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$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

$2,999,999
Lower Matecumbe
Mat Ocean Beach   - MM: 75.00
3 Bed, 3 Baths, 1,400 SqFt Days Listed: 210
-7.69% ($250,001) 1 Price Change : Last Change 67 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are enjoyed from upper porch, lower level covered patio, living room and 2 of the 3 bedrooms.Fully remodeled in 2021, this charming get-away has been entirely refreshed with new everything...including impact windows and doors, metal roof, flooring, new appliances, central air, pool equipment and electric gate. Furnishings and finishes reflect the coastal cottage style creating the epitome of relaxation and embodying the Florida Keys lifestyle.

$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.

$3,150,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
4 Bed, 4 Baths, 2,576 SqFt Days Listed: 822
-1.56% ($50,000) 2 Price Changes : Last Change 133 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 400ft.

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today.Owner is Florida licensed real estate agent.

$3,225,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 2,478 SqFt Days Listed: 41
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift70ft

LOOKING FOR THE PREMIER DEEP WATER OCEAN/BAY ACCESS COMMUNITY? Discover the epitome of waterfront living in the exclusive community of Venetian Shores in Islamorada. Renowned for its expansive 100-foot-wide canals, this neighborhood provides unparalleled access to both the Atlantic Ocean and Florida Bay via Snake Creek--ideal for boating enthusiasts. This meticulously updated residence boasts 4 spacious bedrooms and 4 bathrooms. The upper level features three en-suite bedrooms, ensuring privacy and comfort for all occupants. The main living area is highlighted by soaring tongue-and-groove vaulted ceilings and 8-foot impact-resistant French doors that open to a screened lanai overlooking the saltwater pool and canal. The gourmet kitchen is equipped with stainless steel appliances and a gas stove, catering to culinary enthusiasts.The ground floor offers a legal apartment complete with a bedroom and full bath, perfect for guests. Entertain effortlessly on the expansive covered porch, which provides a serene setting to enjoy the outdoors.The saltwater pool is designed for year-round enjoyment, featuring both heating and cooling capabilities, along with a retractable cover for added convenience. A dedicated, air-conditioned mancave offers ample space for storing boating, fishing, and diving equipment. For boating aficionados, a 20,000-pound boat lift was installed, and the property is fully fenced with a sliding gate, ensuring privacy and security.With nearly $80,000 invested in recent improvements, this home is move-in ready. Embrace the Florida Keys lifestyle with world-class fishing and diving just minutes away. Dont miss the opportunity to own this exceptional waterfront property-- Your Florida Keys Dream Home Awaits!

$3,249,000
Plantation Key
Plantation Tropical Park   - MM: 91.00
3 Bed, 3 Baths, 2,938 SqFt Days Listed: 108
-9.49% ($340,800) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock60ft.

This brand-new tri-level home in the FL Keys perfectly captures the essence of sophisticated luxury & relaxed island living. With both bay & ocean access, 60 ft. of canal frontage + private concrete dock, its ideal for saltwater enthusiasts. The home flows seamlessly from the rec room & summer kitchen to pool area, all set in a fenced yard - perfect for kids & pets. The 2nd level offers open living & dining, kitchen island, sleek wet bar & laundry room. An expansive balcony is perfect for family dinners & unwinding. Upstairs, elegant finishes & water views offer a peaceful master retreat. Just blocks from Tavernier Marina & fuel station, close to the top dining spots in Islamorada & only 90 mins. from Miami, this home is an ideal vacation retreat w/no HOA & great rental income potential.

$3,275,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
4 Bed, 4 Baths, 2,782 SqFt Days Listed: 56
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Located in a private, gated community in the heart of Islamorada, 109 South Drive is a rare waterfront retreat that perfectly blends luxury, comfort, and the ultimate Florida Keys lifestyle. The main home features 4 spacious bedrooms and 3.5 beautifully designed bathrooms upstairs, while a separate 1-bedroom, 1-bath apartment downstairs offers privacy for guests or rental potential. Enjoy a custom resort-style pool surrounded by lush, tropical landscaping and a brand-new designer kitchen by Allabastro Designs. Boaters will appreciate the protected dockage with an ipe dock and direct ocean access -- no bridges, no long idle canals. Relax on the rooftop balcony with panoramic ocean views or entertain on expansive outdoor patios. With its unmatched access, thoughtful upgrades, and serene island ambiance, this property is a true Islamorada gem.

$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
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
4 Bed, 4 Baths, 2,519 SqFt Days Listed: 201
-10.59% ($450,000) 2 Price Changes : Last Change 79 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

The Ospreys are back! Welcome to The Ospreys Nest; your perch by the Ocean in one of Islamoradas most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20 dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story primary suite and beachside pool with heater and chiller for those hot summer days. True island living is here on Sunset Drive. Listing includes canal parcel with dock across the street RE#00389220-000100

$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
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

$3,995,000
Upper Matecumbe Key Islamorada
Caribee Beach   - MM: 80.00
2 Bed, 2 Baths, 1,578 SqFt Days Listed: 29
-6.00% ($255,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Seize the rare opportunity to build your dream home in one of Islamoradas most coveted locations! Located directly across from the iconic Alligator Reef Lighthouse. Across the street from a protected preserve that will never be developed, and featuring a deep water channel capable of accommodating boats up to 40 feet, this property offers unmatched privacy and access.Imagine living just a short stroll from the legendary Square Grouper, Midway Cafe, Robbies. Down the road from some of the best restaurants in Islamorada like Ziggies, Mad Dogs, and Chef Michaels. This oversized lot, just shy of an acre, provides the perfect canvas for a builder, developer, or savvy end user to craft a stunning, custom-designed home in an unparalleled location. Dont miss your chance to secure this exceptional piece of paradisean extraordinary opportunity to live where others only dream!

$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.

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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