Refine Search
Map
Sort by
$2,700,000
3 Beds ⋅ 4 Baths ⋅ 619060 MLS
Paradise found--experience the best of Florida Keys waterfront living in this beautifully updated, lushly landscaped lakefront home offering exceptional privacy and tranquil water views. Boaters will appreciate easy access from the lake to the bay and direct ocean access through nearby Tavernier Creek. Inside, soaring ceilings and impact-rated windows and doors fill the home with natural light, creating a bright, open atmosphere. The spacious great room flows onto an expansive waterfront deck just steps from the lake--perfect for relaxing or entertaining. The chef's kitchen features maple cabinetry, granite countertops, Thermador refrigerator and oven, Bosch dishwasher, commercial ice maker with filtration, and a GE Profile wine cooler. The oversized island showcases etched glass panels depicting an underwater seascape, illuminated with remote-controlled LED lighting. The main level includes two guest bedrooms and two updated bathrooms, including one ensuite. A custom tamarind wood serpentine staircase leads to the private third-floor primary suite with beautiful water views. The primary bath offers a whirlpool tub, walk-in steam shower, and skylights. Additional features include an oversized two-car garage with 12-foot ceilings and ample storage, plus a large ground-level storage area currently configured as a guest apartment with a permitted full bath. Outdoors, enjoy a secluded heated pool surrounded by tropical landscaping and a 60-foot concrete dock finished with durable IPE (Brazilian walnut). With no neighbors behind, on one side, or across the water, this property offers rare privacy and quick access to both Florida Bay and the Atlantic Ocean--capturing the essence of relaxed Keys living.

151 Lake Rd, Islamorada
$2,050,000
3 Beds ⋅ 3 Baths ⋅ 619722 MLS
Impeccably Designed Islamorada Waterfront Retreat! Welcome to your private island oasis! This stunning 3BR/3BA solid concrete waterfront home on Lower Matecumbe Key combines comfort and style with the ultimate Florida Keys lifestyle. Beautifully updated, this turnkey residence is move-in ready for immediate enjoyment. The inviting floor plan features a well-appointed kitchen with quartz countertops and stainless appliances with open living concept, a spacious primary en suite, and a versatile downstairs guest suite with bedroom and living area--perfect for hosting family and friends or creating your own private retreat. Situated on a canal with immediate ocean access, the property includes 75 feet of concrete dockage with boat lift for the boating enthusiast. The resort-style backyard is designed for endless entertaining with a heated pool, expansive sun deck, screened porch, and multiple indoor-outdoor living spaces--your personal vacation paradise. Located just minutes from Islamorada's acclaimed restaurants, local marinas, world-class fishing, and island attractions, this exceptional home offers the perfect balance of waterfront tranquility and vibrant Keys living. Whether you're lounging poolside, departing for a day on the water, or gathering with loved ones, every day feels like a getaway. Low Flood Insurance currently $2075 available to transfer.

137 Cortez Dr, Islamorada
$275,000
2 Beds ⋅ 2 Baths ⋅ 620217 MLS
ISLAMORADA OCEANFRONT LIVING! Located in the highly desirable Plantation by the Sea community, this rare opportunity allows you to create your own island retreat. Currently gutted and ready for renovation, this 2-bedroom, 1.5-bathroom townhome offers a blank canvas to design and finish to your personal taste within one of Islamorada's premier gated oceanfront communities. The floor plan features a spacious living area that opens to a screened balcony, providing the perfect setting to enjoy the tropical breeze and outdoor living. Upstairs, you'll find two bedrooms and a full bathroom, while a convenient half bath is located on the main level. Plantation by the Sea offers an impressive collection of resort-style amenities, including an oceanfront swimming pool with expansive sundeck, clubhouse with full kitchen, fitness center overlooking the Atlantic Ocean, sauna, kayak and paddleboard storage, fishing pier and fish-cleaning station, BBQ area, and guest parking. Ideally located near Founders Park, residents enjoy access to a wide range of recreational amenities, including an Olympic-size swimming pool, sandy beach, marina, tennis and pickleball courts, ball fields, playgrounds, dog park, and amphitheater. If you are looking for an investment property, this is your chance to customize a townhome in one of Islamorada's most sought-after oceanfront communities and enjoy the unparalleled Florida Keys lifestyle.

