Islamorada FL Real Estate & Homes for Sale

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Beds:
3
Baths:
4.00
Sq.Ft.:
5,559
Status:
Active
MLS#:
620441
Type:
Single Family
Subdivision:
Venetian Shores (86.0)
Lot size:
0.23 Acres
Year built:
2027
Courtesy: RE/MAX All Keys Real Estate 305-451-0060
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ADDITIONAL INFORMATION

An Unfinished Masterpiece Awaits in the prestigious **Venetian Shores**, one of Islamorada's most desirable waterfront communities, known for its deep-water canals and quick access to both the Florida Bay and the Atlantic Ocean via Snake Creek. This extraordinary opportunity allows you to complete what was envisioned as one of the Florida Keys' most premier luxury estates. 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, providing an exceptional foundation for your dream home. Designed with **5,559 square feet of air-conditioned living space**, the residence offers an ideal blend of luxury and boating lifestyle. The first level includes **1,467 square feet** of living space, an oversized **897-square-foot garage**, and plans for an expansive entertainment area, fishing gear room, and direct waterfront access. The second level features **2,361 square feet** of living space plus over **1,100 square feet of covered porches**, with plans for three spacious guest suites, each with a private bath, a half bath, laundry room, chef's kitchen, and open-concept living area. The entire third floor is dedicated to the **1,731-square-foot primary retreat**, designed with ocean views, a spa-inspired bath, oversized custom closet, executive office, and private covered porch. An elevator shaft is already in place for easy access to every level. Plans also include a canal-front pool and cabana overlooking Snake Creek Bridge. With a concrete dock, 100 feet of waterfront, deep-water boating, and one of the Keys' finest locations, this property offers the rare opportunity to complete a truly remarkable custom estate while selecting every finish to reflect your own vision. Property is being sold as is. Some images are AI computer generated to show future potential.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,014
Status:
Active
MLS#:
620430
Type:
Single Family
Subdivision:
Plant Beach (87.5)
Lot size:
1.82 Acres
Year built:
1999
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege. With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership. A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout. Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout. Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.

Beds:
6
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A12042996
Type:
Other
Subdivision:
LOWER MATECUMBE BEACH
Year built:
1972
Courtesy: American Caribbean Real Estate
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ADDITIONAL INFORMATION

Islamorada Beach House in Lower Matecumbe. This 6 bedroom, 4 bathroom home is situated directly on Sea Oats Beach, a mile-long sea turtle nesting beach, with stunning Atlantic Ocean views, sunrise skies, and a sandy beach backyard just steps from the water. The home captures the essence of relaxed coastal living with expansive beachside outdoor space and turquoise water. Enjoy exceptional access to the nearby grass flats, known for wade fishing for bonefish and tarpon. An additional nearby smaller canal front lot is included. A special opportunity to own direct beachfront property in Islamorada, where the Atlantic Ocean is your backdrop and the beach is your backyard.

Beds:
4
Baths:
6.00
Sq.Ft.:
8,194
Status:
Active
MLS#:
A12050889
Type:
Other
Subdivision:
Matecumbe Ocean Bay (75.0)
Lot size:
1 Acres
Year built:
2011
Courtesy: Ocean Sothebys Intl Realty Annie Hagen 305-304-1762
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,088
Status:
Active
MLS#:
620412
Type:
Single Family
Subdivision:
Venetian Shores (86.0)
Lot size:
0.16 Acres
Year built:
1991
Courtesy: Coldwell Banker Schmitt Islamorada 305-664-4470
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ADDITIONAL INFORMATION

