Chokoloskee - Chokoloskee, FL Homes for Sale - Search All Homes & Real Estate for Sale in Chokoloskee Chokoloskee, Florida

Escape the ordinary and own a piece of Old Florida at 1227 Mangrove Lane! Set in the heart of historic Chokoloskee, this spacious multi-family property delivers 5 bedrooms and 4 baths with incredible flexibility for owner occupants, investors, seasonal owners, extended families, or anyone dreaming of an island retreat with income potential. Concrete block construction and a durable metal roof provide a solid foundation, while public water and sewer, central HVAC and room for a pool add everyday convenience. Step outside and you’re surrounded by the legendary beauty of the Ten Thousand Islands—where world-class fishing, boating, kayaking and endless backwater adventures are part of the lifestyle. Use one side and rent the other, create a seasonal getaway, or build your investment portfolio in one of Southwest Florida’s most unique coastal communities. This isn’t cookie-cutter Florida—it’s laid-back, authentic island living where the water, wildlife and adventure are never far away. Bring your boat, bring your fishing rods, and bring your vision!

1227 Mangrove Lane, Chokoloskee

Listing courtesy of RE/MAX PROFERE. 612-865-3158

$494,900

5 Beds ⋅ 4 Baths ⋅ 2026036883 MLS

Escape the ordinary and own a piece of Old Florida at 1227 Mangrove Lane! Set in the heart of historic Chokoloskee, this spacious multi-family property delivers 5 bedrooms and 4 baths with incredible flexibility for owner occupants, investors, seasonal owners, extended families, or anyone dreaming of an island retreat with income potential. Concrete block construction and a durable metal roof provide a solid foundation, while public water and sewer, central HVAC and room for a pool add everyday convenience. Step outside and you’re surrounded by the legendary beauty of the Ten Thousand Islands—where world-class fishing, boating, kayaking and endless backwater adventures are part of the lifestyle. Use one side and rent the other, create a seasonal getaway, or build your investment portfolio in one of Southwest Florida’s most unique coastal communities. This isn’t cookie-cutter Florida—it’s laid-back, authentic island living where the water, wildlife and adventure are never far away. Bring your boat, bring your fishing rods, and bring your vision!

1227 Mangrove Lane, Chokoloskee

Listing Courtesy of RE/MAX Profere

$87,000

226026883 MLS

Build your dream home on this cleared 0.25-acre residential lot in the heart of historic Chokoloskee. This oversized homesite offers approximately 10,890 square feet with paved road frontage and city water available. Just moments from public boat ramps, marinas, world-class fishing, Everglades National Park, and the Ten Thousand Islands, this property offers the perfect blend of Old Florida charm and modern convenience. Enjoy easy access to boating, kayaking, waterfront dining, and endless outdoor recreation while still having utilities readily available nearby. Whether you’re looking to build a primary residence, seasonal retreat, or investment property, this island lot provides an exceptional opportunity in one of Southwest Florida’s most unique coastal communities.

Chokoloskee

Listing Courtesy of Epique Realty, INC

$360,000

3 Beds ⋅ 3 Baths ⋅ 226026860 MLS

Beautifully updated custom 3-bedroom, 3-bath island home with a den/flex room and an additional connected sleeping room, showcasing exceptional craftsmanship, quality finishes, and thoughtfully designed indoor and outdoor living spaces. Nestled on historic Chokoloskee, this one-of-a-kind residence blends coastal charm with custom woodwork and outstanding attention to detail. Inside, you’ll find beautiful cedar and pine tongue-and-groove walls and ceilings throughout much of the home, complemented by custom trim, handcrafted built-ins, decorative millwork, and attractive tile and laminate flooring. The spacious open floor plan flows seamlessly from the inviting living room into the dining area and beautifully appointed kitchen featuring custom wood cabinetry, breakfast bar seating, stainless steel appliances, and abundant storage. The flexible floor plan includes three bedrooms, a den, and an additional sleeping room that is accessed through one of the bedrooms making it 4 bedrooms, offering excellent possibilities for family, guests, a home office, hobby space, or a vacation retreat. The primary suite offers a beautifully updated bath with a custom vanity and a spacious glass walk-in shower. Throughout the home, you’ll appreciate the warmth and character created by the extensive cedar and pine finishes, custom shelving, and quality craftsmanship. The laundry room includes a utility sink, storage cabinetry, shelving, and a dedicated utility area for added convenience. Outdoor living is truly exceptional. The expansive screened lanai serves as an additional living space complete with a custom outdoor kitchen, wet bar, cooktop, stainless steel sink, refrigerator, handcrafted wood bar, and seating areas, making it the perfect place to entertain after a day on the water. The refrigerator does not convey. The beautifully landscaped backyard features tropical palms, mature landscaping, decorative lighting, privacy fencing, a workshop, and a dedicated fish-cleaning station. Boat owners will appreciate the oversized concrete parking area with room for multiple boats, trailers, golf carts, and additional guest parking. There’s enough room to store a motorhome or a travel trailer. Additional features include a metal roof, fiber cement siding accented with beautiful cedar and pine exterior trim, municipal water, private septic system, irrigation, custom built-ins throughout, and a high-efficiency Goodman HVAC system. Located just minutes from two marinas, Everglades National Park, the Ten Thousand Islands, and world-class fishing and boating, this remarkable property offers the perfect combination of island living, quality craftsmanship, and outdoor adventure. With its flexible layout, desirable location, and strong appeal to visitors seeking a unique coastal experience, this property also presents an excellent opportunity for use as a vacation rental or income-producing investment in a popular Airbnb and VRBO destination.