87455 Old Hwy Unit 235, Islamorada
$580,000
4 Beds ⋅ 2 Baths ⋅ 618000 MLS
ANCHOR IN PARADISE- 4 BEDROOM, 2 BATH IN ISLAMORADA- EXECUTIVE BAY CLUB, THIS IMMACULATE CONDO WILL CONVEY FULLY FURNISHED ALL COMPLETELY RENOVATED & UPDATED W/HURRICANE IMPACT WINDOWS, SLIDING GLASS DOORS, WASHER/DRYER DOWNSTAIRS. PERFECT RETREAT W/SANDY BEACH, POOL, TENNIS COURTS, CLUBHOUSE FOR GATHERINGS, DOCKAGE AVAILABLE, BRAND NEW ONSITE MARINA, WALKING DISTANCE TO 'FOUNDER'S PARK' & FINE DINING!

87200 Overseas Hwy Unit M2, Islamorada
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 619919 MLS
Experience luxury island living in the heart of Islamorada at Bay Harbour, one of the Florida Keys' most desirable waterfront communities. Unit 204 offers breathtaking ocean and lagoon water views and an exceptional blend of elegance, comfort, and investment potential. This spacious 3-bedroom, 2.5-bath residence has been fully remodeled and impeccably maintained, featuring beautiful high-end finishes throughout and a stunning designer kitchen perfect for entertaining. The oversized primary suite offers a true retreat with a spacious bedroom and a beautifully appointed spa-inspired primary bathroom. Offered 100% turnkey, this residence is ready for immediate enjoyment or income production, with the flexibility of 7-day rentals and a strong established, impressive rental history. Boaters will appreciate the assigned boat slip and private 20,000-pound boat lift, providing easy access to some of the best fishing and boating in the Florida Keys. Bay Harbour is known for its upscale amenities, prime location, and relaxed coastal lifestyle, making this an exceptional opportunity for both personal enjoyment and investment.

101 Gulfview Dr Unit 204 & 30' boat slip with lift, Islamorada
$825,000
2 Beds ⋅ 2 Baths ⋅ 617666 MLS
Beacon Reef is calling your name! This beautifully designed 2-bedroom, 2-bath residence spans approximately 1,275 square feet of light-filled living space. Enjoy the charming balcony with a steady breeze and lovely ocean views from the primary and balcony. With a spacious primary suite complete with an en-suite bath and charming sitting area and an oversized guest suite offering flexibility and comfort, this unit offers generous space for all! The open-concept living area seamlessly connects to a well-appointed kitchen featuring ample cabinetry and an abundance of counter space and a breakfast bar, perfect for entertaining. Additional highlights include impact windows, designated laundry space, a new air conditioner and refrigerator in 2025, a new stackable washer/dryer, and a large balcony designed for indoor-outdoor living. This unit is also ADA accessible and includes a larger parking space with ADA parking to accomodate a van. Residents of Beacon Reef enjoy gated, resort-style amenities including an oceanfront lovely pool, fitness center with water views, and first come/first serve boat slips accommodating vessels up to 35 feet. The property also offers a fishing pier, tiki hut, BBQ area, and lush tropical landscaping. Just minutes from world-class fishing, diving, dining, and art galleries and within walking distance to Publix and several restaurants, Unit 301 offers the perfect balance of tranquility and access to the best of the Florida Keys. Whether as a primary residence, weekend escape, or seasonal retreat, this exceptional residence is your invitation to live the true Islamorada lifestyle!

83201 Old Hwy Unit 301, Islamorada
$225,000
1 Beds ⋅ 1 Baths ⋅ 619702 MLS
The perfect spot to call home. Plantation Villas unit G101 is a ground-level end unit in the quiet back corner of the community. This one-bedroom, one-bath home has been updated this past year with a new kitchen featuring all new appliances, Quartz stone countertops, under-cabinet LED lighting, and LED ceiling lights. The bathroom features a tile shower and a built-in Bluetooth music speaker. When you are away from home, an app-controlled thermostat and smoke detector make monitoring things a breeze. Plantation Villas features assigned parking and guest parking. A community pool and clubhouse for your enjoyment. And the location within the Village of Islamorada allows the owner access to the benefits of Founders Park, with sandy beach, swimming pools, tennis, pickleball, walking paths, sports fields, and daily fun activities.FYI - Plantation Villas has recently renamed Building G to Building #2 and the unit to #210. The HOA dues include the building insurance.

