Chestnut Estates
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.
As of September 2026, the MLS records 16 closed sales in Chestnut Estates Ph 2 in Winter Springs, FL since 2013, the most recent in July 2026. 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).
Chestnut Estates Ph 2 is a tightly built pocket of 48 homes, all raised between 1995 and 1998, with a median build year of 1996. That narrow construction window means the housing stock reads consistently: similar-era construction, similar-era systems, and a median living area of roughly 2,643 square feet that skews toward larger single-family footprints rather than starter-sized homes.
There is no recent closings activity in the current snapshot, so we are not pricing this community off fresh transaction data right now. That is not a red flag on its own for a small, built-out subdivision of this size — it just means any pricing conversation here has to lean on condition, comparable sales from the broader Winter Springs market, and a careful look at what has actually sold nearby rather than relying on turnover inside the community itself.
Nearby homes for sale
No active listings inside Chestnut Estates Ph 2 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.
The 60-Second Overview
A small, fully built subdivision in Winter Springs where nearly 9 in 10 homes carry a homestead exemption — a strong signal of owner-occupancy and longer hold periods rather than frequent resale or rental turnover.
Stellar MLS sales records identify 30 homes in Chestnut Estates that have changed hands since 2005, built between 1995 and 1998 (median 1996), with a median living area of about 2,636 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.
Who Chestnut Estates is best for.
Best for
- Buyers prioritizing interior square footage over community amenities.
- Move-up buyers comfortable evaluating a mid-1990s home on its individual condition and updates.
- Buyers planning a longer hold who are less concerned with amenity-driven resale appeal.
Probably not for
- Buyers who want on-site amenities like a pool, clubhouse, or organized common areas.
- Buyers who need very recent comparable sales data inside the community to feel confident pricing a home.
- Buyers seeking a smaller, lower-square-footage starter home.
The market around Chestnut Estates
Chestnut Estates is too small for its own price trend, so here is the market around it.
In ZIP 32708, 150 homes are on the market and 33% are under contract — a fast-moving corner of Winter Springs.
Across Seminole County, 1,646 homes are active and 585 pending (26% under contract).
In ZIP 32708 (Winter Springs), 668 homes closed in the last 12 months at a median of $412K ($242/sq ft), down 1.5% year over year, with a median 33 days on market. Right now 32 active and 21 pending listings put supply at about 1.9 months — a healthy market. See the live ZIP 32708 housing market and the Seminole County market.
ZIP and county figures describe the wider market, not Chestnut Estates specifically. Momentum Research analysis of MLS records.
The Chestnut Estates buying strategy.
If we were buying in Chestnut Estates 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 Estates.
A built-out, owner-held pocket
With only 48 homes and construction confined to a four-year window in the mid-1990s, Chestnut Estates Ph 2 is not a community that adds new inventory or evolves architecturally over time — what you see is close to what you get, era-wise. The median living area near 2,643 square feet puts the typical home here above a starter-home footprint, which tends to appeal to buyers looking for more interior space rather than a compact or entry-level layout.
Current MLS listings show no identified community amenities — no clubhouse, pool, or similar shared facility tied to this phase. That does not mean the location lacks nearby recreation or services, but it does mean the value proposition here is the home and lot themselves, not a bundled amenity package. Buyers should treat this as a standalone housing decision and evaluate the immediate lot and structure on their own merits.
The location and the amenities are priced into every listing in Chestnut Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, thinly traded community like this one, the publicly available data only tells part of the story. We pull comparable sales from the surrounding Winter Springs market, factor in the age and typical square footage of this specific phase, and give you a grounded read on where a home should price — rather than leaning on a single automated number or guesswork.
Chestnut Estates in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
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 Estates 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 Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chestnut Estates, 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 Estates home worth?
Get a no-obligation home value based on real comparable sales in Chestnut Estates, 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 all homes for sale in Winter Springs →
Should you buy in Chestnut Estates?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2013 (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 local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Chestnut Estates Ph 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Chestnut Estates
Where is Chestnut Estates?
Chestnut Estates is a community in Winter Springs, Seminole County, Florida, ZIP 32708.
Are there homes for sale in Chestnut Estates right now?
No active listings inside Chestnut Estates at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Chestnut Estates have an HOA or CDD?
No HOA is on record for Chestnut Estates in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Chestnut Estates with Momentum Realty’s local guides.