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$3,200,000
5 Beds ⋅ 4 Baths ⋅ 620230 MLS

139 Tequesta St, Islamorada
$1,180,000
2 Beds ⋅ 3 Baths ⋅ 619466 MLS
One of the most sought after Islamorada Oceanside canals in a prestigious neighborhood where most homes have been completely remodeled or built new. Easy walking distance to both Plantation Key Elementary School and Coral Shores Highschool. Immediate Ocean access and Bay/Backcountry fishing via Tavernier Creek. 128 Plantation drive is located just south of Old Tavernier restaurant. This older 2 Bedroom/2 Bath stilt Cedar home has an 8 foot deep covered back porch, full walkaround deck and a 300 SqFt storage area downstairs with a half bath. Impact Window and Sliding Doors throughout. Cathedral ceilings in the Living/Dinning room and Kitchen. Property is on an XL lot of 70' x 115' including a 12' x 70' Concrete dock with Davits. The previous owners were Fishing Guides, Capt. Ron and Barb Green, and built a really nice fish cleaning table with a hip roof. Easy to show just call the listing agents to set up an appointment.

128 Plantation Dr, Islamorada
$11,500,000
5 Beds ⋅ 8 Baths ⋅ 617575 MLS
A rare architectural masterpiece by renowned architect Max Strang, this modern coastal estate in Port Antigua, Islamorada, redefines luxury waterfront living. Set on a private sandy beach, the residence offers 5 bedrooms, 6 full baths and 2 half baths across 6,367 SF of interior space and 10,483 total SF. Strang's signature tropical modernist design showcases natural materials, clean lines, and expansive glass walls framing panoramic ocean views. Amenities include a gym, golf simulator room, movie theater living area and a spectacular summer kitchen for entertaining. Outdoor living shines with a resort-style pool, spacious terraces and direct beach access. Every detail embodies refined elegance, relaxed sophistication and the timeless allure of Islamorada's coastal beauty. Being offered fully furnished.

236 Costa Bravo Dr, Islamorada
$630,000
2 Beds ⋅ 2 Baths ⋅ 617693 MLS
Charming, light-filled townhouse-style condo featuring 2 bedrooms and 2 baths, tucked away on a quiet cul-de-sac on Lower Matecumbe Key. Enjoy resort-style amenities and excellent boating and fishing access to both the Ocean and the Bay. The open-concept living and dining area flows seamlessly into a well-designed kitchen. Each bedroom and bathroom occupies its own level, providing exceptional privacy for you, your family, and your guests. Vaulted ceilings throughout enhance the bright, modern aesthetic. Two spacious screened balconies capture the ocean breeze, with the upper balcony offering a peek of the water. An oversized garage accommodates your car, bikes, fishing and outdoor gear, plus laundry appliances and a bait freezer. Recent upgrades include all new hurricane-impact windows and doors, new porcelain flooring, and newly installed wooden interior stairs. Resort-level amenities elevate everyday living: a large pool surrounded by lush tropical landscaping, dockage for boats up to 25 feet, multiple shaded fish-cleaning stations, boat and trailer storage, a boat ramp, pickleball and tennis courts, a shuffleboard area, and a clubhouse with restroom facilities and mail/package storage. Perfect as a primary residence, weekend retreat, vacation home, or investment property, this Keys gem offers an exceptional opportunity to enjoy the best of island living.

118 Cortez Dr Unit A, Islamorada
$610,000
2 Beds ⋅ 2 Baths ⋅ 619524 MLS
Welcome to Executive Bay Club in beautiful Islamorada, Florida Keys! Located at Mile Marker 87 bayside, just north of Founders Park, this highly sought-after, pet-friendly waterfront community offers the perfect blend of convenience and Florida Keys living. This completely remodeled 2-bedroom, 2-bath condo is move-in ready and thoughtfully upgraded throughout. Unlike many units, this property features two full bathrooms (one upstairs and one downstairs) and no spiral staircase, offering improved functionality and ease of living. The interior boasts a brand-new kitchen with new appliances, new cabinetry, updated flooring, and fresh paint throughout, creating a clean, modern coastal feel. An indoor laundry room with stackable washer and dryer adds everyday convenience. The bright, open floor plan flows seamlessly to a private patio through sliding glass doors, providing a shaded outdoor space with added privacy--perfect for relaxing after a day on the water. Executive Bay Club is a gated, amenity-rich community featuring a pool, tennis courts, sandy bayfront beach, lush tropical landscaping, and a manned entrance. Boating enthusiasts will appreciate 31 boat slips for vessels up to 28 feet (first come, first serve), 6 mooring pilings, fishing areas, fish cleaning stations, and a kayak launch. Ideally located within the community, this unit is just steps from the pool, tennis courts, and community center. If you're searching for a waterfront condo in Islamorada or a Florida Keys retreat, this property offers an exceptional opportunity to enjoy island living at its best.

