Chesterbrook Condos is a neighborhood in east Leesburg, in the 34748 zip code, built mostly in the 1980s. Homes are stucco and wood frame, predominantly single story. Most homes fall between about 1,100 and 1,400 square feet under air, and the median lot is about 0.03 acres.
Homes here carry an HOA, billed monthly, typically around $450. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Mostly built in the 1980s, with homes from 1975 to 1980.
Construction Stucco and wood frame. Shingle roofs are near universal.
Size Most homes fall between about 1,100 and 1,400 square feet under air.
Bedrooms Two bedrooms is the most common plan, then three.
Lot The median lot is about 0.03 acres.
HOA Billed monthly, typically around $450. Confirm on a specific parcel before relying on it.
Where Chesterbrook Condos is
Chesterbrook Condos, centered at 28.816515, -81.855472. Drag to explore.Street level, inside the neighborhood. Drag to look around.
Drive times below are measured on the road network from the center of Chesterbrook Condos, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.
Nearest is not the same as zoned. The schools above are the closest ones to Chesterbrook Condos by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Lake County Public Schools before it matters to a decision.
Places and drive times from Google, checked 12 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Chesterbrook Condos actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 5 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.
Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.
What homes sold for in Chesterbrook Condos
$64,000Median sale price
$53Median per square foot
113 daysMedian days to contract
5Homes sold in 12 months
Sale prices ran from $55,000 to $95,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
By size
Home size
Sales
Median price
Median $/sq ft
Median days
Under 2,000 sq ft
5
$64,000
$53
113 days
Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Never reduced 2 sales, closed at 93.6% of asking81 days
Reduced at least once 3 sales, closed at 91.8% of the reduced price121 days
Sellers who priced correctly and held their number went under contract in a median 81 days. Sellers who had to reduce took 121 days and still closed at 91.8% of their already reduced price, after a typical cut of $20,000. Opening high costs time and money, in that order.
How buyers paid
Cash 5 sales100%
Cash was 100% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.
Questions about a specific home in Chesterbrook Condos, or want to know what yours would sell for? Call or text Brenden Rendo at 407-616-9019 or send a message.
About this data. Source is the Stellar MLS feed for Chesterbrook Condos in Leesburg, Lake County, covering closed sales from 18 September 2025 through 13 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.
