Chatham Square Homes with Tennis Court(s) Amenities

Welcome to Chatham Square, an exquisite subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community seamlessly blends the tranquility of suburban living with the vibrant lifestyle that Naples is renowned for. Chatham Square is not just a neighborhood; it’s a lifestyle choice, offering residents an array of amenities that cater to both relaxation and recreation.

One of the standout features of Chatham Square is its exceptional homes, many of which boast private tennis courts. Imagine stepping out of your beautifully designed home and onto your own court, ready for a friendly match or an intense game with friends. These properties are perfect for tennis enthusiasts and anyone looking to incorporate an active lifestyle into their daily routine. The well-maintained courts provide the ideal setting for honing your skills or simply enjoying a sunny afternoon with family.

Beyond tennis, Chatham Square is surrounded by the natural beauty that Naples has to offer. With stunning beaches just a short drive away, upscale shopping, and gourmet dining options nearby, residents can enjoy the best of both worlds. The community fosters a warm, welcoming atmosphere, making it easy to connect with neighbors and create lasting friendships.

Whether you’re a retiree seeking a peaceful retreat or a family looking for a vibrant community, Chatham Square has something for everyone. Discover your dream home in this idyllic subdivision and embrace the Naples lifestyle today!

Newest Chatham Square Homes with Tennis Court(s) Amenities

$249,000

2 Beds ⋅ 2 Baths ⋅ 226036221 MLS ⋅ Chatham Square BLDG.

FULL GOLF MEMBERSHIP INCLUDED! Experience the best of the Naples golf lifestyle in this beautifully updated second-floor residence at Glen Eagle Golf & Country Club. This stylish 2-bedroom, 2-bath condo combines modern updates, beautiful golf-course views, and an exceptional location just minutes from downtown Naples. The thoughtfully updated interior features a refreshed kitchen with quartz countertops, brushed nickel hardware, and brand-new stainless-steel appliances. Brazilian laminate flooring enhances the living area and kitchen, while both bedrooms offer newly installed carpeting. A new 2025 A/C system provides added comfort and peace of mind. Step onto the private lanai and start your morning with coffee while enjoying beautiful sunrises and views of golfers heading out on the course. It’s the perfect setting to relax, entertain, and enjoy the year-round Southwest Florida lifestyle. Glen Eagle offers an outstanding array of amenities and social activities, including an 18-hole golf course, Har-Tru tennis courts, state-of-the-art fitness center, pools, dining, and a vibrant calendar of activities and clubs. Best of all, full golf membership is included. Ideally located less than three miles from Fifth Avenue South, you’ll be close to Naples’ renowned restaurants, boutique shopping, art galleries, and pristine Gulf beaches. Updated, beautifully positioned, and ready to enjoy—this is the Naples lifestyle you’ve been waiting for.

6945 Dennis CIR Unit 203, Naples

$329,000

2 Beds ⋅ 2 Baths ⋅ 226035819 MLS ⋅ Chatham Square BLDG.

1st floor condo with FULL GOLF MEMBERSHIP and a GARAGE. Eat in kitchen with stainless appliances, upgraded cabinets and granite countertops. Beautiful view of lush courtyard from the kitchen table. Split floor plan with King size owners bedroom with en suite bath with tiled shower and walk in closet. King size guest bedroom with updated guest bath and granite counters. Great room and dining room open up to a screened lanai with golf course views of the 9th hole. Southern exposure to enjoy beautiful sun rises and sun sets. Electric shutters on lanai. One car detached garage with storage. Walk to community pool , tennis courts and pickleball courts as well as the restaurant and club house. Close to beaches and restaurants on 5th Avenue, Glen Eagle is an active community with tennis, bocce, and a fitness center with lots of classes.

6740 Dennis CIR Unit 103, 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.