Chesterhill Estates
Chesterhill Estates: Local Questions Answered
Where is Chesterhill Estates located?
Chesterhill Estates is off Old Highway 441 near Tangerine Road, in the Tangerine area, on Chesterhill Circle, Chesterhill Lane, Sinisi Drive and Norne Lane. Homes have Mount Dora 32757 mailing addresses, but the neighborhood is in unincorporated Orange County, outside Mount Dora city limits.
What types of homes are in Chesterhill Estates?
Custom single-family homes only. Orange County property records show 72 homes, built from 1984 to 2025 apart from one 1951 home, from about 1,710 to 5,600 square feet, with a median of about 2,760, on lots of about 0.5 to 3.2 acres, and 42 have pools. MLS listings show 3 to 5 bedrooms.
How much do homes cost in Chesterhill Estates?
Over the past two years (MLS data, October 2026), homes in Chesterhill Estates sold 5 times for a median of about $630,000, from about $439,000 to $890,000. Vacant lot sales are not included. For today's listings, see the top of this page.
What are the HOA fees in Chesterhill Estates?
Chesterhill Estates has three homeowners associations, by phase: Chesterhill Estates Association, Inc., Chesterhill Estates Phase II Homeowners' Association, Inc. and Chesterhill Phase IV Homeowners' Association, Inc. Recent MLS listings show HOA dues of about $12 to $25 per month as of October 2026, depending on the phase. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Chesterhill Estates, but check the property tax bill for any special assessments.
What schools serve Chesterhill Estates?
Orange County Public Schools' 2026-27 school zones place Chesterhill Estates in Zellwood Elementary, Wolf Lake Middle and Apopka High School.
Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.
Are there lots for sale in Chesterhill Estates?
Orange County property records show 13 vacant lots, 9 of them in Phase 4, where lots are about 1 acre and homes have been built as recently as 2025. Chesterhill Estates is a resale neighborhood with occasional custom building, not a builder community. Stoneybrook Hills, Elysium Club and Oakfield at Mount Dora are separate communities in the same area.
Can you rent homes in Chesterhill Estates short term?
No Chesterhill Estates-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
