Refine Search
Map
Sort by
$2,275,000
4 Beds ⋅ 4 Baths ⋅ 620004 MLS
Welcome to your own private slice of Islamorada paradise! This canal-front home offers easy access to Florida Bay along with stunning lake views and unforgettable sunsets. This home features CBS construction, a metal roof, accordion shutters, living areas above base flood elevation, and plenty of parking. The upstairs main living area offers over 2,000 square feet of living space with 3 bedrooms and 2.5 bathrooms. Vaulted ceilings and an open, spacious layout are designed to capture natural light and water views. The large kitchen flows seamlessly into the living and dining areas, making it ideal for entertaining or simply enjoying the relaxed Keys lifestyle. The bedrooms are located down the hallway, creating a nice separation from the main living spaces. The primary suite features a walk-in closet and a beautifully appointed spa-like bathroom with marble finishes, dual vanities, granite countertops, soaking tub, and a glass-enclosed steam shower with multiple shower heads. All bedrooms are generously sized with ample closet space. The downstairs living space offers over 770 square feet and is separate from the upstairs, creating a great private area for guests to enjoy, complete with sliding glass doors that open directly to the pool area. Outside, enjoy lush tropical landscaping, a canal-front pool with heater, 60' of dockage with a 15,000 lb boat lift, and quick boating access to Florida Bay. The outdoor living space is ideal for entertaining with plenty of room under the carport along with an outdoor kitchen. Whether you are heading out for a sunset cruise, fishing trip, or waterfront dining, this location puts the best of the Florida Keys lifestyle right at your fingertips.

316 Woods Ave, Islamorada
$1,010,000
2 Beds ⋅ 3 Baths ⋅ 618212 MLS
ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community that allows Vacation Rentals, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades include Brazilian Cherry hardwood floors, kitchen with granite countertops and SS appliances with 2 breakfast bars & tons of cabinet space. The home also has a composite decking & railing, a metal roof & impact doors & windows. The community features 2 sandy beaches, a pool & marina on the Atlantic Ocean. Home has been in rental program for many years with a good following. Own your vacation home for free & more. Great investment. Call today for a showing!

102 Anglers Way, Islamorada
$573,000
3 Beds ⋅ 3 Baths ⋅ 619364 MLS
Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setting. This nicely updated 3-bedroom plus loft townhouse offers a spacious and versatile layout designed for easy everyday living and entertaining. Upstairs, you'll find three inviting bedrooms, two full baths, and a charming loft--perfect for additional guests, a home office, or a cozy retreat. Downstairs, thoughtful updates create a seamless flow, with a level floor plan that connects the living and dining areas--no step-down interruptions--enhancing both function and openness. The expanded kitchen is a standout feature, showcasing stainless steel appliances, generous counter space, and a peninsula with double-sided storage, ideal for both cooking and gathering with friends and family. A full bath on the main level adds convenience for guests. Beyond your front door, Executive Bay Club offers an array of amenities to complement the coastal lifestyle. Enjoy two tennis and pickleball courts, newly expanded first-come, first-serve dockage for your boating adventures, and a beautifully renovated pool area complete with updated pool deck and bath facilities. The refreshed clubhouse provides an inviting space to relax and connect with neighbors. Whether you're seeking a full-time residence or a weekend escape, this welcoming townhouse delivers the perfect blend of elegance, comfort, and laid-back island living.

87200 Overseas Hwy Unit S3, Islamorada
$420,000
2 Beds ⋅ 2 Baths ⋅ 620997 MLS
BEAUTIFUL CONDO WITH OCEAN VIEWS FOR LESS THAN $430,000! LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY IN THE HIGHLY DESIRABLE PLANTATION BY THE SEA ON THE OCEAN IN THE BEAUTIFUL FLORIDA KEYS! LOCATED ON HIGHLY SOUGHT AFTER MILLIONAIRES ROW! UPON ENTERING THIS GATED COMMUNITY, THE OCEAN GREETS YOU AS YOU PARK IN YOUR DESIGNATED COVERED PARKING SPACE. UPON ENTERING YOUR CONDO, THIS PARTIALLY UPDATED CONDO WITH OPEN CONCEPT KITCHEN, WELCOMES YOUR HOME TO A CHEF'S DREAM KITCHEN WITH PLENTY OF CABINET SPACE. NEW WATER HEATER, SCREENED IN PATIO ON THE FIRST FLOOR AND GORGEOUS OCEAN VIEWS FROM THE SECOND FLOOR. CLUBHOUSE/COMMUNITY ROOM, FITNESS ROOM, SAUNA, KAYAK STORAGE, LONG AND WIDE FISHING PIER/DOCK ALLOWS YOU TO TIE UP YOUR BOAT FOR LOADING AND UNLOADING WALK TO WORLD CLASS RESTAURANTS, SHOPPING, AND FOUNDER'S PARK. ALL ARE CLOSE! TAKE ADVANTAGE OF THIS AMAZING OPPORTUNITY TO LIVE FULL TIME WHERE OTHERS VACATION, OR START A VACATION RENTAL BUSINESS HERE IN THE BEAUTIFUL FLORIDA KEYS!

