Chatham Woods Real Estate

Welcome to Chatham Woods, an enchanting subdivision nestled in the heart of Florida, where suburban tranquility meets vibrant community spirit. This charming neighborhood offers a perfect blend of comfort and convenience, making it an ideal place for families, retirees, and everyone in between.

Chatham Woods is characterized by its picturesque tree-lined streets, well-maintained homes, and lush green spaces that invite outdoor activities and leisurely strolls. The community boasts a variety of architectural styles, ensuring that there’s a perfect fit for every taste. From cozy single-family homes to spacious townhouses, the residences here are designed with modern living in mind, featuring open floor plans, updated kitchens, and inviting backyards.

One of the standout features of Chatham Woods is its prime location. Residents enjoy easy access to major highways, making commutes to nearby cities a breeze. The subdivision is also in close proximity to top-rated schools, shopping centers, and recreational facilities, ensuring that all your daily needs are just a stone's throw away. For those who love the outdoors, nearby parks and nature trails provide ample opportunities for hiking, biking, and picnicking.

The sense of community in Chatham Woods is palpable, with friendly neighbors and regular social events that foster connections and create lasting friendships. Whether you’re looking to relax by the pool, join a local book club, or participate in community events, there’s always something happening here.

Discover the charm of Chatham Woods, where your dream home awaits in a vibrant, welcoming community. Experience the perfect blend of suburban serenity and convenient living in this delightful Florida subdivision!

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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