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$2,849,000
4 Beds ⋅ 4 Baths ⋅ 621261 MLS
Exceptional Brand New Waterfront Home in a prime Plantation Key location. This striking three-level contemporary residence offers 60 feet of protected deep-water dockage and seawall with direct canal access to Tavernier Creek, providing immediate Atlantic Ocean and Florida Bay access, truly a boater's dream. The ground level features an open-air two-car garage and generous covered space. On the first living level, an expansive recreation room/possibly 4th bedroom, opens seamlessly to the poolside patio, complete with a full cabana bathroom, creating an ideal setting for entertaining and relaxed island living. The second level showcases a bright, open-concept design with an expansive living area, dining space, and a gourmet chef's kitchen outfitted with European Italian cabinetry and premium finishes, in addition to a well-appointed laundry room with sink and built-ins. Living areas extend to a covered waterfront terrace, perfect for indoor-outdoor living. The third level features a luxurious primary suite featuring a walk-in closet, spa-inspired bath with a two-person shower, and a private open-air balcony overlooking the water. Two additional guest bedrooms and a beautifully finished guest bathroom complete the level. Outdoor amenities include a pool, covered terrace, and a professional outdoor kitchen, ideal for entertaining year-round. Ideally located in the Upper Florida Keys with walking distance to multiple desirable restaurants, a quick boat ride to Tavernier Creek Marina for fuel, ice and snacks, and minutes to boutiques, breweries and 5-star dining in Islamorada. A rare blend of modern luxury and the ultimate Florida Keys waterfront lifestyle. SELLER WILL ENTERTAIN DESIRED REVISIONS OR OFFER CREDIT FOR UPGRADES.

124 Orchid St, Tavernier
$487,500
2 Beds ⋅ 2 Baths ⋅ 621201 MLS
Welcome to your Florida Keys retreat at Summer Sea! Enjoy bay views from your private open deck area. This 2-bedroom, 1.5-bath condo offers updates throughout and coastal living in the highly sought-after, gated Summer Sea community. Bright, stylish, and filled with natural light, this home is your key to island paradise. Unwind while soaking in breathtaking sunsets from the private beach or the rooftop observation deck with panoramic views of the Florida Keys. Community resort-style amenities include a heated/chilled swimming pool, fully equipped fitness center, on-site storage, and a shared freezer/ice machine. Boaters take note: first-come, first-served dockage accommodates vessels up to 26 ft (tip-to-tip) with quick, easy access to the backcountry and open ocean. Spend your days fishing, kayaking, paddleboarding, or diving in crystal-clear waters. Located just minutes from dining, shops, and local favorites.

88500 Overseas Highway Unit 407, Tavernier
$3,700,000
3 Beds ⋅ 3 Baths ⋅ 621153 MLS
Private. Luxurious. Waterfront. Boater-focused. This is more than a home it is an opportunity to experience the Florida Keys exactly as they were meant to be enjoyed. This stunning 3-bedroom, 3-bath Waterfront - Pool home nestled within a private gated community and offers an exceptional combination of sophisticated upgrades and effortless ocean access. This property is designed with the discerning boater in mind, the property features a large, navigable basin offering easy access to the ocean or the Florida bay through one of the near by cuts making it an ideal home base for fishing, diving, cruising, and exploring the Florida Keys and beyond. With two boat lifts and a floating dock, your vessels are securely accommodated and ready for your next adventure. Inside, the home showcases beautiful luxury upgrades, thoughtfully designed for both elegant entertaining and comfortable island living. Expansive impact windows invite abundant natural light while providing peace of mind. As if this was not enough, this property has a roof top deck where you will have beautiful views of the sunrise sky in the morning and enjoy the sunset sky at night. Whether you're enjoying a quiet morning on the water, entertaining friends and family, or heading out for an offshore adventure, this exceptional property delivers the quintessential Islamorada lifestyle. Boat lift 1 -30,000# can accommodate up to apx. a 42 ft Center Console boat. Lift 2 20,000# can accommodate up to apx. a 36 ft. Center Console boat. There is also a floating dock for additional watercraft. Home was Originally built in 1987 Property appraiser shows Effective Year Built 2018.