253 Worley Street, Chokoloskee

Listing Courtesy of Epique Realty, INC

$114,900

226011235 MLS

Opportunity to build your island getaway on historic Chokoloskee Island in Everglades City. This approximately 0.22-acre (9,147± sq ft) residential lot is ideally located on Smallwood Drive and features a cleared homesite with paved road frontage, making it ready for your future build. Positioned within an established neighborhood, the property offers a desirable layout with excellent access and flexibility for a primary residence, seasonal retreat, or fishing camp. Chokoloskee Island sits at the gateway to the Ten Thousand Islands and Everglades National Park, known worldwide for exceptional fishing, boating, kayaking, and wildlife viewing. The property is conveniently located approximately 3 miles from the Marjory Stoneman Douglas Everglades National Park Visitor Center, as well as near public boat ramps, marinas, local restaurants, and the historic Smallwood Store. Enjoy the laid-back Old Florida lifestyle while still being within driving distance of Marco Island and Naples. Whether you’re looking for a quiet island residence or a base for exploring the Everglades and Gulf waters, this property offers a rare opportunity to own land in one of Southwest Florida’s most unique coastal communities.

261 Smallwood Drive, Chokoloskee

Listing Courtesy of Epique Realty, INC

$55,000

226008133 MLS

BUILD YOUR DREAM WEEKEND GET AWAY!!! CHOKOLOSKEE IS KNOWN FOR FAMOUS BACKWATER FISHING AND GORGEOUS SUNSETS. ONLY 1/4 MILE TO THE BOAT RAMP AND WALKING DISTANCE TO HAVANA CAFE.

Chokoloskee

Listing Courtesy of LPT Realty,LLC

$139,000

226006906 MLS

Water-view residential lot on Chokoloskee Island! Rare opportunity to own approximately ¼ acre in the heart of Chokoloskee with potential water views and existing utility connections. Previously improved property, offering elevated building area and established footprint. Located just minutes from Everglades National Park and world-class fishing in the Ten Thousand Islands. Enjoy island living with boating, wildlife, and sunset views nearby. Village Residential zoning allows for a variety of residential uses (buyer to verify permitted uses and building requirements). Utilities previously connected (water, electric, septic) – buyer to verify current status. Great opportunity to build your island retreat or investment property in one of Southwest Florida’s most unique waterfront communities.

1160 Rewis Drive, Chokoloskee

Listing Courtesy of Epique Realty, INC

$295,000

2 Beds ⋅ 2 Baths ⋅ 226002201 MLS

Bonus: Property has an assumable VA loan at an attractive rate for qualified buyers (subject to lender approval and verification of terms). Family/Fisherman’s Paradise in the Heart of the 10,000 Islands! Welcome to this 2016-built, Category 5 rated stilt home, offering peace of mind above flood levels and over 1,000 square feet of living space. There’s no HOA. This 2-bedroom, 2-bath gem sits directly on the water with a dock and direct Gulf access—a dream for any boating or fishing enthusiast. Located on Chokoloskee Island, you’re surrounded by the breathtaking beauty of Everglades National Park, with three marinas, the Historic Smallwood Store, and a vibrant local restaurant just a short walk away. Whether you’re looking for a full-time residence, a seasonal getaway, or a perfect Airbnb investment, this location offers unbeatable potential. Embrace the laid-back island lifestyle—live, fish, and explore in one of Florida’s last untouched coastal communities. Bonus: Property has an assumable VA loan at an attractive rate for qualified buyers (subject to lender approval and verification of terms).

