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Islamorada Homes on the Bay / Gulf Side of the Island For Sale

Total Listings 56
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$2,790,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 2,229 SqFt Days Listed: 40
-5.42% ($160,000) 1 Price Change : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 70ft.

Welcome to your turn-key waterfront oasis in the heart of the Florida Keys! This beautifully updated 4-bedroom, 3-bath concrete home captures the essence of island living, offering direct access to both the bayside and oceanside--truly a boaters paradise. The expansive 70 x 12.5 freshly painted concrete dock provides plenty of room for all your watercraft, whether youre heading out for a day of fishing or cruising the turquoise waters. Completely updated and tastefully furnished in 2024, this residence blends modern coastal design with solid construction. A brand-new stucco finish and full exterior paint give the home a fresh, crisp look. Most windows and doors are impact rated and all are paired with new roll-down and accordion shutters, delivering peace of mind year-round. Inside, youll find a gorgeous, fully renovated kitchen and bathrooms with high-end finishes that reflect the relaxed elegance of Keys living. The open layout flows easily to the outdoors, where a brand-new heated and chilled pool with spa invites you to unwind canal-side. The shaded summer kitchen and BBQ area are ideal for entertaining, and the low-maintenance artificial turf adds a lush, polished look without the upkeep. A large air-conditioned tackle shed offers plenty of space for fishing gear, tools, or hobbies. Upstairs, the main living area includes three bedrooms and two baths, while the lower level features a permitted bath and bedroom plus a kitchenette and flexible office space -- perfect for hosting extended family or weekend visitors. Must see! Meticulously maintained, move-in ready, and thoughtfully designed for both relaxation and recreation--this is island living done right. Dont miss the chance to own a slice of paradise!

$2,799,999
Plantation Key
Lake Harbor   - MM: 89.50
4 Bed, 4 Baths, 2,476 SqFt Days Listed: 33
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.

This new construction 4-bedroom, 4-bathroom waterfront residence doesnt just check all the boxes -- it redefines them. Spanning 2,476 square feet, this home seamlessly blends modern design with exquisite craftsmanship, complete with top-tier amenities. At the heart of the home is a gourmet chefs kitchen featuring handcrafted fine Italian cabinetry, top-of-the-line appliances, and stunning custom finishes that flow into every room -- from the bathrooms to the doors, closets, and beyond. Designed for entertaining, this home boasts an illuminated 165-bottle wine cellar, a Sonos surround sound system indoors and out, and expansive balcony overlooking the canal. Step outside into your private oasis featuring a pool and spa framed by stone pavers, lush architect-designed tropical landscaping, and a fully fenced yard for ultimate privacy. Boaters will appreciate 60 feet of dockage, a 15,000 lb. boat lift, the popular KillerDock setup, and a state-of-the-art summer kitchen just steps from the water. Located in one of Islamoradas most desirable neighborhoods, youre just a short walk to A-rated schools, local restaurants, and the neighborhood homeowners park. Whether youre seeking a full-time residence or a weekend escape, this one delivers it all -- and then some.

$2,800,000
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 4,537 SqFt Days Listed: 150
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Basi

Discover Your Private Tropical Oasis in Islamorada.Welcome to your dream retreat in the heart of the Florida Keys in the sport fishing capital of the worldaa stunning Key West-style home nestled amidst lush greenery in an exclusive gated bayfront private club community. This residence is more than just a home; its a lifestyle defined by serenity, elegance, and the natural beauty of Islamorada.From the moment you pass through the palm-lined gated front entrance, you will notice the manicured tropical beauty of this community as you make your way to the classic architectural gem that will captivate you. Vibrant hues, large sitting porches, and timeless craftsmanship create a warm, inviting ambiance. Inside, open living spaces are bathed in natural light, blending seamlessly with the lush surroundings visible through every window.Step outside and find yourself in your very own tropical sanctuary. Towering palms, old growth trees, vibrant bougainvillea, and lush greenery surround the property, offering privacy and tranquility. Relax by the pool, host unforgettable gatherings on the expansive patio, or simply unwind as the breeze carries the scent of salt air.Nestled within a private club community, this home offers access to a range of world-class amenities, including a marina, sunset point, beach, and community pool. Plus, the vibrant culture and stunning waters of Islamorada are yours to explore from the protected marina.Whether youre seeking a permanent residence or a vacation escape, this property provides the perfect balance of seclusion and connection. From sunrise strolls on pristine beaches to evenings under the stars, every moment here feels like a slice of paradise.Dont just dream of the Keys, live it. Schedule your private tour today and experience firsthand what makes this home and private community so extraordinary.