313 North 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
$999,988
3 Beds ⋅ 2 Baths ⋅ 621110 MLS
OCEANFRONT PENTHOUSE -- STRONG RENTAL INCOME. Welcome to PH701 at Sea Gulls, a rare and incredibly unique 3-bed, 2-bath oceanfront penthouse. With over 2,100 sq ft of living space and two expansive private balconies, this top-floor residence offers panoramic ocean views from every room. Offered FULLY FURNISHED and turnkey, this property has excellent rental income potential and is a high-performing investment. The open layout is light, breezy, and perfect for entertaining, complete with in-unit laundry. As one of just two penthouses in the building, PH701 provides exceptional privacy and prestige. Sea Gulls offers resort-style amenities including an oceanfront gym, heated seaside pool, kayak launch/storage, clubhouse, and secure access. Located in the heart of Tavernier near dining, shops, and schools, this penthouse combines luxury, income potential, and lifestyle flexibility. Don't miss your chance--schedule a private tour today!

200 Wrenn St Unit PH 701, Islamorada
$6,195,000
4 Beds ⋅ 5 Baths ⋅ 620986 MLS
Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

144 N Rolling Hill Rd, 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
$795,000
2 Beds ⋅ 3 Baths ⋅ 620945 MLS
Island Opportunity is knocking! Enjoy your own Islamorada vacation home...with the option to generate excellent rental income when you're not using it. Set in a private, peaceful oceanfront community of just 10 townhomes, you'll have a beach, pool and your own slip for boat up to 30'. Spend the day on the water, relax by the pool or head up to the rooftop deck for ocean breezes & a peekaboo water view. There are four balconies - so you can enjoy some shade at any time of day. Although this seller never rented, the home is eligible for a coveted weekly rental license, giving a new owner the flexibility to enjoy it personally while also taking advantage of the strong Keys vacation rental market. The 2 bedroom, 2.5 bath townhome has a comfortable layout, with a private bath for each bedroom, a half bath on the main living level, and *straight interior* stairs rather than a spiral staircase. It's also refreshingly low maintenance, with concrete construction, a concrete roof, impact windows and doors, and an HOA that takes care of the grounds. Because this is a townhome rather than a condo, owners choose how much insurance to carry, and current insurance costs are surprisingly low. It's even in an X flood zone, so no flood insurance is required. Covered parking and an entry from underneath the home are two more practical touches that make coming and going easy, rain or shine. Trailer/boat storage is allowed under the home. The location works just as well by water as it does by land, with fantastic fishing and diving just steps from home and a great Old Highway location close to Founders Park, restaurants and everything you come to Islamorada to enjoy. Breezy and relaxed when you're here, with the ability to generate income when you're not. It's a rare and excellent combination.. good for your heart and your wallet.

136 Aregood Ln, 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
$499,900
2 Beds ⋅ 2 Baths ⋅ 620763 MLS
Welcome to Summer Seas, a desirable waterfront community in the heart of the Florida Keys! This beautifully maintained 2-bedroom, 1.5-bath condominium offers the perfect blend of comfort, convenience, and island living. Enjoy a bright and inviting layout with an open living area, comfortable bedrooms, and a private balcony to relax and take in the tropical surroundings. The community features waterfront amenities, including a marina, pool, and easy access to the beautiful waters of the Florida Keys. Conveniently located near restaurants, shopping, boating, and everything Islamorada and Tavernier have to offer. Whether you are looking for a full-time residence, vacation getaway, or investment opportunity, this charming Keys retreat is ready to welcome you home.

