Cheshire Woods
Homes for Sale in Ocoee, FL
All 144 homes for sale in OCOEE, FL · median $447,498 · 88 homes for sale in 34761 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Cheshire Woods in Ocoee, FL has 1 home for sale. As of September 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, 400 homes closed in the last 12 months at a median of $474,990, 38 median days on market, with 53 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).
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 12, 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 September 15, 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, 204 homes are on the market and 35% are under contract — a fast-moving corner of Ocoee.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
ZIP and county figures describe the wider market, not Cheshire Woods specifically. Momentum Research analysis of MLS records.
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 2026-09-14, 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.
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 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 6 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 6 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 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 →
CHESHIRE WOODS Market Scorecard
CHESHIRE WOODS is currently a strong buyer's market. About 12.0 months of supply, a median asking price of $479,499, and homes go under contract in about 212 days.
Typical home value in the 34761 ZIP is $413,418, about 8.4% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · 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.
Frequently Asked Questions
Is Cheshire Woods a buyer's or seller's market right now?
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?
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 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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