87200 Overseas Hwy Unit M4, Islamorada
$900,000
2 Beds ⋅ 2 Baths ⋅ 618264 MLS
Rare offering at Sandy Point Condo in Port Antigua! Enjoy the best of both worlds - beachfront living & protected dockage for your boat. Enter through the ground level & up the stairs to the main living area, where you'll find water views from your living space, an expansive galley kitchen with upgraded Fisher Paykel appliances & dining room, and a convenient half bathroom. The second set of stairs leads to the primary bedroom, guest bedroom & full bathroom. Interior highlights to note - impact windows upgraded in 2022, new AC unit, beach facing windows expanded by 18 inches to improve water views & remodeled kitchen. The ground level offers covered parking for your vehicle, enclosed laundry room, storage, and a patio space to relax in your backyard. Other features include protected concrete dockage up to 30FT & fish cleaning table, access to private bay-front beach & boat ramp. Enjoy sunset views from the living room & primary bedroom! Easy bay & ocean access through Channel Two & Five bridges. Use as your full time residence, weekend getaway or income producing rental!

109 Costa Bravo Dr, Islamorada
$1,435,000
3 Beds ⋅ 3 Baths ⋅ 618650 MLS
Peaceful Palms - Luxury Oceanfront Living in the Florida Keys Welcome to Peaceful Palms, a newly developed gated coastal community offering 15 exclusive high-end townhomes in the heart of the Florida Keys. This oceanfront retreat boasts breathtaking views of the renowned Sandbar and Alligator Reef Lighthouse, providing the perfect blend of luxury, relaxation, and investment potential. Each three-bedroom, three-bathroom townhome is thoughtfully designed with expansive balconies on both the second and third floors, a spacious garage, and pet-friendly accommodations. Owners and guests can enjoy stunning sunrises, an oceanfront pool, and dockage available for rent, making it an ideal escape for those who love life on the water. Additionally, Peaceful Palms is designed to accommodate weekly rentals with the proper permitting, offering an incredible opportunity for investors. With the possibility of new building permits becoming unavailable in the Florida Keys, now is the time to secure your place in this sought-after destination. Don't miss the chance to own a piece of paradise!

84745 Old Hwy Unit 7, Islamorada
$2,600,000
4 Beds ⋅ 5 Baths ⋅ 618956 MLS
Pickle Ball Estate is a stunning new luxury retreat in the heart of Islamorada, masterfully crafted by 4 Keys Construction. This brand-new four-bedroom, five-bathroom residence is a true standout, blending refined coastal design with resort-style living. Designed for both relaxation and entertainment, the home features a private pickleball court, making it a rare and exciting find in the Florida Keys. Spacious interiors, high-end finishes, and thoughtful craftsmanship throughout reflect 4 Keys Construction's latest masterpiece, including a gourmet kitchen equipped with premium Miele appliances. Ideally located, Pickle Ball Estate offers access to a community boat ramp, perfect for days on the water, and is just minutes from Founders Park, where you can enjoy beaches, events, sports facilities, and family-friendly amenities. Whether you are seeking a primary residence, a vacation home, or an investment property, Pickle Ball Estate delivers the ultimate Islamorada lifestyle with luxury, recreation, and island living at its finest.

