Chatham Woods Real Estate

Welcome to Chatham Woods, a picturesque subdivision nestled in the heart of sunny Florida. This charming community offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone seeking a serene lifestyle without sacrificing access to modern amenities.

Chatham Woods features beautifully landscaped streets lined with mature trees, creating a warm and inviting atmosphere. The homes here boast a variety of architectural styles, from cozy single-family residences to spacious two-story designs, ensuring there's something for everyone. Many properties come with generous lots, allowing for ample outdoor space to enjoy Florida's beautiful weather year-round.

One of the standout features of Chatham Woods is its family-friendly environment. The community is home to several parks and recreational facilities, perfect for weekend picnics, leisurely strolls, or playdates with friends. Residents can take advantage of nearby walking trails and nature preserves, making it easy to embrace an active lifestyle while surrounded by the beauty of Florida’s natural landscape.

Chatham Woods is conveniently located near major highways, providing easy access to local shopping, dining, and entertainment options. Whether you're in the mood for a night out or a day of retail therapy, you'll find plenty of choices just a short drive away. Additionally, the community is served by highly-rated schools, ensuring that families have access to quality education.

Discover the charm and warmth of Chatham Woods, where community spirit thrives and every day feels like a vacation. Your dream home awaits in this delightful Florida enclave!

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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