$2,800,000
Lower Matecumbe
Port Antigua   - MM: 74.50
4 Bed, 4 Baths, 2,098 SqFt Days Listed: 26
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp6

Stunning canal-front home at the rare T-junction of two crystal-clear waterways in Port Antigua--one of Islamoradas most sought-after communities. This fully updated 4 bed, 3 bath pool home is offered turnkey and ready for immediate enjoyment.Upstairs features an open split floor plan with two spacious ensuite bedrooms, new porcelain wood-look tile throughout, fresh paint, all-new LED lighting, and a sleek kitchen with quartz countertops. The living area opens to a screened balcony overlooking your private dock and wide water views.Downstairs offers a beautifully renovated 2 bed, 1 bath guest suite with its own full kitchen--ideal for visitors or extended family.Enjoy a brand-new pool with fountain, a stylish louvered pergola for sunbathing or shade, a wraparound porch, and a screened upper balcony. Dual A/C units and water heaters add comfort and convenience.Port Antigua residents enjoy a private white sand beach, boat ramp, and direct ocean access--making this a must-see waterfront retreat.

$2,850,000
Upper Matecumbe Key Islamorada
Tarpon Flats   - MM: 81.50
3 Bed, 3 Baths, 2,072 SqFt Days Listed: 33
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock150ft

Experience refined coastal living at Tarpon Flats, Islamoradas 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.

$2,975,000
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 2,250 SqFt Days Listed: 9
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift90ft.Concre

UNIQUE & SPACIOUS BOATERS & OUTDOOR ENTHUSIASTS WATERFRONT HAVENThis nearly quarter acre waterfront property, tucked away with steps from Sunset Point in the coveted and secluded Islamoradas Indian Mound Waterways Neighborhood, is a solid concrete block home secured with automatic and aesthetic roll down hurricane screens. It offers unobstructed views of the Florida Bay with extensive views of the two canals converging. From the homes wide upper living room deck or the 93 feet of concrete dock, observe the dolphins swim and play. Throughout the day, manatees glide by. The four aquarium view underwater lights attract multiple tarpon that linger throughout the night. Soak in the soothing sounds of the coconut fronds. spurred by Florida Bays gentle breeze. Fishermen and boating enthusiasts can easily launch and secure their boats on either of the two boatlifts with walk-on platforms, decked with dual power and water pedestals. The outdoor custom kitchen is equipped with a killer dock fish cleaning station, all stainless steel ice-maker, sink with faucet, refrigerator, large stove and grill with granite countertops. Guests can relax in the hammocks, in the private Bahamian sandy beach adjacent to the kitchen. Dip and swim in the deep and wide lap pool that is cooled or warmed by the homes large 36-panel solar generation system. Propane-fueled tiki torches illuminate the property. The large concrete firepit adds warmth after a cool swim. Gated grounds are landscaped with delicious tropical fruit trees and plants such as mangoes, pineapples, key limes, coconuts, and bananas. Secure your Recreational Vehicle with RV hookup within the gates. Property amenities include access to the neighborhoods local private beach and dock. As a Plantation Key property owner, enjoy Islamoradas amenities: additional bayside beaches, pickleball, tennis, boat docking, amphitheater, and more. The property is move-in-ready or refer to the Architectural Drawings for remodel ideas.

$2,995,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
4 Bed, 4 Baths, 2,928 SqFt Days Listed: 108
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin70ft.

Coastal Elegance Meets Timeless Craftsmanship in Safety Harbor- Welcome to Piece of Quiet, a winner of the Miami Herald Fame award for custom homes with unique architecture. Nestled in the coveted Safety Harbor neighborhood, this CBS construction home is a masterful blend of strength, style, and coastal luxury. Wrapped in island-style siding, the home exudes character and seaside charm, while grandeur arched French doors in the main living area flood the space with natural light and frame stunning waterfront views. Delight your senses with the custom terrace floors that were modeled after those at the Historic Cheeca Lodge & Spa. Step inside to the rich beauty of white oak flooring, offering both durability and sophistication throughout. The open-concept design seamlessly connects indoor and outdoor living, perfect for entertaining or enjoying peaceful moments by the water. Boating enthusiasts will revel in the 70 feet of dockage on a serene, protected deepwater basin, providing direct access to the bay and quick ocean access via the two bridges at Channels 2 and 5. Whether youre setting sail at sunset or savoring the gentle breezes from your private dock, or waterfront decks, this home is a rare gem not to be missed.Dont miss the opportunity to own this waterfront retreat--schedule your private showing today!

