Chestnut Hill
Homes for Sale in Lake Mary, FL
True comps, carrying-cost math, and listings before the portals.
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.
The 60-Second Overview
Chestnut Hill market snapshot (as of July 15, 2026): the median sale price is about $1.64M ($302 per sq ft over the trailing 12 months of closed sales), and a median 6 days on market for closed sales.
Chestnut Hill is a community of 38 homes in Lake Mary, Seminole County, built between 1984 and 2012 (median 1995.0), with a median living area of about 4,172 square feet. 79% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
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 July 15 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.64M) IS the median in the snapshot above.
Windows contain 0 to 4 sales each (4 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 %s through %s. Deemed reliable but not guaranteed.
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
- Mandatory HOA — confirm current dues
- 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 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.
See homes for sale in Chestnut Hill on the map →
Frequently Asked Questions
What is the median home price in Chestnut Hill?
How long do homes in Chestnut Hill take to sell?
How many homes are in Chestnut Hill?
What share of Chestnut Hill is owner-occupied?
When were the homes in Chestnut Hill built?
Do cash buyers compete in Chestnut Hill?
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?
Should you buy in Chestnut Hill?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 15, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (3 streets, ZIP 32746)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| 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 your area 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.