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$2,790,000
3 Beds ⋅ 2 Baths ⋅ 621394 MLS
Wake up to endless ocean views and the effortless simplicity of life on the beach. This pristine three-bedroom, two-bath oceanfront retreat offers a private, gated setting with a pool, spacious covered patio, and beautiful beach and ocean views from the upper porch, lower-level patio, living area, and two of the three bedrooms. Fully remodeled in 2021, this charming getaway was thoughtfully refreshed throughout, including impact windows and doors, a metal roof, new flooring, appliances, central air conditioning, pool equipment, and an electric entry gate. Coastal cottage-inspired furnishings and finishes create a casual, welcoming atmosphere designed for effortless island living. From mornings overlooking the ocean to afternoons by the pool, this beautifully maintained home captures the relaxed simplicity of the Florida Keys lifestyle.

75055 Overseas Hwy, Islamorada
$1,950,000
3 Beds ⋅ 2 Baths ⋅ 621340 MLS
Perfect fishing retreat/home. A boater's and angler's paradise in Venetian Shores! This 3-bedroom, 2-bath home at 161 Palermo Drive offers deep water and immediate access to the bay and ocean. Enjoy an open floor plan and screened porch, plus concrete construction, a concrete roof, impact windows & doors. A lift makes carrying heavy items upstairs easier. A spacious downstairs rec room with storage, covered parking, and a separate A/C shed for your fishing gear make it easy to enjoy life on the water.

161 Palermo Dr, Islamorada
$699,000
3 Beds ⋅ 2 Baths ⋅ 621332 MLS
Looking for a private 3-bedroom condo with dockage that feels like home? Coral Harbour Club's distinctive open-sided building design provides windows on multiple exposures--including in the kitchen and in every bedroom and bath--filling the home with natural light and tropical views. Shared community boat slips and an excellent on-site marina make boating part of everyday life, with fuel and ice available on the property. Head out for fishing, diving, sandbar days or exploring the Florida Keys, then return to your peaceful retreat. Unlike most waterfront condos squeezed onto a narrow strip of shoreline, Coral Harbour Club spans approximately 14 lush acres with mature landscaping and remarkably spacious, private grounds. Two pets any size are welcome, with shaded walks and access to the Atlantic. Nearby covered parking provides convenient access to the building's central elevator up to the third floor, which is shared with only four other residences. Inside, this spacious split-plan condo has been thoughtfully updated for timeless Keys living. The kitchen features a classic Tuscan-style renovation with newer appliances, while both baths have been updated in elegant island style. One bedroom currently serves as a custom built-in office and can easily convert back. Additional features include new central A/C, full-size washer and dryer, generous closets and additional hall storage. A large wrap-around screened porch extends from both side bedrooms across the living area--perfect for morning coffee or unwinding after a day on the water. Impact windows and doors offer peace of mind, while accordion shutters protect the porch while you're away. Amenities include an oceanfront pool, expansive clubhouse, saltwater lagoon with sandy beach, tennis, pickleball and bocce ball courts, and extensive waterfront grounds with shady seating spots for enjoying shimmering sunrises and ever-changing ocean views.

88181 Old Hwy Unit APT G31, Islamorada
$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
$2,250,000
3 Beds ⋅ 3 Baths ⋅ 621121 MLS
Welcome to your private island home retreat, The Belle House. Highlighted on the Netflix series Bloodline as the home of Kevin & Belle Rayburn. Set on an expansive half-acre double lot enveloped by lush, tropical native plantings, this beautifully updated home offers a rare combination of privacy, tranquility, & effortless Keys living. This home offers room to breathe, unwind & genuinely enjoy your surroundings. Mature landscaping creates a secluded, garden-like setting that feels more like a private resort than a traditional residential property. Featured on the Upper Keys 40th Anniversary Garden Walk, this concrete home with metal roof, Anderson impact windows & doors throughout, & lovely, relaxing wraparound porch is situated in an X flood zone. The neighborhood boasts one of Islamorada's nicest homeowners' parks offering a boat ramp, temporary dockage, a beach & wade in swimming area. Depart from your driveway, launch your boat, & be in Florida Bay in under 10 minutes! Located walking distance to Islamorada's Founder's Park. The interior provides casual, timeless elegance with vaulted ceilings & hand sculpted walnut flooring. The main level consists of free-flowing living & dining, chef's kitchen featuring Wolf, Sub Zero & Meile appliances with honed granite countertops, large pantry/laundry area, very spacious primary suite, as well as guest bedroom, bath and under stair storage. The second level provides privacy for your guests or older children, offering a second guest bedroom and bath as well as a sitting room with mini fridge and breakfast bar. This area could easily transition into a 4th bedroom. There is a detached, all concrete garage on the second lot w/ ample space for parking a flats boat and RV ready with 30-amp service. Two driveways provide plenty of parking for multiple vehicles. This unique home is move in ready. It has been beautifully maintained and cared for and is ready for you and your family to make new memories on Palm Lane!