$2,995,000
Lower Matecumbe
Port Antigua   - MM: 74.50
4 Bed, 4 Baths, 2,683 SqFt Days Listed: 283
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift70ft.

Welcome to Latitudes in Islamorada, where luxury living meets coastal elegance. This stunning 4-bedroom, 2.5-bath, three-story residence is nestled within the prestigious Port Antigua community on Lower Matecumbe Key in the Florida Keys, a sought-after enclave known for its live-work-play lifestyle. The neighborhood shares a natural white sand beach and boat ramp with private access. This exceptional property offers unparalleled features, including breathtaking 360-degree views from the top floor, a custom-designed pool and spa, a spacious tiki hut complete with a grill and bar, an elevator that goes up to the top floor, and dual boat lifts (12,000# & 20,000#) with deep water and 70+ ft of seawall.The three-story layout at Latitudes is a masterful showcase of an open-concept living space on the top floor, where the dining, living, and kitchen areas flow seamlessly--all in the design of an upscale penthouse. Expansive covered balconies offer additional outdoor living spaces. The home is fortified with impact-resistant doors and windows throughout, ensuring both security and peace of mind.The second floor is dedicated to comfort, featuring a luxurious master suite and bath, along with spacious guest rooms, guest bath and half bath. The ground level includes an enclosed garage and a finished storage area, offering ample space for all your needs. At Latitudes, every detail has been carefully considered to provide a perfect blend of style, functionality, and luxury.

$2,999,987
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,374 SqFt Days Listed: 90
-8.54% ($280,013) 3 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift90ft.Concre

Sellers will consider contributing to buyers closing costs depending on price and terms. Are you looking for a newly renovated Port Antigua home that has plenty of outside entertaining space and 90 ft. of dockage? Youve found it! This home is a top-performing 5-Star vacation rental, projected to generate approx. $70,000 rented just 6 months of the year. Home is being sold with furniture, professional decor and everything you need for a turn-key income producing vacation rental. With a welcoming open floor plan, the 4 sets of impact sliding glass doors and large windows let in ample natural light to the main living level. Impact windows and doors were installed in the entire home in 2019. The kitchen features Bosch stainless appliances, double thickness granite counters, 2 reach in pantries and plenty of seating for the chefs helpers. On this level there is also a guest bedroom and bath and a large, open canal front terrace. The laundry room has additional storage and the on-demand tankless water heater. Interior stairs lead to the primary suite with large en-suite bath, as well as, another guest bedroom with en-suite bath. On the ground level the large driveway covered with concrete pavers offers ample parking, carport and fabulous entertaining space cooled by the east breeze in the summer. A garage and air conditioned workshop to store all your fishing gear and golf cart and is only steps away from the 90 ft. wide concrete dock with a 10,000 lb. boatlift, mooring whips and a fish cleaning station. Dock was resurfaced in 2024. Located in a quiet location on a cul-de-sac in the best private bay-beach community in Islamorada, Port Antigua. Port Antigua provides a degree of anonymity that other Islamorada communities cannot equal, despite being just a short drive from the areas most popular attractions. Its beautiful white sandy beach, complete with Tikis, picnic tables, and grills, along with our large canals and private boat dock, assist in making thi

$3,100,000
Lower Matecumbe
Port Antigua   - MM: 74.50
4 Bed, 4 Baths, 2,937 SqFt Days Listed: 409
-16.19% ($599,000) 12 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.

72 West Plaza Granada is looking for an offer. 4 bedrooms 3.5 bath gorgeous waterfront home in Islamoradas Port Antigua awaits a new owner! Freshly painted, recent new roof, impact windows, Roll down shuttered second level outside balcony for entertaining, top of the line kitchen with Miele and Sub Zero appliances and Faber exhaust island stove, exquisite baths, wine cooler, ice machine (negotiable) grand staircase entry way, alarm system, wired for stereo inside and out, covered parking, room for pool, great entertainment and storage area on ground level along with spacious tackle and storage. Tropical fruit trees, shady side of the canal and a superior neighborhood park with ramp and private homeowners beach round out this Keys Treasure. 27500lbs elevator lift for your big boat. The 2022 42ft Custom Freeman Catamaran offshore fishing boat can go with the house for an additional1.1 Million. This can truly be the fishing package youve been looking for. Shown by appointment only. Contact agent for your personal tour.