40 High Point Rd Unit G101, Islamorada
$350,000
619014 MLS
This is for the sale of 1 (one) Waterfront Transferable Development Right (TDR aka TBR) for use in The Village only. Buyer to pay ALL closing costs associated with the transaction and the transfer fee to The Village. The sale DOES NOT include any real property. Buyer must have an eligible property to which the rights can be transferred.

Waterfront Waterfront Tdr, Islamorada
$1,230,000
3 Beds ⋅ 3 Baths ⋅ 619607 MLS
EXCEPTIONAL FLORIDA KEYS OPPORTUNITY! Lowest priced home in Indian Waterways. This is it!! Your Florida Key Oasis! Quintessentially Key-z, this home has it all ... and then some. Located in the very desirable Indian Waterways Community of Tavernier on Plantation Key. Stylish Two Bedroom / Two Bath Main house plus a super inviting 1/1 guest house that your guests will never want to leave! Relax and entertain in the canal front Tiki hut as you enjoy tropical breezes. Cool off on the Custom Outdoor Shower after you dock your boat. Composite Dock ensures longtime enjoyment. And an Outstanding Double-sided Garage + storage room for a major Bonus!!! Also features a personal boat ramp, that is perfect for launching/storing a flats boat, skiff, Jet Ski, or Kayak. Both the Main House and Guest House boast gorgeous, exposed wood-beamed ceilings that are gleaming works of Art. Large Bedrooms and stylishly updated Bathrooms. Great privacy with a nature preserve across the Street. CBS Construction and a White Picket Fence add to the irresistible charm of this property that personifies 'Tropical Chic.' Super Close proximity to Tavernier Creek via the famous 'Toilet Set Cut'. World Class deep water, reef, and backcountry fishing are mere minutes away, as are incredible diving, snorkeling, Lobstering, and sandbar-ing! Come Grab a slice of Florida Keys Living!

157 Caloosa St, Islamorada
$400,000
619916 MLS
This 10,000 sq ft, double sized, vacant residential parcel offers a fantastic opportunity to build your Florida Keys dream home with the convenience of being within walking distance to Publix, local restaurants, and everyday essentials. Ideally suited for enjoying the laid-back Islamorada lifestyle, the property is just moments from blue-green waters, boating, dining, and outdoor recreation, offering a rare blend of accessibility and island living. Call list agent for details on development rights.

104 S Hammock Rd, Islamorada
$3,000,000
3 Beds ⋅ 2 Baths ⋅ 620319 MLS
Tucked away on a quiet cul-de-sac in the highly sought-after Port Antigua neighborhood, this beautifully updated waterfront home is designed for effortless Florida Keys living. With an impressive 145 feet of dockage, a 15,000 pound boat lift, sparkling pool, and quick access to the water, it's the perfect setting for boating, fishing, and entertaining. Inside, vaulted ceilings and an open floor plan create a bright, airy atmosphere, while two expansive 10 foot sliding glass doors seamlessly connect the living space to the waterfront terrace overlooking the pool and canal. The stunning kitchen serves as the heart of the home, featuring stainless steel appliances, a waterfall-edge island with seating for five, and plenty of space for gathering with family and friends. A separate laundry room and pantry add convenience and functionality. The spacious primary suite enjoys peaceful water views and features an en-suite bath with a double vanity and separate shower. Two generously sized guest bedrooms and a well-appointed guest bath provide comfortable accommodations for family and friends. Downstairs, a versatile bonus room offers additional space for a home office, gym, hobby room, or overflow guests. Impact windows and doors, along with a durable metal roof, provide peace of mind, allowing you to focus on enjoying the laid-back waterfront lifestyle that makes the Keys so special. Whether you're heading out for a day on the water, relaxing poolside, or enjoying sunset breezes from the terrace, this exceptional Port Antigua property is ready to become your island retreat.

