Who Chesterbrook fits
Suits budget-focused retirees or seasonal residents who prefer a low purchase price and an all-inclusive monthly fee.
Amenities
Clubhouse, pool, bathhouse, fitness center, shuffleboard, park, sidewalks.
What's near Chesterbrook
- UF Health Leesburg Hospital, 600 E. Dixie Ave., Leesburg. Full-service hospital in central Lake County.
- UF Health The Villages Hospital, 1451 El Camino Real, The Villages. Hospital serving Lady Lake and The Villages area.
- Venetian Gardens: seven-island waterfront park on Lake Harris with walking bridges
- Lake Harris and Lake Griffin, part of the Harris Chain of Lakes
- Lake Griffin State Park in nearby Fruitland Park
- Historic downtown Leesburg
- US-27 and US-441 corridors for shopping and services
- Florida's Turnpike connects Leesburg to Orlando and I-75
- Orlando International Airport via the Turnpike
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Frequently asked questions
Is Chesterbrook a 55+ community?
Yes. Chesterbrook is listed as 55+ (per listings). Under the federal Housing for Older Persons Act, at least 80% of occupied homes must have at least one resident aged 55 or older; check the community's own rules for guests, younger spouses and renters.
What are the HOA fees at Chesterbrook?
Reported dues are $870 per month as of October 2026. Reported inclusions: Cable, water, sewer, trash, pool, pest control. Fees vary by home and change over time, so confirm with the HOA.
Is Chesterbrook gated?
We have not yet confirmed whether Chesterbrook is gated.
Does Chesterbrook have a golf course?
There is no golf course in Chesterbrook.
How far is Chesterbrook from a hospital?
About 5 minutes (1.5 mi) by car to UF Health Leesburg Hospital, the nearest Lake County hospital. Times are measured from the community entrance or sales center without traffic and will vary by home.
What healthcare is near Chesterbrook?
The nearest urgent care is UF Health Leesburg Hospital Urgent Care, about 5 minutes away. The nearest pharmacy is Walgreens, about 7 minutes away. Veterans can use the Tavares VA Clinic, about 18 minutes away. Times are by car without traffic.
Does Chesterbrook have a CDD fee?
We have not yet confirmed whether this community carries a Community Development District (CDD) assessment. Check the non-ad valorem assessments on a current Lake County tax bill for any home you're considering.
More 55+ communities in Leesburg
Heritage - The Cottages of Sanders Grove
Arlington Ridge
Hawthorne at Leesburg
Last checked October 2026. Sources: public community listings and MLS data. Something out of date? Tell us.
Listings call Chesterbrook a 55+ community, but we could not confirm a recorded age restriction. Ask the association before you buy.