114 Royal Ln, Islamorada
$975,000
3 Beds ⋅ 3 Baths ⋅ 618807 MLS
Welcome to Unit 116D at Bay Harbour, an elegant and spacious residence in one of Islamorada's most desirable waterfront communities. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of comfort, style, and resort-level amenities, all within a gated, private setting in Lower Matecumbe. Step inside to an inviting open-concept layout featuring high ceilings, abundant natural light, and a generous living and dining area ideal for relaxing or entertaining. The well-appointed kitchen with a propane Viking Range also includes ample cabinetry, granite countertops, and a convenient breakfast bar, making meal preparation both easy and enjoyable. A large, covered terrace extends the living space outdoors, providing the perfect spot for morning coffee, evening breezes, or dining al fresco. The primary suite is a peaceful retreat with direct access to the terrace, a spacious walk-in closet, and an en-suite bath with dual vanities, soaking tub, and separate shower. Two additional guest bedrooms offer flexibility for family, visitors, or a dedicated home office. Bay Harbour is known for its exceptional amenities, including a heated resort-style pool, spa, fitness center, tennis courts, and a clubhouse. The property also features a marina with available boat slips, making it an excellent choice for boating and fishing enthusiasts. Covered parking, a private storage unit, and elevator access add convenience and ease to everyday living. Located just minutes from world-class fishing, dining, beaches, and the natural beauty of the Florida Keys, Unit 116D delivers a low-maintenance, luxury lifestyle in a prime Islamorada location. Whether you're seeking a full-time residence or a seasonal escape, this condo offers the perfect blend of comfort, convenience, and coastal living. Bay Harbour allows weekly rentals with a Village of Islamorada license. For virtual tour www.116BayHarbourCondo.com

101 Gulfview Dr Unit 116D & 30' boat slip, Islamorada
$6,500,000
3 Beds ⋅ 3 Baths ⋅ 619209 MLS
The prettiest, most perfect Keys home you ever did see. Discover one of the most beautifully updated homes in the Florida Keys, set on two spacious lots on Sapodilla Drive. This exceptional property has been completely reimagined with high-quality upgrades throughout, including a brand-new metal roof, a stunning pool and spa, and a private dock with boat lift offering protected dockage and peaceful bay views. Thoughtfully designed for both everyday living and entertaining, the home features tasteful, modern finishes and a striking shell stone privacy wall that enhances its sense of seclusion. Positioned at the end of the street, the setting offers rare privacy and a quiet, tucked-away feel. Two garages provide ample room for vehicles, watercraft, and gear, making this property as practical as it is refined. A truly turnkey home with standout features in a highly desirable location.

158 Sapodilla Dr, Islamorada
$850,000
2 Beds ⋅ 2 Baths ⋅ 617715 MLS
This classic Florida bungalow is located on a rare DOUBLE Lot on Plantation Key in Islamorada. The Dade County Pine ceilings and classic Saltillo tile floors are paired with modern updates to the kitchen with new appliances, including an induction range and oven, quartz counter tops and tile backsplash. The primary bedroom includes an en suite bathroom and walk in closet. Off the kitchen you will find an entertaining space and bar area which leads to your backyard paradise, complete with a lush turf lawn and 100 sqf Tiki hut perfect for entertaining complete with ambient lighting and fans. The entire property is surrounded by professional, mature landscaping which offers both privacy and a tropical oasis. Additional features include a versatile storage outbuilding for all your outdoor gear, extra flex space or guest suite. The lot has plenty of room for parking your boat, vehicle, toys or transforming into your own personal retreat with a pool or addition. The neighborhood incudes an optional $100/yr. HOA park just a block away with a boat ramp or kayak access, dock, fish cleaning station or enjoy the breathtaking sunsets over the bay. This home is in a quiet residential neighborhood on Plantation Key and only a mile and half from Founders Park where you can enjoy pickleball, tennis, swimming, dog park and marina or many of Islamorada's local events. Don't miss this unique opportunity to own a slice of paradise.

