Chatham Square Real Estate

Welcome to Chatham Square, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming subdivision is renowned for its tranquil atmosphere, lush landscaping, and a community spirit that makes it feel like home from the moment you arrive.

Chatham Square boasts a variety of beautifully designed single-family homes, each exuding a unique blend of modern elegance and classic Florida charm. With spacious layouts, inviting outdoor spaces, and an abundance of natural light, these residences are perfect for families, retirees, and anyone looking to embrace the Naples lifestyle. Many homes feature private pools, manicured gardens, and expansive patios ideal for entertaining or simply enjoying the serene surroundings.

One of the standout features of Chatham Square is its prime location. Situated just minutes away from the stunning beaches of Naples, residents can easily indulge in sun-soaked days by the Gulf of Mexico. The subdivision is also conveniently located near an array of shopping, dining, and entertainment options, including the upscale boutiques and gourmet restaurants of Fifth Avenue South and the vibrant Mercato district.

For those who appreciate the outdoors, Chatham Square is in close proximity to beautiful parks, golf courses, and nature preserves, providing endless opportunities for recreation and relaxation. Additionally, the community is served by top-rated schools, making it an ideal choice for families.

Discover the charm and convenience of Chatham Square, where a vibrant lifestyle awaits you in one of Florida's most desirable cities. Whether you're looking for your forever home or a seasonal retreat, Chatham Square is the perfect place to begin your next chapter.

Newest Listings in Chatham Square

$365,000

2 Beds ⋅ 2 Baths ⋅ 226031805 MLS ⋅ Chatham Square BLDG.

Welcome to Chatham Square at Glen Eagle Country Club. This Condo offers a full golf membership along with the opportunity to enjoy all that Glen Eagle has to offer. Perfectly situated within the Chatham Square community, only steps to the sparkling pool, relaxing hot tub, popular pickleball courts, and friendly neighborhood social gatherings. The nearby clubhouse is the heart of the community, featuring indoor and outdoor dining, a full bar, social activities, table tennis, billiards, card rooms, library, golf simulator, and newly renovated pro shop. Visit the Divot for breakfast and lunch while viewing the course or playing Bocce. Next door, the fitness center offers additional amenities, including a weight room, activities and many fitness classes. There's something for everyone. The condo comes with a one-car garage for additional storage and convenience. Glen Eagle Country Club is located just minutes from Naples’ beautiful white-sand beaches and renowned restaurants. Whether you’re looking to relax, entertain, stay active, or simply enjoy Southwest Florida, this beautifully appointed condo delivers! Come enjoy the exceptional location, outstanding amenities, golf membership, and the scenic lifestyle of Glen Eagle Golf Country Club.

6780 Dennis CIR Unit M103, Naples

$215,000

2 Beds ⋅ 2 Baths ⋅ 226009100 MLS ⋅ Chatham Square BLDG.

Positioned within Chatham Square at Glen Eagle, this inviting residence offers a sought-after bundled golf membership along with tranquil lake and golf course views. Enjoy tranquil views from your private screened lanai overlooking the lush fairways and sparkling lake, creating a peaceful backdrop for everyday living and relaxed outdoor enjoyment. With a desirable second-floor vantage point and a dedicated carport space, this two-bedroom, two-bath condominium presents an exceptional opportunity to embrace Naples golf lifestyle. The thoughtfully designed floor plan features a bright and open living and dining area with direct lanai access, allowing the beautiful lake and golf course views to become part of your daily experience. A formal dining space flows seamlessly into the living room, making the layout ideal for relaxed evenings and entertaining guests. The screened lanai, complete with a ceiling fan, provides comfortable outdoor living year-round while capturing sweeping views of the course and water. The kitchen is functional and inviting, offering a convenient pass-through window to the living room, a pantry for added storage, and a charming breakfast area set by a window with a ceiling fan. Appliances include a range, microwave and refrigerator/freezer, providing everything needed for effortless meal preparation. The primary suite serves as a comfortable retreat, featuring a ceiling fan and golf course views. The en-suite bath includes a sink vanity with a framed mirror and a shower-tub combination. The guest bedroom is thoughtfully positioned adjacent to a full bath with a shower-tub combo and includes ceiling fans for added comfort, making it ideal for visitors or flexible use as a home office. Residents of Glen Eagle Golf & Country Club enjoy an active, amenity-rich lifestyle centered around the 18-hole championship course. Additional offerings include tennis courts, a fitness center, resort-style pool, clubhouse dining and a vibrant year-round social calendar. Ideally in South Naples, this community is just minutes from the white sand beaches of the Gulf and renowned destinations of Old Naples, Fifth Avenue South, Third Street South, Naples Pier, Waterside Shops, Artis—Naples, Venetian Bay, Bayfront and Mercato, offering the best of Naples living.

7025 Dennis CIR Unit G202, Naples

$225,000

2 Beds ⋅ 2 Baths ⋅ 225084882 MLS ⋅ Chatham Square BLDG.

FULL GOLF Membership included!! Freshly painted 2-bedroom, 2-bathroom ground-floor condo offered at a very reasonable price! The A/C unit was replaced in 2024. Updated bathrooms, a newer refrigerator, and much more- you won’t be disappointed! One covered parking space comes with the property, plus plenty of open guest parking nearby. Enjoy beautiful sunrises and picturesque golf course views from the spacious screened lanai. The subdivision amenities are just steps from the unit, including a community pool with hot tub/spa and pickleball/tennis court, in addition to the main Glen Eagle Golf & Country Club amenities. Glen Eagle Golf & Country Club is a bundled golf community featuring an 18-hole championship golf course and a wealth of social activities and amenities, including a resort-style pool, pro shop, restaurant and lounge, tennis, bocce, card room, billiards, and a separate fitness center with a café. Conveniently located in one of South Naples’ most desirable areas, just minutes from Naples’ sugar-sand beaches, shopping plazas, restaurants, fine dining, boutique shopping, art galleries, theaters, and museums. A short drive to downtown Naples attractions such as Olde Naples, Fifth Avenue South, Third Street South, Naples Pier, Waterside Shops, Artis-Naples, Venetian Bay, Bayfront, and Mercato.

6945 Dennis CIR Unit I-107, 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.