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Single Family Homes for Sale in Islamorada, FL

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Welcome to your dedicated resource for single family homes for sale in Islamorada, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Islamorada, FL agent, Marc Plotkin specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the single family properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Single Family Homes for Sale in Islamorada, FL

$11,700,000
6 Beds ⋅ 8 Baths ⋅ A12056007 MLS ⋅ Matecumbe Ocean Bay Sec 2 BLDG.
Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom suites, media room, an elevator, and a custom kitchen showcasing mahogany cabinetry and Thermador appliances. Expansive balconies extend the living spaces into the natural surroundings. The third-level Sunset Lounge elevates entertaining with a full bar, wine storage, generous seating, a mega-TV, and views toward Florida Bay. Outdoors, the property features a saltwater pool and spa, covered dining and entertaining areas, a private pickleball court, and a dock with boat lift. A detached guest house provides comfortable accommodations with added separation from the main residence. This distinctive Islamorada estate brings together natural beauty, recreation, boating access, and elevated island living.

77350 Overseas Hwy, Islamorada
$29,000,000
4 Beds ⋅ 6 Baths ⋅ A12050889 MLS ⋅ Matecumbe Ocean Bay (75.0) BLDG.
Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre of bayfront property, a dramatic arrival unfolds beneath soaring 30ft ceilings, leading into a grand living space framed by turquoise bay views. An arcaded hallway with a hand-tiled barrel-vaulted ceiling connects interiors featuring Italian finishes, exquisite marble details, five fireplaces, hand-painted ceiling frescoes, and a one-of-a-kind imported tile roof. Florentine windows, Juliette balconies, wrought-iron railings, copper gutters, and hand-carved marble corbels. The floor plan includes four bedrooms, with three guest suites on the main level and a private third-floor primary retreat. The chef's kitchen is appointed with top of the line appliances, a walk-in pantry, and dedicated prep kitchen. A pass-through window connects to the outdoor kitchen and covered dining. A formal dining room with a hand-painted ceiling fresco, wellness room, sauna, theater, and billiards lounge. Outside, an infinity-edge pool, sunken gazebo with swim-up seating, putting green, fountains, and tropical landscaping. Deep dockage, sand beach, and clear waters provide immediate access to fishing, diving, snorkeling, and boating. An air-conditioned boat room, skiff ramp, 4,000+ SF collector's garage, elevator servicing all 3 levels, C4/Sonos smart home, secure walled & gated grounds.

75090 Overseas Highway, Islamorada
$2,795,000
3 Beds ⋅ 3 Baths ⋅ A12051290 MLS ⋅ Venetian Shores No 2 BLDG.
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
$6,999,000
4 Beds ⋅ 5 Baths ⋅ A12032087 MLS ⋅ Plantation Beach BLDG.
Private Bayfront Estate in desirable Islamorada offering a serene ambiance on an oversized parcel of pristine bayfront with breathtaking sunsets and unobstructed panoramic views of the Florida Bay. This exceptional waterfront retreat features an irreplaceable protected boat basin, concrete jetty, and T-dock providing superior deep-water dockage. Encompassing 4,000 square feet of beautifully designed living space, this remarkable residence includes 4 spacious bedrooms and 4.5 bathrooms. This home showcases an inviting kitchen and multiple expansive living areas all thoughtfully designed for ultimate comfort and entertaining, ideal for hosting family and guests or enjoying a private coastal escape. Step outside to your own tropical sanctuary with unforgettable sunsets, year-round outdoor living, and the sparkling waters of Florida Bay creating the ultimate Florida Keys lifestyle. A rare opportunity to own in one of Islamorada's most exclusive waterfront settings.

88110 Overseas Hwy, Islamorada
$3,350,000
4 Beds ⋅ 4 Baths ⋅ A12028354 MLS ⋅ White Marlin Beach Sec 1 BLDG.
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 Drive, Islamorada
$25,000,000
7 Beds ⋅ 10 Baths ⋅ A12022973 MLS ⋅ Islamorada BLDG.
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 four 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 home's architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. 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 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.

82768 Overseas Highway, Islamorada
$298,000
1 Beds ⋅ 1 Baths ⋅ A12017273 MLS ⋅ Windley Key Mobile Home P BLDG.
Escape to your own slice of paradise with this cozy and beautifully kept 1-bedroom, 1-bath Jayco RV. Whether you’re looking for a peaceful weekend retreat, a seasonal getaway, or a spot with great rental potential, this charming hideaway has it all. Wake up to the soothing sounds of the Atlantic and enjoy unforgettable sunrises and sunsets right from the jetty. Nestled in a rare, intimate oceanfront community, you’ll love the relaxed lifestyle and low association fees. Spend your days soaking up the sun, launching your kayak or small boat, or taking advantage of the fish-cleaning station and marina. It’s the perfect chance to own a tranquil oceanfront retreat—simple, serene, and full of coastal charm.