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

107 Valencia Dr, Islamorada
$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
$999,999
3 Beds ⋅ 3 Baths ⋅ 621101 MLS
Embrace the ultimate island lifestyle in this beautifully renovated waterfront home on Lower Matecumbe Key, featuring 36 ft of private dockage and effortless ocean access. Meticulously updated, tastefully decorated, and completely move-in ready, this costal retreat is perfectly suited as a full-time residence or a premier weekend getaway. Enjoy the financial freedom of no HOA fees, along with the unique flexibility of possible owner financing. The layout is exceptionally well-suited for hosting and entertaining, with two bedrooms and two bathrooms on the main living level, and a large separate guest suite and bonus area on the lower level providing privacy and flexibility. Enjoy peaceful views from the screened-in porch, perfectly positioned to capture a straight, open view down the canal, while the spacious backyard offers plenty of room to relax, entertain, and a blank canvas to further enhance your outdoor living experience to your liking. Boaters will appreciate quick access to the ocean, with a beautiful sandbar/beach nearby, perfect for anchoring up for a day of sun, as well as convenient routes to the bay via Channel 2 or Channel 5 bridges. Additional features include a rare garage space, ideal for storing a golf cart, jet skis, and gear while keeping everything protected from the elements. This property provides a walkable Keys lifestyle. Stroll down to the fishing pier to catch dinner and take in a sunset view or hop in the golf cart and ride down to the locals favorite, Habanos restaurant and their new tapas bar right on the ocean for dining and drinks. This is a must-see waterfront opportunity combining comfort, functionality, and the best of island living.

100 Iroquois Dr Unit Unit 5, Islamorada
$999,000
3 Beds ⋅ 2 Baths ⋅ 621074 MLS
Discover easy bayfront living in this beautifully updated townhome at Executive Bay Club, where breathtaking views of Florida Bay take center stage. The open living area and kitchen enjoy beautiful, unobstructed bay views, while the upstairs primary bedroom offers its own spectacular waterfront perspective. The main living level features level tile flooring and a comfortable, inviting layout designed to take full advantage of the setting. Upstairs, you'll find three bedrooms plus a versatile loft and a spacious bath with a jetted tub and separate shower. Executive Bay Club has recently completed significant community improvements, including a replaced and expanded dock, an updated clubhouse, pool, pool deck and pool bathrooms, all completed within the past two years. With these improvements already made, there are no pending assessments. Move-in ready and ideally positioned on Florida Bay, this is a wonderful opportunity to own a waterfront townhome in one of the Keys' most desirable communities. Don't miss your chance to enjoy bayfront living, beautiful sunsets and the relaxed Florida Keys lifestyle at Executive Bay Club.

87200 Overseas Hwy Unit J 6, Islamorada
$2,400,000
3 Beds ⋅ 4 Baths ⋅ 621073 MLS
Simply the best location, exclusive & extremely private. This is a rare find and a single-family home that's rarely available. It's tucked away in the prestigious ''Plantation Lake Estates,'' a highly sought-after gated community with an on-site boat ramp and park. This Coastal-Styled Beach Home is in a prime location at Mile Marker 87, across the street from Founders Park, which has a beach, tennis courts, a full-service marina, a dog park, sports fields, and Olympic-size lap pools. This home boasts a stunning great room with a gorgeous coral fireplace and soaring wood beam ceilings. They all overlook the glistening Atlantic Ocean, providing priceless views and sunrises. The home has a metal roof, a modern kitchen, updated baths, and impact windows and doors. The exterior has been reinforced with rebar and stucco. There are three inviting bedrooms, including a third-floor master en-suite with a private porch. A large ''rec room'' with a cabana kitchen is perfect for indoor-outdoor entertaining. You'll have world-class fishing and diving right in your own backyard.