87455 Old Hwy Unit 248, Islamorada
$1,030,000
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
$285,000
620621 MLS
50' X 22' boat slip at the World famous Lor E Lei marina. Excellent in-town location, you know you're going to boat over here anyway so you might as well tie up for the night! Enjoy the sunsets, unwind, Uber home, or use for your fishing business, so many possibilities. A rare find.

96 Madeira Rd Unit # 10, Islamorada
$11,500,000
7 Beds ⋅ 7 Baths ⋅ 619776 MLS
LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pristine bayfront offering deep-water dockage with a 20,000 lb boat lift, a white sandy beach and stunning unobstructed panoramic views of the Florida Bay located in desirable Lower Matecumbe. Spanning nearly 6,000 square feet of extraordinary living space with 7 bedrooms and 7 bathrooms. Thoughtfully designed for ultimate comfort, this estate features two separate guest wings, each offering three private bedroom suites, ideal for family, guests or an unparalleled private retreat. The gourmet chef's kitchen, perfect for entertaining, leads to an expansive and inviting great room, elegant tray ceilings, designer finishes, and sophisticated architectural details throughout. A private elevator offers effortless access between levels. Step outside to your own tropical sanctuary, where a stunning pool deck overlooks the sparkling waters of Florida Bay. Lush tropical landscaping provides privacy, while spacious covered terraces provide the perfect backdrop for unforgettable sunsets and year-round outdoor living. With WEEKLY rentals permitted with a Vacation Rental license, this rare offering combines luxurious personal enjoyment with outstanding investment potential. Experience the Florida Keys lifestyle in one of Lower Matecumbe's most exclusive waterfront settings. SELLER FINANCING AN OPTION WITH 50% DOWN.

75840 Overseas Hwy, Islamorada
$5,550,000
5 Beds ⋅ 7 Baths ⋅ 620457 MLS
Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf of thoughtfully designed living space, set just 2 lots from the bay and across from a tranquil mangrove preserve that enhances both privacy and natural beauty. Boaters will love the setup - 100' of dockage with 2 elevator boat lifts (20,000lb and 15,000lb), plus easy access to Everglades National Park and the Atlantic Ocean through the 65' Channel 5 Bridge. Inside, the home feels open, bright, and refined. There are 5 ensuite bedrooms and 2 half baths, each bedroom featuring its own ductless A/C along with the central system. The primary suite includes a cozy sitting area, his-and-hers closets, and partial bay views. A secondary primary suite opens directly to the pool deck, offering privacy for guests or family. The top level centers around a stunning great room with vaulted ceilings, fireplace, and a chef's kitchen with high-end appliances - the perfect setting for entertaining. On the lower level, a relaxed family room with fireplace and wet bar creates another comfortable gathering space. Additional features include laundry on both floors, an elevator, 2-car garage, and gated circular drive. Out back, the saltwater pool, outdoor kitchen, and sound system create a true resort-style atmosphere. The east-facing orientation means warm morning sunshine, shady afternoons, and gentle ocean breezes. With CBS construction, metal roof, whole house generator and impact windows and doors, this home blends luxury, comfort, and peace of mind. This is waterfront living for those who value both elegance and ease - the Keys lifestyle at its finest.

