Displaying: For Sale
Location: Leesburg
Property Type(s): Condos
Price: $0 to $99,000
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Leesburg - 4 properties found
500 NEWELL HILL RD #101A, LEESBURG, FL 34748
$63,000120 Days on yellowkey MLS ID: G5108494
REDUCED by $5,000 (7.4%) on 06/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1134 Built: 1975 Tax: $1,041 (2025)Community: Leesburg Chesterbrook CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,041
Elementary School: Beverly Shores Elem
High School: Leesburg High
Tax Year: 2025
Middle School: Oak Park Middle
Remarks: 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.
Listing is courtesy of: RE/MAX PREMIER REALTY (352-735-4060)
Listing Agent: James Donovan (352-552-8195)
500 NEWELL HILL RD #108A, LEESBURG, FL 34748
$48,000323 Days on yellowkey MLS ID: G5100448
1 Days Off yellowkey (back on 6/11/2026)
REDUCED by $11,000 (18.6%) on 05/27/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1413 Built: 1980Monthly Fee: $645 Tax: $1,273 (2024)Community: Leesburg Chesterbrook 02 CondoSpa: NoCondo
Taxes:$1,273
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Motivated Owner says make an offer. This 3/2 condo in the 55+ community of Chesterbrook is looking for a new owner. This community is close to everything Leesburg has to offer, restaurants, health care facilities, mall, auto dealers and 20 minutes from the Villages. The unit has a large primary bedroom with ensuite bath and dual sinks. Sit out in the morning on the porch. Call for your appointment today. Community has completed the new roofs and unit has been freshly painted.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Nicky Lerch (571-212-2077)
500 NEWELL HILL RD #106D, LEESBURG, FL 34748
$50,000184 Days on yellowkey MLS ID: S5140606
REDUCED by $5,000 (9.1%) on 06/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1134 Built: 1979Monthly Fee: $870 Tax: $1,049 (2025)Community: Chesterbrook 2 CondoCondo
Taxes:$1,049
Remarks: New Roof!! Welcome to this cozy and well-maintained 2-bedroom, 2-bath condo located in a 55+ community. This second-floor unit features a private entry, convenient parking, and no neighbors above for added privacy. The interior has been freshly painted and includes an enclosed porch a perfect for relaxing and enjoying the Florida lifestyle. Chesterbrook Condo offers excellent amenities, including a clubhouse, community pool, and shuffleboard. The HOA covers water, sewer, garbage, and cable, making for easy, low-maintenance living. Centrally located near shopping, dining, entertainment, and medical facilities, with a bus stop conveniently located within the community for easy access to daily needs. Enjoy!
Listing is courtesy of: PROFESSIONAL REAL ESTATE TEAM (407-483-4964)
Listing Agent: Diana Perez (407-483-4964)
1112 W MAIN ST #C4, LEESBURG, FL 34748
$92,50028 Days on yellowkey MLS ID: G5112767
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 638 Built: 1973 Tax: $682 (2025)Community: Spanish Oaks CondoCondo
Taxes:$682
Middle School: Carver Middle
Remarks: Rare first-floor condo in the heart of downtown Leesburg! Enjoy the convenience of walking to local dining, shopping, and Beacon College while living in a beautifully remodeled condo with a modern feel throughout. Step inside to an open dining and living room combination featuring new luxury vinyl plank flooring, fresh white paint, and a bright, clean design. The updated kitchen offers wood cabinetry, backsplash, open wood shelving, and butcher block countertops that create a stylish modern touch. The bathroom has been fully updated with a beautifully tiled shower, new vanity, elegant gold fixtures, and updated lighting. Additional features include a 2017 hot water heater, and the condo association maintains the roof for added peace of mind. Community amenities include an assigned parking space, guest parking, and community pool. Whether you are looking for a low-maintenance full-time residence, investment property, or downtown retreat, this rare first-floor unit is a must-see!
Listing is courtesy of: MORRIS REALTY AND INVESTMENTS (352-435-4663)
Listing Agent: Lindsay Sanders (352-661-0232)
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