Islamorada Real Estate Search

Newest Islamorada Homes and Condos for Sale

$400,000
619203 MLS
This is for the sale of 1 (one) Waterfront Transferable Development Right (TDR aka TBR) for use in The Village only. Buyer to pay ALL closing costs associated with the transaction and the transfer fee to The Village. The sale DOES NOT include any real property. Buyer must have an eligible property to which the rights can be transferred.

Waterfront Waterfront Tdr, Islamorada
$3,800,000
4 Beds ⋅ 5 Baths ⋅ 619187 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 15, Islamorada
$4,000,000
4 Beds ⋅ 5 Baths ⋅ 619186 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 8, Islamorada
$4,000,000
4 Beds ⋅ 5 Baths ⋅ 619185 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for either full time residency or effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 7, Islamorada
$4,445,000
8 Beds ⋅ 4 Baths ⋅ 619083 MLS
Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique and valuable than others, we offer 100 linear feet of dockage. There is a 30,000 pound lift for your large boats and a 10,000 lift for your smaller boats. And there is still room for another vessel or personal water crafts. This home offers three levels, the main level has three bedrooms a full bath a kitchenette and living area with great views of the water. The second level, large living area with soaring ceilings, a massive kitchen, 2 bedrooms and a full bath. The third level offers 3 bedrooms and 2 full baths. There is an abundant pool and bar area for entertaining family and friends. Looking for a home to accommodate the large extended family, this is it or put it out in the Airbnb world, it would make a great income property.

136 San Remo Dr, Islamorada
$3,999,999
2 Beds ⋅ 2 Baths ⋅ 619064 MLS
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, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. An existing legal nonconforming home with a waterfront swimming pool currently sits on the property and may be used as a residence or rental while architectural plans and permits are finalized, offering flexibility during the planning process. For buyers who understand the value of land in the Florida Keys, this offering represents something increasingly difficult to find: the opportunity to create a custom waterfront estate tailored entirely to your vision, rather than inheriting someone else's. A remarkable parcel for a remarkable build.

77340 Overseas Hwy, Islamorada
$630,000
3 Beds ⋅ 2 Baths ⋅ 619040 MLS
If you're looking for a property with potential in a highly desirable area of Islamorada and are prepared to put in the work, this is an opportunity worth considering. Sellers are motivated and will entertain offers. This 3-bedroom home offers a chance to purchase in one of Islamorada's most desirable areas and update the property to fit your needs, investment goals, or long-term plans. The home sits on an oversized lot and features a functional floor plan with generously sized rooms and a kitchen that opens to the living and dining areas. The concrete construction and larger homesite provide a solid starting point for renovation and improvement. Located directly across from Founder's Park, the property offers convenient access to a bayfront beach, community pool, public boat ramp, baseball fields, playgrounds, dog park, and community events throughout the year. The oversized lot also provides additional outdoor space compared to many nearby properties.

110 E Ridge Rd, Islamorada
$4,500,000
3 Baths ⋅ 618928 MLS
Beautiful 100' of oceanfront property on Lower Matecumbe Key. This offering consists of a 100' lot with a triplex apartment building (3 TDRs),.This gives you lots of possibilities for redevelopment of the property. Fantastic near 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Note: One of the owners is a State of Florida Real Estate Licensee

75131 Overseas Hwy, Islamorada
$4,900,000
618920 MLS
Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal for a comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This remarkable bayfront estate offers endless possibilities in an unparalleled setting.

150 List St, Islamorada
$4,900,000
1 Beds ⋅ 1 Baths ⋅ 618918 MLS
Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to secure a premier bayfront parcel in one of Islamorada's most sought-after locations. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This vision blends refined indoor living with outdoor elegance, creating a seamless waterfront sanctuary. Whether you envision a private coastal retreat or an entertainer's paradise, this remarkable bayfront estate offers endless possibilities in an unparalleled setting.

150 List St, Islamorada
$15,990,000
6 Beds ⋅ 9 Baths ⋅ 618911 MLS
Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival. Set on over 2 usable acres with 210 feet of private sandy beachfront and a protected cove, the residence spans 7,590 square feet of interior living space & 1,736 square feet of exterior living, with an expansive 230-foot dock. Designed for seamless indoor-outdoor living, the home features a dramatic great room with 23-foot ceilings, panoramic Atlantic exposure, and expansive covered terraces with summer kitchen and outdoor dining areas. A 65-foot heated lagoon-style pool with swim-up bar and fire-pit lounge creates a resort-caliber setting. The chef's kitchen is appointed with Sub-Zero, Wolf, and Thermador appliances. Additional highlights include dual primary suites, private orchid garden, lounge & recreation room, elevator, Sonos surround sound, impact windows and doors, metal roof, double-height garage, water-sports storage room and a full home generator. The essence of beachfront living in Islamorada, combining impressive scale and ultimate privacy. ***A contiguous 0.7-acre lot with development rights for an ancillary building with upstairs storage is available separately.