177 Lopez Lane, Chokoloskee

Listing Courtesy of Epique Realty, INC

Selling Office: .

$210,000

2 Beds ⋅ 2 Baths ⋅ 225038576 MLS

Island Retreat for Sale – Chokoloskee Island Discover your perfect island escape with this 2 bed, 2 bath home nestled on some of the higher ground on Chokoloskee Island. Featuring an open and spacious living area, a screened front porch for relaxing evenings, and two large storage sheds out back, this home offers both comfort and convenience. Whether you’re looking for a peaceful retreat or a high-potential seasonal rental, this property is a true gem. Located in the heart of the 10,000 Islands—just steps from three marinas, the Havana Café, and the historic Smallwood Store—this is a fisherman’s paradise and an ideal getaway. Don’t miss your chance to own a slice of island life! The property next door is adjoining and available for purchase too, ask listing agent about it if your interested!

264 Mamie Street, Chokoloskee

Listing Courtesy of Epique Realty, INC

Selling Office: .

$254,900

2 Beds ⋅ 2 Baths ⋅ 225020414 MLS

Unique opportunity to own a Chokoloskee Island property that includes an additional adjoining parcel for added space and flexibility. This offering includes a 2-bedroom, 2-bath mobile home with approximately 828 sq. ft. of living area situated on approximately 0.17 acres, plus an additional adjoining vacant lot of approximately 0.06 acres, for a combined total of approximately 0.23 acres. The home offers a flexible floor plan with multiple living areas to fit a variety of needs (buyer to verify all intended uses and permitted occupancy). Enjoy island living with convenient access to the Gulf of Mexico and some of Southwest Florida’s best backcountry fishing. Located near multiple marinas, this property is ideal for boating, fishing, seasonal enjoyment, or creating your own island retreat. Additional adjoining lot included—don’t miss this chance to own extra land in historic Chokoloskee.

224 Mamie Street, Chokoloskee

Listing Courtesy of Epique Realty, INC

$160,000

2 Beds ⋅ 1 Baths ⋅ 225038513 MLS

Island Retreat on Chokoloskee – Priced to Sell! Welcome to your perfect island getaway! Located in the heart of this close-knit Chokoloskee Island community, this charming single-family home is ideal for weekend escapes, cozy year-round living, or a seasonal Airbnb in this beloved fishing destination. Set against the backdrop of the breathtaking Ten Thousand Islands, it’s a haven for anglers and outdoor enthusiasts alike. With space to park your boat and trailer, and an oversized porch, this property is built for enjoying the laid-back island lifestyle. Thoughtfully renovated in 2022, the home features updated plumbing, wiring, and air conditioning—giving you peace of mind and modern comfort and its on some of the higher ground on the island. Its within walking distance to three Marinas, the HavAnnA Café, and the iconic Smallwood Store and museum, adventure and local charm are always within reach. Plus, a nearby boat ramp means you can be on the water in no time. Don’t miss your chance to own a slice of paradise—whether you’re looking for a peaceful retreat or a savvy rental opportunity, this island gem won’t last long! The property next door is adjoining and available for purchase too, ask listing agent about it if your interested!

268 Mamie Street, Chokoloskee

Listing Courtesy of Epique Realty, INC

Selling Office: .

$324,900

3 Beds ⋅ 2 Baths ⋅ 225021065 MLS

This property at 228 Mamie Street, Chokoloskee Island, Florida 34138 is an inviting and renovated home priced to sell. It features: • 3 Bedrooms • 2 Full Bathrooms • 960 sq. ft. of living space • 0.17 Acres of land • Built in 1993, renovated in 2021 • Style: One-Story Mobile Home Interior Highlights include: • Kitchen with stainless steel appliances, induction stovetop, and conventional/air fry oven • Master Bedroom with a walk-in closet and ensuite bathroom featuring a garden tub • Ceramic Tile flooring throughout • Central A/C for cooling Additional Features: • Elevated home with extra space below for storage or workshops • Screened porch at the entry • Carport and an open backyard • Three marinas within approximately 1 mile, offering easy access for boating, kayaking, or canoeing, perfect for nature lovers or fishing enthusiasts. With its recent updates and access to the serene Everglades, this could be a fantastic home, vacation getaway or seasonal rental property.