Coastal elegance meets the ultimate boating lifestyle in this beautifully updated Venetian Shores home. Designed for effortless Keys living, the open floor plan is filled with natural light, highlighted by a dramatic floor-to-ceiling wall of windows in the living area that brings the outdoors in. An inviting entrance foyer welcomes you inside, with interior stairs to the main living level. The spacious kitchen is the heart of the home, featuring stainless steel appliances, a large island for gathering, and a separate laundry room and pantry for added convenience. The main living level offers two guest bedrooms and two full baths, including one bedroom with a private en-suite bath. Direct access from the second-floor living area to the pool deck creates a seamless connection between indoor and outdoor living. The open floor plan offers plenty of room for dining, watching TV, conversation and even some ping pong. Upstairs, the expansive primary suite provides a peaceful retreat with a walk-in closet and luxurious en-suite bath. A fourth bedroom on the third floor offers flexibility for guests, family, or a home office. Separate air-conditioning systems for each floor ensure year-round comfort. Outside, 70 feet of dockage and a 27,000-pound boat lift make this property a dream for boating enthusiasts, with quick access to both the Atlantic Ocean and Florida Bay. The resort-style backyard is ready for endless summer fun, featuring a sparkling pool, expansive sun deck, shady lounging area, and abundant storage for all your fishing, diving, and water sports gear. Whether you're entertaining friends, heading out for a day on the water, or simply relaxing poolside, this exceptional Venetian Shores home offers the perfect blend of coastal sophistication and waterfront adventure.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,352
Status:
Active
MLS#:
620393
Type:
Condo/Townhouse
Subdivision:
Executive Bay (87.0)
Year built:
1980
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada 305-664-4444
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ADDITIONAL INFORMATION

Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. The main level features an open-concept floor plan with a spacious living area and kitchen, plus full bath, creating an inviting space for entertaining and everyday living. Upstairs, you'll find an expansive primary suite, a generously sized guest bedroom and full bathroom, and a thoughtfully finished loft accessed from the hallway that serves as an ideal bonus sleeping area or home office. Step outside and enjoy the exceptional amenities that make Executive Bay Club one of Islamorada's most sought-after waterfront communities. Residents have access to the newly expanded first-come, first-serve dockage, a bayfront beach area, unforgettable sunsets, and a new heated swimming pool complete with an updated pool deck, clubhouse and bath facilities, pickleball and tennis courts, kayak storage and 24/7 staffed gated entry. Whether you're searching for a full-time residence, vacation retreat, or investment opportunity, this welcoming townhouse offers the ideal blend of island charm to enjoy the Florida Keys lifestyle.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,384
Status:
Active
MLS#:
620353
Type:
Single Family
Subdivision:
Lower Mat Bch (74.0)
Lot size:
0.15 Acres
Year built:
1984
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of newly decked dockage along the tranquil ''Sleepy Lagoon'', this exceptional property combines relaxed island living with effortless boating access to both the ocean and bay. The light-filled second floor features an open-concept living, dining, and kitchen area with soaring cathedral ceilings and new vinyl flooring throughout. The recently remodeled kitchen showcases new cabinetry, stainless steel appliances, and an inviting layout ideal for entertaining. Two bright bedrooms with laminate flooring are located on this level, including a spacious primary with en-suite bath. Step outside onto the expansive second-floor balcony and enjoy breathtaking lagoon views while watching manatees glide by and fish jump in the tranquil waters below. The first floor offers additional flexible living space with an open bedroom/living area and full bath, featuring sliding glass doors that lead directly to the tropical backyard, pool, and dock. Designed for comfort and convenience, this fully turnkey home includes well-maintained accordion shutters on all non-impact windows, generous storage space for water toys and gardening equipment, and a securely anchored storage shed. Outdoor living is truly exceptional. Relax beneath the airy chickee hut, cool off in the in-ground pool after a day on the water, or entertain family and friends with freshly grilled BBQ favorites in the private backyard oasis. Additional features include a JetDock, fish cleaning station, spacious outdoor shower, fenced backyard for pets, and ample parking for boats, trailers, RVs, and recreational equipment. Residents may enjoy access to a beautiful sandy beach within the subdivision through a voluntary HOA membership. The beach is a protected turtle nesting habitat.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,845
Status:
Active
MLS#:
620271
Type:
Condo/Townhouse
Subdivision:
Sandglass (74.5)
Year built:
1989
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly sought-after Lower Matecumbe. This exceptional 5-bedroom, 3-bath residence combines contemporary design with breathtaking water views, creating a truly unique island retreat. The thoughtfully designed layout features three spacious bedrooms on the lower level and two additional bedrooms upstairs, connected by a spectacular modern staircase that serves as a striking architectural centerpiece. Soaring ceilings and expansive windows fill the home with natural light, while the open-concept floor plan seamlessly connects the living, dining, and entertaining spaces. The sleek, modern kitchen is perfectly positioned to serve both everyday living and waterfront gatherings. Generously sized bedrooms and beautifully appointed bathrooms provide comfort and privacy for family and guests alike. Step outside to an impressive 667-square-foot waterfront screened deck overlooking the tranquil lagoon, offering the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Boaters will appreciate the deep-water dockage featuring a large boat slip and 16k boat lift, with convenient access to both the Atlantic Ocean and Florida Bay. Enjoy stunning views of the bayside lagoon and the ocean, along with world-class fishing, diving, and boating right from your backyard. Additional amenities include covered parking and ample storage space for all your water toys. Offering the perfect blend of modern elegance, waterfront living, and premier boating access, this remarkable Lower Matecumbe property is a rare opportunity to own a piece of paradise in one of Islamorada's most desirable locations. Onsite property management for true peace of mind.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,337
Status:
Active
MLS#:
620243
Type:
Condo/Townhouse
Subdivision:
Misc Plantation Key (85.0)
Year built:
1980
Courtesy: EXP Realty, LLC 888-883-8509
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ADDITIONAL INFORMATION

Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situated next to Founders Park, this gated bayfront community offers an unbeatable combination of location, lifestyle, and investment potential. One of the standout features of this residence is the rare open kitchen layout, creating a more spacious and inviting main living area ideal for everyday living or entertaining. EBC is highly desirable for boaters and investors alike, with first-come, first-served dockage available for boats, immediate bay access, and quick ocean access via Snake Creek and Tavernier Creek. Residents and guests enjoy a private sandy beach with beautiful sunset views, plus community amenities that include a renovated pool and clubhouse, tennis courts, pickleball courts, BBQ area, kayak launch, kayak storage, trailer parking, and secure gated entry. Short-term rentals are allowed with a 28-day minimum, making this an excellent opportunity for full-time living, a vacation getaway, or an income-producing property. Located in the heart of Islamorada and within walking distance to Founders Park events, recreation, and nearby dining, this property offers the ideal blend of waterfront enjoyment, boating convenience, and rental flexibility in one of the Florida Keys' most desirable communities.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,352
Status:
Active
MLS#:
A12034985
Type:
Other
Subdivision:
EXECUTIVE BAY CLUB
Year built:
1980
Courtesy: EXP Realty, LLC Luis Ruiz 305-978-4463
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ADDITIONAL INFORMATION

Discover the Florida Keys lifestyle at Executive Bay Club Unit K5, one of Islamorada’s hidden gems and an ideal retreat for boaters, vacation-home buyers, investors, and anyone seeking the perfect island escape. Located just about one hour from Miami, this residence offers the best of Keys living with easy access to world-class fishing, boating, dining, beaches, and waterfront recreation. Perfectly positioned steps from the community pool, Unit K5 also allows you to enjoy beautiful bay views right from your backyard, creating the ideal setting for morning coffee, sunset relaxation, and effortless island living. Executive Bay Club is a gated bayfront community offering resort-style amenities, including a private beach, renovated clubhouse, sparkling pool, tennis courts, basketball, pickleball, and beautifully maintained common areas. Boaters will appreciate the first-come, first-served dockage and convenient access to both Tavernier Creek and Snake Creek, making ocean and bay adventures easily accessible. Perfect as a primary residence, weekend getaway, vacation home, or income-producing property, Unit K5 offers excellent short-term rental and Airbnb potential, subject to community and local rental guidelines. Close to Founders Park, local marinas, restaurants, shops, and everything that makes Islamorada one of the most desirable destinations in the Florida Keys.

Beds:
2
Baths:
2.00
Sq.Ft.:
989
Status:
Active
MLS#:
620217
Type:
Condo/Townhouse
Subdivision:
Plant By The Sea (87.5)
Year built:
1977
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada 305-664-4444
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ADDITIONAL INFORMATION

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.