430 Palm Dr, Islamorada
$1,500,000
4 Beds ⋅ 3 Baths ⋅ 619331 MLS
Island Living in Prestigious Venetian Shores! Welcome to this newly custom-built 4bd/3ba residence ideally positioned on a tranquil plugged canal in one of the most sought-after subdivisions in the Florida Keys. Upstairs, enjoy a spacious open porch that flows seamlessly into a light-filled open concept floor plan. The designer kitchen features solid wood cabinetry, quartz countertops, a large island with waterfall edges, and accent-colored cabinetry for a modern coastal touch. The lower level offers the perfect guest quarters, complete with a private bedroom overlooking the pool, a large bathroom, and a generous living space. Concrete construction with metal roof and impact windows and doors allows you to enjoy the benefits of newer construction. Outdoor entertaining is a breeze with multiple seating areas and a large gazebo, and paver driveway that extends into a beautifully designed pool area. The concrete pool includes a water feature and LED lighting. Additional features include tall covered parking suitable for RVs and boats, and spray foam Icynene insulation in the attic for energy efficiency and reduced cooling costs. Buyers of new hones like this one can save an average of $25,335 over the first 10 years in lower utility bills and reduced repair costs compared to 20 year old homes - Based on recent study, Realtor.com. Boaters will love the nearby Venetian Shores marina with available boat slip rentals and convenient nearby access to boat ramps at Founders Park which also offers a sandy beach, pool, dog park and sports fields. Whether you're looking for a full-time residence or a weekend escape, this exceptional home captures the best of Florida Keys living! SELLER WILL PAY FOR A YEAR OF STORAGE FOR UP TO A 30' BOAT AT SNAKE CREEK MARIN

124 Venetian Way, Islamorada
$4,200,000
4 Beds ⋅ 4 Baths ⋅ 617501 MLS
Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene. The home enjoys unobstructed water views and nightly sunsets that paint the sky in brilliant hues. A Tiki at the water's edge provides a perfect perch for morning coffee or evening cocktails, while mature landscaping adds privacy and tropical charm. Boaters will appreciate the deep-water dockage with davits, ideal for quick access to open water. The 2,478-square-foot residence features 4 bedrooms and 4 bathrooms, with tile flooring throughout and expansive windows that frame the bay. The open-concept living and dining areas flow into a well-appointed kitchen. The primary suite offers direct water views and private outdoor access. Outdoor living is elevated with a spacious pool and deck area, balcony, and brick paver walkways. The white picket fencing and lush landscaping complete the coastal aesthetic. Additional features include CBS construction, off-street parking, FKAA water service, septic system, and low HOA fees. Pets are welcome. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, 166 Bayview Drive delivers unmatched location, views, and lifestyle in the Florida Keys.

166 Bayview Dr, Islamorada
$1,000,000
2 Beds ⋅ 2 Baths ⋅ 620889 MLS
Unit 21 & 22 building within Kon Tiki resort. An exceptional opportunity to own one of Islamorada's most recognizable waterfront hospitality properties. The iconic Kon Tiki Resort is a beloved Old Florida destination on the tranquil shores of Florida Bay in the heart of the Sportfishing Capital of the World. This family-owned resort offers a collection of charming villa-style accommodations surrounded by mature tropical landscaping, a private marina, and unforgettable sunset views. Designed for boaters and outdoor enthusiasts, the property features one of the few private boat ramps in Islamorada, complimentary dockage, trailer parking, a temperature-controlled pool, sandy swimming lagoon, picnic areas, and direct access to both Florida Bay and the Atlantic Ocean. Its central location places guests within minutes of world-renowned fishing, dining, diving, and the vibrant lifestyle that defines the Florida Keys. With decades of established goodwill, a loyal repeat clientele, and a reputation for authentic Keys hospitality, Kon Tiki represents a rare investment opportunity to acquire units within an operating waterfront resort with tremendous long-term potential in one of the most desirable destinations in the Florida Keys.

81200 Overseas Hwy Unit 2122, Islamorada
$2,100,000
3 Beds ⋅ 3 Baths ⋅ 621166 MLS
Turnkey waterfront living with exceptional boating access in the heart of Plantation Key. Beautifully remodeled and designed for the Florida Keys lifestyle, this inviting canal-front home offers 70 feet of waterfront on a wide canal, a spectacular new pool surrounded by expansive brick-paver decking, and direct access to the Atlantic Ocean. The light-filled main living level features an open-concept design with a beautifully updated kitchen, generous island seating and an easy flow into the living and entertaining spaces. The main level offers two bedrooms and two baths, while a separate one-bedroom, one-bath guest area downstairs provides additional space for family and friends. A garage adds valuable storage for all the Keys essentials. Outside is where this property truly shines. Lush tropical landscaping surrounds the new pool and spacious waterfront entertaining areas, creating a private, resort-like setting for relaxing after a day on the water. Enjoy 70 feet of canal frontage with plenty of room for your boating lifestyle. Boaters will appreciate quick, direct ocean access, with Tavernier Creek just minutes away providing convenient passage to Florida Bay. This exceptional location makes both the Atlantic and Florida Bay easily accessible for fishing, diving, cruising and days on the water. Fresh, beautifully updated and ready to enjoy, this is a wonderful opportunity to embrace the best of Plantation Key living, where boating, entertaining and laid-back island life come together.

