Chatham Square Homes under $250,000

Welcome to Chatham Square, a hidden gem nestled in the heart of Naples, Florida, within the charming Collier County. This vibrant subdivision offers a unique blend of affordability and community spirit, making it an ideal choice for first-time homebuyers, retirees, or anyone looking to enjoy the Naples lifestyle without breaking the bank.

Chatham Square is known for its welcoming atmosphere and well-maintained properties, where residents take pride in their homes and surroundings. Here, you can find a delightful selection of homes priced under $250,000, making it an attractive option for those seeking value in one of Florida's most sought-after locations. These homes often feature open floor plans, cozy living spaces, and outdoor areas perfect for enjoying the beautiful Florida weather.

Living in Chatham Square means having access to a wealth of amenities and attractions. The nearby beaches are just a short drive away, offering sun-soaked days by the Gulf of Mexico. For those who love the outdoors, numerous parks and recreational areas are within reach, providing endless opportunities for hiking, biking, and enjoying nature.

Additionally, Chatham Square is conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a stone's throw away. With its friendly community and affordable housing options, Chatham Square is the perfect place to call home in Naples. Discover the charm and convenience of this delightful subdivision today, and see why so many are choosing to make Chatham Square their home sweet home!

Newest Chatham Square Homes under $250,000

$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

$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.