228 Mamie Street, Chokoloskee

Listing Courtesy of Epique Realty, INC

$677,500

3 Beds ⋅ 2 Baths ⋅ 225041122 MLS

Olde Florida Island Living – A Rare Gem on Chokoloskee Bay Discover the essence of Olde Florida living in this truly one-of-a-kind water front island retreat. Set on nearly half an acre of lush, fenced land, this unique property is the only one on the island with its own private boat basin—a true haven for those who love the water and nature. Wake up to the call of shorebirds and end your days with breathtaking sunsets over the untouched beauty of Chokoloskee Bay. This beautifully restored Olde Cracker home offers a front-row seat to nature’s wonders, with sweeping water views from the open-concept family room and kitchen. This beautifully renovated Olde Cracker-style home has been thoughtfully restored using only top-of-the-line materials and finishes. Features include: Original Dade County Pine and Cypress pilings Andersen hurricane-rated and PVG windows New electric, PEX plumbing, and PVC drains Foam insulation with pest-resistant treatment 7mm luxury vinyl plank flooring Stainless steel appliances fenced fruit trees The elevation of this home is high, and importantly, it did not flood during Hurricanes Irma or Ian. With countless upgrades and unmatched charm, this is more than a home—it’s a sanctuary of timeless Florida beauty.

1155 Hamilton Street, Chokoloskee

Listing Courtesy of LPT Realty,LLC

Selling Office: .

$330,000

3 Beds ⋅ 2 Baths ⋅ 223084896 MLS

This quaint 3 bedroom 2 bath stilt home has the lower level concrete block has garage and workshop downstairs. The home has recently been remodeled and boost a covered balcony to enjoy your morning cup of coffee or sunset cocktails. The yard is fenced with plenty of room for a pool, boat, off road toys or RV. The boat ramps, HavAnnA Cafe and Smallwood museum is a short distance from your home. Enjoy the fishing, sightseeing or kayaking in the 10,000 island. Chokoloskee is Olde Florida living at it's best.

266 Gator Lane, Chokoloskee

Listing Courtesy of LPT Realty,LLC

Selling Office: .

$1,125,000

4 Beds ⋅ 4 Baths ⋅ 223079234 MLS

H12401 Discover a charming, spacious Old-Florida-style home boasting four bedrooms, two full baths, and two half baths, including a convenient main-floor primary suite. Upon entry, you'll be captivated by elevated front doorways, high-volume ceilings, and terra cotta flooring that seamlessly flows through the main living areas, while wood-look vinyl flooring adds character to the guest bedrooms. The primary suite, kitchen, and living room are thoughtfully placed on the main floor, taking advantage of breathtaking water views and providing access to a balcony for a serene retreat. Upstairs, you'll find guest suites, one of which enjoys its own private balcony with equally enchanting water vistas. For avid boaters, this exclusive street of just four homes grants you the convenience of a private boat launch, ensuring your nautical adventures are mere moments away. The property also offers a large four-plus-car garage, providing ample space for your vehicles, watercraft, and even a workshop. Additionally, there's a separate bonus room on the garage level, offering versatile options to suit your specific needs. This home is the ultimate coastal haven for those seeking a waterfront lifestyle.

1251 Mangrove Lane, Chokoloskee

Listing Courtesy of John R Wood Properties

Selling Office: .

$425,000

3 Beds ⋅ 2 Baths ⋅ 223024906 MLS

Florida Style 3 bedroom 2 bath single family home in Charming Chokoloskee FL with an attached bonus room /in-law suite. There is a large galley style eat-in kitchen, large bedroom, and a split living design. There is also a Genink, a whole house serge senior, Reverse Osmosis water system with a whole house water filter. This stilt home features ia covered car port, a golf cart garage for 2 golf carts, covered boat parking, and a work shop. There is a private lush backyard that can be enjoyed from both the upper screened lanai and the lower screened lanai. Chokoloskee is a unique Olde Florida community surrounded by the Everglades, Everglades National Park and its 10,000 islands. This is a designated golf cart community that has its own museum, Smallwood, the Havanna Cafe, 3 private boat ramps and access to the greatest snook fishing int he world. Don't miss this opportunity to experience the old world charm of Florida and still be close to Miami, Marco Island and Naples, FL.

294 Smallwood Drive, Chokoloskee

Listing Courtesy of DomainRealty.com LLC

Selling Office: .

$80,000

3 Beds ⋅ 2 Baths ⋅ 223025138 MLS

Over a quarter of an acre totally fenced lot. Just of State Road 29. Perfect for the weekend getaway for the outdoorsman. Short distance to Everglades city for wonderful fishing in the 10,000 islands, and hunting and riding the dirt roads. There is a mobil home on the property.

214 Turnstile Drive, Chokoloskee

Listing Courtesy of MVP Realty Associates LLC

Selling Office: .

Chokoloskee - Chokoloskee Florida Homes for Sale

Chokoloskee - Chokoloskee, FL Homes for Sale