123 Harbor Dr, Islamorada
$1,062,000
2 Beds ⋅ 2 Baths ⋅ 620551 MLS
A unique opportunity to enjoy the Florida Keys boating lifestyle without the cost of waterfront ownership. This well-maintained dry lot home in desirable Tollgate Shores includes a deeded boat slip directly across the street, complete with a new dock, 20k boat lift, water, power, and a fish cleaning station. Enjoy the convenience of direct sight lines to your boat from the living room and front porch, with peekaboo views of Florida Bay and the iconic Channel 5 Bridge beyond. Upstairs, the home features two generously sized bedroom suites, each with its own ensuite bathroom. A pantry and laundry room are conveniently set off of the well-appointed, modern kitchen. The open-concept living area is highlighted by vaulted ceilings with exposed wood trusses and bamboo flooring. A clean interior offers a comfortable, move-in-ready space, with furnishings negotiable. The lower level includes covered parking, an air conditioned garage, a spacious bonus room, and a dedicated tackle storage closet, providing ample space for boating gear, hobbies, and everyday storage. A metal roof, high quality insulation and impact windows and doors add to the integrity and efficiency of this home. Located adjacent to the neighborhood park, the property benefits from additional open green space. The voluntary HOA is $250 annually. With quick boating access to both Florida Bay and the Atlantic Ocean via Channel 5, this property is well suited as a full-time residence, weekend retreat, or investment opportunity. Whether your priority is boating, fishing, or embracing the relaxed Florida Keys lifestyle, 321 Tollgate Shores offers a distinctive combination of convenience, functionality, and value with a niche setup.

321 Tollgate Shores Dr, Islamorada
$1,300,000
3 Beds ⋅ 2 Baths ⋅ 619311 MLS
Desirable Venetian Shores 3 bedroom / 2 bath home just steps to your boat slip! Enjoy a direct sight line view of your boat and surround yourself with peaceful water views from almost every window of this bright, open-concept residence on one of the neighborhood's premier streets. This home offers the truly rare treat of wrap-around views of coastal living with a wide panorama of the private community marina and direct view of your assigned boat slip, plus water views of the closed canal in back. Don't miss this opportunity to live in Islamorada's most desirable neighborhood and enjoy the best boating in the Keys! With just minutes from your boat slip to Florida Bay and easy ocean access through Snake Creek to the Atlantic Ocean, you can delight in fishing, diving, offshore sandbars and boating to more than a dozen nearby waterfront restaurants and bars. This stilt home, built on reinforced concrete pilings, has all the living space on one level upstairs including an open kitchen with newer appliances (2023), large pantry, great room with high ceilings and a sun porch. There are also three large bedrooms in a split plan all with ample closet space. This family home offers the security of a reinforced metal roof, outdoor cameras and an alarm system, and the front door and most of the windows have also been upgraded to impact glass. Downstairs are two carports with workshop, a central tackle/storage room, and a sizable back yard with a sunken outdoor kitchen area/patio for enjoying afternoon barbecues after a day on the water. The expansive front yard has low maintenance landscaping and offers lots of parking for family, friends and all your toys. Relax with your favorite beverage on your covered front porch for a perfect view of the famous Florida Keys sunsets over the marina every night. Marina includes power/water and allows a variety of boat lifts to suit your boat. Ready to enjoy the best Islamorada has to offer with your boat steps from your door? Call today!

113 San Juan Dr Unit & Boat Slip, Islamorada
$220,000
1 Beds ⋅ 1 Baths ⋅ 618855 MLS
Nice and quiet 1/1 located in the desirable Plantation Villas on Plantation Key. This is a upper corner unit with Tile throughout. Impact Cat 5 hurricane windows and newer AC. Tub shower combination in bath. Large walk-in closet in bedroom with lots of storage and ceiling fans throughout. Beautiful Yard area for outdoor enjoyment. This development has a pool, clubhouse and picnic area. Located near Founders Park with lots of activities and beautiful beach.

