Islamorada Homes with Fence Exterior features

Islamorada Homes with Fence Exterior features

Welcome to Islamorada, a tropical paradise nestled in the heart of the Florida Keys, Monroe County. Renowned for its stunning ocean views, vibrant marine life, and laid-back island lifestyle, Islamorada is often referred to as the "Sportfishing Capital of the World." With its pristine beaches, charming boutiques, and exquisite dining options, this idyllic village offers a unique blend of relaxation and adventure.

As you explore the real estate opportunities in Islamorada, you'll discover a variety of homes that perfectly capture the essence of island living. One of the standout features of many properties here is the presence of fenced exteriors, providing both privacy and security for your family and pets. These beautifully designed homes often boast spacious yards, ideal for outdoor gatherings, gardening, or simply soaking up the sun in your own personal oasis.

Imagine waking up to the gentle sound of waves lapping against the shore, stepping out onto your patio surrounded by lush tropical landscaping, all while feeling safe and secure within your fenced yard. Whether you’re looking for a cozy retreat or a luxurious waterfront estate, Islamorada’s real estate market has something for everyone.

With its breathtaking sunsets, a plethora of water activities, and a strong sense of community, Islamorada is not just a place to live; it's a lifestyle. Discover your dream home in this enchanting village, where every day feels like a vacation and the beauty of nature is right at your doorstep. Come experience the magic of Islamorada, where your dream home awaits!

Newest Islamorada Homes with Fence Exterior features

87455 Old Hwy Unit APT 234, Islamorada
$399,000
2 Beds ⋅ 2 Baths ⋅ 621854 MLS
Enjoy a tropical retreat at Plantation By The Sea, an oceanfront community in Islamorada. Relax beside the sparkling oceanfront pool or cast a line from the community fishing pier, then head out for waterfront dining, live music, and eclectic local shops. This inviting 2-bedroom, 1.5-bath condo offers a two-level layout with living spaces downstairs and both bedrooms upstairs. Bamboo flooring adds warmth to the living and dining areas and bedrooms. The updated kitchen features white cabinetry and generous counter and storage space. The open living and dining area flows onto a covered balcony nestled among tropical greenery - a pleasant spot for morning coffee or unwinding after a day exploring the island. Both upstairs bedrooms feature sliding glass doors opening to balcony spaces. An updated full bathroom with a tiled walk-in shower, a convenient downstairs half bath, and an in-unit Bosch washer and dryer add everyday comfort. Assigned covered parking and a ground-level storage room provide added convenience. Community amenities also include an oceanfront clubhouse with a kitchen, a pool table, and a ping-pong table - a great place to entertain friends and family. Take in ocean views while working out in the fitness center, or unwind in the men's and women's saunas. Gated entry and kayak and paddleboard storage add to the community's appeal. Nearby Founders Park offers a beach, Olympic-size swimming pool, tennis and pickleball courts, ball fields, and an amphitheater. Whether you're seeking a seasonal getaway or a year-round home, this welcoming condo puts the best of Islamorada within reach.

87455 Old Hwy Unit APT 234, Islamorada
131 Ojibway Ave, Islamorada
$3,200,000
4 Beds ⋅ 4 Baths ⋅ 621841 MLS
Experience the ultimate Florida Keys waterfront lifestyle! Discover this exceptional 4-bedroom, 4-bathroom waterfront residence featuring solid concrete construction, a concrete roof, and a spacious custom-designed kitchen. Enjoy the ultimate boating lifestyle with a private boat lift and direct water access with no bridges. This remarkable property also features a beautiful swimming pool, a spacious garage, an outdoor summer kitchen perfect for entertaining, and breathtaking ocean views from the rooftop. Offering generous living spaces and endless opportunities for boating, fishing, and entertaining, this beautiful Islamorada home combines quality construction, comfort, and coastal elegance. Experience waterfront living at its finest!

131 Ojibway Ave, Islamorada
16 Avacado St, Islamorada
$23,500,000
9 Beds ⋅ 11 Baths ⋅ 621766 MLS
Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.

16 Avacado St, Islamorada
74501 Overseas Hwy, Islamorada
$4,850,000
5 Beds ⋅ 4 Baths ⋅ 621750 MLS
Discover a rare oceanfront paradise in the Florida Keys, situated on 1.35 acres of private oceanfront property featuring an extraordinary stretch of natural sandy beach, a feature seldom found in the Keys. Perfectly positioned next to iconic Sea Oats Beach, known for its pristine shoreline and seasonal sea turtle nesting, this exceptional estate offers privacy, coastal elegance, and breathtaking turquoise waters, just minutes from Islamorada's renowned dining and shopping. Enter through a private electric gate with ample parking for vehicles, boats, and trailers, plus an oversized three-car garage with pull-through access. An expansive ground-level storage area, currently utilized as a private gym, provides additional space for recreational equipment and boating gear. Built with concrete construction, the residence features impact-resistant windows and doors, along with a 25kW propane generator. Inside, marble floors, granite countertops, stainless steel appliances, a wine refrigerator, built-in ice maker, and spectacular open living spaces create an inviting coastal retreat. Four sets of double sliding impact glass doors frame panoramic ocean views and abundant natural light. The residence features five bedrooms and four full bathrooms, including two guest suites with private baths. The oceanview primary suite offers a walk-in closet, dual vanities, soaking tub, and walk-in shower. Outside, a lagoon-style pool, Jacuzzi, and wraparound balcony create an exceptional setting for entertaining and enjoying the ocean breezes. Offered below its 2026 appraised value, this remarkable oceanfront estate presents a rare opportunity to own 1.35 acres of private oceanfront property with a natural sandy beach, stunning open-water views, and convenient access to Islamorada's restaurants, shopping, and marinas.