125 Porto Vista Ct, Islamorada
$3,800,000
4 Beds ⋅ 5 Baths ⋅ 619832 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for either full time residency or effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. *Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 16, Islamorada
$396,000
5 Beds ⋅ 4 Baths ⋅ 617023 MLS
New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Tucked within the coveted White Marlin Beach enclave, this canal-front retreat captures the essence of refined Florida Keys living. Framed by swaying palms and a gracious front entry, the 5-bedroom, 3.5-bathroom residence offers a seamless blend of comfort and coastal elegance. The open-concept main level is bathed in natural light, with soaring ceilings, oversized windows, and glass doors that connect the living area to the private pool and tranquil canal beyond. A bright, gourmet kitchen anchors the space with JennAir appliances, dual sinks, and generous cabinetry—ideal for effortless entertaining. A bay window in the dining area frames serene views of the pool. The main-floor primary suite features a custom walk-in closet and direct access to the patio and pool. Upstairs, a second spacious bedroom offers a large closet and a Jack-and-Jill bath shared with an adjoining guest room. Two additional bedrooms provide ample accommodations for family and guests. The home comes fully furnished and professionally decorated.

134 Nautilus Dr, Islamorada
$650,000
2 Beds ⋅ 3 Baths ⋅ 618206 MLS
Welcome to Islamorada living at its finest in one of the most sought-after bayfront communities. This beautifully appointed townhome features 2 bedrooms plus a large loft, 2.5 baths and offers an effortless blend of comfort, style, and coastal charm. Thoughtfully designed to comfortably sleep seven or more, the versatile layout is ideal for hosting family and friends or maximizing rental potential. Inside, the remodeled kitchen shines with quartz countertops, stainless appliances and generous workspaces. Updated tile flooring flows throughout the living areas, while a custom wood-and-steel staircase adds architectural interest and easy access to the second floor bedrooms. Upstairs, you'll find a serene primary suite with private bath, along with a comfortable guest bedroom and full guest bath. The loft, accessed from the hallway, has been thoughtfully finished to provide added privacy from the primary bedroom, making it an ideal bonus sleeping area, home office, or peaceful retreat. Natural light fills the home, creating a bright, welcoming atmosphere that reflects the relaxed Keys lifestyle and impact-rated windows and doors throughout offer peace of mind. Step outside to the expansive patio surrounded by lush garden views--perfect for grilling and chilling, morning coffee, evening cocktails, or simply unwinding after a day on the water. Tucked within a quiet, central location of the community, this residence offers a peaceful retreat while remaining just steps from world-class amenities. Executive Bay Club is renowned for its resort-style living, featuring a bayfront beach area perfect for watching unforgettable sunsets, dockage for boating enthusiasts, a new heated pool, tennis and pickleball courts, clubhouse, tiki huts, kayak storage and 24/7 staffed gated entry. Whether you're seeking a full-time home, a vacation escape, or an investment, this townhome delivers the best of Islamorada, where every day feels like a getaway. A true Florida Keys gem!

87200 Overseas Hwy Unit O8, Islamorada
$405,000
2 Beds ⋅ 2 Baths ⋅ 618126 MLS
LIVE THE DREAM IN THIS OCEANFRONT BUILDING ON MILLIONAIRES' ROW IN THE BEAUTIFUL FLORIDA KEYS! LARGER THAN OTHER UNITS UNDER AIR AT 1100 SQ FT. TURN KEY STUNNING AND PARTIALLY REMODELED, FRESHLY PAINTED, FURNISHED SINGLE STORY 2 BEDROOM 2 FULL BATH CONDO, MOVE IN READY! OR START MAKING MONEY AS A VACATION RENTAL RIGHT AWAY! $10,000.00 WORTH OF VACATION RENTAL BOOKINGS AND CONSULTING ARE INCLUDED WITH THIS CONDO SALE! CHEF'S KITCHEN, HUGE PANTRY, BOSCH WASHER/DRYER INCLUDED WHICH IS NOT FOUND IN MOST OTHER UNITS. SPLIT BEDROOM PLAN, WOOD CABINETS IN KITCHEN AS WELL AS NEW REFRIGERATOR AND DISHWASHER. NEW WATER HEATER AND MAIN BEDROOM HAS LARGE WALK IN CLOSET. ADDITIONAL STORAGE UNIT ON MAIN FLOOR. 1 DESIGNATED COVERED PARKING SPACE & PLENTY OF GUEST PARKING, HEATED POOL, 400 FOOT DOCK/FISHING PIER ALLOWS YOU TO TIE UP YOUR BOAT FOR LOADING AND UNLOADING FOR A WONDERFUL DAY ON THE WATER, COMMUNITY ROOM AVAILABLE WITH KITCHEN TO GATHER WITH THE RESIDENTS FOR A PARTY OR RENT OUT THE SPACE FOR YOUR OWN PRIVATE EVENT, FITNESS AREA, SAUNA, AND SO MUCH MORE! WALK TO RESTAURANTS, SHOPPING, AND FOUNDER'S PARK CLOSE BY AS WELL AS THEATRE OF THE SEA.