88500 Overseas Highway Unit 208, Tavernier
$3,450,000
4 Beds ⋅ 3 Baths ⋅ 620762 MLS
This exceptional waterfront estate situated on two lots and on a deep water canal with a 50ft dock is situated in the heart of Plantation Key. The property features a grand three story residence framed by established palm trees and a striking, patterned paver driveway. The expansive grounds are clean but unplanted, offering a clear blank canvas for you to design your ultimate custom tropical landscaping and privacy screening. The backyard focuses entirely on the water, featuring a lagoon style pool with cascading waterfalls, rock formations, and elevated sun decks. A private waterfront dock provides instant access to boating, fishing, or cruising to the open waters of Florida Bay. Inside, this well maintained home is incredibly clean and move in ready. The living spaces are generous and bright, with large windows that seamlessly connect to outdoor terraces overlooking the canal. Enjoy breathtaking, panoramic sunset views from the spacious rooftop observation deck, which provides vistas over the mangrove preserve and surrounding waterways. This property is perfect for someone looking for an immaculate, turnkey home with significant upside potential to add value and personality through their own landscaping vision. It offers the true keys lifestyle just minutes from world class fishing and attractions. This is more than a home; it is a true island destination.

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

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

87851 Old Hwy Unit P3, Islamorada
$619,995
2 Beds ⋅ 2 Baths ⋅ 620555 MLS
Welcome to Futura Yacht Club! Your island getaway awaits in this highly desirable Plantation Key community. Unit 304 is a 2 bed, 2 bath, beautifully maintained condo. Florida Bay views make this third floor perch heavenly. A hideaway murphy bed is an additional feature adding to the desirability of this coastal condo as an ideal second home or rental. Owners and renters benefit from extensive community amenities, including a boat ramp, on-site boat and trailer storage, a large pool with adjacent club area, kayak storage, paddleball and basketball courts, and well-maintained grounds with shaded picnic spots. The on-site management team maintains the serenity of this community. This immaculate condo is being sold fully furnished. Futura is the place to be for boating, with short run times to the Ocean and Florida Bay. Easy boating and spectacular Florida Bay sunsets make for a beautiful investment in island living.

88540 Overseas Hwy Unit APT 304, Islamorada
$2,899,000
4 Beds ⋅ 4 Baths ⋅ 620278 MLS
Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily lot, giving you both immediate rental income and room to grow. In the Village of Islamorada, it is rare to find side-by-side multifamily parcels in such a convenient, desirable Upper Keys neighborhood. 127 Monroe Drive is a concrete triplex of roughly 2,400 sq ft on a 7,500 sq ft lot, with 3 rental units (1/1, 1/1, 2/2), full kitchens and baths, abundant on-site parking, and comfortable outdoor living areas. Units 1 and 3 were renovated with fresh finishes and updated interiors that attract solid tenants and keep maintenance in check. In 2025, the dock electric was upgraded with a dedicated meter for the dock power, one on each property. Next door, 121 Monroe Drive is an additional multifamily parcel of about 7,500 sq ft, now vacant and ready for your next phase of development. Consider adding more units, a pool, covered parking with storage, or enhanced outdoor spaces to create a cohesive compound and boost rental revenue. Multifamily waterfront land in Islamorada is limited, and demand for quality rentals remains strong. With recent upgrades already completed and easy access to the mainland, this combined offering is a great opportunity for investors, 1031 buyers, or owner-operators who want a flexible Keys property with income today and room for future build-out and long-term appreciation. Free access to Founders Park, with sandy beach, swimming pool, boat ramp, playground, tennis, pickleball, walking paths, sports fields, dog park and daily fun activities and regular events.

