Chestnut Hill
Homes for Sale in Lake Mary, FL
All 206 homes for sale in Lake Mary, FL · median $450,000 · 187 homes for sale in 32746 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 3 recorded sales closed at a median of $1,449,000, $344 per square foot, a median 1 days on market, sellers accepting 98% of original asking. Homes listed or recently sold were built 1984–1986; 3 of 4 report an HOA (median $85/mo). At the median price and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $22,000 ($21,400 with the full homestead exemption).
Chestnut Hill prices off size and land, not amenities. With no community amenity package showing in current MLS data, the median price near $1,643,500 is being driven almost entirely by square footage — a median living area over 4,100 square feet — and by scarcity, with only 38 homes total in the neighborhood.
A median of 5.5 days on market tells you this is not a place where buyers get to negotiate on time. When something in this size range and price point comes up, it moves fast. Sellers should price to the recent comps, not test the market, and buyers need financing and a decision ready before they tour.
Nearby homes for sale
No active listings inside Chestnut HillHomes for Sale in Lake Mary, FL 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
Chestnut Hill market snapshot (as of September 12, 2026): the median sale price is about $1.45M ($344 per sq ft over the trailing 12 months of closed sales), and a median 1 days on market for closed sales.
In ZIP 32746 (Lake Mary), 650 homes closed in the last 12 months at a median of $422K ($231/sq ft), up 0.8% year over year, with a median 34 days on market. Right now 75 active and 36 pending listings put supply at about 2.6 months — a healthy market. See the live ZIP 32746 housing market and the Seminole County market.
Stellar MLS sales records identify 7 homes in Chestnut Hill that have changed hands since 2009, built between 1984 and 1990 (median 1985), with a median living area of about 7,085 sq ft and a typical 6-bedroom, 6-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.
Chestnut Hill is a low-volume enclave of larger-format homes built mostly in the 1990s and early 2000s, where value sits in square footage and lot rather than a branded amenity package.
Who Chestnut Hill is best for.
Best for
- Buyers who need a genuinely large floor plan and are budgeting near the mid-$1.6M range
- Buyers comfortable acting fast in a market where homes typically move in about a week
- Buyers who prioritize house and lot size over community amenities
Probably not for
- Buyers expecting a clubhouse, pool, or other organized amenity package as part of the purchase
- Buyers who want a wide selection to compare, given the total pool is only 38 homes
- Buyers on a tight timeline who need weeks to deliberate before offering
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.45M) IS the median in the snapshot above.
Windows contain 0 to 3 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2007 through 2026. Deemed reliable but not guaranteed.
Chestnut Hill Market Scorecard
Chestnut Hill is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32746 ZIP is $470,893, about 15.4% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Chestnut Hill on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
The Chestnut Hill buying strategy.
If we were buying in Chestnut Hill 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 Hill.
Size drives the number, not upgrades
The math here is straightforward: a median price/square foot of $301.72 against a median home size over 4,100 square feet produces a median price in the mid-$1.6M range. That is a size story more than a finish-out story — this is not a neighborhood where a handful of premium renovations are pulling the median up. The homes themselves, built between 1984 and 2012 with a median year built of 1995, are simply large.
With a homestead exemption share near 79%, most owners here are in it long-term rather than treating these as investment or rental holdings. Combined with a small total inventory of 38 homes, that means listings are infrequent and, per the 5.5-day median DOM, get absorbed quickly once they hit the market. Anyone tracking this community for a specific home type should expect to move on it, not wait it out.
The location and the amenities are priced into every listing in Chestnut Hill. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this thin — 38 homes and a handful of closings in the recent window — pricing precedent is hard to read from public portals alone. We track the actual comps as they close, not stale averages, so sellers price correctly on day one and buyers know within days, not weeks, whether an offer is competitive.
Chestnut Hill in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $85/month (about $1,020/yr) · median of 21 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $85 per month ($1,020 a year) — the median AssociationFee across 21 MLS records, normalised to a monthly figure; most are billed quarterly. 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 Hill 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 Hill sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chestnut Hill, 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 Hill home worth?
Get a no-obligation home value based on real comparable sales in Chestnut Hill, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Chestnut Hill?
How long do homes in Chestnut Hill take to sell?
Who is the best real estate agent for Chestnut Hill?
How do I find a top Lake Mary real estate agent who knows Chestnut Hill?
Can Momentum Realty connect me with an agent for Chestnut Hill?
Where is Chestnut Hill, and what county is it in?
Should you buy in Chestnut Hill?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 17, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2007 (8 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.
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See how Chestnut Hill fits the bigger picture — live prices, inventory, and Momentum Scores:
More Lake Mary & 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.
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