$3,450,000
Lower Matecumbe
Port Antigua   - MM: 74.50
5 Bed, 5 Baths, 3,052 SqFt Days Listed: 31
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift75ft.

Located in the highly sought-after neighborhood of Port Antigua, this newly renovated 5-bedroom, 3-bathroom canal-front home offers the ideal combination of space, style, and boating convenience. The main living area is on the upper level, featuring 3 bedrooms and 2 bathrooms with a desirable split floorplan. Soaring ceilings and a large open-concept living space create the perfect environment for entertaining family and friends. Step out onto the spacious back porch to enjoy peaceful canal views, enhanced by electric roll-down shutters for added convenience and protection.For boating enthusiasts, the 75-foot concrete dock with a 15,000 lb boat lift is a dream, and the extra-wide 80-foot canal allows for easy navigation and turning for larger vessels. Downstairs, a fully independent 2-bedroom, 1-bathroom guest quarters--with its own kitchen and built above flood--offers flexibility for hosting guests or extended family.The exterior is equally impressive, with a low-maintenance turf front yard, a fenced backyard, outdoor bar, and a fish cleaning station--everything you need to enjoy the ultimate Florida Keys lifestyle. Theres also ample room to add a pool, should you choose. With access to Port Antiguas private beach, community boat ramp, and quick access to the bay, this home is the complete package. Come see it for yourself--you wont be disappointed.

$3,750,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
4 Bed, 4 Baths, 3,182 SqFt Days Listed: 101
-1.32% ($50,000) 1 Price Change : Last Change 52 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift65ft.

LUXURY CANAL FRONT HOME IN ISLAMORADA!Brand new offering of the most exquisite coastal designed home offering spacious floor plans, entertaining spaces, and oversized rooms. This meticulously maintained home offers a split floorplan with a living room, wet bar, sizeable bedroom and full bathroom on the ground floor overlooking the outdoor kitchen and in ground pool. The second level boosts 3 bedrooms and 2.5 bathrooms, a great living room, pristine kitchen, and walk in laundry room/ office. The fenced in backyard welcomes you to enjoy your private yard surrounded in turf, low maintenance landscaping, and no neighbors directly across. The concrete dock holds a 20,000 lb boat lift and room for multiple boats! Along with this stunning home, you will also have access to the White Marlin Private Homeowners Beach, and all the close amenities in the area!

$3,750,000
Lower Matecumbe
Port Antigua   - MM: 74.50
5 Bed, 5 Baths, 2,425 SqFt Days Listed: 94
-6.13% ($245,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits100ft.

Exquisite Canal Front Retreat in Prestigious Port Antigua, IslamoradaWelcome to your dream waterfront oasis in the highly coveted Port Antigua community of Islamorada. This meticulously remodeled 5-bedroom, 3-bath (3 Up / 2 Down) residence embodies luxury coastal living with 100 feet of premier dockage, offering effortless access to Florida Bay, Channel 2, and Channel 5, placing the Atlantic Ocean just minutes away.This turnkey masterpiece has been completely redesigned and built with high-end finishes and state-of-the-art craftsmanship. On the exterior you have board & batten downstairs and hardy board upstairs. Step inside to soaring high ceilings, driftwood tile flooring with clean lines, hurricane-impact windows and doors that flood the home with natural light while framing breathtaking sunrise views.The gourmet designer kitchen is a chefs delight, featuring sleek stainless steel appliances, a professional-grade hood, wet bar with wine cooler and custom cabinetry, creating an elegant and functional space for entertaining. Each bathroom is a statement of sophistication, boasting exquisite decorator designs, while built-in custom closets and all-new interior finishes enhance the homes refined aesthetic.The outdoor living spaces are just as impressive, this oversized pie-shaped lot on the canal is a rare find, ensuring privacy and abundant space for waterside relaxation. There is room for a pool and all the poolside entertaining space one could yearn for. Residents of Port Antigua enjoy exclusive community amenities, including a private beach with tiki huts and BBQ grills, a boat ramp, and access to the Port Antigua sandbar, where endless days of sun-soaked adventure await.Whether youre seeking the perfect boaters paradise, a serene Florida Keys retreat, or an entertainers dream, this exceptional home offers it all. Experience waterfront luxury at its finest - schedule your private showing today!

