Upper Matecumbe Key Islamorada Homes for Sale, Single Family Houses, MLS Home Listings

This lovely home is classic Keys on the outside, with modern elegance on the inside. Secluded on high ground in the heart of downtown Islamorada, this accommodating three-bedroom, two-bath residence offers abundant space for relaxation and entertainment, including an inviting back porch, surrounded by lush landscaping that enhances the serene atmosphere. The expansive front and back yards provide ample room for outdoor activities and gatherings. Ideally situated, you are within easy walking distance to the beaches, great restaurants, and grocery shopping. Experience the perfect blend of comfort and convenience in this idyllic retreat.

Welcome to 100 Parker Drive, a delightful 2-bedroom, 2-bath all-concrete home nestled in one of Islamoradas most sought-after neighborhoods. Tucked away between the Overseas Highway and the Old Highway, this quaint, quiet, and family-friendly street is a hidden gem, offering the perfect blend of island charm and small-town community living.This partially updated retreat boasts a private, fenced-in paver patio, ideal for outdoor entertaining, morning coffee, or a peaceful evening under the palms. Surrounded by lush tropical landscaping, it offers a serene escape just minutes from the heart of downtown Islamorada.Whether youre looking for a full-time residence, a seasonal getaway, or an investment property, this home is turn-key and a prime opportunity for both long- and short-term (28 day or more) rentals. The Parker Drive community is vibrant and welcoming, with plenty of families and children, making it an excellent choice for those seeking a neighborhood feel with the perks of island life.Location is everything! From here, you can bike to Islamoradas best restaurants, boutiques, art galleries, breweries, and marinas--all just a short ride away. Take a quick drive to the local schools, parks, and waterfront attractions that make Islamorada one of the most desirable places to call home.Dont miss your chance to own a piece of paradise! This unbeatable location and potential for return on investment make it a rare find in Islamorada. Schedule a showing today!

Beautiful Downtown Islamorada Cottage! This newly constructed home is located on an oversized lot with a pool, outdoor entertaining area, plenty of storage, parking, and handicap access. The home features 3 bedrooms & 3 bathrooms with two of the bedrooms ensuite. The home offers a great floor plan and has been tastefully decorated with a beautiful kitchen including stainless steel appliances. This is a great investment with rental history. Dont miss the opportunity to own where you can walk and ride your bike to all the places downtown Islamorada has to offer including shopping, restaurants, bars, and all the amenities The Sports Fishing Capital of the World has to offer!

Located in downtown Islamorada, this property offers an ideal lifestyle with a great floor plan for work-life balance. The separate office guest quarters overlooking the pool creates a perfect work environment. This home offers 3 bedrooms & 3 bathrooms, and a split floor plan, ideal for a family that is looking for privacy and space. Enjoy the large private inground pool, & outdoor entertainment area along with access to a sandy beach with dock, boat launch, and stunning ocean views, all within walking distance to restaurants, shops, and art galleries.

Welcome to Turtles Nest, a charming home offering the perfect blend of comfort, flexibility, and Florida Keys lifestyle, all set on an oversized, lushly landscaped corner lot in the heart of Islamorada. A 3 Beds - 2 Baths + Office & Two-Car Garage - 2,128 Sq. Ft. under Air conditioning on an oversized, 12,300 Sq. Ft. lot. This beautifully maintained home with a private office/flex space features a spacious, sun-filled layout with impact-resistant windows. The enclosed wraparound sunroom is ideal for year-round enjoyment. Enjoy the convenience of two full laundry rooms, a rare bonus for seasonal or full-time residents. The private office with its own exterior entrance offers the perfect setup for remote work or guests. The home also boasts a fully air-conditioned and heated 2-car garage, perfect as a workshop, gym, or storage space. Step outside to find an outdoor shower with hot water, an electric gated entry, and dedicated boat trailer parking. The tropical landscaping with mature greenery and fruit trees surrounds the home, providing privacy and a true island retreat vibe. Located in an exclusive neighborhood with deeded access to the renowned and historic Green Turtle Beach, private oceanfront park, perfect for enjoying sunrises, walks, kayaking, or beach picnics for just $33 a month. Just minutes from world-class restaurants, galleries, spas, pickleball courts, and more. This home offers a peaceful island living with a walkable, vibrant lifestyle. Furnishings available and negotiable.