Beds:
6
Baths:
7.00
Sq.Ft.:
5,100
Status:
Active
MLS#:
620190
Type:
Single Family
Subdivision:
Safety Harbor (74.0)
Lot size:
0.24 Acres
Year built:
2025
Courtesy: Fairchild Partners, Inc. 305-668-0620
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ADDITIONAL INFORMATION

Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the home's exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the property's thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. Not included in the listed square footage is a 488 SF garage and over a thousand square feet of covered patio. This home is perfect for the indoor/outdoor entertainer. A true statement of coastal luxury—this is Florida Keys living at its finest.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,672
Status:
Active
MLS#:
620173
Type:
Condo/Townhouse
Subdivision:
Coral Harbour (88.0)
Year built:
1979
Courtesy: Coldwell Banker Schmitt Key Largo 305-451-4422
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ADDITIONAL INFORMATION

''Rare 30' Deeded Boat Slip Included Ocean & Lagoon Views Direct Ocean Access'' The Ultimate Florida Keys Waterfront Lifestyle. Boaters, anglers, and waterfront enthusiasts will appreciate this exceptional opportunity to own a spacious 2-bedroom, 2-bath residence with a highly sought-after 30-foot deeded boat slip and direct ocean access in the gated Coral Harbour Club community. Offering 1,672 square feet of living space and one of the largest floor plans in the community, this bright and open residence captures stunning ocean views, peaceful lagoon vistas, and spectacular Florida Keys sunsets. The expansive open-concept design seamlessly connects the living, dining, and kitchen areas, creating an inviting space for entertaining or simply relaxing after a day on the water. Step outside and enjoy immediate access to some of the world's best fishing, diving, snorkeling, and boating destinations. Whether heading offshore, exploring nearby reefs, or cruising to waterfront restaurants, your boat is conveniently located just steps from your residence. Additional features include an elevator located directly outside the unit, covered parking beneath the building, and a nearby electric vehicle charging station. Coral Harbour Club offers an unmatched collection of resort-style amenities, including a private sandy lagoon beach, full-service marina with boat ramp, fuel and ice services, direct ocean access, oceanfront swimming pool, tennis and pickleball courts, bocce ball, kayak storage, compressed air station, and beautifully maintained grounds. Whether you're searching for a full-time residence, vacation retreat, or investment property, this waterfront escape delivers the perfect combination of boating convenience, resort amenities, and the relaxed luxury of the Florida Keys lifestyle.

Beds:
1
Baths:
1.00
Sq.Ft.:
550
Status:
Active
MLS#:
B26036550
Type:
Residential
Subdivision:
HOTEL CONDOMINIUM AT CHEECA LODGE, BLDGS 1 8 (6
Year built:
1988
Courtesy: United Realty Group, Inc 561-235-2127
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ADDITIONAL INFORMATION

Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Great vacation and income producing condotel in the Sport Fishing Capital of the World. This 27-acre oceanfront Islamorada resort set in a lush tropical landscape has everything from fine dining restaurants, spa and wellness, fitness center, three resort style pools, two tiki bars, par 3 golf course, four lighted tennis courts, pickleball, basketball, bicycles, huge pier for fishing, kayaking, paddleboarding, and more. This top floor corner unit is a beautifully appointed one king bedroom with expansive master bath, kitchen and private screened in balcony. Accomplished on-site professional management has delivered high occupancy and rental rates far above many other lodging properties in the Keys!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,079
Status:
Active
MLS#:
A12029820
Type:
Other
Subdivision:
ISLAMORADA SOUTH
Year built:
1980
Courtesy: Pena Realty, Inc. Ralph Pena 305-448-5241
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ADDITIONAL INFORMATION

This island resort unit offers stations for dockage up to 25-foot boats daytime only, trailer storage and boat ramp. There is a pool for the development, pickle ball and tennis courts. The unit has hurricane impact windows as well as updated balcony area. It offers a large garage area with plenty of storage space. Injoy island living in the Keys .