87465 Old Hwy Unit 102, Islamorada
$3,003,000
4 Beds ⋅ 3 Baths ⋅ 612438 MLS
The Ospreys are back! Welcome to The Osprey's Nest; your perch by the Ocean in one of Islamorada's most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20' dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story primary suite and beachside pool with heater and chiller for those hot summer days. True island living is here on Sunset Drive. Listing includes canal parcel with dock across the street RE#00389220-000100

133 Sunset Dr, Islamorada
$7,600,000
4 Beds ⋅ 5 Baths ⋅ 619928 MLS
Discover paradise in Islamorada, with beautiful ocean views, protected canal dockage, and resort-style amenities that you'll never want to leave! Blending luxury living with the Florida Keys lifestyle, this home is designed with both entertaining and relaxation in mind. You'll find modern touches throughout this fully-furnished 4 bed, 5 bath home with an abundance of natural light enhancing it's coastal charm. The main level showcases ocean views from the large kitchen, living and dining areas, a French door sunroom and a massive elevated patio for seamless indoor/outdoor entertaining. Head downstairs and bring your resort experience to life. Relax under the poolside beach cabana, complete with an outdoor kitchen and furnished interior bonus room with a full bath connected by interior stairs or elevator. Sunbathe on your sandy beach complemented by a well-manicured backyard with privacy landscaping, mangroves, palm trees and a turf lawn. Take a dip in the resort-style pool/spa, play a little putt-putt golf, or use the access steps to the canal and explore the oceanside bonefish flat. Located in the heart of the sportfishing capital of the world, this home has the avid fishermen and watersport enthusiasts covered. With 200' of waterfrontage and 90' of dockage, safely secure your boats on the 40,000# or 15,000# lifts in the deep protected canal. Within minutes you could head offshore chasing big game fish or run bayside to fish the backcountry or explore the Everglades park. Just steps away from your dock is a dedicated tackle room complete with a chest freezer, commercial ice machine, rigging bench, rod racks and tool storage. Accompanied by an oversized 2 car garage, you'll have plenty of room to store all your toys and cars. Concrete construction, newer Interlock Aluminum Slate Roofing and equipped with impact windows & doors, this home was built to withstand anything. Start living your dream today in this true Florida Keys retreat on beautiful Lower Matecumbe.

91 Iroquois Dr, Islamorada
$600,000
3 Beds ⋅ 2 Baths ⋅ 615921 MLS
Island Life in the Heart of Islamorada, a ground-level, 3 bed, 2 bath home with all the charm and comfort you need to enjoy life in the Keys. Solid CBS construction with Bahama shutters, central air, and an updated kitchen ready for entertaining. The yard is fully fenced plus there's a large bonus shed out back. Walking distance to Publix, restaurants, and all the best local spots. Easy, laid-back living in one of the best neighborhoods in Islamorada. Brand new Roof.

