Islamorada Single Family Homes Under $5 Million

We found 15 Islamorada Single Family Homes for sale in Islamorada.

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Single Family Home
Venetian Shores

115 Villa Bella
Islamorada, FL 33036

4 Beds / 4 Baths
Courtesy of American Caribbean Real Estate
$4,899,000
Virtual Tour
RAPB
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 ready to enjoy from day one, including linens, bathroom essentials, a fully stocked kitchen, and three ... More Info...
Single Family Home
Venetian Shores No 2

155 Palo De Oro Drive
Islamorada, FL 33036

4 Beds / 5 Baths
Courtesy of RE/MAX All Keys Real Estate
$4,500,000
Under Contract Virtual Tour
RAPB
An unfinished masterpiece awaits in prestigious Venetian Shores, one of Islamorada’s most desirable waterfront communities with deep-water canals and quick access to Florida Bay and the Atlantic Ocean via Snake Creek. Elevated above flood on 100 feet of canal frontage, this solid concrete home features a striking concrete roofline and nearly all impact-rated windows and doors already installed.D ... More Info...
Single Family Home
Matecumbe Ocean Bay Sec 2

77340 Overseas Highway
Islamorada, FL 33036

2 Beds / 2 Baths
Courtesy of Coldwell Banker Schmitt Real E
$3,799,999
Oceanfront Virtual Tour
RAPB
Estate Opportunity - Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, ... More Info...
Single Family Home
Lower Matecumbe Beach

74049 Overseas Highway
Islamorada, FL 33036

4 Beds / 4 Baths
Courtesy of Luxe Properties
$3,750,000
Marina Oceanfront Virtual Tour
RAPB
Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing propert ... More Info...
Single Family Home
Port Antigua Plat No 3 &

59 Plaza Del Sol
Islamorada, FL 33036

5 Beds / 3 Baths
Courtesy of Pine River Realty, LLC.
$3,275,000
Oceanfront Virtual Tour
RAPB
Spectacular turnkey luxury meets the ultimate boater's paradise, nestled in Islamorada's coveted Port Antigua community! Built with solid concrete construction, this exceptional waterfront residence offers a rare Florida Keys feature: a full lower level, seamlessly connected by an interior staircase. Offering nearly 3,000 SF, 5 bedrooms, 3 bathrooms. The lower level features 3 spacious bedrooms, a ... More Info...
Single Family Home
Indian Waterways

131 Ojibway Avenue
Islamorada, FL 33070

4 Beds / 4 Baths
Courtesy of Golden International Realty Corp
$3,200,000
Foreclosure Virtual Tour
RAPB
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 spaci ... More Info...
Single Family Home
Coral Cove

80902 OLD Highway
Islamorada, FL 33036

4 Beds / 3 Baths
Courtesy of Coldwell Banker Schmitt Real E
$2,950,000
Oceanfront Virtual Tour
RAPB
RARE OPPORTUNITY IN CORAL COVE! Welcome to Island Hopper, an award-winning tropical plantation-style home in one of Islamorada's most private gated communities. Set on an oversized double lot, this beautifully updated 4-bedroom, 3-bath home offers 3,550 sq. ft. of living space plus 1,200 sq. ft. of covered outdoor living. A spectacular wraparound porch, soaring windows, and abundant natural light ... More Info...
Single Family Home
Port Antigua Plat No 5 &

122 Court Contessa
Islamorada, FL 33036

3 Beds / 3 Baths
Courtesy of The Keyes Company
$2,740,000
Foreclosure Intracoastal Oceanfront Virtual Tour
RAPB
Rarely available turnkey Deepwater Boater's retreat with a Private Bayside beach in the heart of the fishing capital of the world. Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in the Florida Keys, this fully renovated 3-bedroom, 3.5-bath concrete residence delivers the ultimate Florida Keys lifestyle - where luxury, durability, and world-class boating converge. Built fo ... More Info...
Single Family Home
Venetian Shores No 2

107 Valencia Drive
Islamorada, FL 33036

3 Beds / 2 Baths
Courtesy of Keller Williams Legacy
$2,500,000
Virtual Tour
RAPB
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. ... More Info...
Single Family Home
Plantation Key Colony 1st

