Chatham Square Homes under $350,000

Chatham Square Homes under $350,000

Welcome to Chatham Square, a hidden gem nestled in the heart of Naples, Florida, within Collier County. This charming subdivision offers a unique blend of affordability and the quintessential Florida lifestyle, making it an ideal choice for first-time homebuyers, retirees, or anyone looking to embrace the sunny allure of Naples.

Chatham Square is known for its welcoming community atmosphere, where neighbors become friends, and the spirit of camaraderie thrives. The subdivision features a variety of well-maintained homes, many of which are available for under $350,000, making it an attractive option for those seeking quality living without breaking the bank. These homes often come equipped with desirable amenities and are situated on picturesque lots, providing a perfect setting for relaxation and outdoor activities.

Residents of Chatham Square enjoy easy access to Naples' stunning beaches, vibrant shopping districts, and an array of dining options that cater to every palate. The proximity to top-rated schools, parks, and recreational facilities further enhances the appeal of this community, ensuring that families and individuals alike can thrive in this beautiful area.

Whether you're looking for a cozy starter home or a tranquil retreat, Chatham Square offers a diverse selection of properties that cater to various lifestyles and budgets. Experience the charm of Naples living in a community that feels like home. Discover your dream home in Chatham Square today, where affordability meets the beauty of Florida living!

Newest Chatham Square Homes under $350,000

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, 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 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
6945 Dennis Circle Unit I-107, Naples
$225,000
2 Beds ⋅ 2 Baths ⋅ Chatham Square SubDv.
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 Circle Unit I-107, Naples
Start Your Search

How much is your home worth?

Get instant property value now!