130 N Hammock Rd, Islamorada
$1,260,000
4 Beds ⋅ 2 Baths ⋅ 619672 MLS
Welcome to 310 North Drive, located in the gated community of Plantation Lake Estates. This solid concrete 4-bedroom, 2-bath home offers 1,975 sq ft of living space and sits on a rare 16,000 sq ft double lot with no neighbors on three sides, providing exceptional privacy. The home features recently renovated kitchen and bathrooms, a spacious wraparound porch, and an oversized 1,500+ sq ft garage/workshop. The seller is installing all impact windows and doors prior to closing, adding significant value and peace of mind. Enjoy access to the neighborhood's newly updated homeowners park, complete with a boat ramp and 72-hour dockage. Conveniently located directly across from Founders Park, offering beaches, a marina, pool, and pickleball courts. A rare opportunity combining concrete construction, privacy, boating access, and a prime location in one of Islamorada's most desirable gated communities.

310 North Dr, Islamorada
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 616594 MLS
Seller will consider seller financing. Florida Keys waterfront home, offered fully furnished, no homeowners association, 1,786 SqFt living area (larger than tax roll) fully renovated 3 bedroom, 3 bath waterfront property situated in Lower Matecumbe Key with 7,500 SQ FT lot. New seawall was completed & elevated in 2021. Boaters paradise w/75FT of dockage, under 5 minute ride to open ocean + easy access to bay as well, plenty of space to install a boat lift. There is also a private neighborhood concrete boat ramp that can be used. Canal depth is estimated 10-12 FT. Unique layout offers 2 bedrooms & 2 baths on the second floor with full kitchen & spacious living room area, washer & dryer. First floor offers 1 bedroom & 1 bath, washer & dryer, full kitchen (separate living units). New roof/hurricane impact windows. Easy storage space. Ample parking.

126 Columbus Dr, Islamorada
$900,000
3 Beds ⋅ 2 Baths ⋅ 617056 MLS
3-bedroom, 2-bath pool home brings vacation vibes! Custom built with thoughtful details, this home features updated vinyl flooring (2023), open eat-in kitchen (new appliances in 2021), and updated bathrooms that feel fresh, bright, and modern. The vaulted ceilings and natural light create a breezy, island-style atmosphere throughout. A pool with a new pump installed in 2024, a screened-in porch perfect for barbecues and morning coffee, and a fully fenced yard on a spacious 7,700 sq ft lot. The community boat ramp just down the street makes getting on the water a breeze, whether you're heading to the reef or cruising the bay. Located in the desirable Treasure Harbor neighborhood of Plantation Key, you're close to everything you love about the Keys — fishing, boating, restaurants, and A-rated schools!

223 Treasure Harbor Dr, Islamorada
$395,000
1 Beds ⋅ 2 Baths ⋅ 619718 MLS
The Palms of Islamorada is one of Islamorada's true sweet spots! Enjoy the oceanfront pool with nearby steps leading directly into the water where you can take a refreshing dip while soaking in panoramic open ocean views. This spacious one-bedroom residence features a large primary bedroom and bathroom with a dressing area, plus an additional half bath for guests. Recent updates include newer appliances, water heater, and A/C for added comfort and peace of mind. Fresh interior paint and motorized blinds throughout plus impact doors and windows as well. Ideally located near Bud N' Mary's Marina and some of Islamorada's most celebrated restaurants, this property offers the perfect blend of relaxation, convenience, and the Florida Keys lifestyle.

79901 Overseas Highway Unit 320, Islamorada
$5,325,000
4 Beds ⋅ 4 Baths ⋅ 617285 MLS
Discover Serenity Cove: Where Privacy Meets the Ease of Keys Living Serenity Cove is a distinctive waterfront estate that offers an exceptional blend of privacy, space, and comfort along the calm waters of Florida Bay. Set on nearly 1.75 acres stretching from the main highway to the bay, this custom designed property invites you to enjoy the easy, relaxed lifestyle that has made the Florida Keys famous. From first light to sunset, Serenity Cove captures the spirit of the Keys. Wake up to water views, prepare your favorite meals in a chef inspired kitchen, and spend days boating, fishing, or swimming directly from your own dock. Evenings can be enjoyed watching beautiful sunsets on the private beach watching the sky change colors over the bay. This property is ideal for those who appreciate a quiet setting and an easy flow between indoor comfort and outdoor adventure. Its thoughtful design and quality finishes reflect craftsmanship and care, while the expansive grounds provide room to relax, gather, or simply take in the natural beauty around you. Convenient access to Islamorada's dining, shopping, and services completes the picture—making Serenity Cove not just a house, but a lifestyle destination in the Florida Keys.

