Cheshire Woods
Homes for Sale in Ocoee, FL
All 155 homes for sale in OCOEE, FL · median $446,990 · 137 homes for sale in 34761 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, Cheshire Woods in Ocoee, FL has 1 home for sale. As of October 2026, the MLS records 23 closed sales in Cheshire Woods in Ocoee, FL since 2006, the most recent in November 2025. Across Ocoee as a whole, 405 homes closed in the last 12 months at a median of $474,990, 38 median days on market, with 57 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $7,920 ($7,250 with the full homestead exemption).
| Location | OCOEE, Orange County, FL · ZIP 34761 |
|---|---|
| Homes in the community | 75 (FL DOR 2025 assessment roll) |
| Years built | 1997–1999 (median 1998) |
| Typical living area | 1,842 sq ft (median) |
| Amenities listed by sellers | Clubhouse, Gated, Gated Community - Guard, Pickleball Court(s), Playground, Pool |
| For sale right now | 1 active, 0 pending · median asking $479,499 · 12.0 months of supply |
| Owner-occupied (homestead) share | 84% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Cheshire Woods key facts,” movewithmomentum.com/neighborhoods/cheshire-woods-ocoee, data as of September 20, 2026.
Cheshire Woods right now
🟢 Buyer-leaning market. 12.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 20, 2026. Confidence: Low (1 active and pending listings, 1 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 5, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The market around Cheshire Woods
Cheshire Woods is too small for its own price trend, so here is the market around it.
In ZIP 34761, 211 homes are on the market and 37% are under contract — a fast-moving corner of Ocoee.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
ZIP and county figures describe the wider market, not Cheshire Woods specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Cheshire Woods, OCOEE
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.
Homes For Sale Right Now in Cheshire Woods
Live MLS inventory for Cheshire Woods. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Cheshire Woods listings as of 2026-10-01, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2025. Tap any home to ask about it.
Every Home for Sale in Cheshire Woods Ocoee Right Now (1)
All 1 active and pending Cheshire Woods Ocoee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 457 Mickleton Loop · $465,000 · 4 bd / 2 ba · listed Jul 6, 2026 · listed by Russu Realty & Associates Pa
Life at Cheshire Woods
- Gated · reported on 2 of 2 listings
- Pickleball Court(s) · reported on 2 of 2 listings
- Playground · reported on 2 of 2 listings
- Pool · reported on 2 of 2 listings
- Tennis Court(s) · reported on 2 of 2 listings
- Clubhouse · reported on 2 of 2 listings
- Gated Community - Guard · reported on 2 of 2 listings
- Basketball Court · reported on 1 of 2 listings
- Cable TV · reported on 1 of 2 listings
- Wheelchair Access · reported on 1 of 2 listings
- Gated Community · reported on 1 of 2 listings
- Fitness Center · 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.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Westbrooke Elementary · Elementary
- SunRidge Middle · Middle
- West Orange High · High
Zoned schools reflect the assignments reported on recent Cheshire Woods listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Cheshire Woods address.
Shop the zone: Homes zoned for West Orange High High School
The Cheshire Woods buying strategy.
If we were buying in Cheshire Woods 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 Cheshire Woods.
A closer look at the Cheshire Woods market
Inventory runs at 12.0 months of supply, a buyer-leaning market.
The housing stock is 75 homes built between 1997 and 1999, and 84% 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 Cheshire Woods. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- HOA dues reported around $176/month (about $2,112/yr) · median of 44 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $176 per month ($2,112 a year) - the median AssociationFee across 44 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, 2026-10.
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 Cheshire Woods 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 Cheshire Woods sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cheshire Woods, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Cheshire Woods home worth?
Get a no-obligation home value based on real comparable sales in Cheshire Woods, 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 Ocoee →
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange 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 · Orange 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.
32% of homes for sale in ZIP 34761 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-05).
Frequently Asked Questions
Is Cheshire Woods a buyer's or seller's market right now?
How many homes are in Cheshire Woods?
What share of Cheshire Woods is owner-occupied?
When were the homes in Cheshire Woods built?
Who is the best real estate agent for Cheshire Woods?
How do I find a top Ocoee real estate agent who knows Cheshire Woods?
Can Momentum Realty connect me with an agent for Cheshire Woods?
Where is Cheshire Woods, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 34761)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (23 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 Cheshire Woods fits the bigger picture — live prices, inventory, and Momentum Scores:
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