127 & 121 Monroe Dr Unit 1-3, Tavernier
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 620148 MLS
Futura Yacht Club Rare 3 Bed/2 Bath Condo with 39 ft. Deeded Boat Slip AND 24,000 lb. Boat Lift in desirable Futura Yacht Club! Located in the heart of Plantation Key in Islamorada, this is one of the most coveted boating locations in the Florida Keys with crystal clear water, spectacular nightly sunsets and easy boating access to both the bay and the ocean! This spacious condo is nicely updated inside and offers a private balcony overlooking the sports courts, grounds and gardens. Owners and renters alike enjoy the abundant community amenities, including an easy boat ramp, onsite boat/trailer storage, a huge pool with poolside club area, kayak storage, tennis and basketball courts and spacious grounds with shady picnic areas. After a day on the water, grab a cocktail and stroll over to the sandy beach area with sunset seating and shaded hammocks to enjoy spectacular Florida Keys sunsets! This first level condo allows for easy access via a single flight of nearby stairs or take the elevator to the lobby. Don't miss this opportunity and make sure you see the property video and 3D tour. Call today to arrange a private showing.

88540 Overseas Hwy Unit 101 & Boat Slip 22, Islamorada
$13,500,000
8 Beds ⋅ 8 Baths ⋅ 620067 MLS
Private Helicopter Estate in the Florida Keys. Behind private gates on prestigious Million Air Row, this exceptional oceanfront estate spans nearly 2.5 acres and offers a rare blend of luxury, privacy, and future potential. The recently renovated residence features 8 bedrooms, 7.5 bathrooms, double-height ceilings, spacious bedroom suites, abundant storage throughout, solid CBS construction, impact windows and doors, and a new concrete roof. Designed for the ultimate Florida Keys lifestyle, the property boasts protected basin dockage with a 24,000 lb boat lift, a private helicopter pad, hot yoga studio, resort-style pool with waterslides, waterfall, and spa, plus two covered carports and a large garage. Expansive grounds provide endless opportunities to add additional amenities such as pickleball, volleyball, guest accommodations, or a private beach retreat. A truly unique waterfront compound offering the space and exclusivity rarely found in the Florida Keys.

89401 Old Hwy, Tavernier
$369,000
2 Beds ⋅ 2 Baths ⋅ 620020 MLS
Located in Plantation by the Sea, this Islamorada townhouse offers 2 bedrooms, 1.5 bathrooms, covered parking, and a storage unit in a gated oceanfront complex. Inside, the unit has been updated with renovated kitchen, bathrooms, and flooring. Both upstairs bedrooms feature open balconies, along with an additional balcony off the living room for added outdoor space. The upstairs layout includes 2 bedrooms and 1 full bathroom, while the half bath is conveniently located downstairs. Community amenities include a covered parking space, plenty of guest parking, storage unit, workout room, sauna, kayak and paddleboard storage, bicycle storage, clubhouse, and gated entry. Conveniently located near Founders Park, Islamorada's community park offering a beach, Olympic-size swimming pool, tennis courts, pickleball courts, ball fields, and an amphitheater.

87455 Old Hwy Unit 244, Islamorada
$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
$645,000
2 Beds ⋅ 2 Baths ⋅ 619878 MLS
Welcome to Summer Sea Condominium Apt 424, a beautifully remodeled and fully furnished bayfront residence in the heart of Islamorada. This turnkey, 2-bedroom, 2-full bath condominium offers 1,148 square feet of light-filled living space with open water bay views from an oversized double-width balcony perched among the treetops on the top floor. Designed for both comfort and entertaining, the open-concept floor plan features a spacious living area, modern kitchen, generous storage throughout, and a custom wet bar with a second refrigerator -- ideal for boating and fishing enthusiasts. Both bedrooms are well-appointed and offer comfortable accommodations for owners and guests alike. Summer Sea is a gated waterfront community known for its beautifully maintained grounds, welcoming residential atmosphere, and outstanding amenities. Residents enjoy two swimming pools including a large heated pool, sandy beach area, fitness center, game rooms, community gathering spaces, elevator access, and breathtaking sunset views over Florida Bay. This community has successfully completed its milestone inspection and continues to reflect exceptional pride of ownership with numerous recent improvements, including 2 new elevators, composite dock, remodeled poolside bathrooms, and storm-rated windows and more-- all completed with no special assessments. Whether you are seeking a full-time residence, weekend retreat, or investment opportunity, this exceptional bayfront condominium captures the very best of the Islamorada lifestyle.