113 Key Heights, Islamorada
$5,400,000
3 Beds ⋅ 3 Baths ⋅ 617408 MLS
Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada within walking distance of your favorite spots! Custom built in 2014, this concrete fortress is storm-resilient and also offers a host of sustainability features including a whole-house solar array. Situated on a peninsula with 250+ feet of crystal-clear open waterfront, the gated estate provides unparalleled privacy. This open water home has no neighbors looking through side yards and of course, no neighbors across a canal. Designed to offer the ultimate combination of location, deep-water dockage, storm resiliency and open water views, this luxurious home also boasts marble floors throughout and a gorgeous ''floating'' staircase. Begin your day by stepping out of your bedroom to your private bayfront terrace and into a stunning second floor Infinity Edge pool, complete with a heater/chiller. In the evening, experience the brilliance of Islamorada's sunsets from every room, the rooftop or outdoor lanais, which provide a grand total of almost 6,000 sf of combined indoor and outdoor living space. Floor-to-ceiling sliding glass doors disappear into pockets, bringing the indoors out and the outdoors in. Just one step outside the main kitchen is a full outdoor kitchen and bayside dining, al fresco. For stargazing, venture up to the rooftop deck for a breathtaking front row seat. Ready to get on the water? Your boats will comfortably berth on the 100' deep water dock with two lifts and are kept safe by built-in storm protection. Other functional luxuries include an elevator, an enormous three-car 2,200 sf garage with workshop/storage, camera/security system and mature landscaping with fruit trees. A fourth bedroom with bath can be easily added without modifying the structure at a reasonable cost. With all living space above flood and built to withstand sustained 200 mph winds, this concrete home has accordion shutters over impact for ultimate storm resiliency.

100 List St, Islamorada
$850,000
2 Beds ⋅ 2 Baths ⋅ 616013 MLS
Stunning Ocean Views in Islamorada - the Fishing Capital of the World! Enjoy panoramic views of the Atlantic Ocean and iconic Alligator Lighthouse from this beautifully new and upgraded modular home in desirable Windley Key. Surrounded by water views from every window, this newer construction offers hardy board siding built to withstand 180mph winds, impact windows and doors, and an elevator lift for convenience. Step inside to find a bright and open floor plan featuring an attractive kitchen with quartz countertops, stainless steel appliances, a center island, and stylish window treatments, comfortable living area with 2 bedrooms and 2 bathrooms. Composite decking and exterior staircases lead to a spacious covered area perfect for relaxing or entertaining while enjoying the ocean breeze. Additional highlights include a large storage room/workshop, covered parking, and possible dockage and boat trailer parking privileges. Whether you're searching for a primary residence or the perfect Keys retreat, this oceanfront gem is an exceptional opportunity to own a piece of paradise. DOCKAGE may be available for rent. YOU OWN THE LAND.

84961 Old Hwy Unit 21, Islamorada
$834,000
4 Beds ⋅ 2 Baths ⋅ 617660 MLS
Back on market with Huge Price Improvement! Rare Downtown Islamorada Opportunity... Just steps to the ocean, sunrises and sunsets. Walk to everything you love in Islamorada! Located just off the Old Hwy, oceanside, in the sought-after Matecumbe Beach neighborhood on Upper Matecumbe Key. This versatile property features two charming cottages on one property, just steps from festivals, the Arts District, Library Beach, Cheeca Lodge, Historical Hurricane Monument and some of the island's finest dining. The front cottage offers 2 bedrooms and 1 bath with +/-866 sq. ft., while the back cottage includes 2 bedrooms and 1 bath with +/-900 sq. ft. Enjoy the option to live in one and rent the other, or maximize income by renting both. An exceptional investment in a prime location, right in the heart of Islamorada's most vibrant and walkable district. Important Note: This property is also listed separately in the MLS under 2 different classifications intentionally: Single Family Home and Duplex/multifamily as it can be used for both.

219 Preston St, Islamorada
$5,475,000
5 Beds ⋅ 7 Baths ⋅ 614879 MLS
Welcome to your private tropical retreat in the heart of Islamorada, Florida Keys. This stunning gated oceanfront estate showcases unparalleled beauty with a private walk-in sandy beach, offering direct access to crystal-clear waters. Designed for both relaxation and recreation, the property features 5 spacious bedrooms, 6.5 luxurious bathrooms, a resort-style pool, a pickleball court, and a putting green, all set amidst lush, tranquil landscaping. Wake up to spectacular ocean views from nearly every room, and enjoy the serenity of your tropical surroundings. This property is offered turn-key, fully furnished and equipped, making it an ideal primary residence, second home, or lucrative vacation rental opportunity in one of the Keys' most desirable locations.Your dream oceanfront lifestyle awaits in Islamorada — where every day feels like a vacation.