Open Bay Views, Boat Dockage and more... all in the Heart of Downtown Islamorada! Have you been dreaming of living downtown, but cant find a home with dedicated boat dockage and open water views? If so, this custom home in Madeira Bay is your dream come true! Enjoy open water views from the porch, living room, kitchen, loft and bedroom plus soaring ceilings and lots of living space. The Madeira Bay gated community is a hidden treasure of only 8 homes tucked in behind one of Islamoradas most beloved local restaurants in a peaceful private neighborhood. In addition to the community dock there is also a community pool and a gradual shoreline for launching a boat, paddle board or kayak or for wading directly into the bay with your rafts and floats! Stunning great room opens to the bay view porch on the main living level where there are also three bedrooms and two full baths in a split plan. There is also an open loft bedroom with full bath upstairs off the great room featuring beautiful bay views. The fully permitted downstairs is connected by internal spiral stairs and adds a separate ground level entrance plus a spacious second living room, wet bar area for entertaining, plus a private guest bedroom with a full bath and outdoor porch. There is also an attached garage for protected parking and/or storage. The downtown location offers immediate access to shopping, fine dining, bars, galleries, art studios and all the regular local art festivals, full moon parties and events. Madeira Bay homes rarely come on the market and this one is a must see!

Discover Your Private Tropical Oasis in Islamorada.Welcome to your dream retreat in the heart of the Florida Keys in the sport fishing capital of the worldaa stunning Key West-style home nestled amidst lush greenery in an exclusive gated bayfront private club community. This residence is more than just a home; its a lifestyle defined by serenity, elegance, and the natural beauty of Islamorada.From the moment you pass through the palm-lined gated front entrance, you will notice the manicured tropical beauty of this community as you make your way to the classic architectural gem that will captivate you. Vibrant hues, large sitting porches, and timeless craftsmanship create a warm, inviting ambiance. Inside, open living spaces are bathed in natural light, blending seamlessly with the lush surroundings visible through every window.Step outside and find yourself in your very own tropical sanctuary. Towering palms, old growth trees, vibrant bougainvillea, and lush greenery surround the property, offering privacy and tranquility. Relax by the pool, host unforgettable gatherings on the expansive patio, or simply unwind as the breeze carries the scent of salt air.Nestled within a private club community, this home offers access to a range of world-class amenities, including a marina, sunset point, beach, and community pool. Plus, the vibrant culture and stunning waters of Islamorada are yours to explore from the protected marina.Whether youre seeking a permanent residence or a vacation escape, this property provides the perfect balance of seclusion and connection. From sunrise strolls on pristine beaches to evenings under the stars, every moment here feels like a slice of paradise.Dont just dream of the Keys, live it. Schedule your private tour today and experience firsthand what makes this home and private community so extraordinary.

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

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today.Owner is Florida licensed real estate agent.

Waterfront Elegance in Venetian Shores - A Turnkey Coastal GemDiscover the pinnacle of Florida Keys living in this impeccably remodeled waterfront oasis, located in the highly sought-after Venetian Shores. This sophisticated 4-bedroom, 3-bathroom retreat spans over 3,000 square feet of thoughtfully designed living space, blending contemporary luxury with island-inspired charm.From the moment you step inside, youll be captivated by the refined finishes and custom upgrades throughout -- including a gourmet chefs kitchen, spa-quality bathrooms, and expansive open-concept living areas ideal for relaxing or entertaining.This home is truly move-in ready, featuring a brand-new roof, sparkling new pool, all-new impact windows and doors, a state-of-the-art 27,000 lb boat lift, and premium craftsmanship in every detail.Boaters will appreciate 70 feet of deepwater dockage with instant access to Snake Creek -- offering seamless navigation to both the Atlantic Ocean and Florida Bay.Whether youre searching for a permanent residence or a high-end vacation escape, this home offers the perfect blend of luxury, comfort, and unbeatable location.Exclusively offered in Venetian Shores -- where world-class boating and refined coastal living come together.