75560 Overseas Hwy, Islamorada
$940,000
2 Beds ⋅ 2 Baths ⋅ 616998 MLS
Welcome to Ocean Harbour Condominiums, one of Islamorada's most sought-after addresses where tropical luxury meets Keys serenity. Built in 1989 and meticulously maintained, this gated oceanfront community is a true hidden gem boasting lush, resort-style grounds with hundreds of swaying palms and panoramic views that stretch endlessly across the caribbean blue Atlantic ocean. This 2-bedroom, 2-bath condominium offers an immaculate, light-filled interior — the perfect clean slate for your own personal design vision. Featuring upgraded hurricane-impact windows and doors, the residence invites gentle sea breezes and showcases tranquil ocean views from sunrise through sunset. Enjoy world-class amenities including a stunning free-form oceanfront pool and jacuzzi, tennis and pickleball courts, a spacious clubhouse with full gym, social area, and TV lounge, plus two TIKI huts with community BBQ areas ideal for gatherings under the stars. The property also offers a boat ramp, assigned covered parking for each unit, trailer storage, and available boat slips for daily or long-term use. Whether you're seeking a permanent island retreat, a vacation getaway, or an income-producing property with a proven rental clientele, Ocean Harbour delivers the ultimate in Florida Keys living — beauty, convenience, and that peaceful ''toes-in-the-sand'' lifestyle you've been dreaming of.

87851 Old Hwy Unit M32, Islamorada
$1,065,000
2 Beds ⋅ 2 Baths ⋅ 617512 MLS
Resort-style living at Ocean Harbour. 2BR/2BA oceanfront condo with sweeping Atlantic Ocean views, new kitchen appliances, impact windows/doors and a 6,000-lb boat lift. Boat slip #36 is currently leased from the Association for $100 per month. Boat ramp, trailer storage, and covered parking space included. Enjoy the luxury island lifestyle on 12 gated acres with an oceanfront pool, beach areas, clubhouse, gym, pickleball/tennis, tiki with BBQ, EV charging station, impeccably maintained tropical grounds. Prime Plantation Key location at MM 87.5, close to restaurants, shops, health care, and galleries. The best of Islamorada waterfront living awaits—this Ocean Harbour condo is refreshed and ready for its new owner.

87851 Old Hwy Unit M24, Islamorada
$775,000
2 Beds ⋅ 2 Baths ⋅ 618074 MLS
Ground-level living in the heart of Islamorada! Situated on an oversized parcel, this beautifully completely remodeled 2-bedroom, 2-bath home offers comfort and an unbeatable location. This FULLY FURNISHED tastefully updated interior includes porcelain tile throughout the home including showers, quartz countertops and brand new LG appliances and offers an open living area and flows seamlessly to a large screened porch--perfect for relaxing or entertaining while overlooking the expansive backyard and enjoy the attached spacious storage room. Weekly Rentals Allowed once the property meets the required assessed value. Zoned Village Center (VC), the property provides exceptional potential with a wide range of mixed-use and commercial options, making it ideal as a primary residence, investment, or live/work opportunity. Enjoy a superior central location with walking distance to neighborhood beach access, local breweries, shopping, and some of Islamorada's best dining. A rare opportunity to own a versatile property in one of the Keys' most desirable areas.

82207 Old Hwy, Islamorada
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 617822 MLS
VA Assumable! Experience refined waterfront living in the Florida Keys, where luxury meets effortless access to world-class boating and fishing. This exceptional canal-front residence is thoughtfully designed for discerning buyers who value privacy, convenience, and a true connection to the water. A private dock with newly added 15,000 lb boat lift provides seamless access to open water, allowing you to leave your backyard and reach premier fishing grounds in minutes. A utility elevator lift enhances everyday comfort, making it easy to move gear, provisions, and luggage between levels with ease. Outdoor living is elevated for both entertaining and function. A custom storage shed equipped with an ice machine and two deep freezers caters perfectly to avid anglers and boating enthusiasts, offering an ideal setup for bait, ice, and fresh catch storage—an uncommon and highly desirable feature in the Keys. Inside, the home offers a bright, coastal interior that complements the surrounding water views, creating a calm and inviting retreat. Designed for both full-time living and elegant escapes, the residence balances relaxed island style with upscale practicality. Whether hosting sunset gatherings, heading offshore at first light, or enjoying quiet evenings by the water, this property delivers a lifestyle defined by ease, sophistication, and the unparalleled beauty of the Florida Keys. An exceptional opportunity for those seeking a premier waterfront home that supports both luxury living and an active boating lifestyle.