40 High Point Rd Unit 601, Islamorada
$1,050,000
3 Beds ⋅ 4 Baths ⋅ 617029 MLS
ACTIVE BUILDING AND DOCK PERMITS. BUILD RIGHT AWAY. Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. Imagine waking up to sunlit mornings, salty breezes, and the soft embrace of warm sand beneath your feet. Welcome to White Marlin Beach, where your vision of paradise comes to life. Vacant lots with active building permits are a rare find, and this one is ready for you to create your dream retreat. Picture a three-bedroom, four-bathroom island escape blending coastal charm with modern luxury. Two spacious, sunlit stories are designed for relaxation, complete with an elevator to ensure comfort and convenience. Expansive porches invite you to unwind, sip your morning coffee with bay views, feel the ocean breeze in your hair, and enjoy evenings under a canopy of stars. New construction offers more than a fresh start—it brings favorable insurance rates, a solid foundation, and the confidence of quality craftsmanship. This is your gateway to maritime bliss. The private homeowners' park features one of the few sandy beaches in the Keys, perfect for building sandcastles, watching sunsets, and creating cherished memories. This property offers convenient access to vibrant dining, boutique shopping, and an inspiring arts scene. It's more than just a property; it's an invitation to embrace the island lifestyle. Opportunities like this don't wait. Ready to turn your dream into reality? Dive into your future at White Marlin Beach—your tropical oasis is calling!

142 Gulfview Dr, Islamorada
$500,000
2 Beds ⋅ 2 Baths ⋅ 620524 MLS
This is the exceptional deal you've been waiting for! Opportunity knocks on this 2 story townhouse in Islamorada's gated bayfront community, Executive Bay Club. These spacious units are highly desired for their well laid out floor plan, perfect for full time residence, a vacation home or as a seasonal rental (30 day minimum) Amenities include a Bayfront sandy beach, newly renovated marina with first come first serve dockage, a newly renovated pool lined with cabana chickee huts and a gorgeous clubhouse. Tennis and pickleball courts, a 24 hour gated security guard and 2 pets are allowed per townhouse. This unit is mostly original inside. Perfect for those looking to transform a unit to their desired style and preference. Townhouse B6 is in a great location within the community with a tastefully done back patio, it is ready for back yard summer time BBQ's! The sale is subject to Monroe County Probate court approval. Don't hesitate to call for a showing. This is priced to sell and won't last long. Easy to show. Must have an appointment to get into the community. All information to be verified by buyers.

87200 Overseas Hwy Unit APT B 6, Islamorada
$1,280,000
6 Beds ⋅ 3 Baths ⋅ 620458 MLS
3 plex ( 3 separate units) in the heart of downtown Islamorada. A total of 6 bedrooms and 3 baths. Two of the units are remodeled. Walk to Shopping, Boutiques, Bars, Restaurants, World Wide Sportsman/Bas Pro Shops, Florida Keys Brewery. Or take your street legal golf cart. Currently fully rented on annual leases. Would make great 30 days rentals or really great employee housing. Do not miss this opportunity. Two separate electric meters and one water meter.

81160 Old Hwy, Islamorada
$1,275,000
3 Beds ⋅ 2 Baths ⋅ 620016 MLS
Ocean Harbour condo with Atlantic ocean views and a boat slip in Islamorada. 3 bedroom, 2 bathroom luxury condo offers expansive ocean views and comfortable living space. The thoughtfully redesigned floor plan enhances the primary suite layout, adds a third bedroom, updates both bathrooms, and expands the living area by enclosing the porch as additional interior living space; maximizing functionality, comfort, and guest accommodations. Features updated appliances, hurricane impact glass, boat slip #33 and one covered parking space. Elevated waterfront living within this premier gated community featuring beach areas, oceanfront clubhouse, swimming pool, spa, gym, pickleball and tennis courts, EV charging station, boat ramp, and boat trailer storage. The beach tiki is ideal for entertaining with a grill, ice maker, and TV. Pets allowed with restrictions. Enjoy boating, fishing, kayaking, paddle boarding, nearby restaurants, medical care, boutique shopping, and art galleries. Bring your boat and experience the best of Florida Keys waterfront living.

