Leesburg Chesterbrook Condos

Leesburg Chesterbrook Condos in Leesburg, FL, offer an exceptional real estate opportunity for those seeking comfortable living in a 55+ community. These well-designed condos provide a range of amenities and features tailored to meet the needs of mature residents. With an emphasis on convenience and quality, Leesburg Chesterbrook Condos offer a low-maintenance lifestyle, allowing residents to focus on enjoying their retirement years.

The condos boast a variety of amenities, including a clubhouse where residents can gather for social events and activities. The community also offers a swimming pool and walking trails, providing opportunities for exercise and relaxation. The well-maintained grounds and landscaped areas create a serene atmosphere for residents to enjoy.

Located in Leesburg, FL, residents of Chesterbrook Condos benefit from easy access to local attractions, including shopping centers, restaurants, and medical facilities. The vibrant community offers a range of recreational opportunities, including golf courses and nearby lakes for fishing and boating enthusiasts. With its desirable location and array of amenities, Leesburg Chesterbrook Condos provide an appealing option for those seeking a comfortable and active 55+ lifestyle in Florida.

Available Leesburg Chesterbrook Condos For Sale

$82,500
3 Beds ⋅ 2 Baths ⋅ G5114410 MLS ⋅ N/A BLDG.
DISCOVER EASY FLORIDA LIVING-in the desirable Chesterbrook Condominiums in Leesburg! This centrally located 3-bedroom 2- bath home is nestled in a welcoming 55+ community featuring a community pool and clubhouse. NEW ROOF 2026, AND NEWER AC. The HOA also covers water, sewer, trash, and cable making for a truly hassle-free living. Whether you're looking for a full time residence or the perfect winter retreat , this is an opportunity you want to miss!!

500 Newell Hill Road Unit 108D, Leesburg

Courtesy of MORRIS REALTY AND INVESTMENTS

$99,900
2 Beds ⋅ 2 Baths ⋅ G5113323 MLS ⋅ 110 BLDG.
Discover elegance and ease in this beautifully remodeled 2-bedroom, 2-bath condo, tucked away in the premier 55+ community of Chesterbrook. Glowing with natural warmth, the spacious open-concept layout effortlessly connects the living and dining area to a serene enclosed porch, the perfect spot for your morning coffee. A bonus is additional storage in the attic space located on the enclosed porch, so nice to have that space you will not find on the 1st floor. High-end finishes elevate every corner, featuring Venatino Italian tile, durable laminate flooring, granite countertops, and custom maple cabinetry. Both bathrooms have been stunningly upgraded with Mirasol glazed ceramic wall tiles, including a luxurious jacuzzi jetted tub in the guest bath. Retreat to the generous primary suite, which easily accommodates a king-size bed and boasts an impressive, oversized walk-in closet. The large second bedroom offers fantastic flexibility, making it an ideal space for guests, a home office, or a hobby room. Outside, Chesterbrook’s sparkling community pool is ready for summer relaxation. Perfectly positioned, you are just minutes from Lady Lake, The Villages, and Lake Griffin. Your stylish, low-maintenance retreat awaits, in addition to the remodel, please note excellent mechanical updates: a BRAND NEW ROOF (February 2026) and AC (2020).

500 Newell Hill Rd Unit 110D, Leesburg

Courtesy of GARRISON REALTY GROUP LLC

$63,000
2 Beds ⋅ 2 Baths ⋅ G5108494 MLS ⋅ 101a BLDG.
NEW LOW PRICE!!!! — a quiet, well-kept 55+ community just minutes from downtown Leesburg, The Villages, and the sparkling waters of Lake Griffin on the renowned Chain of Lakes. This beautifully updated 2-bedroom, 2-bathroom ground-floor condo offers comfort, convenience, and a relaxed Florida lifestyle. Step inside to an inviting open floor plan with premium ceramic tile in the kitchen, baths and living areas for added durability and style. As an end-unit you will enjoy extra privacy and a peaceful setting. The enclosed patio provides the perfect spot to unwind on warm afternoons — a cozy indoor-outdoor retreat you can enjoy year-round. Parking is just steps from your front door, making daily living effortless. RETIRE YOUR LAWN MOWER Chesterbrook residents enjoy a friendly, active community with amenities that include: A refreshing community pool A welcoming clubhouse A convenient bathhouse Shuffleboard courts for leisurely afternoons You’ll love the unbeatable location — close to restaurants, shopping, medical facilities, and only a short 15-minute drive to all the entertainment and conveniences of The Villages. Outdoor lovers will appreciate quick access to the Chain of Lakes for boating, fishing, and scenic adventures. The condo fee covers water, sewer, trash, and grounds maintenance, giving you true low-maintenance living. Community roof replacement is already underway. Whether you’re looking for a comfortable full-time home or a smart investment opportunity, this move-in-ready condo checks all the boxes. Come see why Chesterbrook is such a special place to call home.

500 Newell Hill Road Unit 101A, Leesburg

Courtesy of RE/MAX PREMIER REALTY

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