This remarkable 34,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay.One of the key highlights of the lot is its exceptional dockage, (65 ft), which has previously accommodated a 36-foot bertram, making it perfect for boating enthusiasts. The property also offers plenty of room for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds creating a tranquil atmosphere for evening relaxation.The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aquatic species like fish, birds, manatees and a multitude of different birds. Its a perfect canvas for your dream residence or vacation retreat.With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this property is one of the best properties on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation.May also purchase the vacant lot up front that has a Market Rate TDR on it. This would make an exceptional family compound in the heart of Islamorada. Possible owner financing. ,Owner / Agent

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 boasts 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 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 warranty2. New Dock and Stair Brick Pavers3. New third-floor Impact Windows4. Two New third-floor Impact French Doors5. Two New third-floor electric Rolladen Hurricane Shutters6. Swimming poll resurfacing with new glass edge surround7. Dock has a 220-volt pedestal to service dock-side marine electric needs

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

Built in 2014, Bahia Bonita is an ultra-private, luxury bayfront estate found in the heart of Islamorada. Situated on a peninsular parcel with 250+ linear feet of open water frontage of crystal-clear water teeming with marine life, this home is within walking distance of Islamoradas favorite dining spots. Designed to offer the ultimate combination of location, deep-water dockage, storm resiliency and unobstructed open water views from every room, this home boasts marble floors throughout and a spectacular floating staircase. Begin your day by stepping out of your master suite to your private and secluded bayfront terrace and into a second floor Infinity Edge pool. Just one step away from the main kitchen is an outdoor kitchen with adjacent bay view, al fresco dining. In the evening, slide open the numerous walls of glass to experience year-round, unobstructed open water views and the brilliance of Islamoradas sunsets from the privacy of your great room, bedrooms, gourmet kitchen or outdoor decks. For stargazing, venture up the spiral stairs to the rooftop deck for a breathtaking front row seat. Your boats will comfortably berth on the 100 dock with two boat lifts fitted with hurricane and storm surge protection. Other functional luxuries include an elevator, an enormous three-car, 2200 sf garage, complete with workshop and storage, professional camera/security system, central wet-dry vacuum system and mature landscaping with fruit trees. A fourth bedroom and bathroom can be easily added without modifying the structure or footprint at very reasonable expense. Built to withstand sustained 200 mph winds, this solid concrete constructed home also includes accordion shutters over impact glass for ultimate storm resiliency. Call today to view this private piece of paradise!

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost comfort. Located in a serene cove with a pristine natural beach, the home features floor-to-ceiling windows that offer stunning 180-degree panoramic views of the ocean. Every corner is meticulously designed with tasteful decor, exuding elegance while providing a personal, comfortable atmosphere. The property is in downtown Islamorada, Florida Keys, and includes a private beachfront terrace, a third-story private balcony, and a tranquil pool with a tiki hut, making it ideal for relaxation and entertaining. The outdoor spaces feature a cozy firepit, offering the perfect setting for intimate gatherings with the sound of the waves as a backdrop. As a vacation rental, this residence is a lucrative investment opportunity in a highly sought-after area. This home is a true masterpiece, offering unparalleled luxury, privacy, and breathtaking views.

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Dont miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly 4 acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the sparkling waters of the bay while lush gardens create a serene oasis. The homes architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. Spanning over 6,900 square feet, the interior is a seamless fusion of open-concept living spaces and private retreats. Soaring vaulted ceilings and vast windows invite abundant natural light and spectacular views of the bay, creating an indoor-outdoor flow. The primary suite serves as your personal sanctuary, complete with private terrace, spa-inspired bathroom, and walk-in closets fit for a connoisseur of fine living. Each guest has direct access to outdoor spaces and views. A bonus, versatile bunk room/media center sits just off the west wing of the home. The charming guest house is the perfect complement to the main home, nestled in its own secluded on site location this delightful addition exudes a warm, welcoming ambiance ideal for hosting guests, or as a private office or creative studio. This downtown Islamorada estate in an incomparable location; walking distance to shopping, dining, and local culture, also has appeal that extends to those with a passion for the great outdoors. Two protected docking basins and boat lift, sandy lounging beach, expansive outdoor lanai and outdoor kitchen offers the ideal space for entertaining or enjoying a quiet evening watching the sunset. Fly the seaplane in or land the helicopter. Premier boating access just moments away from the Intracoastal waterway and Ocean channels. Serenity Cay is not just a home, its an experience.