87851 Old Hwy Unit M42, Islamorada
$3,510,000
3 Beds ⋅ 3 Baths ⋅ 619454 MLS
Welcome to Casa Tranquila in the highly desirable Venetian Shores neighborhood of Islamorada, where boating convenience meets tropical serenity. With 105 feet of dockage just one home from Snake Creek, this property offers immediate access to both the bay and the ocean--perfect for effortless days on the water. A brick-pavered driveway leads to a welcoming foyer and interior staircase, guiding you to the light-filled main living level. Here, an open floor plan creates an inviting space for gathering. The well-appointed kitchen features stainless steel appliances and flows effortlessly into the dining and living areas, making entertaining both easy and enjoyable. Just off the dining space, a convenient dry bar provides the perfect spot for preparing cocktails and serving guests. Two sets of sliding glass doors extend the living area onto a spacious screened terrace--ideal for enjoying breezes and waterfront views. This level also offers two comfortable bedrooms, two full baths, and a dedicated laundry room for added convenience. The private third-floor primary suite is a true retreat, complete with an ensuite bath and an expansive open terrace overlooking the water--your own peaceful escape for sunrise coffee or evening relaxation. Surrounded by lush, mature landscaping--including ponytail palms, queen palms, ginger, and fishtail palms--the property feels like a secluded tropical oasis. The backyard is designed for both relaxation and entertaining, featuring a heated saltwater pool with spa and waterfall, a charming tiki hut with lighting and fan, and fruit-bearing key lime and mango trees that enhance the island ambiance. With its prime location, thoughtful layout, and beautifully curated indoor and outdoor spaces, this home captures the essence of the Islamorada lifestyle--elegant, inviting, and effortlessly connected to the water.

131 Bayview Isle Dr, Islamorada
$4,000,000
618904 MLS
Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with an active permit and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus another .24 acres of bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

75750 Overseas Hwy, Islamorada
$430,000
2 Beds ⋅ 2 Baths ⋅ 618199 MLS
🌊 Spectacular Direct Ocean Views! ✨ Islamorada's Best-Kept Secret! This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront balcony. Step outside and enjoy a refreshing swim in the oceanfront pool or take a dip directly in the crystal-clear Atlantic. Perfectly situated near Bud & Mary's Marina and just minutes from Islamorada's most beloved restaurants, this location captures the very best of island living. This property is truly a must-see--and it's priced to sell. Seller will consider all reasonable offers.

79901 Overseas Highway Unit 204, Islamorada
$2,350,000
3 Beds ⋅ 3 Baths ⋅ 618461 MLS
Located in the highly desirable Venetian Shores neighborhood in Islamorada, this canal front home offers 70 feet of dockage with a brand new concrete dock and seawall, making it an excellent opportunity for boating enthusiasts. Enjoy quick and convenient access to both the Atlantic Ocean and Florida Bay through Snake Creek, one of the most sought-after boating access points in the Florida Keys. This prime location allows for easy navigation whether heading offshore or exploring the backcountry. Situated on a 7,000 square foot lot, the property features a two-bedroom, two-bathroom layout upstairs, along with a one-bedroom, one-bathroom downstairs, offering additional flexibility for guests, extended family, or bonus space. The home has been freshly painted and is ready for immediate enjoyment, while also presenting an opportunity to update, expand, or build new in a neighborhood known for redevelopment and custom homes. For boaters, this property is ready to go--complete with a new concrete dock and seawall, ideal for accommodating a large vessel. A boat lift permit has already been applied for and approved by the Village of Islamorada, providing added value and convenience for the next owner. Venetian Shores is known for its wide canals, excellent water access, and close proximity to dining, marinas, and local amenities. Whether you're looking for a primary residence, vacation home, or future investment, this property offers strong potential in one of Islamorada's most desirable waterfront communities.