88351 Old Hwy, Islamorada
$4,645,000
618904 MLS
Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with an active permit and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus another .24 acres of bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

75750 Overseas Hwy, Islamorada
$1,150,000
2 Beds ⋅ 3 Baths ⋅ 618212 MLS
ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community that allows Vacation Rentals, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades include Brazilian Cherry hardwood floors, kitchen with granite countertops and SS appliances with 2 breakfast bars & tons of cabinet space. The home also has a composite decking & railing, a metal roof & impact doors & windows. The community features 2 sandy beaches, a pool & marina on the Atlantic Ocean. Home has been in rental program for many years with a good following. Own your vacation home for free & more. Great investment. Call today for a showing!

102 Anglers Way, Islamorada
$3,995,000
5 Beds ⋅ 3 Baths ⋅ 618653 MLS
Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling approximately 1,500 square feet, and 2 bedrooms and 1 bathroom downstairs totaling approximately 1,140 square feet. The private resort-style backyard features a heated pool with sun shelf, hot tub, expansive patio, hammock lounge, and mature palms creating a true tropical setting. Enjoy deep-water canal frontage with 70 feet of dockage and two boat lifts rated at approximately 15,000 pounds and 20,000 pounds, providing exceptional boating capacity. Located on one of Venetian Shores' desirable 100-foot-wide canals, the property offers generous maneuvering space and convenient access to both the Atlantic Ocean and Florida Bay through nearby Snake Creek, making offshore fishing and backcountry boating easily accessible within minutes. The custom tiki pavilion includes a full outdoor kitchen with built-in grill, refrigeration, sink, bar seating, mounted TV, and generous space for hosting gatherings year-round. Inside, the bright open-concept living area showcases vaulted ceilings with exposed beams, abundant natural light, and French doors that create seamless indoor-outdoor flow to the balcony overlooking the canal. The primary suite offers balcony access, dual vanities, soaking tub, glass-enclosed shower, and walk-in closet. A gated brick driveway provides generous parking, and the home is offered furnished for immediate enjoyment or continued use as a full-time residence, seasonal escape, or investment opportunity. This Venetian Shores waterfront property delivers the location, spacious layout, wide canal setting, and boating infrastructure buyers are searching for in the Florida Keys.

105 Palo De Oro Dr, Islamorada
$15,950,000
6 Beds ⋅ 8 Baths ⋅ 618816 MLS
BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The residence includes 6 bedrooms, 7.5 bathrooms and was designed to blend coastal elegance with effortless waterfront living. In addition to the bedrooms, the main home provides a complete gym and office. A separate guest house includes a living room, full kitchen, laundry room, and two bedrooms with ensuite bathrooms. Located in the heart of Islamorada, the home is walkable to several restaurants. Agents Welcome

20 Avacado St, Islamorada
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Islamorada Homes for Sale

Stretching across just over seven square miles halfway between Key West and South Miami, the waterfront community of Islamorada is a great place to buy a home in Monroe County, Florida. Encompassing Tea Table Key, Upper and Lower Matecumbe Key, Windley Key, and Plantation Key, the community is also called Village of Islands. The community was just a part of Upper Matecumbe Key until it was incorporated in 1977. It is located in the center of the one-hundred-mile-long Florida Keys, between Mile Markers 72 and 90. Altogether its four islands span eighteen linear miles with a thin land area of just under four thousand acres.

This naturally beautiful community has strict land development regulations as do most of the islands in the Florida Keys. It is an incredibly popular destination for anglers, particularly in the backcountry that abuts the Gulf of Mexico. In fact, it is known as the Sport Fishing Capital of the World. It also has fabulous fishing opportunities on the opposite shore, conveniently out of reach from the Gulf Stream. Home to just over six thousand, six hundred people, Islamorada sees a lot of second-home owners and vacationers and offers a wide variety of services and amenities. For example, there are some fabulous micro-beer breweries, art galleries, shops, and restaurants here, including must-try places like Whale Harbor Restaurant, Pierre’s, Kaiyo Grill & Sushi Bar, Ziggie & Mad Dogs, and Chef Michaels, to name a few.

Islamorada is also home to beautiful sandbars and parks, including Founders Park which encompasses a sandy beach, aquatic center, and Plantation Yacht Harbor Marina and its eighty-three wet slips. All of these advantages contribute to the irresistibility of Islamorada real estate. Real estate in Islamorada include stunning oceanfront estates, two- and three-story stilt homes, and a variety of oceanfront condos. There are roughly five thousand seven hundred homes in this Village of Islands, and they include Islamorada oceanfront homes and inland properties. These also include Islamorada vacation homes. Whatever it is you seek, we would love to share details about specific properties available in Islamorada, Florida, so please contact us today so we can help you with your Islamorada home search.

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