Leesburg Chesterbrook 02 Condo Homes with 55+ Only

Welcome to Leesburg Chesterbrook 02 Condo, a vibrant 55+ community nestled in the heart of sunny Leesburg, Florida. This charming subdivision offers an idyllic blend of comfort, convenience, and camaraderie, making it the perfect place for active adults seeking a fulfilling lifestyle in a serene setting.

As you explore the Leesburg Chesterbrook 02 Condo, you’ll discover a variety of well-appointed residences designed with your needs in mind. Each home features spacious layouts, modern amenities, and inviting outdoor spaces, allowing you to enjoy the beautiful Florida weather year-round. The community is thoughtfully designed to foster connections among residents, encouraging a friendly and supportive atmosphere.

Living in Leesburg means you are just moments away from a plethora of recreational opportunities. From picturesque lakes and lush parks to golf courses and walking trails, the natural beauty of Lake County is at your doorstep. Enjoy leisurely strolls along the waterfront or indulge in a round of golf with friends. Additionally, the community is conveniently located near shopping, dining, and healthcare facilities, ensuring you have everything you need within reach.

At Leesburg Chesterbrook 02 Condo, you’ll find more than just a home; you’ll discover a vibrant lifestyle filled with social activities and events tailored to enrich your golden years. Join clubs, participate in fitness classes, or simply relax by the pool with neighbors who quickly become friends. Embrace the joys of 55+ living in this delightful community where every day is an opportunity for new adventures!

Newest Leesburg Chesterbrook 02 Condo Homes with 55+ Only

$82,500

3 Beds ⋅ 2 Baths ⋅ Leesburg Chesterbrook 02 Condo SubDv. ⋅ 34748 Zip Code

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

$99,900

2 Beds ⋅ 2 Baths ⋅ Leesburg Chesterbrook 02 Condo SubDv. ⋅ 34748 Zip Code

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

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