Chokoloskee, FL Real Estate Sold

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!

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!

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.

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.

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.

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.

Three homes on .67 acre parcel, totally fenced located on chokoloskee island. The main house has three bedroom and 2 bath with carport and large wooden deck to enjoy the outdoors. The second home is currently an airbnb. It is a 1 bedroom, 1 bath open concept home with den and screen porch. 2nd guest home is 1 bedroom, 1 bath manufactured home with attached screen porch. There is a large shed with electric and water. All structures are permitted!!! Just minutes to the marina and off to the best fishing and nature exploring in the 10, 000 island. Great family compound or great investment property.

Small town olde florida living at it best. Chokoloskee is a 141 acre island surround by the 10, 000 islands. Known for the one of the best fishing destinations and nature at its finest. Just minutes to the boat ramp, smallwood museum and havana café. This home built in 1962 has been completely redone. 2 bedroom and 2 bathroom with open floorplan. Enjoy the sunsets on your screen porched. Air conditioner 5yrs. Water heater 1.5 yrs. Carport is 1 yr. And 2 sheds on the property.

Fisherman's paradise in the heart of chokoloskee. This is true olde florida home built in the 1930. Three bedroom each with their own bathroom. This property has two lots. Detached garage and workshop, plenty room to park your boat, rv and other toys and still add your pool.

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 marco island and naples, fl.

Prime waterfront location on the southern end of chokoloskee island, this lot sits directly on the bay with gulf of mexico access. Accessible by bridge from everglades city, chokoloskee is an island sanctuary at the southernmost tip of southwest florida's gulf coast. Enjoy daily views of both sunrise and sunset. Prime waterfront location provides the ultimate private setting to build a weekend getaway or year-round home for anglers and wildlife lovers alike.

Fisherman's paradise, this very unique property has a two bedroom stilt home, a storage shed, a large quonset hut and includes five lots which are fenced! Plenty of room to build a pool, other homes and store your toys. This home is known as "the tree house in chokoloskee" the quonset hut is being rented month to month. The five parcels have individual ids.

This renovated home presents a haven of comfort and style. Boasting a thoughtfully redesigned layout, it features 2 bedrooms, 2 baths, and an inviting open floor plan that seamlessly blends modern living with island charm. Step outside to the screened patio, where you can savor the island breeze and scenic views. Updates abound, including a newer air conditioner, hot water heater, and a convenient carport. Storage is plentiful with two sheds onsite, providing ample space for your belongings. Don't miss this opportunity to experience island living at its finest in this beautifully updated retreat. Discover the allure of chokoloskee, a captivating 141-acre island enveloped by the enchanting expanse of the 10, 000 islands. Renowned as one of the premier fishing destinations, this idyllic locale showcases nature at its most splendid. Within mere minutes, you can access marinas, the smallwood museum, and the charming havanna cafe, adding to the island's appeal.

Spacious island living – perfect for families and outdoor enthusiasts! Located on the tranquil chokoloskee island, this 3-bedroom, 2-bathroom home offers over 1, 200 sq. Ft. Of open living space on an oversized lot—ideal for families and adventure lovers alike. The generous yard provides ample room to store boats, four-wheelers, lawn equipment, and more. Inside, enjoy a bright, open layout, shower/tub combos in both bathrooms, and a luxurious jacuzzi-style tub in the master suite. Just a short walk to three marinas, a local restaurant, and the historic smallwood store, this peaceful, laid-back community is a fisherman’s dream. With so much space and such a prime location, this property is priced to sell fast! The commercial property next door is adjoining and available for purchase too, ask listing agent about it if your interested!

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.

This parcel includes 2 lots located on a quiet street in chokoloskee. This home is a stilt home cbs ground floor and pilings, 2 car garage with plenty of storage space. The upper level is a 3 bedroom plus large den and 2 bath. The kitchen boasts granite countertops, stainless steel appliances with a breakfast bar flowing into the dining room. The family room is very spacious. All the rooms have plenty of natural light. French doors throughout the home with access to the wrap around deck. There is plenty of room for parking your boats, off road toys or rv. The pool is 25 x 40 with a paver patio, great for relaxing after an amazing day on the water in the 10, 000 islands.

Experience the chokoloskee waterfront lifestyle in this elevated canal-front home designed for boating, fishing and relaxed coastal living. The main living level offers 2 bedrooms and 2 bathrooms, an open floor plan with vaulted ceilings, wood-look luxury vinyl plank flooring and a bright living area that opens through sliding-glass doors to a spacious screened waterfront porch. Enjoy canal views and year-round outdoor living from the tiled porch, complete with room for dining and entertaining. The open kitchen features wood cabinetry, stainless-steel appliances, a decorative backsplash, pantry storage and a brand-new stainless-steel microwave. Additional highlights include a large walk-in primary closet, recently repainted interior, hurricane shutters and a payne hvac system installed in may 2026. An elevator provides convenient access to the main living level, with separate staircases offering additional entry points. Beneath the elevated home are covered parking, extensive concrete parking and workspace, a separate laundry area with bathroom & whirlpool washer and dryer, and a ground-level storage/workshop with double doors, workbench, shelving and space for fishing and recreational equipment. The canal-front setup includes a concrete seawall, boat lift, separate boat davit, covered fish-cleaning station and stainless-steel waterfront ladder. The oversized concrete area provides excellent space for boats, vehicles and outdoor activities. Seller intends to convey select furniture and furnishings, two televisions, and an exceptional recreational package that includes a 2023 tracker bass tracker classic xl boat, mercury 50-horsepower four-stroke motor, trolling motor, trailer and club car golf cart, subject to the sales contract and separate personal-property addendum. Enjoy waterfront living near the ten thousand islands and everglades national park!

This renovated home presents a haven of comfort and style. Boasting a thoughtfully redesigned layout, it features 2 bedrooms, 2 baths, and an inviting open floor plan that seamlessly blends modern living with island charm. Step outside to the screened patio, where you can savor the island breeze and scenic views. Updates abound, including a newer air conditioner, hot water heater, and a convenient carport. Storage is plentiful with two sheds onsite, providing ample space for your belongings. Don't miss this opportunity to experience island living at its finest in this beautifully updated retreat. Discover the allure of chokoloskee, a captivating 141-acre island enveloped by the enchanting expanse of the 10, 000 islands. Renowned as one of the premier fishing destinations, this idyllic locale showcases nature at its most splendid. Within mere minutes, you can access marinas, the smallwood museum, and the charming havanna cafe, adding to the island's appeal.

Charming waterfront home on quaint chokoloskee island discover the perfect blend of tranquility and adventure with this 2-bedroom, 2-bath stilt home, located on the serene chokoloskee island. With direct gulf access from your private dock, you're just minutes from the stunning ten thousand islands, renowned for world-class fishing, wildlife viewing, and outdoor exploration. Ideally situated within walking distance to the local favorite, havana café, and close to the smallwood museum and marinas, this property offers an exceptional location for both relaxation and entertainment. Whether you're looking for a weekend getaway, a profitable airbnb, or a peaceful forever home, this property checks all the boxes. Start your mornings with a peaceful coffee on the screened porch or unwind with evening cocktails as you soak in the natural beauty that surrounds you. The home boasts ample storage with a 3-car garage beneath, while a convenient chairlift makes the transition from garage to home effortless. Embrace island life and make this charming stilt home your own personal retreat.

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. This 2-bedroom, 2-bath gem sits directly on the water with a dock, direct gulf access—a dream for any boating or fishing enthusiast. Located on chokoloskee island, you’re surrounded by the breathtaking beauty of the 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. Your next adventure starts here.