88500 Overseas Hwy Unit APT 424, Tavernier
$999,000
4 Beds ⋅ 3 Baths ⋅ 619796 MLS
Spacious 4 bed, 3 bath home in the desirable Indian Mound neighborhood on Plantation Key. Sitting on two lots totaling about 11,000 sq ft, there's plenty of privacy and extra space to enjoy. As you enter, you're welcomed by a large, open floor plan with high ceilings, giving the home a bright and airy feel. The kitchen features granite countertops, upgraded stainless steel appliances, and high-output tankless water heater with instant hot water. Tile flooring runs throughout the main level, with carpet upstairs. Just off the living room, there's a large screened-in outdoor space that's perfect for relaxing or entertaining. This ground-level, above-flood CBS home was built in 2010 and includes a metal roof, impact windows and doors, split-zone A/C, and ceiling fans throughout. It offers 2,361 sq ft of living space, along with exterior lighting and a fenced backyard. Located at 148 Iroquois St and close to local schools, it's a great option for anyone needing both space and convenience. The oversized lot gives you room for kids, pets, or even future additions, while the fenced yard adds an extra layer of privacy. The neighborhood also offers a boat ramp, making it easy to enjoy everything the Keys lifestyle has to offer.

148 Iroquois St, Tavernier
$875,000
2 Beds ⋅ 2 Baths ⋅ 619533 MLS
Islamorada luxury condo and boat slip for boats to 44' - the perfect combination for serious boaters! Located within a 14-acre, resort-style ocean front community of just eight buildings, this home sits in a peaceful low-rise building with only three units. As an end unit with no one above or below, it feels very much like a single-family home. Windows on three sides bring in natural light and a comfortable, airy feel throughout. The kitchen and baths are up-to-date and beautiful. The layout includes 2 bedrooms and 2 baths, plus a screened porch and an expansive 650+/- sq ft open patio overlooking a peaceful swimming lagoon, surrounded by mature trees. You'll want to dine outdoors every night! It's a quiet, private setting that still keeps you close to everything. Impact windows and doors throughout - and - electric roll down shutters for the screen porch. For boaters, the marina is a standout. There's a ramp, shore power, ice, and a private fuel dock exclusively for owners which is an uncommon and valuable feature. It's not just more convenient to gas up at home... it's less expensive than local marinas too! This unit comes with a slip that can accommodate up to a 44' boat and is in a prime location, close to shore and just a short distance from the unit. It's also near a popular gathering spot where owners tend to unwind and connect at the end of the day. Community amenities include an oceanfront pool, clubhouse, a lighted tennis court, and an additional court for tennis or pickleball. The grounds are lush, green, well-kept and spread out, giving the entire property a relaxed, uncrowded feel. Pet-friendly with no size restrictions. If you're looking for a low-maintenance Keys home with excellent dockage and a true Keys boating lifestyle, this one checks the boxes. Offered beautifully furnished. An absolute must-see! Slip #24. Using exterior measurements, total footprint is 2,650 sf +/-.

88181 Old Hwy Unit B3, Islamorada
$700,000
2 Beds ⋅ 2 Baths ⋅ 619480 MLS
TOP FLOOR oceanfront living awaits in this beautifully updated 2-bedroom, 2-bath condo located in desirable Sea Gulls development in Plantation Key. Enjoy breathtaking Atlantic Ocean views from the main living area, primary suite, and an expansive private balcony, perfect for soaking in stunning sunrises and refreshing ocean breezes. The tastefully renovated interior is offered turnkey, fully furnished, allowing for immediate enjoyment as a full-time residence or the ideal vacation retreat. Sea Gulls is a gated, resort-style oceanside community offering exceptional amenities, including an oceanfront pool, sandy beach, kayak and paddleboard storage with launch access, chickee huts, outdoor grilling areas, and a fully equipped renovated oceanfront fitness center and a spacious clubhouse featuring a kitchen and game room. Residents and guests are welcomed through an interior foyer with elevator access and beautiful oceanviews. Experience the best of the Florida Keys lifestyle in this exceptional oceanfront offering.