Beds:
5
Baths:
3.00
Sq.Ft.:
2,759
Status:
Active
MLS#:
620127
Type:
Single Family
Subdivision:
Venetian Shores (86.0)
Lot size:
0.16 Acres
Year built:
1995
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada 305-664-4444
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ADDITIONAL INFORMATION

Welcome to one of Islamorada's finest homes! Located in Venetian Shores the premier boating community of Islamorada. One of only two streets in the neighborhood with curbs and street drainage system. 70ft of deep water dockage and 100ft wide canal. Direct Ocean and Bay access via Snake Creek. Draw bridge to ocean for yachts and tower boats. This home is a must see! Extremely clean and well maintained home. Fantastic layout. Upstairs you have a little over 1,900 sq ft of living space all on one floor - which includes your kitchen, living room, dining room, 3 large bedrooms and 2 bathrooms. Downstairs you have your rec room with 2 bedrooms, cabana bath and tackle room/workshop. Solid concrete construction designed to offer peace of mind during hurricane season. Conveniently located close to restaurants, shopping, Publix, schools, and hospital.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,182
Status:
Active
MLS#:
A12028354
Type:
Single Family
Subdivision:
WHITE MARLIN BEACH SEC 1
Lot size:
0.16 Acres
Year built:
2017
Courtesy: Langley Knight Gardner Islamorada Kelsey Caputo
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ADDITIONAL INFORMATION

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.

Beds:
1
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
620105
Type:
Mobile Home
Subdivision:
Galen Beach (85.0)
Lot size:
0.03 Acres
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada 305-664-4444
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ADDITIONAL INFORMATION

ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this charming home is perfectly situated in the heart of Islamorada. Offering 1 bedroom, 1 bathroom, and a versatile loft space, the interior provides comfortable living with a relaxed Florida Keys atmosphere. Step outside to the open porch, the perfect spot to enjoy the island breeze. Ideally located near renowned waterfront dining, local breweries, boutique shopping, and all the attractions that make Islamorada one of the most desirable destinations in the Keys. Residents benefit from a recently completed sewer system upgrade, with no known upcoming assessments. Low monthly HOA fees of just $149 cover common area and road maintenance. Don't miss this opportunity to own your own slice of paradise in the Sport Fishing Capital of the World and experience the laid-back lifestyle that makes the Florida Keys so special.

Beds:
6
Baths:
9.00
Sq.Ft.:
6,573
Status:
Active
MLS#:
620077
Type:
Single Family
Subdivision:
Misc Plantation Key (85.0)
Lot size:
3.2 Acres
Year built:
2014
Courtesy: Coldwell Banker Schmitt Islamorada 305-664-4470
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ADDITIONAL INFORMATION

Yes, you can have it all! Tucked away behind mature tropical landscaping and stretching across an expanse of more than 250 feet of sandy bayfront shoreline, 139 Gimpy Gulch is a rare Islamorada estate designed for those who value privacy, boating, sunsets and effortless luxury in equal measure. This one-of-a-kind compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through private gates to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, a new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. This one-of-kind package also includes a 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The 100 ft. long resort-style pool with large spa create the centerpiece of the property, surrounded by multiple lounging areas, outdoor kitchen with covered bar, shady terraces and intimate gathering spaces. The estate's flexible layout includes two homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes offer chef kitchens with high-end appliances including SubZero and La Cornue. Not only is this estate ready for fun, it's also ready to enjoy with furniture, decor, kitchenware and even linens included! This remarkable property includes 2 acres of upland, 1.2 acres of baybottom, the separate vacant lot plus valuable development rights. It is also conveniently located next to Islamorada's crown jewel Founder's Park for near instant access to seasonal festivals, sports fields, dog park, playground, tennis and pickleball courts and much more. All of these features elevate the property into a true legacy holding--ideal as a luxury residence, family compound, or private bayfront retreat.

Beds:
1
Baths:
1.00
Sq.Ft.:
468
Status:
Active
MLS#:
620039
Type:
Mobile Home
Subdivision:
Unplatted Windley Key (88.0)
Lot size:
0.03 Acres
Year built:
2015
Courtesy: American Caribbean Real Estate, Christie's International Real Estate 305-664-4966
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ADDITIONAL INFORMATION