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

155 Plantation Ave, Islamorada
$3,000,000
3 Beds ⋅ 3 Baths ⋅ 620907 MLS
Welcome to your Venetian Shores retreat, where relaxed coastal living meets effortless waterfront luxury. This completely updated pool home is designed for easy living and unforgettable entertaining, with an open floor plan, beautiful finishes, and seamless indoor-outdoor flow. The heart of the home is a spacious kitchen with a generous island, opening to the living area and a wall of sliding glass doors. Step outside to a covered terrace overlooking the resort-style pool and waterfront, with plenty of pool deck for soaking up the sun and a shaded poolside area for lingering over long lunches or evening cocktails. Boaters will love the 70 feet of dockage, complete with a 20,000-pound boat lift. Venetian Shores is known for its 100-foot-wide canals and exceptional boating access, with a quick route to the ocean or bay through Snake Creek. Built with CBS construction and a concrete roof, the home offers an elevator plus both interior and exterior stair access between floors. Upstairs, you'll find the main living area and two bedrooms and two baths, while the downstairs offers an additional bedroom and bath. A bonus room, ample storage, and cabana bath add flexibility and convenience. With its resort-style pool, generous waterfront, easy boating access, and beautifully updated interiors, this is the kind of home that makes everyday life feel like a vacation, casual, polished, and unmistakably coastal.

121 Severino Dr, Islamorada
$2,890,000
3 Beds ⋅ 3 Baths ⋅ 620743 MLS
Welcome to your coastal retreat in the highly sought-after Port Antigua neighborhood--where relaxed Keys living meets exceptional boating access and resort-style amenities. Residents enjoy a private homeowner's beach and boat ramp, enhancing the ease of life on the water. This solid CBS construction home offers approximately 75 feet of dockage, a 12,000 lb boat lift, and a convenient fish cleaning station--perfect for avid boaters and anglers alike. After a day on the water, unwind by the beautifully designed pool where a spa cascades into the water, complete with a swim jet, heater, and chiller for year-round enjoyment. Upstairs, the open floor plan is bright and inviting, anchored by a well-appointed kitchen featuring stainless steel appliances, quartz countertops, and a generous island ideal for gathering. Two spacious bedrooms and baths provide comfort and privacy, while a versatile Florida room serves perfectly as a home office and gym. Built for durability and peace of mind, the home includes a concrete roof, impact windows and doors, and an Arlo security system. A rooftop deck offers additional space to relax and take in the coastal surroundings. Downstairs, an expansive covered entertaining area flows seamlessly to the pool and tiki hut--thoughtfully equipped with lighting, ceiling fan, grill, side burner, sink, and refrigerator--creating the ultimate setting for outdoor living. Elevated above flood, the guest quarters feature a private living area, bedroom, and bath with access from both the pool and interior, making it ideal for visitors. A perfect blend of comfort, function, and island charm--this is Port Antigua living at its finest.

101 Madeira Ct, Islamorada
$2,485,000
3 Beds ⋅ 3 Baths ⋅ 620704 MLS
Refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket. This three-story home offers a thoughtful layout and spectacular bay views throughout. The ground floor features covered parking, a versatile multi-purpose room, and access through a gracious foyer entry. Upstairs, the main living level boasts an open-concept kitchen and dining area with panoramic bay vistas, two bedrooms, two bathrooms, and a tranquil porch ideal for enjoying sunset skies. The top floor is reserved for the expansive master suite, complete with a private balcony and sweeping waterfront views. Tarpon Flats offers an amenity-rich lifestyle tailored to the discerning buyer. Enjoy a waterfront pool and gazebo, private beachfront access, generous dockage for your skiff, a charming greenhouse, and a tennis court with shaded seating for guests. Adding to the ease of ownership, the community provides a full-time concierge service and an on-site handyman, ensuring both comfort and convenience year-round. Sophistication, privacy, and natural beauty converge in this exceptional Islamorada retreat--come discover what makes Tarpon Flats truly one of a kind.

