Chatham Square Real Estate

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 serene ambiance, lush landscapes, and a tight-knit community that embodies the essence of Florida living.

Chatham Square boasts a variety of beautifully designed single-family homes, each exuding unique character and style. Residents here enjoy spacious layouts, modern amenities, and private outdoor spaces perfect for soaking up the sun or hosting family gatherings. The well-maintained streets and vibrant gardens create an inviting atmosphere, making it an ideal place for families, retirees, and everyone in between.

One of the standout features of Chatham Square is its prime location. Just a short drive away, you’ll find Naples’ stunning beaches, upscale shopping at Waterside Shops, and a plethora of dining options that cater to every palate. For those who appreciate the great outdoors, the nearby parks and nature preserves offer ample opportunities for hiking, biking, and enjoying Florida’s natural beauty.

Chatham Square is also conveniently located near top-rated schools and healthcare facilities, ensuring that residents have access to essential services and a quality lifestyle. The community spirit here is palpable, with friendly neighbors and regular social events that foster connections and create lasting memories.

Whether you’re looking for your forever home or a seasonal retreat, Chatham Square in Naples, FL, offers a delightful blend of comfort, convenience, and community. Discover the lifestyle you’ve always dreamed of in this enchanting subdivision!

Newest Listings in Chatham Square

6985 Dennis Circle Unit 204, Naples
$424,900
2 Beds ⋅ 2 Baths ⋅ Chatham Square SubDv.
One or more photo(s) has been virtually staged, AI generated or rendered. 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 Circle Unit 204, Naples
6945 Dennis Circle Unit 205, Naples
$299,000
2 Beds ⋅ 2 Baths ⋅ Chatham Square SubDv.
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 Circle Unit 205, Naples
6945 Dennis Circle Unit 203, Naples
$249,000
2 Beds ⋅ 2 Baths ⋅ Chatham Square SubDv.
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 Circle Unit 203, Naples
6740 Dennis Circle Unit 103, Naples
$329,000
2 Beds ⋅ 2 Baths ⋅ Chatham Square SubDv.
1st floor condo with FULL GOLF MEMBERSHIP and a GARAGE. Eat in kitchen with stainless appliances, including new refrigerator, 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 Circle Unit 103, Naples
7025 Dennis Circle Unit G202, Naples
$215,000
2 Beds ⋅ 2 Baths ⋅ Chatham Square SubDv.
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 Circle Unit G202, Naples
Start Your Search

How much is your home worth?

Get instant property value now!