74501 Overseas Hwy, Islamorada
101 Orange Ln, Islamorada
$735,000
4 Beds ⋅ 3 Baths ⋅ 621604 MLS
Solid Concrete Home on Plantation Key! Live the Islamorada lifestyle from this solid concrete home in a desirable Plantation Key subdivision. The home is ground level and built above flood. It offers 4 bedrooms, 3 bathrooms, a comfortable living area, and a large dining room for entertaining family and friends. Out back, a spacious, fully fenced yard has plenty of room for a pool, a garden, or simply relaxing outdoors. Owners can use the neighborhood HOA park, its boat ramp for direct bay access, with the ocean a short run away and short term dockage. Founders Park is just minutes away, with a swimming pool, sandy beach, boat ramp, playground, dog park, and tennis and pickleball courts. Acclaimed restaurants, shopping, schools, and the hospital are all close by. This home puts you in the middle of everything Islamorada has to offer. Orange Lane is a great fit for investors, renovators, or buyers who want to build equity.

101 Orange Ln, Islamorada
154 Carroll St, Islamorada
$2,699,000
4 Beds ⋅ 4 Baths ⋅ 621562 MLS
Location! Location! Location! This incredible custom designed home is located on a quiet lane in the heart of Islamorada, 154 Carroll Street offers privacy, modern construction, and easy access to some of the area's best restaurants, shops, private clubs, and resorts, and beaches. Completed in 2018, the home combines clean coastal design with comfortable and abundant indoor-outdoor living. Mature tropical landscaping creates a private setting around the pool and spa. The handcrafted tiki pavilion is designed for outdoor cooking and entertaining, complete with a mosquito misting system, refrigerator, ice maker, grill, cooktop, all made of marine grade stainless steel, in NatureKast exterior cabinets--an ideal gathering spot for afternoons by the pool, evening entertaining or star gazing in the hot tub. Inside, the two floor cathedral ceilings enhance the interior with bright light, and the open layout features porcelain floors and coastal finishes. Two primary suites offer flexibility, including an upstairs suite with a private balcony and a downstairs suite with an oversized walk-in closet. Additional guest suites and a loft offer plenty of space for family, visitors, or a home office. Built above flood, the home includes impact-rated openings and spray-foam insulation for incredible efficiency. Practical features include a rare attached garage, Tesla charging station, exterior security cameras & wired interior system and a fenced area with room for a boat and trailer. Located within Islamorada's golf cart district, the home makes it easy to leave the car behind and enjoy nearby restaurants, shops, resorts, and local favorites by golf cart, bike, or on foot. Sandy neighborhood beach access at the end of the block puts the Atlantic just a short walk away, while the Islander Resort and the amenities of Upper Matecumbe are close at hand. 154 Carroll Street combines the privacy and features of a new home with a central location designed for tranquil living.

154 Carroll St, Islamorada
75055 Overseas Hwy, Islamorada
$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
115 Villa Bella Dr, Islamorada
$4,899,000
4 Beds ⋅ 4 Baths ⋅ 621387 MLS
Experience turnkey luxury in the renowned Venetian Shores community with this exceptional 4-bedroom, 4-bath concrete waterfront residence, completely rebuilt from top to bottom with designer finishes and thoughtful details throughout. Offered fully furnished and completely outfitted, this home is truly ready to enjoy from day one. Everything is already in place, including linens, bathroom essentials, a fully stocked kitchen, and three mini-bar setups. Currently operating in a highly successful vacation rental program, the property has been thoughtfully designed and equipped for effortless personal use, entertaining, or continued rental operation. The beautifully finished interiors offer a sophisticated coastal feel, while an additional bonus space downstairs provides exceptional flexibility as a potential 5th bedroom, private office, game room, or lounge. Outdoor living is equally impressive. The resort-style pool is both heated and chilled for year-round enjoyment, while extensive landscape and architectural lighting creates an incredible atmosphere after sunset. Under-dock lighting illuminates the water below, perfect for nighttime fish watching and feeding. An outdoor shower provides the ideal place to rinse off after a swim or a long day on the water. Adding even more to the Keys lifestyle, the property includes a customized golf cart, making it easy to cruise through Venetian Shores and enjoy everything this highly sought-after neighborhood has to offer. From the complete rebuild and designer interiors to the turnkey furnishings, flexible living spaces, resort-style outdoor amenities, and established vacation rental operation, every detail of this home has been carefully considered. Simply arrive, unpack, and start enjoying the Florida Keys lifestyle.