75851 Overseas Hwy, Islamorada
$330,000
1 Beds ⋅ 1 Baths ⋅ 609266 MLS
Islamorada South....One of the BEST kept secrets in Islamorada! This is a one bedroom, fully updated unit with a screened porch includes a GARAGE! The Spacious garage perfect for storing your weekend toys. Bring your boat! There is always space on the dock for your 25' boat. Clean your catch dockside on the cleaning table. Secured boat and trailer storage is available. It is just a short jaunt to the ocean or the bay. Immediate ocean access from the dock gets you to some of the best fishing, diving & crystal clear waters these islands are known for. Conveniently located on Lower Matecumbe Key yet just minutes from downtown Islamorada's famous restaurants, shops, galleries & breweries. For an intimate complex, the amenities are grand. Play a game of pickle ball in the morning, tennis in the afternoon, cool off in the pool or enjoy a game of horseshoes or shuffleboard with your neighbors after dinner or meditate under the tikis. Islamorada South provides a real community feel....come join the community!

119 Cortez Dr Unit G5, Islamorada
$645,000
3 Beds ⋅ 2 Baths ⋅ 618498 MLS
Enjoy resort-style living in this spacious, fully furnished 3-bedroom, 2-bath condominium located in the exclusive Coral Harbour Club. This residence features an open and airy floor plan where the kitchen, dining, and living areas blend seamlessly, creating an inviting space ideal for both relaxing and entertaining. The primary suite offers privacy and comfort with a modern en-suite bathroom featuring a large walk-in shower, along with a generous-sized walk-in closet. On the opposite side of the living area is a guest suite with two separate guest bedrooms, a full bathroom conveniently located between them, and ample storage throughout the unit. A standout feature of this home is the expansive screened wrap-around balcony, accessible through multiple large glass sliding doors from the living room, primary bedroom, and one guest bedroom. This outdoor space extends the living area beautifully and is perfect for al fresco dining or relaxing while enjoying the tranquil surroundings. Lush, mature landscaping provides exceptional privacy and a serene atmosphere for this second-floor residence. The kitchen is appointed with warm wood cabinetry and granite countertops, offering both style and functionality. Additional highlights include a laundry closet next to the kitchen, a designated covered parking space, nearby guest parking, and a private storage unit conveniently located on the same floor. Coral Harbour Club is a gated community with on-site management, ensuring privacy, security, and convenience. The amenities include a private sandy beach with a chickee hut overlooking the ocean, an oceanfront full-service marina, boat ramp, large community pool, saltwater lake, tennis courts, and a spacious clubhouse that hosts weekly social events and is available for private gatherings. All amenities are surrounded by beautifully maintained, mature tropical landscaping. Experience the lifestyle you've been dreaming of—island living at its finest in the Florida Keys.

88181 Old Hwy Unit G21, Islamorada
$2,000,000
2 Beds ⋅ 2 Baths ⋅ 617174 MLS
Tucked away on a peaceful, hidden boat basin, this diamond in the rough embraces natural privacy from its setting within a broad expanse of native surroundings. Clear waters, endless skies, and unforgettable sunsets. With +/-135 feet of concrete seawall on a private basin, this property offers exceptional space for boating, water-sports, or simply soaking in the tranquil beauty of the Florida Keys. Resting on a rare double lot totaling +/-18,975 square feet, the home provides an incredible sense of privacy and potential. The generous property size allows for lush landscaping, outdoor entertaining, and ample room to expand or design your dream retreat by the water's edge. Inside, the living space unfolds across three levels. A spacious double garage anchors the ground floor, while the second level features the main living area and a guest bedroom with water views. The top floor is dedicated to the primary suite—a private sanctuary with broad views of the basin, frequented by manatees and tarpon. This weekend escape can be your canvas for a future Keys masterpiece, in perfect harmony with nature.