200 Wrenn St Unit 606, Tavernier
$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
$625,000
2 Beds ⋅ 2 Baths ⋅ 619284 MLS
Elevated direct oceanfront living from a 5th-floor 2 bedroom 2 bath residence in Sea Gulls on Plantation Key in Islamorada. This all concrete building offers peace of mind and stunning Atlantic Ocean views from a full-length private balcony that spans the entire unit, providing water views from every room. The renovated interior is offered turnkey and ready for immediate enjoyment, ideal as a full-time residence or vacation retreat. Sea Gulls is a gated oceanside community featuring a resort-style oceanfront pool, lounging area overlooking Atlantic & sandy beach, kayak/paddleboard storage & launch area, chickee huts, outdoor grilling areas, oceanfront fitness center w/dedicated yoga room, clubhouse w/kitchenette & game room. Owners and guests are welcomed through an interior foyer with elevator access w/scenic water views, enhancing both convenience and arrival experience. Enjoy the best of the Florida Keys lifestyle with breathtaking sunrises, refreshing ocean breezes, and exceptional amenities all within a beautifully maintained waterfront setting.

200 Wrenn St Unit APT 510, Tavernier
$1,075,000
2 Beds ⋅ 2 Baths ⋅ 619193 MLS
Experience the relaxed lifestyle of Islamorada at its finest, at Ocean Harbor Condominiums. This first-floor unit sits directly above its assigned covered parking space and is conveniently closest to the elevator for easy access. A private backyard staircase leads you straight to the pool, and the beach is just steps from your door. This home can serve as a personal retreat or monthly vacation rental, and offers the perfect mix of comfort, convenience, and coastal charm. Inside, the spacious 2 bed/ 2-bath split floor plan offers 1,536 square feet of thoughtfully designed living space, providing privacy for guests, family, or friends. The primary suite features unobstructed ocean views, allowing you to wake up to the beauty of the sea each morning. The living room shares these sweeping vistas, perfect for tranquil sunrises. Enjoy your morning coffee on the porch or take a short walk to the Tiki Hut at the point, which offers ample entertainment space complete with barbecue grills and ice makers ideal for gatherings. Ocean Harbor is a gated community known for its extremely well maintained grounds, with meticulously raked beaches, freshly cut grass, and lush tropical landscaping. Resort style amenities include a large pool and jacuzzi, tennis courts, and a jetty with a Tiki Hut offering breathtaking, unobstructed ocean views. The beautifully appointed clubhouse features a gym, co-working space, and lounge areas. Outdoor grills are located throughout the beach area and near the clubhouse for casual entertaining. For boating enthusiasts, there's a boat launch for trailers, on-site boat storage, and slips available for rent for long term, which just might be cheaper than owning one and paying property taxes on the slip you own. Additional conveniences include electric vehicle charging stations, a pet-friendly policy allowing up to two pets of any size, and one assigned covered parking space. Call today for your private showing!

