Chestnut Ridge
Homes for Sale in Winter Springs, FL
All 126 homes for sale in WINTER SPRINGS, FL · median $422,445 · 62 homes for sale in 32708 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
Nearby homes for sale
No active listings inside CHESTNUT RIDGE right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
As of September 2026, the MLS records 16 closed sales in Chestnut Ridge in Winter Springs, FL since 2012, the most recent in November 2025. Across Winter Springs as a whole, 253 homes closed in the last 12 months at a median of $446,000, 33 median days on market, with 32 homes for sale today. At that median and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $6,770 ($6,170 with the full homestead exemption).
The market around Chestnut Ridge
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.
ZIP and county figures describe the wider market, not Chestnut Ridge specifically. Momentum Research analysis of MLS records.
Life at Chestnut Ridge
- Golf · reported on 2 of 2 listings
- Deed Restrictions · reported on 1 of 2 listings
- Park · reported on 1 of 2 listings
- Playground · reported on 1 of 2 listings
- Tennis Court(s) · reported on 1 of 2 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
The Chestnut Ridge buying strategy.
If we were buying in Chestnut Ridge today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Chestnut Ridge.
A closer look at the Chestnut Ridge market
The housing stock is 51 homes built between 1992 and 2001, and 96% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Chestnut Ridge. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- HOA dues reported around $43/month (about $516/yr) · median of 6 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $43 per month ($516 a year) - the median AssociationFee across 6 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Chestnut Ridge buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Chestnut Ridge sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chestnut Ridge, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chestnut Ridge home worth?
Get a no-obligation home value based on real comparable sales in Chestnut Ridge, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See homes for sale in Chestnut Ridge on the map →
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Seminole County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Seminole County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
CHESTNUT RIDGE Market Scorecard
CHESTNUT RIDGE is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32708 ZIP is $427,790, about 2.4% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
How many homes are in Chestnut Ridge?
What share of Chestnut Ridge is owner-occupied?
When were the homes in Chestnut Ridge built?
Do cash buyers compete in Chestnut Ridge?
Who is the best real estate agent for Chestnut Ridge?
How do I find a top Winter Springs real estate agent who knows Chestnut Ridge?
Can Momentum Realty connect me with an agent for Chestnut Ridge?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32708)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2012 (16 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.
Looking to buy here? Search homes for sale →
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More Winter Springs & Seminole County & North Orlando guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Seminole County & North Orlando or the full Neighborhood Finder.
See how CHESTNUT RIDGE fits the bigger picture — live prices, inventory, and Momentum Scores:
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