Chatham Woods Real Estate

Welcome to Chatham Woods, a hidden gem nestled in the heart of Florida that perfectly blends tranquility with modern living. This charming subdivision offers a unique opportunity for homebuyers seeking a peaceful retreat without sacrificing convenience.

Chatham Woods is characterized by its picturesque tree-lined streets, spacious homes, and a welcoming community atmosphere. With a variety of architectural styles, from contemporary designs to classic Florida charm, there’s a home for every taste and lifestyle. The meticulously landscaped yards and vibrant gardens add to the neighborhood's appeal, creating a warm and inviting environment for families and individuals alike.

One of the standout features of Chatham Woods is its proximity to a wealth of amenities. Residents enjoy easy access to top-rated schools, shopping centers, and recreational facilities. The nearby parks are perfect for weekend picnics, jogging, or simply enjoying the beautiful Florida sunshine. For those who love the outdoors, the stunning beaches and nature reserves are just a short drive away, offering endless opportunities for adventure and relaxation.

Chatham Woods is not just a place to live; it’s a community where neighbors become friends. The neighborhood hosts regular events and gatherings, fostering a sense of belonging and camaraderie among residents. Whether you’re looking to raise a family, retire in peace, or find a vibrant place to start anew, Chatham Woods has something for everyone.

Discover the charm and convenience of Chatham Woods today, and let this delightful subdivision be the backdrop for your next chapter in sunny Florida!

Newest Listings in Chatham Woods

$1,059,000

4 Beds ⋅ 2 Baths ⋅ Chatham Woods SubDv.

One or more photo(s) has been virtually staged, AI generated or rendered. Turnkey doesn't begin to cover it. No Flood Zone • Low HOA Fees • Private Fenced Backyard • Pool with Sun Shelf • Custom Outdoor Kitchen • Impact-Resistant Front Windows & Doors • Electric Hurricane Shutters • Motorized Bug Screens • Move-In Ready. This meticulously maintained Gulfstream-built 3-bedroom + den (or optional 4th bedroom), 2-bath home sits on a completely fenced, private lot and has been thoughtfully upgraded throughout. Every detail has been carefully maintained, making this a home you can enjoy from day one. Recent updates include a new refrigerator (2023), new dishwasher (2025), new pool pump (2025), updated bathroom vanity lighting, upgraded cabinet hardware, custom window treatments, and fresh interior paint. The tile floors have been professionally sealed, the driveway and pool deck pavers have been cleaned and sealed, the HVAC has been serviced, the gutters have been cleaned, the roof has been inspected, and all permits have been properly closed. Step outside to your private backyard oasis featuring a pool with sun shelf, a custom outdoor kitchen, electric hurricane shutters, and motorized bug screens that allow you to enjoy the lanai year-round. The fully fenced backyard provides both privacy and functionality, creating the perfect space for relaxing or entertaining. Ideally located just minutes from Mercato, Vanderbilt Beach, Waterside Shops, Artis–Naples, world-class dining, shopping, golf, and downtown Naples, this home offers the perfect balance of privacy, convenience, and the Naples lifestyle.

37 Johnnycake Drive, Naples

$328,900

3 Beds ⋅ 2 Baths ⋅ Chatham Woods SubDv.

THIS GORGEOUS 3 BED/2.5 BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NESTLED NEAR MAITLAND IN A COMMUNITY CALLED CHATHAM WOODS. THIS ELEGANT HOME FEATURES 1,233 SQ. FT. OF LIVING SPACE, PORCELEN TILE AND WOOD FLOORS. STAINLESS STEELE APPLIANCES INCLUDE RANGE, RANGE HOOD, REFRIGERATOR AND MICROWAVE. VAULTED CIELING THAT FLOWS TO THE BEAUTIFUL WOOD FLOORS. LOVELY DESIGNED MASTER AND QUEST BATHROOMS WITH STAINLESS STEELE FIXTURES, WOOD FLOORING, LIVING ROOM AND FAMILY ROOM. NEWER ROOF 2018. UPDATED PLUMBING, NEW ELECTRICAL UPDATES AND NEWER AC HANDLER & CONDENSER. LANDSCAPING READY FOR YOUR VISION TO GIVE ULTIMATE CURB APPEAL. THIS HOME IS APPROXIMATELY 15 MINUTES FROM DOWNTOWN ORLANDO, APPROXIMATELY 25 MINUTES TO ORLANDO INTERNATIONAL AIRPORT, APPROXIMATELY 15 MINUTES TO RETAIL SHOPPING AND RESTUARANTS ON PARK AVE., APPROXIMATELY 15 MINUTES TO VALENCIA STATE COLLEGE, APPROXIMATELY 25 MINUTES TO UCF AND APPROXIMATELY 30 MINUTES TO DISNEY WORLD.

5501 Chatham Woods Court, Orlando

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