Chokoloskee, FL Real Estate Sold

Collier County | Updated
Results 6 of 6
268 Mamie St, Chokoloskee, Florida 34138, image 1
Sold - Jul 28, 2025
$160,000
  • 2 Beds
  • 1 Baths
  • 648 SqFt
  • $247/SqFt
House sold
268 Mamie St, Chokoloskee, FL 34138
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!
264 Mamie St, Chokoloskee, Florida 34138, image 1
Sold - Jul 28, 2025
$210,000 $89K
  • 2 Beds
  • 2 Baths
  • 862 SqFt
  • $244/SqFt
House sold
264 Mamie St, Chokoloskee, FL 34138
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!
1251 Mangrove Ln, Chokoloskee, Florida 34138, image 1
Sold - Dec 29, 2023
$1,125,000
  • 4 Beds
  • 2 2/2 Baths
  • 1,670 SqFt
  • $674/SqFt
House sold
1251 Mangrove Ln, Chokoloskee, FL 34138
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.
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266 Gator Ln, Chokoloskee, Florida 34138, image 1
Sold - Dec 20, 2023
$330,000
  • 3 Beds
  • 2 Baths
  • 1,008 SqFt
  • $327/SqFt
House sold
266 Gator Ln, Chokoloskee, FL 34138
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.
294 Smallwood Dr, Chokoloskee, Florida 34138, image 1
Sold - Dec 08, 2023
$425,000
  • 3 Beds
  • 2 Baths
  • 1,473 SqFt
  • $289/SqFt
House sold
294 Smallwood Dr, Chokoloskee, FL 34138
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.
1155 Hamilton St, Chokoloskee, Florida 34142, image 1
Pending
$800,000
  • 3 Beds
  • 2 Baths
  • 1,584 SqFt
  • $505/SqFt
House for sale
1155 Hamilton St, Chokoloskee, FL 34142
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.

Chokoloskee, FL Snapshot

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