109 Milano Dr, Islamorada
$2,500,000
3 Beds ⋅ 2 Baths ⋅ 620603 MLS
Welcome to 154 Biscayne Boulevard in the heart of Islamorada. This beautifully maintained 3 bedroom, 2 bathroom concrete home is designed for those who want to enjoy life on the water. Located in the highly sought after Port Antigua neighborhood, this home offers the perfect balance of comfort, durability, and island living. Whether you are searching for a full time residence, a weekend retreat, or an investment opportunity in the Florida Keys, this is your chance to own a piece of paradise and experience everything Islamorada has to offer. Built for lasting peace of mind, the home features a concrete roof, full impact windows and doors, and an inviting open concept floor plan that seamlessly connects the kitchen, dining, and living areas. Natural light fills the space, creating a bright and welcoming atmosphere that is perfect for everyday living or entertaining family and friends. Step outside to the spacious screened balcony overlooking the canal, the perfect place to enjoy your morning coffee or unwind in the evening while taking in the tropical breeze. Downstairs, the covered outdoor living area offers exceptional space for entertaining, relaxing after a day on the water, or storing everything you need for the Florida Keys lifestyle. For boating enthusiasts, this property features a concrete dock with two boat lifts, and quick access to some of the best fishing and boating waters in the world. A large enclosed storage area provides plenty of room for fishing gear, paddleboards, diving equipment, and all of your essentials.

154 Biscayne Blvd, Islamorada
$1,490,000
3 Beds ⋅ 3 Baths ⋅ 620353 MLS
Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of newly decked dockage along the tranquil ''Sleepy Lagoon'', this exceptional property combines relaxed island living with effortless boating access to both the ocean and bay. The light-filled second floor features an open-concept living, dining, and kitchen area with soaring cathedral ceilings and new vinyl flooring throughout. The recently remodeled kitchen showcases new cabinetry, stainless steel appliances, and an inviting layout ideal for entertaining. Two bright bedrooms with laminate flooring are located on this level, including a spacious primary with en-suite bath. Step outside onto the expansive second-floor balcony and enjoy breathtaking lagoon views while watching manatees glide by and fish jump in the tranquil waters below. The first floor offers additional flexible living space with an open bedroom/living area and full bath, featuring sliding glass doors that lead directly to the tropical backyard, pool, and dock. Designed for comfort and convenience, this fully turnkey home includes well-maintained accordion shutters on all non-impact windows, generous storage space for water toys and gardening equipment, and a securely anchored storage shed. Outdoor living is truly exceptional. Relax beneath the airy chickee hut, cool off in the in-ground pool after a day on the water, or entertain family and friends with freshly grilled BBQ favorites in the private backyard oasis. Additional features include a JetDock, fish cleaning station, spacious outdoor shower, fenced backyard for pets, and ample parking for boats, trailers, RVs, and recreational equipment. Residents may enjoy access to a beautiful sandy beach within the subdivision through a voluntary HOA membership. The beach is a protected turtle nesting habitat.

140 Iroquois Dr, Islamorada
$3,250,000
4 Beds ⋅ 4 Baths ⋅ 618873 MLS
TURN KEY Canal-Front Islamorada Home with Pool, Dock & Private Beach Access Luxury canal-front home in Islamorada offering spacious living, refined coastal design, and exceptional outdoor amenities. This meticulously maintained residence features a flexible split floor plan with a main-level living area, wet bar, bedroom, and full bath overlooking the outdoor kitchen and resort-style pool. Upstairs includes 3 additional bedrooms, 2.5 baths, an open living area, pristine kitchen, and walk-in laundry room/office. The fenced backyard is designed for easy living with turf, low-maintenance landscaping, and privacy! Concrete dock with 20,000 lb boat lift and space for multiple boats. Owners also enjoy access to the private White Marlin homeowners beach and close proximity to area amenities. The perfect Florida Keys getaway with strong monthly rental income potential! A rare opportunity for turnkey waterfront living in the heart of Islamorada.

145 Venetian Dr, Islamorada
$2,425,000
3 Beds ⋅ 4 Baths ⋅ 617758 MLS
Welcome to Coral Cove Residence 3, perfectly positioned in the heart of Islamorada. This turn-key, thoughtfully designed three-bedroom, three-and-a-half-bath residence was built in 2020 and features quality construction and well-appointed appliances throughout. A beautiful open floor plan allows natural light to flow effortlessly, creating an inviting coastal living environment. Located within Coral Cove, a private bayfront community of just eight residences, this home offers both exclusivity and convenience. The residence boasts its own private pool, ideal for relaxing or entertaining, while the community also features a stunning bayfront pool with sweeping sunset views over the water. An assigned boat slip in the community marina provides easy access to the bay and ocean beyond, perfect for boating, fishing, and enjoying life on the water. Weekly rentals are permitted, making this an excellent opportunity for a vacation home that can offset carrying costs, an income-producing investment, or a combination of both. The intimate, well-maintained community offers a peaceful retreat while remaining within walking distance to Islamorada's dining, art galleries, boutiques, and local attractions. A rare opportunity to own a turn-key property in one of downtown Islamorada's most desirable bayfront communities.