Memories begin here. Tucked along the ocean's edge and offering the kind of lifestyle buyers spend years searching for, this one-of-a-kind oceanfront retreat delivers the ultimate Florida Keys escape all for under $1M! What is unique about this property is the 40' protected boat slip located right out your back door. This unit is conveniently located offering quick access to the ocean or the bay and the Islamorada sandbar is within view. The elevated tiki with panoramic ocean vistas that make every sunrise, lunch, happy hour, and sunset unforgettable. Inside, the cottage is light, coastal, and move-in ready with an inviting open layout that keeps the focus where it belongs--on the view and the lifestyle. Whether you're looking for a weekend getaway, fish camp, vacation retreat, or memory-making waterfront hideaway, opportunities like this are incredibly rare. Bring the boat. Bring the family. Start making memories.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,736
Status:
Active
MLS#:
620016
Type:
Condo/Townhouse
Subdivision:
Ocean Harbor (87.5)
Year built:
1989
Courtesy: American Caribbean Real Estate, Christie's International Real Estate 305-664-4966
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ADDITIONAL INFORMATION

Ocean Harbour condo with Atlantic ocean views and a boat slip in Islamorada. 3 bedroom, 2 bathroom luxury condo offers expansive ocean views and comfortable living space. The thoughtfully redesigned floor plan enhances the primary suite layout, adds a third bedroom, updates both bathrooms, and expands the living area by enclosing the porch as additional interior living space; maximizing functionality, comfort, and guest accommodations. Features updated appliances, hurricane impact glass, boat slip #33 and one covered parking space. Elevated waterfront living within this premier gated community featuring beach areas, oceanfront clubhouse, swimming pool, spa, gym, pickleball and tennis courts, EV charging station, boat ramp, and boat trailer storage. The beach tiki is ideal for entertaining with a grill, ice maker, and TV. Pets allowed with restrictions. Enjoy boating, fishing, kayaking, paddle boarding, nearby restaurants, medical care, boutique shopping, and art galleries. Bring your boat and experience the best of Florida Keys waterfront living.

Beds:
2
Baths:
2.00
Sq.Ft.:
989
Status:
Active
MLS#:
620020
Type:
Condo/Townhouse
Subdivision:
Plant By The Sea (87.5)
Year built:
1977
Courtesy: Coastal Realty of the Florida Keys 305-664-0077
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ADDITIONAL INFORMATION

Located in Plantation by the Sea, this Islamorada townhouse offers 2 bedrooms, 1.5 bathrooms, covered parking, and a storage unit in a gated oceanfront complex. Inside, the unit has been updated with renovated kitchen, bathrooms, and flooring. Both upstairs bedrooms feature open balconies, along with an additional balcony off the living room for added outdoor space. The upstairs layout includes 2 bedrooms and 1 full bathroom, while the half bath is conveniently located downstairs. Community amenities include a covered parking space, plenty of guest parking, storage unit, workout room, sauna, kayak and paddleboard storage, bicycle storage, clubhouse, and gated entry. Conveniently located near Founders Park, Islamorada's community park offering a beach, Olympic-size swimming pool, tennis courts, pickleball courts, ball fields, and an amphitheater.

Beds:
7
Baths:
10.00
Sq.Ft.:
8,288
Status:
Active
MLS#:
A12022973
Type:
Single Family
Subdivision:
Islamorada
Year built:
2017
Courtesy: Ocean Sothebys Intl Realty Gonzalo Del Negro 305-842-0559
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,152
Status:
Active
MLS#:
619965
Type:
Multi-Family
Subdivision:
Port of Call (88.5)
Lot size:
2,052 Acres
Year built:
1991
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Welcome to Port of Call--an intimate oceanfront enclave on Plantation Key where refined coastal living meets the effortless rhythm of the Florida Keys. Tucked within this exclusive 10-residence boutique community, 136 Aregood Lane offers a rare blend of luxury, privacy, and true serenity. This beautifully appointed 2-bedroom, 2.5-bath townhome is designed for both relaxation and adventure, featuring weekly rental eligibility, assigned dockage, a community pool, and a private rooftop deck with sweeping ocean views. Flooded with natural light, the main living level flows seamlessly to a private balcony where gentle breezes and glimpses of turquoise water set the tone for quiet island living. The thoughtful floor plan provides generous space for entertaining, while the additional half bath on this level ensures comfort for guests. Upstairs, two spacious en-suite bedrooms--each with its own balcony--offer peaceful retreats after a day on the water. With all impact windows and doors, the home delivers both beauty and peace of mind, allowing you to enjoy the Keys lifestyle with ease. For boating enthusiasts, the assigned boat slip with direct ocean access opens the door to world-class fishing, diving, and cruising. Spend your days exploring the Atlantic, then return to unwind by the community pool or stroll the private beach area as the sun dips below the horizon. Perfectly positioned in the heart of Islamorada, you're just minutes from Islamorada's renowned dining, shopping, and cultural experiences--yet worlds away from the everyday. Whether you envision a full-time residence, a weekend escape, or a high-demand investment property, this exceptional townhome delivers unmatched flexibility with its weekly rental capability and coveted oceanfront amenities. Port of Call is a place where luxury feels effortless, the ocean is your backyard, and every day begins with possibility.