87851 Old Hwy Unit M3, Islamorada
$775,000
2 Beds ⋅ 2 Baths ⋅ 618895 MLS
The first thing you notice as you walk up to this home is the view, bright blue ocean over green treetops. Step inside and it opens up even more: ocean, sky, and a wide lagoon with a sandy beach below. Sunset here is stunning. This very spacious 2 bedroom, 2 bath end-unit condo offers 1,330 square feet of single-level living with windows on three sides! Located on the second floor, above covered parking, it's that just-right height that makes all the difference. High enough for the views and breezes, without feeling disconnected. Access is easy by elevator or stairs. The oversized screened porch takes full advantage of the ocean and lagoon views and truly extends your living space. Inside, the home has been thoughtfully upgraded for both style and peace of mind. Gorgeous wood-plank tile flows seamlessly throughout the entire condo, including the expansive screened porch, creating a clean coastal look with easy maintenance. The bright kitchen features quartz countertops and stainless appliances - fresh, modern, and functional. Bathrooms have been tastefully updated, the electrical system has been upgraded, and hurricane impact windows and doors provide security and efficiency. Patio surrounded by smoothly operating accordion shutters. A tankless hot water heater adds to the home's smart improvements. You'll also appreciate the recently expanded storage closets and pantry space - something you don't always find in condo living. The community is shady, green, and peaceful. Amenities include a full-service marina (yes, even fuel) with long-term dockage available, waterfront pool, clubhouse, tennis and pickleball courts - soon to be lit for night play. Pets are welcome here. Coral Harbour Club is just five minutes from Founders Park, with its bay front beach, sports programs, dog park, and year-round community events. An updated, move-in ready condo with real ocean views, boating access, and one of the best locations in the Upper Keys. This one is worth seeing in person!

88181 Old Hwy Unit F24, Islamorada
$3,800,000
5 Beds ⋅ 3 Baths ⋅ 618165 MLS
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 Café, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll 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 you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

87950 Overseas Hwy, Islamorada
$895,000
3 Beds ⋅ 2 Baths ⋅ 617033 MLS
Islamorada Tropical Retreat! Rare 3-bedroom 2-bath split plan condo in desirable Futura Yacht Club. Also available with a 39 ft. boat slip with a 24,000 lb boat lift as MLS#620148 for $1,100,000. Located in the heart of Plantation Key, this condo is in one of the most coveted boating locations in the Florida Keys with crystal clear water, spectacular nightly sunsets and easy boating access to both the bay and the ocean! This spacious condo is nicely updated inside and offers a private balcony overlooking the sports courts, grounds and gardens. Owners and renters alike enjoy the abundant community amenities, including an easy boat ramp, onsite boat/trailer storage, a huge pool with poolside club area, kayak storage, tennis and basketball courts and spacious grounds with shady picnic areas. After a day on the water, grab a cocktail and stroll over to the sandy beach area with sunset seating and shaded hammocks to enjoy spectacular Florida Keys sunsets! This first level condo allows for easy access via a single flight of nearby stairs or take the elevator to the lobby. Don't miss this opportunity and make sure you see the property video and 3D tour. Call today to arrange a private showing.

88540 Overseas Highway Unit 101, Islamorada
$500,000
1 Beds ⋅ 1 Baths ⋅ 617483 MLS
Premier 1 bedroom unit a stunning open water and pool view off your private balcony. Fully updated with the open concept kitchen open to the dining and living room. Stunning white cabinets and modern bathroom, Tile floors and granite countertops throughout the apartment. Comfortable queen size bed with a pull-out couch in the living room. The perfect place to lounge and enjoy your days! The condominium is right on the bay with two pools (one heated), a beautiful beach area, Marina with a new composite Dock, Fish cleaning stations, Tiki huts with BBQ grills and picnic tables, Remodeled workout room and game room, community room, fabulous sunsets and friendly residential atmosphere. Safe and secure gated community with 2 brand new elevator. Summer Sea is a multi-story residential waterfront condominium with a friendly atmosphere with on-site management. The community has successfully completed its milestone inspection and continues to show pride of ownership with numerous recent improvements, including two new elevators, a new composite dock, newly remodeled poolside bathrooms, and storm rated windows -- all completed with no special assessments. This condominium is on Plantation Key, Tavernier at MM88.5, just north of the famous Marker 88 Restaurant, a 5-star gourmet restaurant with outside bar. Four restaurants within walking distance. Marina is first come, first serve, other restrictions apply. One pet per apartment with no size restriction. NOTE: The apartment is rented January, February and March 2027 so rental income is already in place!

88500 Overseas Highway Unit 320, Tavernier