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 offers a perfect blend of tranquility and accessibility, making it an ideal destination for families, retirees, and anyone seeking the quintessential Florida lifestyle.

Chatham Square is known for its beautifully landscaped streets and well-maintained homes, each exuding a unique charm that reflects the vibrant spirit of the community. The neighborhood boasts a variety of architectural styles, ensuring that there’s something to suit every taste. Residents here enjoy a friendly, close-knit atmosphere, where neighbors become friends and community events foster a sense of belonging.

One of the standout features of Chatham Square is its prime location. Just a short drive away, you’ll find the stunning beaches of Naples, renowned for their soft sands and breathtaking sunsets. The area is also home to an array of shopping, dining, and entertainment options, from upscale boutiques to charming cafes, ensuring that you’ll never be far from the action.

For outdoor enthusiasts, Chatham Square is surrounded by lush parks and recreational areas, perfect for weekend picnics, jogging, or simply soaking in the Florida sunshine. Additionally, the nearby golf courses and nature preserves provide endless opportunities for adventure and relaxation.

Experience the best of Naples living in Chatham Square, where community spirit meets the beauty of Florida’s coastal lifestyle. Whether you’re looking to settle down or invest in a vacation home, this subdivision offers a welcoming haven that captures the essence of Southern charm. Come and discover your new home in Chatham Square today!

Newest Listings in Chatham Square

$230,000

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

$299,000

2 Beds ⋅ 2 Baths ⋅ 226007017 MLS ⋅ Chatham Square BLDG.

Welcome to effortless Florida living in this exceptionally maintained first-floor condo with a detached garage, located in the highly desirable Chatham Square community and offering a full golf membership at Glen Eagle Golf & Country Club. This inviting residence features two bedrooms plus a den, two full baths, and 18-inch tile laid on the diagonal throughout, creating a bright, clean, and cohesive feel. Thoughtful upgrades include decorative plantation shutters on every window and roll-down exterior storm shutter for added security. Major mechanicals have been updated, including the air conditioner, water heater, washer, and dryer, providing peace of mind for years to come. Unwind on your screened lanai, sip your morning coffee, and enjoy peaceful sunrise views in your own private retreat. Don’t miss this opportunity to own a piece of paradise in one of the best-valued golf communities in Southwest Florida. Glen Eagle is perfectly located less than 4 miles from downtown Naples, where you’ll enjoy Fifth Avenue’s fine dining, boutique shopping, art galleries, and the stunning Gulf beaches

6700 Dennis CIR Unit A102, Naples

$350,000

3 Beds ⋅ 2 Baths ⋅ 226000172 MLS ⋅ Chatham Square BLDG.

Enjoy beautiful golf course and lake views from this spacious end-unit condo in Glen Eagle Country Club with GOLF MEMBERSHIP INCLUDED. Featuring 2 bedrooms + den, 2 baths, covered parking, plenty of guest parking and walking distance to the community pool and tennis court. 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. Take a short drive to Naples pristine beaches, downtown top-rated restaurants, shopping, theatres and more. The perfect opportunity to enjoy the Naples golf lifestyle.

6945 Dennis CIR Unit I201, 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.