Chatham Woods market snapshot
Homes, condos and townhomes. Source: Naples MLS listing data, updated October 27, 2026. Information deemed reliable but not guaranteed.
About Chatham Woods
Chatham Woods is an intimate community of just 24 single-family homes in North Naples, tucked within the Willoughby Acres area near Immokalee Road and Airport-Pulling Road. The neighborhood offers a distinctly different experience from North Naples’ larger gated and master-planned communities, with a single residential street, generous homesites and no large recreational complex. Its small scale creates a traditional neighborhood atmosphere while still providing convenient access to shopping, dining, beaches and other North Naples destinations.
Homes in Chatham Woods feature contemporary Florida designs with approximately 1,700 to 2,700 square feet of living space, although individual residences vary in configuration and improvements. Floor plans include multiple bedrooms, dens and flexible living spaces, with attached garages and outdoor living areas. Private pools can be found at some residences, while individual lots provide room for landscaping, patios and other outdoor features. Because the homes were built and customized individually, buyers will find differences in architecture, interior finishes, hurricane protection, pools and other improvements from one property to another.
Chatham Woods does not have a clubhouse, community pool or extensive collection of shared recreational amenities. Instead, the focus is on private single-family living and the convenience of the North Naples location. Lawn and landscape maintenance is provided through the homeowners association, adding a lower-maintenance component while allowing residents to enjoy the space and privacy of a detached home.
Why People Like the Chatham Woods Community
- Only 24 Homes: The exceptionally small size creates an intimate residential setting that feels more like a traditional neighborhood than a master-planned development.
- Single-Family Living: Chatham Woods consists of detached residences with private homesites, attached garages and individual outdoor living areas.
- Private Outdoor Space: Some properties feature private pools, outdoor kitchens, screened lanais and fenced yards, with features varying by residence.
- Lawn Maintenance Included: Association-provided lawn and landscape maintenance reduces some of the routine upkeep associated with single-family ownership.
- No Large Amenity Complex: Buyers who do not want to support a clubhouse, golf course or extensive recreational facilities may appreciate the community’s simpler structure.
- Convenient North Naples Location: Immokalee Road, Airport-Pulling Road, U.S. 41 and I-75 provide convenient access to beaches, shopping, dining and destinations throughout North Naples.
What You Need to Know About Living in Chatham Woods
- Chatham Woods Is Not Gated: Unlike many small newer Naples enclaves, Chatham Woods does not have a gated entrance.
- Homes Are Not Uniform: Size, floor plan, architecture, pool configuration, interior finishes and other improvements vary throughout the neighborhood.
- Private Pools Are Property-Specific: Some residences have private swimming pools and expanded outdoor living areas, but these features are not universal.
- HOA Maintenance Has Defined Limits: Lawn and landscape maintenance and certain common services are provided through the association, but buyers should review current documents to understand exactly what is included and which responsibilities remain with the homeowner.
- There Are No Traditional Community Recreational Facilities: Buyers looking for a clubhouse, community pool, fitness center, tennis or pickleball should understand that Chatham Woods is designed around the individual residences rather than shared amenities.
- Association Rules Apply: Leasing, pets, parking, exterior modifications and other property-use matters are governed by the community documents and should be verified as part of the purchase process.
Current listings
Chatham Woods Homes for Sale
See the newest homes for sale in Chatham Woods, updated throughout the day from the Naples MLS. Want a private showing or an honest read on value? Call Renee Hahn at (239) 287-2576.
The source of this real property information is the copyrighted and proprietary database compilation of the M.L.S. of Naples, Inc. Accuracy of this information is not warranted or guaranteed. Information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Chatham Woods Amenities
Chatham Woods takes a deliberately simple approach to community amenities. The neighborhood includes streetlights, underground utilities and maintained lawn and landscape services, but does not have a traditional clubhouse, community swimming pool, fitness center or racquet-sports facilities.
Instead, outdoor recreation and entertaining are centered around the individual residences. Some homes feature private swimming pools, screened lanais, outdoor kitchens and fenced yards, allowing homeowners to create their own private outdoor environments.
For buyers comparing Chatham Woods with larger North Naples developments, this distinction is important. Its appeal is the combination of just 24 detached homes, private residential lots, lawn maintenance and a convenient North Naples location, rather than an extensive shared amenity package.
What Is Near Chatham Woods?
Downtown Naples (5th Avenue South): 9.5 miles
Closest beach: Delnor-Wiggins Pass State Park, 3.7 miles
RSW Airport: 17.9 miles
Nearby golf: Tiburón Golf Club, 1.8 miles
Notable shopping & dining nearby: Mercato, 2.5 miles
Closest park: Veterans Community Park, 1.2 miles
(Distances are approximate straight-line distances.)
Chatham Woods Floor Plans
Floor plans are provided as a complimentary resource to help you understand the layouts available in Chatham Woods. Plans and specifications can change, so confirm details for any specific home.
View Chatham Woods floor plans (PDF)
Where Is Chatham Woods?
Chatham Woods FAQ
Where is Chatham Woods located?
Chatham Woods is in North Naples, within the Willoughby Acres area near Immokalee Road and Airport-Pulling Road. U.S. 41, I-75, beaches, shopping and dining are all convenient.
What types of homes are in Chatham Woods?
Chatham Woods has just 24 single-family homes along a single residential street, with contemporary Florida designs of approximately 1,700 to 2,700 square feet. Homes include attached garages and outdoor living areas, and some have private pools.
Is Chatham Woods gated, and is there an HOA?
Chatham Woods is not gated. It does have a homeowners association that provides lawn and landscape maintenance and certain common services, so the exact coverage should be confirmed in the current documents.
What amenities does Chatham Woods offer?
There is no clubhouse, community pool, fitness center or racquet courts. The neighborhood has streetlights, underground utilities and maintained landscaping, while recreation happens at home with private pools, lanais and fenced yards at some residences.
What makes Chatham Woods different from larger North Naples communities?
With only 24 homes on one street, it feels like a traditional neighborhood rather than a master-planned development. Owners get detached homes and HOA lawn care without supporting a large amenity complex.
Last updated October 2026 by Renee Hahn, Your Naples Expert. Community details, fees and amenities can change, so confirm specifics for any home you are considering.