84961 Old Hwy 17 Hwy, Islamorada
$13,500,000
7 Beds ⋅ 7 Baths ⋅ A12017379 MLS ⋅ Mat Ocean Bay BLDG.
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 and a valuable vacation rental license in place, 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.

75840 Overseas Highway, Islamorada
$3,999,999
4 Beds ⋅ 4 Baths ⋅ A12010138 MLS ⋅ Lower Matecumbe BLDG.
The gated entrance supplies a perfect level of privacy. The approach sets the tone for the entire experience: peaceful, secluded, and authentically 'Old Florida,' yet elevated with the sophistication expected in a luxury Keys residence. Whether used as a full-time home, a seasonal retreat, or a legacy property to be enjoyed for generations, Casa Matecumbe offers a rare combination of location, land, and lifestyle that is nearly impossible to replicate. The main residence is thoughtfully positioned to maximize panoramic ocean views from nearly every room. Expansive windows and glass doors frame the turquoise water, inviting natural light to fill the interior spaces throughout the day. Upstairs there are 3 bedrooms and 2 baths as well as a gorgeous kitchen an open concept with dining under air conditioning or al fresco, Downstairs includes a large en-suite bedroom with water views as well as an additional kitchen and dining living area. Both levels offer a breezy indoor-outdoor living--with modern comforts including updated finishes, impact windows, and spacious living areas. This 4-bedroom House is the perfect vacation home for larger families wishing to enjoy the pool, the beach and the ocean in a private setting.

74049 Overseas, Islamorada
$6,999,000
8 Beds ⋅ 6 Baths ⋅ A12009440 MLS ⋅ Strattons Subdivision Pb2- BLDG.
Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct access to both the Florida Bay and Atlantic Ocean. Seller will consider all reasonable offers. The main residence features 7 spacious bedrooms and 5 beautifully appointed bathrooms designed with both elegance and comfort in mind--perfect for entertaining or hosting large gatherings. A dramatic third-floor Bird's Nest Sky Lounge features 360-degree glass walls and a walkout rooftop deck, capturing breathtaking vistas in every direction. Expansive living areas and thoughtfully designed spaces capture stunning water views from every angle. A private 1-bedroom, 1-bathroom guesthouse provides the ideal retreat for visitors, accommodating extended family, or potential rental income or creating a secluded retreat. For boating enthusiasts, the estate includes an impressive 85+ foot deep-water yacht slip and four boat lifts, offering seamless access to both the Bay and Ocean--an unparalleled fishing advantage in the Florida Keys.

1101 Mastic Street, Islamorada
$6,150,000
5 Beds ⋅ 6 Baths ⋅ A12000712 MLS ⋅ Matecumbe Sandy Beach BLDG.
Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

137 Sapodilla Dr, Islamorada
$18,999,000
6 Beds ⋅ 6 Baths ⋅ A11990479 MLS ⋅ Plantation Beach BLDG.
A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. Designed for elevated living, The Oasis blends resort-style amenities with the privacy and scale of a true Florida Keys compound. The grand porte-cochère entry sets the tone, leading to a single-level main residence with soaring ceilings, white oak floors, and 12' retractable glass walls that frame sweeping ocean views. The chef's kitchen is anchored by a Calacatta marble island, Thermador appliances, and a walk-in pantry, opening to a spacious great room and dining area ideal for entertaining. The main home features four bedrooms, six full bathrooms, and a soundproof theater. The primary suite is a private retreat with a fireplace, dual walk-in closets, a safe room, and a spa-inspired bath with a steam shower. Each additional bedroom includes an en suite bath, private balcony, and ocean views. A detached guest house offers two additional bedrooms and bathrooms, creating a total of six bedrooms across the estate with endless space for expansion. The summer kitchen, alfresco dining areas, and multiple lounging terraces offer seamless indoor-outdoor living. The deepwater basin accommodates larger vessels. Amenities rival a private resort: soundproof theater, fitness center with sauna, golf simulator, and two resort-style pools—each with a spa, sun deck, & outdoor entertaining spaces.

87429 Old Hwy, Islamorada
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