Chatham Woods Homes for Sale

Welcome to Chatham Woods, a hidden gem nestled in the heart of sunny Florida! This charming subdivision is perfect for families, retirees, and everyone in between, offering a serene suburban lifestyle without sacrificing convenience. With its lush landscapes, tree-lined streets, and friendly atmosphere, Chatham Woods is a community where neighbors become friends and memories are made.

The homes for sale in Chatham Woods are as diverse as the residents who call it home. From spacious single-family houses to cozy townhomes, there’s a perfect fit for every lifestyle and budget. Many of these residences feature modern amenities, open floor plans, and beautifully landscaped yards, making them ideal for both relaxation and entertaining. Imagine hosting summer barbecues in your backyard or enjoying quiet evenings on your porch, surrounded by the sounds of nature.

Living in Chatham Woods means you’re just a short drive away from some of Florida’s most beautiful beaches, vibrant shopping districts, and delectable dining options. The community is also conveniently located near top-rated schools and recreational facilities, making it an ideal place for families to thrive.

As you explore the homes for sale in Chatham Woods, you’ll discover not just a house, but a place where you can truly feel at home. Don't miss your chance to be part of this wonderful community—come and see for yourself why Chatham Woods is the perfect place to start your next chapter!

Newest Chatham Woods Homes for Sale

$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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