$3,795,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 4,008 SqFt Days Listed: 25
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.Concr

Welcome to Your Waterfront Oasis in Venetian Shores. Discover the ideal blend of luxury and laid-back island living in this elegant three-story canal-front home, perfectly situated in the coveted community of Venetian Shores. Boasting 100 feet of dockage and a 14,000 lb. boat lift, this property offers effortless access to both the Atlantic Ocean and Florida Bay via scenic Snake Creek--making it a boaters dream. Thoughtfully designed for comfort, convenience, and entertaining, the home features an open-concept main living area that flows seamlessly into the outdoors. Enjoy al fresco dining in the covered entertaining space complete with an outdoor kitchen and a soothing spa--perfect for unwinding after a day on the water. This residence is fully fenced with two gated driveways and a separate walk gate, ensuring privacy and space for guests. A private elevator connects all three levels, adding both accessibility and sophistication. Inside, youll find two spacious guest suites, each with en-suite baths, and a luxurious primary retreat with dual half baths and a separate spa-style shower--designed for ultimate relaxation and convenience. With abundant storage throughout, a whole-house propane generator, and refined coastal finishes, every detail has been curated for peace of mind and island comfort. Whether youre seeking a serene escape or a vibrant place to gather with family and friends, this Venetian Shores sanctuary offers it all.Paradise is calling. Possible seller financing.

$3,800,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 2,464 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 100ft.

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

$3,875,000
Lower Matecumbe
Port Antigua   - MM: 74.50
4 Bed, 4 Baths, 3,004 SqFt Days Listed: 160
+12.32% ($425,000) 1 Price Change : Last Change 70 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp56ft.

Welcome to Paradise in Port Antigua, one of Islamoradas best-kept secrets! This spacious 4-bedroom, 4-bath home, built in 2019, offers the ultimate Florida Keys lifestyle with modern coastal design, deep-water dockage, and exceptionally low insurance premiums with the possibility of assuming a 2.8% interest rate! Located in the highly sought-after Port Antigua community, residents enjoy unique deepwater dockage and over 1,000 feet of private, exclusive beach frontage.This thoughtfully designed home features a well-planned layout with two primary suites--one on each level--providing privacy and comfort for residents and guests. Each floor includes a separate living space, connected by an interior staircase (all above flood!). A kitchenette on the first level adds convenience, making this home ideal for multi-generational living or hosting visitors. Upstairs, the open-concept layout boasts a spacious kitchen island, high-end appliances, and a seamless flow into the dining and living areas. Balconies on both levels provide stunning canal views, offering perfect spots for outdoor relaxation.The upper level offers three bedrooms and two full baths, while the lower level includes an additional primary suite, two full guest baths, a wet bar, and a secondary living area with easy access to outdoor spaces. The generously sized bedrooms feature large closets, enhancing the homes comfort and functionality.Built for durability, this home includes a standing seam metal roof, all impact windows and doors, and tile floors throughout.Outside, the property boasts two garages--one with AC--a commercial-grade ice machine, and 56 feet of concrete dockage on a desirable 90-foot canal with deepwater access. A 20,000-pound boat lift is included, along with ample parking for vehicles and trailers. Theres even room for expansion if you wish to add more dockage or a pool. This home checks all the boxes and is move-in ready! Call today for more information.

$3,900,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 3,088 SqFt Days Listed: 32
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift70ft.

Waterfront Elegance in Venetian Shores - A Turnkey Coastal GemDiscover the pinnacle of Florida Keys living in this impeccably remodeled waterfront oasis, located in the highly sought-after Venetian Shores. This sophisticated 4-bedroom, 3-bathroom retreat spans over 3,000 square feet of thoughtfully designed living space, blending contemporary luxury with island-inspired charm.From the moment you step inside, youll be captivated by the refined finishes and custom upgrades throughout -- including a gourmet chefs kitchen, spa-quality bathrooms, and expansive open-concept living areas ideal for relaxing or entertaining.This home is truly move-in ready, featuring a brand-new roof, sparkling new pool, all-new impact windows and doors, a state-of-the-art 27,000 lb boat lift, and premium craftsmanship in every detail.Boaters will appreciate 70 feet of deepwater dockage with instant access to Snake Creek -- offering seamless navigation to both the Atlantic Ocean and Florida Bay.Whether youre searching for a permanent residence or a high-end vacation escape, this home offers the perfect blend of luxury, comfort, and unbeatable location.Exclusively offered in Venetian Shores -- where world-class boating and refined coastal living come together.