115 Villa Bella Dr, Islamorada
75433 Overseas Hwy, Islamorada
$3,999,000
4 Beds ⋅ 4 Baths ⋅ 621270 MLS
Wake up to the sunrise over the Atlantic from this private oceanfront retreat offering two separate residences, a sandy beach, and direct access from Highway to Ocean. This unique property offers a 3BD/3BA main residence plus a separate 1BD/1BA guest house, ideal for extended family, visiting friends, private home, or income producing estate. Enjoy a sandy beach, pool, two beachside tiki huts, observation pier, concrete boat ramp and rock jetties for tide protection, creating the ultimate setting for entertaining and waterfront living. Extensive upgrades include impact windows and doors, metal roof, A/C, stucco, paint, appliances and more. With abundant parking for cars, boats, trailers, toys and guests, there is room for everyone. Just minutes by boat to Alligator Lighthouse and nearby Caloosa Marina for fuel, ice, boat storage and food. A rare opportunity to own a true oceanfront Keys compound with space, privacy and a stunning view!

75433 Overseas Hwy, Islamorada
107 Valencia Dr, 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
148 Giardino Dr, Islamorada
$3,599,000
5 Beds ⋅ 3 Baths ⋅ 621117 MLS
THIS UPDATED BEAUTY LOCATED IN RENOWNED VENETIAN SHORES IS A TRUE MUST SEE!! LOCATED IN ONE OF VENETIAN SHORES MOST EXCLUSIVE LOCATIONS GIARDINO DRIVE. UPSTAIRS: THREE BEDROOMS AND TWO SPACIOUS BATHROOMS !! COMFORTABLE LIVING ROOM AND DINING ROOM AREA WITH ACCESS TO A LARGE SCREENED IN PORCH WITH BEAUTIFUL WATERFRONT VIEWS !! LARGE KITCHEN WITH BEAUTIFUL CONNECTED ISLAND AND STATE OF THE ART COUNTERTOPS; MODERN APPLIANCES !! WET BAR AND WINE CELLAR CABINET !! INDEPENDENT INDOOR LAUNDRY ROOM WITH PLENTY OF STORAGE !! CUSTOM CLOSETS THROUGHOUT. HIGH END CEILING FANS THROUGHOUT THE ENTIRE HOME !! NEW EFFICIENT A/C !! INDEPENDENT DOWNSTAIRS: TWO SPACIOUS BEDROOMS AND ONE BATHROOM, CUSTOM CLOSETS !! KITCHENETTE WITH MICROWAVE, REFRIGERATOR, SINK AND FILTERED WATER WITH LOTS OF STORAGE SPACE !! LARGE SCREENED IN PORCH WITH GREAT WATERFRONT VIEWS !! OUTDOOR FEATURES: 100 FEET OF WATERFRONT WITH TWO BOAT LIFTS !! UPDATED FLOOR DECK AND LIGHTING. THREE DOORS DOWN FROM SNAKE CREEK WITH EASY ACCESS TO BAYSIDE AND ATLANTIC !! (2) BOAT LIFTS 14,000 LB. AND 10000 LB. FISH CLEANING STATION WITH WATER AND POWER ACCESS WITH LOTS OF STORAGE. LARGE HEATED POOL ( NEW POOL PUMP ) WITH FIRE WATERFALL AND FIREPIT. OUTDOOR POOL SHOWER. GAS TIKI TORCHES AROUND THE POOL AREA !! LARGE TIKI HUT WITH TV AND FAN AND WITH POWER ACCESS. LARGE AREA OF ARTIFICIAL GRASS WITH A FIVE HOLE PUTTING GREEN !! ROOF TOP DECK WITH BEAUTIFUL VIEWS !! LUSH LANDSCAPING THROUGHOUT !! SAFETY,CONVENIENCE, ENERGY FEATURES: CONCRETE ROOF. IMPACT WINDOWS AND DOORS THROUGHOUT THE ENTIRE HOME !! ELECTRIC ROLLER SHUTTERS ON BOTH PORCHES !! SOLAR PANELS THAT POWER THE ENTIRE HOME ( CURRENT CREDIT WITH POWER CO-OP ). TWO TESLA BATTERIES FOR POWER STORAGE, ELECTRIC CAR CHARGER !! TOTALLY FENCED FRONT/BACK; ELEVATOR, ONE CAR GARAGE AND A CARPORT. 2 LARGE STORAGE AREAS. NEAR FOUNDERS PARK AND GREAT RESTAURANTS IN ISLAMORADA. RUN DON'T WALK, THIS A TRUE MUST SEE FOR ANY ISLAMORADA BUYER!!!

148 Giardino Dr, Islamorada
155 Plantation Ave, 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
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