Chatham Woods Real Estate

Welcome to Chatham Woods, a hidden gem nestled in the heart of sunny Florida! This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone seeking a vibrant community atmosphere.

Chatham Woods is characterized by its beautifully landscaped streets, lined with mature trees and well-maintained homes that exude a warm, inviting charm. The neighborhood features a variety of architectural styles, ensuring that every home has its own unique character. Residents enjoy spacious lots, providing ample outdoor space for gardening, play, and relaxation under the Florida sun.

One of the standout features of Chatham Woods is its prime location. Just a short drive away, you’ll find an array of shopping, dining, and entertainment options, catering to every taste. From quaint local cafes to bustling shopping centers, there’s something for everyone. For outdoor enthusiasts, the nearby parks and recreational facilities offer plenty of opportunities for hiking, biking, and enjoying Florida’s natural beauty.

Families will appreciate the top-rated schools that serve the community, ensuring a quality education for children of all ages. Additionally, Chatham Woods fosters a strong sense of community, with regular neighborhood events and gatherings that encourage residents to connect and build lasting friendships.

Whether you’re looking for a peaceful retreat or a lively community, Chatham Woods offers the perfect blend of both. Experience the charm of this delightful subdivision and discover why so many are proud to call Chatham Woods home!

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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