Beds:
1
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A12017273
Type:
Mobile Home
Subdivision:
WINDLEY KEY MOBILE HOME P
Lot size:
0.02 Acres
Year built:
1980
Courtesy: Luft Realty 305-529-6245
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ADDITIONAL INFORMATION

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.

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Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited. © 2026 MIAMI Association of REALTORS®, all rights reserved.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.




Islamorada 33036 Real Estate

Islamorada is located in Florida. Islamorada, Florida 33036has a population of 7,051. Islamorada 33036 is less family-centric than the surrounding county with 16.45% of the households containing married families with children. The county average for households married with children is 20.65%.

The median household income in Islamorada, Florida 33036 is $77,423. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Islamorada 33036 is 55.3 years.

Islamorada Weather

The average high temperature in July is 89.3 degrees, with an average low temperature in January of 62 degrees. The average rainfall is approximately 47.7 inches per year, with 0 inches of snow per year.

Islamorada Map

Islamorada Real Estate Market Conditions

  • Median sales price

    $1,850,000
    26.6%
    change since last quarter
  • # Active listings

    227
    30-day change

Islamorada Schools and Demographics

Education near Islamorada, FL

City County
High School Graduates 96.13 92.07
College Degree - 2 year 10.44 7.93
College Degree - 4 year 39.54 35.69
Graduate Degree 11.76 9.88
Expenditures per Student 20,907 20,907
Students per Teacher 14.7 14.7

Elementary Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Big Pine Academy PK - 08 177 12.6 33043
Gerald Adams Elementary School PK - 05 544 13.3 33040
Horace O'Bryant School PK - 08 1,059 14.3 33040
Key Largo School PK - 08 847 14.1 33037
Key West Montessori Charter School KG - 08 149 16.6 33040
Monroe Virtual Instruction Program (District Provided) KG - 05 6 33040
Ocean Studies Charter KG - 05 104 11.2 33070
Plantation Key School PK - 08 435 12.8 33070
Poinciana Elementary School PK - 05 663 15.1 33040
Sigsbee Charter School KG - 08 478 17.1 33040
Stanley Switlik Elementary School PK - 05 566 14.2 33050
Sugarloaf School PK - 08 526 15 33042
Treasure Village Montessori Charter School PK - 08 213 14.2 33036

Middle Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Glynn Archer Elementary School PK - 05 394 15.8 33040

High Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Coral Shores High School 09 - 12 733 17.4 33070
Key West Collegiate School 09 - 12 78 15.3 33040
Key West High School 09 - 12 1,193 16.8 33040

Ungraded Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
* Keys Center 08 - 12 11 11 33040
Academic Connections for Excellence 06 - 12 11 33040
Adult/Vocational/Community Education AE - AE 0 33040
Hurricane Island Outward Bound 06 - 12 12 33037
Marathon School 06 - 12 667 18.5 33050
Monroe Virtual Academy (Course Offerings) 06 - 12 0 33040
Monroe Virtual Franchise 06 - 12 4 33040
Monroe Virtual Instruction Program KG - 12 0 33040

Demographics near Islamorada, FL 33036

Zip Code City
Neighborhood Type Small town
Population 7,051 82,244
Population Density 1,094 84
Median Age 55.3 48
People per Household 2.2 2.4
Median Household Income 77,423 73,153
Average Income per Capita 60,315 50,050

Real estate near Islamorada