$3,995,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
5 Bed, 5 Baths, 4,131 SqFt Days Listed: 51
-6.98% ($300,000) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift70ft.Concre

Now priced under appraisal! Introducing the Sea Pearl: a rare and refined coastal masterpiece nestled just four parcels from the Gulf. This ultra-modern smart home constructed in 2016 redefines luxury Keys living, offering five spacious bedrooms, five and a half bathrooms, and over 4,100 square feet of meticulously designed and furnished interior space. Boaters will delight in 70 feet of concrete dockage with water and electric, 15,000 lb boat lift, and panoramic sunset views over a protected nature preserve across the canal--ensuring privacy and tranquility that can never be built upon. This concrete haven is fully equipped with a whole-home generator, Control4 smart system (for AC, music, lights, alarm, security cameras, TVs and more), impact windows/doors, metal roof, and a sleek glass elevator connecting all three levels. Nearly 1,500 square feet of open-air porches and patios invite you to unwind and soak in the Gulf breezes. Step inside the ground level to a welcoming foyer that opens to a sitting area, custom wet bar, Anglers room, and guest ensuite bedroom. Just beyond, enjoy a resort-style pool and built-in spa surrounded by shell stone decking that stays cool even in the height of summer. On the second level, a show-stopping modern kitchen features custom cabinetry, Brittanica Cambria quartz countertops, expansive island with waterfall edge, seating for 8, GE Monogram appliances, Viking 6-burner induction cooktop, and wine cooler--perfect for entertaining. This level also offers three additional bedrooms, including a Jack-and-Jill suite, full laundry, and half bath. The entire top floor is reserved for the primary suite: a true sanctuary with sweeping water views and open air porch, spa-like bathroom with soaking tub, glass shower, bidet, and a custom walk-in closet. With optional White Marlin Beach access, this home is the epitome of modern island elegance--where every detail has been curated for comfort, style, and the ultimate Florida Keys lifestyle.

$3,995,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 946 SqFt Days Listed: 176
-16.77% ($805,000) 8 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 65ft.

This remarkable 34,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay. One of the key highlights of the lot is its exceptional dockage (65 ft), which has previously accommodated a 36-foot Bertram, making it perfect for boating enthusiasts. The property also offers ample space for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds, creating a tranquil atmosphere for evening relaxation. The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aquatic species, like fish, birds, manatees, and a multitude of different birds. Its a perfect canvas for your dream residence or vacation retreat. With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this property is one of the best on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation. May also purchase the vacant lot up front that has a Market Rate TDR on it. Combined you would have ability to build 2 large homes on a combined 49,000 of land. This would make an exceptional family compound in the heart of Islamorada. Possible owner financing. Owner / Agent

$4,400,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
4 Bed, 4 Baths, 1,800 SqFt Days Listed: 135
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davit Pads

Panoramic Bay and Sunset Views! Breathtaking Bayfront Home in Safety Harbor.Experience the stunning beauty of panoramic bay views from this exquisite bayfront home in the premier Safety Harbor neighborhood on Lower Matecumbe. This home is in pristine condition and features an irreplaceable cut-in boat slip with a composite dock on the bay ensuring that your views are not obstructed, and providing immediate bay access and quick ocean access via the two bridges at Channels 2 and 5.Inside, youll find four spacious bedrooms and three bathrooms, perfect for comfortable living. An enclosed garage for all of your fishing and diving gear. The home is equipped with a new whole house generator, ensuring uninterrupted power.Step outside and immerse yourself in resort-style living with a luxurious pool and spa, lush low maintenance landscaping, perfect for relaxation and entertaining. Enjoy breathtaking sunsets year-round from your own private oasis either at the tiki bar, the dock, or one of the two bayfront screened porches. Dont miss the opportunity to own this exceptional bayfront home in Safety Harbor. Schedule your private showing today!

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-15-2025.
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