81250 Overseas Highway Unit 2, Islamorada
$1,680,000
3 Beds ⋅ 2 Baths ⋅ 620534 MLS
Prime Islamorada Mixed-Use Investment | Ocean Views | Overseas Highway Frontage Exceptional mixed-use investment opportunity in the heart of Islamorada. Positioned directly on the Overseas Highway at Mile Marker 74.5, this highly visible Neighborhood Commercial (NC) property offers outstanding exposure, excellent accessibility, and panoramic Atlantic Ocean views. Originally permitted as a three-unit apartment building, the property is currently configured with two primary residential/commercial spaces, presenting an opportunity for a future owner to explore the potential for a third apartment or additional income-producing space, subject to local approvals. The flexible layout lends itself to owner-occupancy, employee housing, professional offices, retail, vacation accommodations (where permitted), or a variety of commercial uses allowed under NC zoning. An increasingly rare feature in the Upper Keys, this property combines valuable highway frontage with parking, exceptional visibility, and an oceanfront setting. Investors, business owners, and developers will appreciate the property's versatility, while end users may envision transforming it into a distinctive single-family residence with sweeping Atlantic views. Located in one of the Florida Keys' most desirable markets, the property is surrounded by established businesses, restaurants, marinas, resorts, and world-endless fishing and diving destinations. Its strategic location offers convenient access for both locals and visitors traveling throughout the Keys. Whether you're seeking a long-term investment, owner-user opportunity, redevelopment potential, or a signature live-work property, this unique Islamorada offering delivers location, flexibility, visibility, and exceptional upside in one of Florida's most sought-after commercial corridors.

74450 Overseas Hwy, Islamorada
$1,680,000
3 Beds ⋅ 2 Baths ⋅ 620533 MLS
Rare Mixed-Use Opportunity with Spectacular Ocean Views in Islamorada MM 74.5. Endless possibilities await at this highly visible, commercially zoned property located directly on the Overseas Highway at Mile Marker 74.5. Offering breathtaking open Atlantic Ocean views and exceptional highway frontage, this unique property is ideal for investors, entrepreneurs, or anyone seeking the perfect live-work lifestyle in the Florida Keys. Originally permitted as a three-unit apartment building, the property is currently configured with two primary living/work spaces, creating the opportunity for a buyer to explore the potential for a third apartment or reconfigure the property to suit their vision, subject to local approvals. Whether you're looking to maximize rental income, establish a business with residential accommodations, or create a one-of-a-kind family compound, the flexibility here is exceptional. The Neighborhood Commercial (NC) zoning opens the door to a wide variety of commercial uses while the existing residential layout also lends itself beautifully to conversion into a spacious single-family residence with incredible ocean views. Imagine waking each morning to the sunrise over the Atlantic while operating your business from one of Islamorada's most recognizable and accessible locations. The property offers generous parking, excellent visibility, fenced outdoor space, and a location surrounded by restaurants, shopping, marinas, and the best of the Florida Keys lifestyle. Opportunities with this combination of commercial frontage, residential flexibility, income potential, and unobstructed ocean views are exceptionally rare. Whether your vision is investment, business, residential living, or a combination of all three, this is a property where imagination truly becomes opportunity.

74450 Overseas Hwy, Islamorada
$4,500,000
3 Beds ⋅ 5 Baths ⋅ 620441 MLS
An Unfinished Masterpiece Awaits in the prestigious **Venetian Shores**, one of Islamorada's most desirable waterfront communities, known for its deep-water canals and quick access to both the Florida Bay and the Atlantic Ocean via Snake Creek. This extraordinary opportunity allows you to complete what was envisioned as one of the Florida Keys' most premier luxury estates. Elevated above flood on **100 feet of canal frontage**, this solid concrete home features a striking concrete roofline and nearly all impact-rated windows and doors already installed, providing an exceptional foundation for your dream home. Designed with **5,559 square feet of air-conditioned living space**, the residence offers an ideal blend of luxury and boating lifestyle. The first level includes **1,467 square feet** of living space, an oversized **897-square-foot garage**, and plans for an expansive entertainment area, fishing gear room, and direct waterfront access. The second level features **2,361 square feet** of living space plus over **1,100 square feet of covered porches**, with plans for three spacious guest suites, each with a private bath, a half bath, laundry room, chef's kitchen, and open-concept living area. The entire third floor is dedicated to the **1,731-square-foot primary retreat**, designed with ocean views, a spa-inspired bath, oversized custom closet, executive office, and private covered porch. An elevator shaft is already in place for easy access to every level. Plans also include a canal-front pool and cabana overlooking Snake Creek Bridge. With a concrete dock, 100 feet of waterfront, deep-water boating, and one of the Keys' finest locations, this property offers the rare opportunity to complete a truly remarkable custom estate while selecting every finish to reflect your own vision. Property is being sold as is. Some images are AI computer generated to show future potential.