81906 Overseas Hwy Unit 3, Islamorada
$670,000
2 Beds ⋅ 2 Baths ⋅ 620084 MLS
Spectacular Top-Floor Views and Expansive Covered Porch! Experience the ultimate Florida Keys backdrop from this 5th-floor condo at The Palms of Islamorada. Being on the top floor means you get the absolute best vantage point--boasting a huge covered porch designed for true outdoor living, with breathtaking, unobstructed ocean views and a direct line of sight to Alligator Lighthouse. Offered completely furnished and in excellent condition, the highly desirable split floor plan ensures maximum privacy. The generous primary suite is a true highlight, offering great space and its own beautiful ocean views. Guests will also love the comfortable second bedroom featuring its own private ensuite bath. The bright interior includes a sleek, modern European-style kitchen and the ultimate convenience of an in-unit washer and dryer. The Palms is a secure, gated complex in downtown Islamorada offering fantastic amenities: a resort-style pool, a large oceanfront tiki hut (plus 6 smaller satellite tikis), a community room, separate men's and women's gyms, and assigned covered parking. Best of all, you are within easy walking distance to premier local dining favorites like Lazy Days and Papa Joe's. This is one you definitely don't want to miss out on--call today to schedule your private showing!

79901 Overseas Highway Unit 511, Islamorada
$900,000
2 Beds ⋅ 3 Baths ⋅ 620172 MLS
Wake up to sparkling Atlantic Ocean views and embrace the relaxed elegance of Islamorada living. This fully remodeled 2-bedroom, 2.5-bath townhome at the highly sought-after Port of Call community offers an exceptional blend of luxury, comfort, and investment potential. Designed for effortless coastal living, the residence features an ocean-view primary suite with a private balcony, an expansive rooftop deck, a beautifully updated kitchen, sunlit dining space, open-concept living area, and a screened terrace perfect for enjoying the island breeze. One of the property's most valuable and increasingly rare features is its ability to accommodate weekly vacation rentals. Port of Call is a boutique 10-residence community that offers the rare advantage of weekly vacation rentals, making this property an exceptional opportunity for both personal enjoyment and investment income. Whether you're seeking a personal island retreat, a high-performing vacation rental, or the ideal combination of both, this flexibility creates tremendous value and income potential. Residents and guests enjoy an oceanfront swimming pool, sandy beach, boat slip, covered parking, private storage, and the convenience of an in-unit laundry room and pantry. With luxury updates, ocean views, boating access, resort-style amenities, and highly desirable weekly rental capability, this turnkey Islamorada property represents a rare opportunity in one of the Florida Keys' most sought-after waterfront communities.

141 Aregood Ln Unit # 3B (C1), Islamorada
$950,000
2 Beds ⋅ 3 Baths ⋅ 616461 MLS
Direct Oceanfront Townhome with Private Boat Slip & Rooftop Deck in the Heart of the Keys! Experience panoramic ocean views, direct boating access, and the ultimate coastal lifestyle from this beautifully updated 2-bedroom, 2.5-bath townhouse in Plantation Key. Perched directly on the oceanfront, this residence includes a private boat slip and a rooftop deck offering unobstructed sunrise-to-moonrise vistas. Inside, an open-concept layout welcomes you with abundant natural light and stunning water views from both the main living areas and the primary suite. The kitchen and living room flow effortlessly to a private terrace perfect for morning coffee, al fresco dining, or evening cocktails by the sea. Upstairs, the spacious bedrooms offer comfortable retreats with generous storage, while the rooftop deck serves as your personal oasis in the sky ideal for sunbathing, entertaining, or simply soaking in the views. This property is eligible for a weekly vacation rental license, giving you the option to generate income when you're not enjoying it yourself. Located at MM 88 just off the Old Highway in Islamorada, you're minutes from world-class fishing, diving, dining, and boutique shopping yet tucked away in your own peaceful waterfront retreat. Whether you're searching for a full-time residence, weekend getaway, or investment property, this home delivers the best of the Florida Keys lifestyle. Seller carries wind/flood and hazard insurances.

143 Aregood Ln Unit D1, Islamorada