Chestnut Ridge
Homes for Sale in Winter Springs, FL

A deed-restricted golf community of just 51 homes in Seminole County, Chestnut Ridge is effectively full and rarely trades, with amenities including a park, playground, and tennis courts.

Stellar MLS sales records identify 37 homes in CHESTNUT RIDGE that have changed hands since 2005, built between 1992 and 1997 (median 1994), with a median living area of about 2,902 sq ft and a typical 4-bedroom, 3-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Chestnut Ridge is a small community — 29 recorded sales on file, most recently in 2021 — too few for its own price trend. Here is the market around it.

In ZIP 32708, 185 homes are on the market and 36% are under contract — a fast-moving corner of Winter Springs.

Across Seminole County, 1,574 homes are active and 662 pending (30% under contract).

Homes here are single family residence.

In ZIP 32708 (Winter Springs), 677 homes closed in the last 12 months at a median of $411K ($242/sq ft), down 1.4% year over year, with a median 33 days on market. Right now 38 active and 21 pending listings. See the live ZIP 32708 housing market and the Seminole County market.

ZIP and county figures describe the wider market, not Chestnut Ridge specifically. Momentum Research analysis of MLS records.

The homes here were built within a tight decade, roughly 1992 to 2001, and the median living area of 2,641 square feet points to substantial single-family product rather than starter stock. Because the community is complete, your competition isn't a builder down the road - it's the next resale that comes to market, and those are infrequent. That makes condition, updates, and lot position the real differentiators on price.

Amenities reported across MLS listings include golf, a park, playground, and tennis courts, all under deed restrictions. Verify current access, fees, and rules directly with the HOA, since reported amenities don't always reflect what's active today. The near-total homestead share signals a stable, owner-occupied setting rather than an investor play.

In a 51-home community with no active listings and thin recent turnover, knowing when a home is about to come available matters more than any search filter. We track this pocket of Winter Springs closely, help you read whether a given home's price reflects genuine updates or just scarcity, and keep you ready to act when inventory is this limited.