-round. Inside, the bright open-concept living area showcases vaulted ceilings with exposed beams, abundant natural light, and French doors that create seamless indoor-outdoor flow to the balcony overlooking the canal. The primary suite offers balcony access, dual vanities, soaking tub, glass-enclosed shower, and walk-in closet. A gated brick driveway provides generous parking, and the home is offered furnished for immediate enjoyment or continued use as a full-time residence, seasonal escape, or investment opportunity. This Venetian Shores waterfront property delivers the location, spacious layout, wide canal setting, and boating infrastructure buyers are searching for in the Florida Keys.

105 Palo De Oro Dr, Islamorada
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 618050 MLS
Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada. A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas--perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full bathrooms, including a luxurious primary suite with a sleek modern en-suite bathroom and a large walk-in closet. A versatile bonus room offers endless possibilities as a media room, den, office, or children's retreat. The oversized gourmet kitchen is a chef's dream, showcasing brand-new high-end stainless steel appliances, elegant quartz countertops, and generous storage. Impact-resistant windows and sliding glass doors provide peace of mind while enhancing the home's clean, contemporary style. Step outside to your private backyard and enjoy peaceful sunrise views or savor coffee and cocktails beneath the shaded gazebo. Boaters will love the newly decked 60-foot dock, offering immediate access to both the Atlantic Ocean and Florida Bay. From watching manatees glide by to cleaning the day's catch at the large fish station, every detail is designed for waterfront living. An added bonus is the voluntary HOA, which provides access to a wide sandy beach, known as a turtle-nesting haven. Welcome to your place in paradise. 🌴

159 Iroquois Dr, Islamorada
$4,750,000
5 Beds ⋅ 5 Baths ⋅ 615676 MLS
Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime waterfront location, this beautiful resort-style residence offers generous living spaces, including both upstairs and downstairs primary suites, three additional guest suites, a dedicated office, shaded porches on both levels and a spacious garage for ultimate flexibility. The gourmet kitchen flows seamlessly to a fully equipped outdoor kitchen and shaded lounge area--ideal for al fresco dining by the pool amid lush tropical landscaping. A rare combination of classic design, modern amenities, and timeless island charm. Effortless boating and space for all of your waterfront toys with 75' of deepwater dockage and quick access to both ocean and bay. Nearby homeowner's park provides the added bonuses of a private, sandy beach and boat ramp. With the serene, wide canal views and cooling bay breezes, and this is where luxury, comfort, and natural beauty, convenience converge.

88 W Plaza Del Lago, Islamorada