Chatham Square Real Estate

Chatham Square Real Estate

Welcome to Chatham Square, an enchanting subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community is the epitome of serene living, combining the tranquility of suburban life with the vibrant culture of one of Florida's most sought-after cities.

Chatham Square boasts meticulously maintained homes that reflect a harmonious blend of modern design and classic architecture. The community is characterized by lush landscaping, tree-lined streets, and a warm, welcoming atmosphere that makes it ideal for families, retirees, and everyone in between. With a variety of floor plans and styles, there’s something to suit every taste and lifestyle.

Residents of Chatham Square enjoy easy access to Naples' stunning beaches, renowned shopping, and gourmet dining options. Just a short drive away, you can indulge in the vibrant arts scene, explore the lush parks, or take a leisurely stroll along the famous Naples Pier, where breathtaking sunsets await.

For those who appreciate an active lifestyle, Chatham Square is conveniently located near numerous golf courses, fitness centers, and recreational facilities. The community fosters a sense of belonging, with friendly neighbors and regular social events that encourage connection and camaraderie.

With its prime location, beautiful homes, and an array of amenities, Chatham Square is more than just a place to live; it’s a lifestyle. Discover the charm of this delightful subdivision and make it your new home in sunny Naples, Florida!

Newest Listings in Chatham Square

6985 Dennis Cir Unit 204, Naples
$424,900
2 Beds ⋅ 2 Baths ⋅ 226036427 MLS ⋅ Glen Eagle BLDG.
Enjoy Golf-Course Living at Glen Eagle Golf & Country Club Welcome to this beautifully remodeled condominium at Glen Eagle Golf & Country Club, where full golf membership is included and picturesque views of the 18-hole golf course create an exceptional Naples lifestyle. This spacious 2-bedroom, 2-bath condominium offers an oversized living room and generous lanai, providing plenty of space to relax and entertain while enjoying the beautiful golf-course setting. The residence also features a convenient laundry room and pantry, along with a stylish bar and wine cooler—perfect for entertaining family and friends. Property Features • Full golf membership included • Picturesque views of the 18-hole golf course • Completely remodeled • Oversized living room and spacious lanai • 2 bedrooms and 2 bathrooms • Laundry room and pantry • Stylish bar with wine cooler • All New Appliances • Newer Hot Water, Washer and Dryer • A/C replaced in 2024 • Hurricane shutters throughout • Community swimming pool and pickleball courts just steps from the condo The Glen Eagle Lifestyle Glen Eagle is a private, gated golf community offering an impressive array of amenities and activities. Members enjoy golf, tennis, billiards, bocce ball, card rooms, a library, restaurant, grill room, outdoor dining, swimming pool, planned social events, and so much more. The fully equipped fitness center offers a variety of classes and programs supported by professional instructors, providing residents with plenty of opportunities to stay active, socialize, and enjoy the community. Ideally located near Naples' renowned beaches, restaurants, shopping, entertainment, and attractions, Glen Eagle offers the opportunity to experience the best of Southwest Florida living in a private-club setting. Come experience the comfort, elegance, and exceptional golf-course lifestyle of this beautifully remodeled Glen Eagle condominium.

6985 Dennis Cir Unit 204, Naples
6945 Dennis Cir Unit 205, Naples
$299,000
2 Beds ⋅ 2 Baths ⋅ 226036138 MLS ⋅ Glen Eagle BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. Golf, resort-style amenities, and Naples' sugar-sand beaches come together at this two bedroom, two bath, second-floor residence in Chatham Square at Glen Eagle Golf & Country Club. Enjoy relaxing on the screened lanai and take in the stunning golf course and lake views. The community pool, spa, and pickleball/tennis courts are just moments from your door, while the Club offers an 18-hole championship course, pro shop, restaurant and lounge, tennis, bocce, card room, and a fitness center with café. Full bundled golf membership included. Set in the gated Glen Eagle community, you're minutes from Fifth Avenue South, Third Street South, Waterside Shops, and Mercato. Ideal as a full-time home or a seasonal retreat. Schedule your private showing today.

6945 Dennis Cir Unit 205, Naples
6945 Dennis Cir Unit 203, Naples
$249,000
2 Beds ⋅ 2 Baths ⋅ 226036221 MLS ⋅ Glen Eagle 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
6740 Dennis Cir Unit 103, Naples
$329,000
2 Beds ⋅ 2 Baths ⋅ 226035819 MLS ⋅ Glen Eagle 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. Professional photos coming soon!!

6740 Dennis Cir Unit 103, Naples
7025 Dennis Cir Unit G202, Naples
$215,000
2 Beds ⋅ 2 Baths ⋅ 226009100 MLS ⋅ Glen Eagle 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
6945 Dennis Cir Unit I-107, Naples
$225,000
2 Beds ⋅ 2 Baths ⋅ 225084882 MLS ⋅ Glen Eagle 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
Start Your Search

How much is your home worth?

Get instant property value now!