439 Palm Drive Dr, Islamorada
$4,250,000
6 Beds ⋅ 5 Baths ⋅ 617415 MLS
Exquisite Tri-Level Waterfront Estate in Islamorada! Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence offers an open-concept floor plan with soaring ceilings, a fireplace and a grand living area. Enjoy seamless indoor-outdoor living with an expansive wraparound veranda, perfect for soaking in the breeze and relaxing water views. The beautifully landscaped 10,000sqft lot provides privacy and tranquility, while the salt swimming pool offers the ultimate relaxation. For boating enthusiasts, this property is a dream come true! Featuring 100' of deep-water concrete dockage equipped with a 20,000lb catamaran width elevator boat lift and a 5500lb set of davits you will enjoy immediate access to both the Atlantic Ocean and Florida Bay for excellent offshore and backcountry fishing. A two-car garage with a new A/C unit, plus additional covered carport parking, ensures ample space for vehicles and storage along with a beautifully paved driveway. Come experience the best of the Florida Keys lifestyle in this exceptional waterfront retreat! Updates.... 1. NEW 2-car Air Conditioning Split with 10-year warranty 2. New Dock and Stair Brick Pavers 3. New third-floor Impact Windows 4. Two New third-floor Impact French Doors 5. Two New third-floor electric Rolladen Hurricane Shutters 6. Swimming poll resurfacing with new glass edge surround 7. Dock has a 220-volt pedestal to service dock-side marine electric needs

153 Stromboli Dr, Islamorada
$350,000
2 Beds ⋅ 2 Baths ⋅ 617156 MLS
Experience the best of Keys living in this beautifully maintained townhouse-style condo at Plantation by the Sea. The open floor plan features a bright and airy living area, a convenient half bath, and a screened terrace. Upstairs, you'll find two comfortable bedrooms and a full bath, each with access to its own private screened terrace. This residence includes covered parking, plenty of guest parking, and an assigned storage locker for your gear. The community offers resort-style amenities including an oceanfront pool with ample sundeck space, an air-conditioned clubhouse with a full kitchen, pool table, ping pong table and plenty of seating for gatherings. Stay active in the air-conditioned gym with stunning ocean views, or unwind outdoors with BBQ grills, kayak and paddleboard racks, and a fishing pier featuring composite decking, a fish cleaning station, and seating to take in the breathtaking ocean vistas. Enjoy maintenance-free living in this sought-after oceanfront community — perfect as a primary home, vacation retreat, or investment property.

87455 Old Hwy Unit 240, Islamorada
$1,800,000
4 Baths ⋅ 616246 MLS
Prime Commercial Opportunity in Islamorada! A rare find in the heart of Islamorada. This iconic restaurant property offers exceptional visibility along the world-famous Overseas Highway. Perfectly positioned on the corner of Overseas Highway and Blackwood Drive, this site has excellent traffic exposure, strong curb appeal, and convenient access for both locals and visitors traveling through the Florida Keys. Close proximity to multiple resorts, shopping, and the Morada Way Art District. The building totals 4,942 square feet situated on a 16,746 square feet lot, with ample customer and employee parking available in the front, side, and rear of the property with a 160 seat restaurant and a 5COP liquor license. Zoned Village Center (VC), the site offers tremendous flexibility for a wide range of commercial uses and is located in desirable X flood zone. Currently home to the Islamorada Shrimp Shack, a local staple and internationally recognized restaurant featured on Food Network's ''Diners, Drive-Ins, and Dives'' with Guy Fieri, the property presents a truly unique opportunity. Whether you're looking to continue a restaurant tradition in a turnkey setting or redevelop into a new commercial concept, this property provides a strong foundation for growth.

81901 Overseas Hwy, Islamorada