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Windley Key Homes for Sale, Single Family Houses, MLS Home Listings

Houses for sale in Windley Key, located in the Middle Florida Keys, can be found in the stunning Islamorada real estate market.  Buyers in the market for properties in the Florida Keys that allow for great fishing, eating, and entertaining nearby will find what they are looking for with homes in Windley Key.  The Windley Key real estate market offers spectacular luxury homes in a beautiful setting.  Great Windley Key homes for sale can be found in neighborhoods such as the ever popular Angler's Reef, a stunning oceanfront gated community.  View all Windley Key properties in the Florida Keys MLS.

Total Listings 5
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$449,000
Windley Key
Windy Cove   - MM: 84.00
2 Bed, 2 Baths, 800 SqFt Days Listed: 18
PreConstructi - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Othe

RARE OCEANFRONT LOT OPPORTUNITY IN ISLAMORADA! BUILD w/ NO DELAYS -your dream waterfront home in the fabulous Florida Keys--this prime buildable lot comes with a Development Right Letter in hand from the Village of Islamorada. Enjoy unobstructed ocean views and multi-million dollar scenery, with the flexibility to build a CBS or modular home on stilts (2BD/2BA engineered plans included). The owner also has a $250K quote for a top-of-the-line Jacobsen modular home for a turnkey option. Max height to build 35ft allowing a 2 story home if one desires. Currently, there is a livable 1BD/1BA RV on-site (RV must be replaced with a home). The lot is solid coral rock--no fill needed! This boaters paradise offers dock privileges, boat storage, a private boat ramp, and a fish cleaning station. Located in a private 48-unit community with low HOA fees, pet-friendly policies (two pets, any size), and just minutes from downtown Islamoradas restaurants, shops, grocery stores, the Art District, and a scenic bike path. Experience breathtaking sunrises and sunsets from your future home--dont miss this rare chance to own a slice of paradise in the Florida Keys! ☀️🌊

$1,199,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,376 SqFt Days Listed: 89
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Other Dockage

ANGLERS REEF HOMEf, Islamoradas Upscale Oceanfront Gated Community, 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, 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!

$1,325,000
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,620 SqFt Days Listed: 26
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your perfect getaway in the heart of the Florida Keys! This beautifully updated 2-bedroom, 2.5 bathroom townhouse is located in Islamorarda in a resort-style community with fantastic amenities. Whether youre looking for a vacation home, an investment property, or both, this tropical retreat offers everything you need.Enjoy an open-concept living space with abundant natural light, a fully equipped kitchen, and spacious bedrooms with en-suite bathrooms. Step outside to your private balcony or patio and soak in the island breeze. This townhome is the only property in association that is situated on two lotsThe community features a sparkling pool, a marina with boat dockage. With weekly rentals allowed, this property is a fantastic income opportunity in a high-demand tourist destination.Located just minutes from world-class fishing, boating, snorkeling, and dining, this townhouse offers the ultimate Florida Keys lifestyle. Dont miss out on this rare opportunity--schedule your private tour today!

$1,999,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,674 SqFt Days Listed: 201
-6.98% ($150,001) 1 Price Change : Last Change 35 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip31ft.

ANGLERS REEF OCEANFRONT HOME WITH DEEDED DOCK. RARE OPPORTUNITY to own an oceanfront home in the prestigious Anglers Reef development in Islamorada. Deeded boat slip accommodating up to a 31 ft boat included in offering. A beautiful 2-bedroom, 2.5-bath, 2-story home with 2 porches and a balcony overlooking the Atlantic Ocean. Located in the gated community of Anglers Reef on Windley Key approximately half way between Miami and Key West. This property contains 2 large bedroom suites with bathrooms on the 2nd floor. A living room, kitchen, dining room and powder room on the main level. Looks out on the community pool and marina (see included video). Upgrades include impact windows/doors, metal roof, composite decks/railings, granite counter tops with wood cabinets, tile floors downstairs and bamboo floors upstairs, shutters/blinds, brand new dishwasher and refrigerator. The community features 2 sandy beaches, pool, gated entry, marina, kayaks and paddle boards. Perfect home for primary residence, vacation family home or investment property. Call today for a showing

$2,795,000
Windley Key
Galen Beach   - MM: 85.00
4 Bed, 4 Baths, 2,880 SqFt Days Listed: 342
-6.68% ($200,000) 3 Price Changes : Last Change 17 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

WEEKLY RENTALS to be allowed with new Zoning Change. Potential SELLER FINANCING AVAILABLE!!! Brand new oceanfront Concrete Home. Coastal-inspired masterpiece with wood plank porcelain tile flooring.Panoramic ocean views from the spacious living areas, including the kitchen, dining room, and master suite. Elevator to all 3 floors. The gourmet kitchen with quartz countertops, high-end GE appliances, and a stunning 10 island perfect for entertaining. Stroll directly out onto your private 2nd floor oceanfront pool complete with waterfall and poolside bar.Enjoy gorgeous Ocean Views from the Living Room, Dining Room, Kitchen, and Master Suite. Kitchen features Quartz Countertops, White Cabinetry, 48 Fridge and a 10 Island. Third Floor Primary Bedroom has Vaulted T&G ceiling, Built in Audio, and a Private 12 x 31 Balcony with Stunning Ocean Views of Snake Creek to Alligator Lighthouse.Plans for a 295 Observation Deck are Approved w/ Permit in Hand from Army Core and DEP. Super convenient to Numerous Popular Restaurants and Boat Marina with Storage. DOCKAGE AVAILABLE AT VERY CLOSE BY MARINA. Availability subject to change.* Zoning and FLUM change not complete yet. State and 2nd village council reading still to be completed. Owner is a Licensed Florida Real Estate Agent.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 04-19-2025.
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