179 Azalea Street
Islamorada, FL 33070

4 Beds / 4 Baths
Courtesy of Classic Investments Corp.
$2,450,000
Virtual Tour
RAPB
Captain's Delight! Beautifully updated home in tranquil Plantation Key Colony. Great location for a boater or simply someone that enjoys Keys living. Four bedrooms and four and a half bathrooms. New pool with heater and chiller. Watch the sunset or the sunrise from the rooftop observation / sun deck. No bridges to the bay and take Tavernier Creek to the ocean. More Info...
Single Family Home
Ocean View

82891 Overseas Highway
Islamorada, FL 33036

3 Beds / 3 Baths
Courtesy of Keys Properties of the PB's
$2,100,000
Virtual Tour
RAPB
LIVE, WORK & PLAY IN ISLAMORADA | RARE SC COMBO ZONING! Income + residence at MM 82.8 on high-visibility Overseas Hwy! Walk to beach, shops & dining. Street-to-street 50x150 lot w/ Old Hwy rear access & parking for work trucks, trailers & boats. COMMERCIAL OFFICE: Fully outfitted CBS bldg w/ 6" concrete roof, dual mini-splits, full bath, separate meter, 3-phase electric & impact shutters. RESIDENT ... More Info...
Single Family Home
Venetian Shores No 1

161 Palermo Drive
Islamorada, FL 33036

3 Beds / 2 Baths
Courtesy of Engel & VΓΆlkers Islamorada
$1,950,000
Virtual Tour
RAPB
Perfect fishing retreat/home. A boater's and angler's paradise in Venetian Shores! This 3-bedroom, 2-bath home at 161 Palermo Drive offers deep water and immediate access to the bay and ocean. Enjoy an open floor plan and screened porch, plus concrete construction, a concrete roof, impact windows & doors. A lift makes carrying heavy items upstairs easier. A spacious downstairs rec room with storag ... More Info...
Single Family Home
Anglers Reef

133 Anglers Way
Islamorada, FL 33036

2 Beds / 2 Baths
Courtesy of Douglas Elliman
$1,700,000
Marina Oceanfront Virtual Tour
RAPB
Beautiful 2BR/2.5BA home in Anglers Reef, Islamorada’s upscale gated oceanfront community. Features a 31' deeded BOAT SLIP with direct Atlantic access and no bridges, making it ideal for boating and fishing enthusiasts. Offered turnkey furnished with hardwood floors, granite countertops, stainless steel appliances, impact windows and doors, 2 private carports, two bedroom balconies, a front porc ... More Info...
Single Family Home
White Marlin Beach Sec 2

164 Venetian Drive
Islamorada, FL 33036

4 Beds / 2 Baths
Courtesy of Compass Florida, LLC
$1,449,000
Virtual Tour
RAPB
Boater’s dream home in White Marlin Beach, Islamorada. Unique 2-story single-family home with split layout, two 800 square feet 2BD/1BA units. Separate entrances and laundry in each unit, 70' dock with private boat ramp on a tranquil mangrove canal. This property is facing mangrove with maximum privacy, just 7 homes from the bay! Plenty of parking for RVs/trailers. Enjoy access to the White Marl ... More Info...
Single Family Home
Anglers Reef

111 ANGLERS Way
Islamorada, FL 33036

2 Beds / 2 Baths
Courtesy of Berkshire Hathaway HomeService
$1,199,999
Oceanfront Virtual Tour
RAPB
Experience the Florida Keys lifestyle at Anglers Reef, Islamorada's upscale gated oceanfront community. This beautifully appointed 2 bedroom, 2.5 bath home features a covered carport & four inviting porches, perfect for enjoying the tropical surroundings. Inside, you'll find Brazilian cherry hardwood floors, a spacious kitchen with granite countertops, stainless steel appliances, two breakfast bar ... More Info...

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© 2026 Starfish Real Estate. Listings updated Nov 8, 2026 5:00 am. Listing data is derived from the Broker Reciprocity Program of the Realtor Association of Indian River County (RAIRC) and BeachsMLS. Properties listed by brokers other than Starfish Real Estate are identified with the applicable MLS logo and include the listing broker's name. Not all properties available through either MLS may be displayed. All MLS data is the copyrighted property of the respective MLS and its participants. Data is deemed reliable but is not guaranteed accurate and should be independently verified prior to entering into any transaction.