76434 Overseas Hwy, Islamorada
$5,700,000
5 Beds ⋅ 6 Baths ⋅ 615922 MLS
BRAND NEW CONSTRUCTION WITH BAY VIEWS! Welcome to a stunning new construction residence that redefines luxury waterfront living in the Florida Keys. This elegant three-story home offers 5 bedrooms, 5.5 bathrooms, pool and spa, office, garage, outdoor kitchen and 70 feet of dockage—perfectly positioned to capture sweeping views of the Florida Bay and iconic Keys sunsets. Thoughtfully designed for the discerning buyer, the home blends sleek modern finishes with timeless coastal style. The main living level features an open-concept floor plan with expansive living areas, a gourmet kitchen with premium appliances. This home is equipped with a covered terrace, outdoor kitchen, custom pool, and lounge area—all ideal for entertaining. The primary suite provides his-and-her walk-in closets, a spa-inspired bathroom with a soaking tub and glass-enclosed shower, and direct terrace access. Each bedroom is generously sized, and custom-finished closets provide elegant storage throughout. Additional highlights include a dedicated office, full laundry room, elevator access to all levels, a full garage, and abundant storage space. Impact windows and doors, smart-home prewiring, and designer finishes elevate every detail of the home's craftsmanship. This property combines unmatched convenience and the tranquility of coastal living, with direct bay access, ocean access through Tavernier Creek, and a traffic light at the neighborhood entrance for easy access to U.S. 1. Whether you're looking for a full-time residence or a vacation retreat, this exceptional home delivers modern elegance, thoughtful design, and a prime waterfront lifestyle.

206 Plantation Ave, Islamorada
$1,050,000
2 Beds ⋅ 2 Baths ⋅ 616860 MLS
THIS UNIT COMES WITH COVERED PARKING. Not all units have covered parking. Covered parking is equal to 2+ parking spaces. The additional parking is a plus because you have the option to keep your boat on a trailer with you at the property, and~or space for your golf cart, bikes, etc. Enjoy Islamorada fully with this extra space. The best of everything at Beacon Reef, centrally locacted close to restaurants & shopping, unparalleled amenities, Atlantic Ocean views & dockage. Unit #405

83201 Old Hwy Unit 405, Islamorada
$775,000
2 Beds ⋅ 2 Baths ⋅ 617990 MLS
Downtown Islamorada gem located on a massive 11,000+ square-foot lot on a quiet street. Vaulted exposed wood beam ceilings give the home a spacious, open vibe. New roof installed in 2022, brand new appliances, and a brand new screen-in enclosure on the front porch ready to enjoy. The first floor offers covered parking and a handy storage room. Close to all the shops, restaurants, and fun that downtown Islamorada has to offer. Come check it out!

20 Park Rd, Islamorada
$799,000
2 Beds ⋅ 3 Baths ⋅ 615286 MLS
Welcome to Port of Call, an exclusive low-density, private community nestled on the ocean side of Islamorada. With only 5 buildings with 10 units, this hidden gem offers resort-style amenities and the flexibility of short-term vacation rentals. This beautifully updated 2-bedroom, 2.5-bath townhome is designed for comfort and elegance. A standout feature is the sunroom dining area, where you can enjoy meals with direct ocean views. Step onto two expansive screened balconies, soak in the sun on your private rooftop sundeck, or take in breathtaking sunrises from anywhere in the unit. Undercover parking ensures convenience, while the oceanfront pool, beachside tiki hut, and private boat slips make every day feel like a vacation. Located just minutes from shopping, dining, marinas, and Founder's Park, this is Islamorada living at its finest. Plus, your only hours from Miami or Key West, making this the perfect getaway or full-time retreat. Call today to experience the charm of Port of Call - where paradise meets opportunity!

