Chatham Woods Real Estate

Welcome to Chatham Woods, a hidden gem nestled in the heart of Naples, Florida. This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle in sunny Southwest Florida.

Chatham Woods is characterized by its lush landscaping and well-maintained properties, creating a picturesque environment that residents are proud to call home. The community features a variety of single-family homes, each exuding its own unique charm while adhering to the high standards of Naples living. With spacious lots and thoughtful designs, these homes provide ample room for relaxation and entertainment.

One of the standout features of Chatham Woods is its prime location. Residents enjoy easy access to Naples' stunning beaches, world-class shopping, and exquisite dining options. Whether you’re exploring the vibrant boutiques of Fifth Avenue South or savoring fresh seafood at a waterfront restaurant, the best of Naples is just moments away.

For outdoor enthusiasts, Chatham Woods is surrounded by beautiful parks and recreational facilities, including the nearby Naples Botanical Garden and the scenic Gordon River Greenway. Enjoy leisurely walks, biking trails, and the natural beauty that Southwest Florida has to offer.

Chatham Woods is not just a place to live; it’s a community where neighbors become friends and memories are made. With its friendly atmosphere, convenient amenities, and stunning surroundings, Chatham Woods is the perfect place to start your next chapter in Naples, Florida. Discover the charm of Chatham Woods today and experience the vibrant lifestyle that awaits you!

Newest Listings in Chatham Woods

$1,059,000

4 Beds ⋅ 2 Baths ⋅ 226023110 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Meticulously maintained Hampton model by Gulfstream Homes offering 3 BR + den/4th BR, 2 BA, and a fully fenced private lot surrounded by lush landscaping in Chatham Woods, a newer subdivision within Willoughby Acres where the landscaping and irrigation maintenance is included. Designed for Florida living, the open layout leads to a backyard oasis complete with a private pool & sun shelf, custom outdoor kitchen, and motorized lanai bug screens. Enjoy full peace of mind with motorized hurricane shutters on the lanai, front impact windows/doors, and a non-flood zone location. Notable upgrades include new primary bath lighting (2026), dishwasher, pool pump, and primary bath faucets (2025), plus a new refrigerator (2023). Fresh interior paint, upgraded cabinet hardware, and overhead garage storage make it turnkey. Ideally located under 4 miles to Gulf beaches and minutes from Mercato, Waterside Shops, Artis Naples, world class dining, shopping, golf, and downtown Naples.

37 Johnnycake DR, Naples

Start Your Search

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Regional Multiple Listing Service of Minnesota. Real estate listings held by brokerage firms other this firm are marked with the Broker Reciprocity logo. Information Deemed Reliable But Not Guaranteed. Property locations as displayed on any map are best approximations only and exact locations should be independently verified.

Listing data © 2026 Regional Multiple Listing Service of Minnesota. All rights reserved. By searching, you agree to the EULA.