155 Palo De Oro Dr, Islamorada
$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
$3,199,000
3 Beds ⋅ 2 Baths ⋅ 619869 MLS
Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscaping. This exceptional concrete stilt home has undergone a spectacular extensive coastal renovation, blending modern luxury with the relaxed elegance of the Florida Keys lifestyle. The residence features 3 bedrooms and 3 bathrooms with a bright, open-concept floor plan designed to maximize natural light and panoramic ocean views. The upstairs living quarters include a stunning new chef's kitchen with custom cabinetry, premium countertops, and high-end appliances, along with beautifully renovated bathrooms and spacious living and dining areas that flow seamlessly onto the elevated oceanfront porch. Recent upgrades include a brand new roof, all new impact windows and doors, renovated bathrooms, a fully redesigned kitchen, updated finishes throughout, and extensive coastal improvements designed for both style and durability. Also included is a New Tiki Hut and an enclosed 480 sqft bonus room/storage. The gated and fenced property also features a gorgeous oceanfront swimming pool with updated pool equipment, outdoor shower, covered parking for multiple vehicles and boats, and abundant storage space. Outdoor enthusiasts will appreciate the impressive 90-foot oceanfront fishing pier with concrete pilings and low-maintenance composite decking, creating the perfect setting to fish, relax, entertain, or take in the spectacular sunrise views over the Atlantic Ocean. This is a rare opportunity to own a fully renovated luxury oceanfront retreat in Islamorada, known as the ''Fishing Capital of the World.''

75071 Overseas Hwy, Islamorada
$1,199,000
3 Beds ⋅ 3 Baths ⋅ 619848 MLS
Experience all that Islamorada has to offer from this stunning home that was constructed in 2020. This two-story residence offers 3 spacious bedrooms and 2 full bathrooms on the ground floor. The second floor has a large great room - ideal for a home office, second living room, playroom, or media space--adding extra versatility to the layout. Additionally, there is another full bathroom upstairs. Step into an open-concept main living area with numerous windows to let in the natural light. Easy to clean tile throughout. The heart of the home is a modern kitchen featuring a large island, custom cabinetry, and premium finishes--perfect for entertaining and everyday living. The spacious side and backyard provide ample space for trailers, boats, or a future pool, making it perfect for outdoor enthusiasts. Speaking of pool, there is a current, valid pool permit that has been issued for the property and can be transferred to the next owner. This home is located just minutes from the ocean, marinas, shopping, and dining. It is zoned for highly rated Coral Shores High School. This home offers the rare opportunity to own an almost new, move-in-ready property in the Upper Keys. Don't wait--schedule your private showing today and make this modern island retreat your forever home!

143 N Hammock Rd, Islamorada
$8,000,000
3 Beds ⋅ 3 Baths ⋅ 619592 MLS
Discover your dream retreat in this beautiful oceanfront home, set on 1.5 acres of prime beachfront property with 150 feet of pristine white sandy beach, this is the ultimate getaway for relaxation and adventure. Unwind in the oversized heated pool or customized hot tub after a day of sun and fun. The Tiki Hut provides convenient storage for all your water toys, making your boating and beach days effortless. Enjoy practicing your swing on the private putting golf course, all while surrounded by breathtaking ocean scenery. With a lucrative 7-day rental option and an easily obtainable license, this gem is perfect for both personal enjoyment and investment. Don't miss your chance to own this slice of paradise--schedule a viewing today!