140 Aregood Ln Unit C2, Islamorada
$615,000
2 Beds ⋅ 2 Baths ⋅ 617914 MLS
Welcome to 112 Cortez Drive, a beautifully updated 2 bedroom, 2 bath townhouse-style condo tucked along a quiet street on Lower Matecumbe Key. This inviting updated residence offers a multi-level design that provides wonderful separation of space & a naturally bright, coastal ambiance throughout. The main living area features an open layout with comfortable gathering spaces, as well as a functional kitchen. Each bedroom is situated on its own floor with a dedicated bathroom nearby, giving both owners & guests a true sense of privacy. Vaulted ceilings & large windows enhance the home's airy atmosphere. Two screened balconies that extend the living space outdoors—ideal spots to relax, dine, or simply enjoy the outdoors. The upper-level balcony offers a private sitting area off the primary bedrooms adding to the property's tranquil setting & where you can enjoy sunrise & ocean breezes. It is rare to have an oversized garage -- offering abundant room for a vehicle, outdoor equipment, small boat, paddleboards, kayaks, bikes, fishing gear, & additional storage. There is also convenient space for laundry appliances & a freezer. Carport is used for additional outdoor seating area & gardens but has plenty of room for an additional car or boat that may need to be under cover. Enjoy an impressive list of amenities: a spacious & heated swimming pool surrounded by mature tropical landscaping, dockage w/abundant electric and water stations, a private boat ramp, boat & trailer storage yard, fish-cleaning stations, pickleball & tennis courts, shuffleboard, tiki with BBQ area, & a clubhouse with pool bathroom & mail room. Quick and easy access within minutes to the Atlantic Ocean & Florida Bay Whether you're searching for a primary home, a seasonal escape, or an income-producing property, 112 Cortez Drive delivers the perfect blend of comfort, convenience, & the relaxed lifestyle that defines the Florida Keys & just a 10 min to world famous downtown Islamorada.

112 Cortez Dr Unit B1, Islamorada
$320,000
1 Beds ⋅ 1 Baths ⋅ 618813 MLS
Welcome to this top-floor 1 bdrm, 1-bath condo with slight ocean views in one of the most desirable & affordable waterfront communities in Islamorada. Elevated for added privacy & enhanced views, this residence captures the essence of relaxed island living. The bright & inviting interior features coastal-inspired finishes, an open-concept layout, & abundant natural light throughout. The spacious bedroom & living areas flow effortlessly to your private balcony -- the perfect place to unwind where you can enjoy sunrises & tropical vibes. A very generous garage provides exceptional storage for all your beach, bike, & boating gear. This amenity-rich, community offers dockage, a convenient boat ramp, on-site boat storage, fish cleaning stations, & easy access with approximately one minute to the Atlantic Ocean & just minutes to Florida Bay. Residents also enjoy a heated waterfront pool, tennis/pickleball courts, clubhouse w/bathroom, onsite laundry facilities, & beautifully maintained tropical grounds. This condo makes an ideal full-time residence, weekend getaway, or income-producing investment. Experience the sought-after Florida Keys lifestyle from your own top-floor retreat -- at a price point that remains one of the best values in the area.

119 Cortez Dr Unit APT G11, Islamorada
$2,625,000
4 Beds ⋅ 4 Baths ⋅ 617588 MLS
PRICE IMPROVEMENT!!! 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. Don't miss the opportunity to own this exceptional waterfront property— Your Florida Keys Dream Home Awaits!

112 Leoni Dr, Islamorada
$960,000
4 Beds ⋅ 3 Baths ⋅ 619208 MLS
This fully furnished waterfront townhome offers 36 feet of dockage and a beautifully renovated interior designed for effortless Keys living. Thoughtfully updated and tastefully decorated, the home is move-in ready and ideal for full time living or weekend getaway. The layout is exceptionally well-suited for multigenerational living or hosting family and friends, with two bedrooms and two bathrooms on the main living level, and a large separate guest suite on the lower level providing privacy and flexibility. Enjoy peaceful views from the screened-in porch, perfectly positioned to capture a straight, open view down the canal, while the spacious backyard offers plenty of room to relax, entertain, and a blank canvas to further enhance your outdoor living experience to your liking. Boaters will appreciate quick access to the ocean, with a beautiful sandbar/beach nearby, perfect for anchoring up for a day of sun, as well as convenient routes to the bay via Channel 2 or Channel 5 bridges. Additional features include a rare garage space, ideal for storing a golf cart, jet skis, and gear while keeping everything protected from the elements.Located on Lower Matecumbe Key, this property provides a walkable Keys lifestyle. Stroll down to the fishing pier to catch dinner and take in a sunset view or hop in the golf cart and ride down to the locals favorite, Habanos restaurant and their new tapas bar right on the ocean for dining and drinks. This is a must-see waterfront opportunity combining comfort, functionality, and the best of island living.

