Chestnut Estates is a 1990s neighborhood in east Winter Springs, in the 32708 zip code. Homes are block and stucco. Most homes fall between about 2,300 and 3,300 square feet under air, the median lot is roughly a quarter acre, and a two car garage is standard.
Homes here carry an HOA, billed quarterly, typically around $175. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Essentially all built in the 1990s.
Construction Block and stucco. Shingle roofs are near universal.
Style Contemporary, Traditional
Size Most homes fall between about 2,300 and 3,300 square feet under air.
Bedrooms Four bedrooms is the most common plan, then five.
Garage A two car garage is standard.
Lot The median lot is roughly a quarter acre.
HOA Billed quarterly, typically around $175. Confirm on a specific parcel before relying on it.
Where Chestnut Estates is
Chestnut Estates, centered at 28.668982, -81.231113. 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 Chestnut Estates, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.
Driving to
Time
Miles
Downtown Orlando
25 min
18.5
Orlando International Airport
28 min
24.4
Winter Park
25 min
11.7
Heathrow and Lake Mary offices
28 min
19.5
Public schools nearby
Oviedo High School 5 min, 1.2 mi
Lawton Elementary School 5 min, 1.6 mi
Rainbow Elementary School 7 min, 2.5 mi
Keeth Elementary School 9 min, 3.2 mi
Private schools nearby
Alpine Academy 4 min, 0.9 mi
Bainbridge Academy 4 min, 1.3 mi
CrossLife Christian Academy 5 min, 1.5 mi
Parks and recreation
Aulin Square Dog Park 4 min, 1.0 mi
Sam Smith Memorial Park 4 min, 1.2 mi
Friendship Park 4 min, 1.4 mi
Lawton Grove Park 5 min, 1.6 mi
Groceries and errands
Publix Super Market at Tuscawilla Bend Shopping Center 3 min, 0.6 mi
Nearest is not the same as zoned. The schools above are the closest ones to Chestnut Estates 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 Seminole County Public Schools before it matters to a decision.
Places and drive times from Google, checked 9 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Chestnut Estates actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 2 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 October 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 Chestnut Estates
$661,550Median sale price
$260Median per square foot
128 daysMedian days to contract
2Homes sold in 12 months
Sale prices ran from $625,000 to $698,100.
Price cuts and time to contract
Median days to go under contract. Shorter is better.
Never reduced 1 sale, closed at 100% of asking2 days
Reduced at least once 1 sale, closed at 97.2% of the reduced price253 days
Sellers who held their number went under contract in a median 2 days. Sellers who had to reduce took 253 days and still closed at 97.2% of their already reduced price, after a typical cut of $129,910.
Seller concessions
50%Of sales included a seller credit
$1,900Typical credit when there was one
1 of 2Sales carrying a credit
A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.
How buyers paid
Cash 1 sale50%
Conventional 1 sale50%
Cash was 50% 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 Chestnut Estates, 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 Chestnut Estates in Winter Springs, Seminole County, covering closed sales from 27 October 2025 through 22 October 2026, refreshed monthly and current as of October 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.
