Chatham Woods Real Estate

Welcome to Chatham Woods, an enchanting subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community is a hidden gem that offers a perfect blend of serene living and vibrant lifestyle, making it an ideal choice for families, retirees, and everyone in between.

Chatham Woods boasts a collection of beautifully designed single-family homes, each exuding a unique character and charm. The lush landscaping and well-maintained streets create a warm and inviting atmosphere that welcomes residents and visitors alike. With spacious yards and mature trees, this subdivision offers a sense of privacy and tranquility that is often sought but rarely found.

One of the standout features of Chatham Woods is its prime location. Residents enjoy easy access to Naples’ pristine beaches, upscale shopping, and exquisite dining options. The nearby Mercato and Waterside Shops provide a delightful array of boutiques and eateries, ensuring that you’re never far from the best that Naples has to offer. Outdoor enthusiasts will appreciate the proximity to various parks, golf courses, and nature trails, perfect for leisurely strolls or weekend adventures.

Families in Chatham Woods benefit from highly-rated schools within the Collier County School District, making it a great place to raise children. The sense of community here is palpable, with neighbors often coming together for social gatherings and events, fostering lasting friendships and connections.

Discover the charm of Chatham Woods, where every day feels like a vacation in paradise. Embrace the relaxed Florida lifestyle and make this beautiful community your new home!

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

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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.