88747 Old Hwy, Islamorada
$789,000
3 Beds ⋅ 2 Baths ⋅ 619261 MLS
Nestled in the heart of Islamorada, this ground-level residence captures the essence of timeless Old Florida charm with refined modern updates. Offering 3 bedrooms and 2 bathrooms with 1,300sf of living space, the home has been updated with impact windows and doors, metal roof, renovated kitchen and updated bathrooms, and a newer A/C and water heater. The outdoor spaces are equally inviting. A redesigned side yard with pavers and artificial turf sets the stage for outdoor living and entertaining, while the backyard offers room to create your dream pool and private retreat. A generously sized storage shed adds convenience for all your island lifestyle needs. Ideally positioned in the heart of Islamorada, you are just moments from boutique shopping, renowned waterfront dining, full-service marinas, grocery stores, and pickleball courts. From sunset dinners to days on the water, this location offers a lifestyle where everything you need is right here on this island.

124 S Hammock Rd, Islamorada
$575,000
3 Beds ⋅ 2 Baths ⋅ 619040 MLS
FINANCING OPPORTUNITY -- ASSUMABLE VA LOAN AT 4.9%! The existing VA loan may be assumable by a qualified buyer. Buyer does NOT have to be a Veteran. Loan assumption is subject to buyer qualification, lender/servicer approval, and all applicable terms and conditions. Ask for details! Here's your chance to see the potential beyond the projects. This 3-bedroom home needs extensive updating and remodeling, including a new roof, but it also has something you can't renovate into a property: a desirable Islamorada location, an oversized lot, and Founders Park right across the street. For the buyer with vision, the ingredients are here. Concrete construction, generously sized rooms, a functional floor plan, and a kitchen that opens to the living and dining areas provide plenty of possibilities for reimagining the home. The oversized homesite adds even more potential, with extra outdoor space that can be hard to find in the Keys. And then there's the location. Walk across the street to Founders Park and enjoy the bayfront beach, community pool, public boat ramp, sports fields, playgrounds, dog park, and year-round community events. Whether boating, swimming, enjoying a sunset, or spending the day outdoors, so much of the Islamorada lifestyle is practically at your doorstep. Make no mistake--this home is a project. But for someone prepared to take it on, it's also an opportunity to renovate a home to their own taste rather than paying a premium for someone else's choices. Bring your contractor, bring your ideas, and ask about assuming the existing 4.9% VA loan. Sellers are motivated and will entertain offers.

110 E Ridge Rd, 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
$5,999,000
3 Beds ⋅ 3 Baths ⋅ 608546 MLS
Beautiful 200' of oceanfront property on Lower Matecumbe Key. This offering consists of one 100' lot, vacant with TDR & contiguously, a 100' lot with a triplex apartment building (3 TDRs),.This gives you endless possibilities for redevelopment of the property. The vacant lot has an additional 200' of bay bottom. Fantastic 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Recap: 200' of oceanfront made up of 1 vacant lot with TDR, 1 lot with 3 apartments, bay bottom on the vacant lot, for a total of 4 TDRs on the property Note: One of the owners is a State of Florida Real Estate Licensee

75131 Overseas Hwy, Islamorada
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 618050 MLS
Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada. A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas-perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full bathrooms, including a luxurious primary suite with a sleek modern en-suite bathroom and a large walk-in closet. A versatile bonus room offers endless possibilities as a media room, den, office, or children's retreat. The oversized gourmet kitchen is a chef's dream, showcasing brand-new high-end stainless steel appliances, elegant quartz countertops, and generous storage. Impact-resistant windows and sliding glass doors provide peace of mind while enhancing the home's clean, contemporary style. Step outside to your private backyard and enjoy peaceful sunrise views or savor coffee and cocktails beneath the shaded gazebo. Boaters will love the newly decked 60-foot dock, offering immediate access to both the Atlantic Ocean and Florida Bay. From watching manatees glide by to cleaning the day's catch at the large fish station, every detail is designed for waterfront living. There is enough space to have an in-ground pool. An added bonus is the voluntary HOA, which provides access to a wide sandy beach, known as a turtle-nesting haven. Welcome to your place in paradise. 🌴