100 Iroquois Dr Unit 5, Islamorada
$1,750,000
619538 MLS
This luxury commercial property in the heart of Islamorada offers prime US-1 highway frontage with high visibility, dual access to Old Highway, and a large, lit highway sign for maximum exposure. Built in 2015, this 3,000 SF mixed-use building features 1,500 SF of premium commercial space on the ground floor, including a grand reception area, two executive offices, a spacious conference room, a full kitchen, and an ADA-compliant bathroom, making it ideal for medical, legal, real estate, or executive office use. The 1,500 SF second-floor residential unit includes two bedrooms, two bathrooms, a modern kitchen, and a private balcony, offering luxury accommodations for an owner-user or an excellent rental income opportunity. Never permanently occupied, it remains in brand-new condition with no expenses spared. HC-Highway Commercial zoning allows for flexible use, making this a prime opportunity for a business owner, investor, or real estate professional. This turnkey property has never been leased and has been owner-occupied since completion.

87847 Overseas Hwy, Islamorada
$880,000
3 Beds ⋅ 3 Baths ⋅ 615716 MLS
This renovated treehouse retreat is your picture-perfect getaway or forever island home! Discover a rare opportunity to own a beautifully reimagined Keys haven in the heart of Islamorada. Nestled among lush tropical foliage on an expansive 15,000+ sq ft lot, this fully renovated CBS residence offers a seamless blend of coastal comfort and timeless Old Florida charm. 3 spacious bedrooms, 3 full baths, and a versatile lower-level flex space, the home is designed for both tranquil living and effortless entertaining. Impact doors and windows throughout ensures peace of mind while thoughtful upgrades elevate comfort and style. Enjoy quiet mornings on the deck or explore the nearby serene waters from your shared day dock with easement to access the Bay—perfect for kayaking, paddleboarding, or swimming. (Please note: boating rights are not included.) Tucked away in a secluded yet central location, this private sanctuary offers the ultimate in island living—where nature, easygoing elegance, and serenity converge.

82260 Overseas Hwy, Islamorada
$629,000
2 Beds ⋅ 2 Baths ⋅ 619170 MLS
Welcome to Sand Pebbles Condominium in the heart of Islamorada--an exclusive bayfront community offering privacy, location, and the true Florida Keys lifestyle. This spacious 2-bedroom, 2-bath condo features approximately 1,300 square feet of living space with an open floor plan and abundant natural light. Enjoy tranquil views overlooking the community pool, lush mangroves, and Florida Bay, delivering stunning sunset views right from your living room, kitchen, and private lanai. Sand Pebbles is a boutique 16-unit waterfront community known for its peaceful setting and low-density design. Residents enjoy desirable amenities including a bayfront pool, tiki hut, mangrove nature walk, and beautifully maintained tropical grounds. Boating enthusiasts will appreciate the on-site boat and trailer storage, with convenient access to nearby marinas and boat ramps . World-class fishing, boating, and water sports are all just minutes away. Located in the center of Islamorada, you are close to top-rated restaurants, marinas, shopping, and local attractions, while still enjoying a quiet, tucked-away waterfront setting. Ideal as a full-time residence, vacation home, or investment property, this condo offers the perfect combination of space, location, and island lifestyle in one of the Florida Keys' most desirable areas.

80450 Overseas Highway Unit 302, Islamorada
$1,335,000
3 Beds ⋅ 3 Baths ⋅ 618649 MLS
Peaceful Palms - Luxury Oceanfront Living in the Florida Keys Welcome to Peaceful Palms, a newly developed gated coastal community offering 15 exclusive high-end townhomes in the heart of the Florida Keys. This oceanfront retreat boasts breathtaking views of the renowned Sandbar and Alligator Reef Lighthouse, providing the perfect blend of luxury, relaxation, and investment potential. Each three-bedroom, three-bathroom townhome is thoughtfully designed with expansive balconies on both the second and third floors, a spacious garage, and pet-friendly accommodations. Owners and guests can enjoy stunning sunrises, an oceanfront pool, and dockage available for rent, making it an ideal escape for those who love life on the water. Additionally, Peaceful Palms is designed to accommodate weekly rentals with the proper permitting, offering an incredible opportunity for investors. With the possibility of new building permits becoming unavailable in the Florida Keys, now is the time to secure your place in this sought-after destination. Don't miss the chance to own a piece of paradise!

84745 Old Hwy Unit 4, Islamorada