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Seminole County › Winter Springs › Chestnut Ridge
Chestnut Ridge, Winter Springs
Chestnut Ridge 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 3,100 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 annually, typically around $350. 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, Florida. Predominantly two story.
- Size Most homes fall between about 2,300 and 3,100 square feet under air.
- Bedrooms Four bedrooms is the most common plan.
- Garage A two car garage is standard.
- Lot The median lot is roughly a quarter acre.
- HOA Billed annually, typically around $350. Confirm on a specific parcel before relying on it.
Where Chestnut Ridge is
Drive times below are measured on the road network from the center of Chestnut Ridge, 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 | 28 min | 19.4 |
| Orlando International Airport | 31 min | 25.4 |
| Winter Park | 25 min | 10.2 |
| Heathrow and Lake Mary offices | 30 min | 19.2 |
Public schools nearby
- Rainbow Elementary School 4 min, 1.4 mi
- Keeth Elementary School 7 min, 2.8 mi
- Oviedo High School 8 min, 2.6 mi
- Lawton Elementary School 8 min, 3.0 mi
Private schools nearby
- The Master's Academy 8 min, 3.0 mi
- Alpine Academy 6 min, 2.3 mi
- Circle Christian School 8 min, 2.8 mi
Parks and recreation
- Sam Smith Memorial Park 3 min, 1.3 mi
- Sunrise Community Park 5 min, 1.8 mi
- Trottwood Park 5 min, 2.0 mi
- Trotwood Park 6 min, 2.1 mi
Groceries and errands
- Oviedo Olive Oil 9 min, 3.5 mi
- Target Grocery 9 min, 3.3 mi
- Publix Super Market at Tuscawilla Bend Shopping Center 6 min, 2.0 mi
- Cavallari Gourmet 9 min, 3.1 mi
Nearest is not the same as zoned. The schools above are the closest ones to Chestnut Ridge 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 6 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 Ridge actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 3 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 Chestnut Ridge
Sale prices ran from $552,000 to $956,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Sellers who priced correctly and held their number went under contract in a median 26 days. Sellers who had to reduce took 120 days and still closed at 93.6% of their already reduced price, after a typical cut of $110,000. Opening high costs time and money, in that order.
Seller concessions
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 was 67% 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 Ridge, 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 Ridge in Winter Springs, Seminole County, covering closed sales from 11 September 2025 through 6 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.