Chesterhill Estates
Homes for Sale in Mount Dora, FL
All 262 homes for sale in Mount Dora, FL · median $437,995 · 230 homes for sale in 32757 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 34 closed sales in chesterhill estates in Mount Dora, FL since 2004, the most recent in August 2026. Recorded prices since 2024 ran from $439,000 to $1,160,000 (median $645,000), on homes of 2,095 to 4,214 sq ft. Across Mount Dora as a whole, 292 homes closed in the last 12 months at a median of $464,910, 54 median days on market, with 60 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $10,750 ($10,080 with the full homestead exemption).
Chesterhill Estates is a small, quiet inventory pool right now - zero active listings and no closings in the trailing window means there is no current price signal to react to. What we can read from the snapshot is the housing stock itself: 89 homes spanning a build range from 1951 to 2024, with a median build year of 2000 and a median living area of 2,738 square feet. That is a mix of older, established construction and newer builds sharing the same footprint, which usually means condition and lot position do more to set value here than square footage alone.
The homestead share sitting near 68.5% tells us this is a community where a large majority of owners have filed for the homestead exemption, which typically points to longer hold periods rather than frequent turnover. Combined with zero active listings, a buyer targeting this community should expect to wait for the right listing rather than choose from several, and a seller should expect real interest if a home does come to market, simply because so little is available to compare it against.
Nearby homes for sale
No active listings inside chesterhill estates 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
Chesterhill Estates in Mount Dora spans decades of construction within a single, compact community of 89 homes, giving it a housing stock that ranges from mid-century to recently built rather than a single architectural era.
Stellar MLS sales records identify 40 homes in chesterhill estates that have changed hands since 2004, built between 1951 and 2019 (median 2000), with a median living area of about 2,860 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 Chesterhill Estates is best for.
Best for
- Buyers comfortable waiting for a listing to surface rather than choosing among several
- Buyers who want a larger home footprint, given the community's above-average median living area
- Buyers open to either an older or newer build, given the wide construction-year range
Probably not for
- Buyers on a tight closing deadline, since there is no current active inventory
- Buyers who want a defined amenity package, since none is identified from current MLS listings
- Buyers who want recent comparable sales data to anchor an offer, since there are no closings in the current window
The market around Chesterhill Estates
Chesterhill Estates is too small for its own price trend, so here is the market around it.
In ZIP 32757, 314 homes are on the market and 24% are under contract — a steady corner of Mount Dora.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32757 (Mount Dora), 622 homes closed in the last 12 months at a median of $470K ($206/sq ft), down 1.5% year over year, with a median 51 days on market. Right now 60 active and 18 pending listings put supply at about 2.6 months - a balanced market. See the live ZIP 32757 housing market and the Lake County market.
ZIP and county figures describe the wider market, not Chesterhill Estates specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in CHESTERHILL ESTATES, MOUNT DORA
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Recent Developments in Chesterhill Estates
Development, infrastructure, retail, and school activity affecting Chesterhill Estates, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated August 2026.
- July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The project is about 25 miles southeast of Chesterhill Estates, elsewhere in Orange County.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 18 miles southeast of Chesterhill Estates, elsewhere in Orange County.
Source: Orange County Newsroom - June 2026Development
Mixed-use high-rise redesigned for 924 and 934 North Magnolia Avenue
A redesigned 17-story mixed-use high-rise was proposed for 924 and 934 North Magnolia Avenue in Orlando's North Quarter district by Acram Group. The project would include 350 residential units, about 3,300 square feet of ground-floor commercial space, and a parking garage with 510 spaces, replacing two 1972 office buildings. A public plaza is planned at the corner of Magnolia and Weber Street.
What it may mean for the marketWould replace two aging office buildings with 350 residences, ground floor retail, and structured parking, adding housing density and a public plaza along the Orlando Urban Trail. The project is about 22 miles southeast of Chesterhill Estates, elsewhere in Orange County.
Source: Florida YIMBY - June 2026Development
Planning board approves zoning for 37-story tower at 170 East Washington Street
Orlando's Municipal Planning Board voted to approve a Planned Development amendment for a 37-story, 425-foot mixed-use tower at 170 East Washington Street across from Lake Eola Park. The project would include 252 residential units, a 221-room hotel, a three-story restaurant, and structured parking. It still requires City Council consideration before construction.
What it may mean for the marketWould add a 37 story tower with 252 residences and a hotel to the downtown skyline, replacing a prior approval for a 7 story hotel and increasing high density housing and parking supply. The project is about 23 miles southeast of Chesterhill Estates, elsewhere in Orange County.
Source: Florida YIMBY - October 2025Retail & Dining
New Apopka complex with restaurants and offices set to open in 2026
A new commercial complex in Apopka with restaurants and office space is set to open in 2026, adding retail and workplace space in northwest metro Orlando.
What it may mean for the marketNew retail and office space in Apopka adds everyday conveniences and local jobs, amenity and employment factors that can support nearby housing demand. The project is about 10 miles southeast of Chesterhill Estates, elsewhere in Orange County.
Source: GrowthSpotter - March 2025Development
Lake County approves rezoning for the Wolf Branch Innovation District near Mount Dora
Lake County approved a rezoning for the Wolf Branch Innovation District, a large mixed-use employment district planned near Mount Dora and State Road 46, clearing the way for a long-term jobs and commercial hub in east Lake County.
What it may mean for the marketA large new employment and mixed-use district near Mount Dora points to long-term job growth in east Lake County, a structural demand driver for housing in the surrounding area. The site is about 3 miles northeast of Chesterhill Estates.
Source: GrowthSpotter
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
The Chesterhill Estates buying strategy.
If we were buying in Chesterhill 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 Chesterhill Estates.
A wide build range, a thin market
The build-year spread - 1951 through 2024 - is the defining structural fact about Chesterhill Estates. A community this size holding homes from both eras means condition, updates, and construction era will vary meaningfully from one address to the next, and a buyer cannot assume any two listings are comparable just because they share a neighborhood name. The median build year of 2000 puts the typical home at a point where original systems may be due for evaluation, but it also means a meaningful share of the stock is newer construction built to more current codes.
With zero active listings and no closings in the current window, there is no live pricing data to point to. What the facts do show is a median living area of 2,738 square feet, which is a useful benchmark for size expectations even without a current price to attach to it, and community amenities are not identified from current MLS listings, so any recreational or association features would need to be verified directly rather than assumed.
The location and the amenities are priced into every listing in Chesterhill Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community with no active listings and no recent closings, the value of a broker is knowing how to track a listing the moment it surfaces and how to read a build-range-and-size profile like this one accurately before an offer is written. We watch Chesterhill Estates as part of the broader Mount Dora market so a buyer is not starting from zero when something finally comes available.
Chesterhill 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 Chesterhill 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 Chesterhill Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chesterhill 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 Chesterhill Estates home worth?
Get a no-obligation home value based on real comparable sales in Chesterhill 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 Mount Dora →
Should you buy in Chesterhill Estates?
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 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2004 (34 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.
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Common questions about Chesterhill Estates
Where is Chesterhill Estates?
Chesterhill Estates is a community in Mount Dora, Orange County, Florida, ZIP 32757.
Are there homes for sale in Chesterhill Estates right now?
No active listings inside Chesterhill 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 Chesterhill Estates have an HOA or CDD?
No HOA is on record for Chesterhill 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 Chesterhill Estates with Momentum Realty’s local guides.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Lake 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 · Lake 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.
CHESTERHILL ESTATES Market Scorecard
CHESTERHILL ESTATES is currently a thin data market. Limited supply, a median asking price of n/a.
Go deeper: 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.