159 Iroquois Dr, Islamorada
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 617148 MLS
Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This newly remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect blend of modern comfort and island living. The unique layout features 1 bedroom and 1 bathroom downstairs, and 2 bedrooms and 2 bathrooms upstairs--ideal for guests or extended family. Built with solid concrete construction and impact windows, this home is elevated above flood and designed for peace of mind. Inside, enjoy an open-concept living area perfect for entertaining, a spacious kitchen with stainless steel appliances and granite countertops, and bright, generously sized bedrooms. Modern finishes and high-quality craftsmanship shine throughout. Step outside to a large deck perfect for soaking up the Florida Keys sunshine. Located on a quiet street with beach access at the end of the road, this property offers convenience and tranquility. Close to world-class restaurants, shops, and some of the best fishing and diving in the world. Excellent rental potential--buy one or both adjoining homes for added opportunity. 'The adjacent residence offers a rare opportunity to expand into a multi-residence estate or income-producing property.' 'The neighboring home may be acquired to create an exceptional multi-home setting ideal for extended family living or rental income.' 'Purchasing the nearby residence allows for a flexible use property, suitable for private family living or investment purposes.' 'The adjoining property presents a unique opportunity to establish a private multi-home arrangement or enhance rental potential.' 'With the option to acquire the neighboring home, buyers can create a distinctive residential setting with income potential. Home currently leased for 1 yr.

191 Carroll St, Islamorada
$3,150,000
3 Beds ⋅ 3 Baths ⋅ 618699 MLS
74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence, and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. The existing structure features expansive wraparound windows framing sweeping Atlantic views, plus a top-floor penthouse suite suited for owner occupancy, executive housing, or premium rental use (subject to approvals). The building configuration can also accommodate a rooftop helipad. Commercial Fishing zoning allows for uses such as a destination restaurant, seafood market, marine outfitter, charter or backcountry fishing headquarters, marina-support retail, or other enterprises aligned with the working waterfront. This is a high-visibility, commercial platform where housing, marine access, and US-1 frontage intersect to create compelling long-term value.

74560 Overseas Hwy, Islamorada
$2,495,000
3 Beds ⋅ 4 Baths ⋅ 617838 MLS
Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions. Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes and was completed in 2020 with refined design, upscale finishes, all stainless-steel Bosch appliances, and exceptional craftsmanship throughout. Elegant interiors and thoughtful details create a sophisticated yet relaxed island lifestyle. The home features a private pool with a wood deck at the rear--ideal for entertaining or unwinding in complete privacy, while residents also enjoy access to a community bayfront pool overlooking breathtaking sunset views. An assigned boat slip on the bay provides effortless access to Florida Bay and the Atlantic beyond. Boat lift currently in place can hold boats up to 5,000 lbs. Adding to its appeal, 7-day rentals are permitted, making this property a rare and superior investment opportunity in one of Islamorada's most walkable and desirable locations. Ideal for a full-time residence, island getaway, or income-producing asset, this home offers an exceptional blend of luxury, lifestyle, and flexibility. Coral Cove is located in an X flood zone, providing additional peace of mind.

81906 Overseas Hwy Unit 2, Islamorada
$750,000
3 Beds ⋅ 2 Baths ⋅ 613083 MLS
All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms plus oversized loft with additional queen and three twin beds. This Townhouse has ALL NEW kitchen, new bar, new built-ins, new custom fishing closet & storage, brand new 4 ton AC unit, 2 brand new Bathrooms with showers, new extended loft area, new full size Washer/Dryer, new BBQ area with new patio chicago brick pavers plus private patio shaded area with beautiful palms trees, serena & lily furniture inside, new electric panel, new electric water heater, new 80' smart OLED TV, new area just for refreshments, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. New Electric car charging electric panel exclusive to this unit. Best area in the community next to pool and marina with two pickleball courts and basketball court in the rear. Sleeps easily over 10 people. King bed in the master bedroom, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for over $6,500 a month! Call today! This community features a new private beach, marina, dock and clubhouse. Being SOLD fully furnished and fully equipped with high end appliances (FRIGIDAIRE), high end furniture (SERENA & LILY) and furnishings. See 3 Videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

87200 Overseas Hwy Unit V9, Islamorada