Westchester Place in Winter Garden

Westchester Place
Homes for Sale in Winter Garden, FL

All 709 homes for sale in WINTER GARDEN, FL · median $584,900 · Orange County homes for sale

Community in Winter Garden · Orange County · ZIP 34777
76 homesBuilt 1915–2024
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Built fromLive Stellar MLS data20 years of closingsFL DOR public recordsUpdated twice daily

As of September 2026, Westchester Place in Winter Garden, FL has 1 home for sale. Homes listed or recently sold were built 1952 - 2004; none of the 3 geocoded homes sit in a FEMA special flood hazard zone (median elevation 117 ft).

Westchester Place key facts
LocationWINTER GARDEN, Orange County, FL · ZIP 34777, 34787
Homes in the community76 (FL DOR 2025 assessment roll)
Years built1915–2024 (median 1956.5)
Typical living area1,072 sq ft (median)
For sale right now1 active, 0 pending · median asking $342,000 · 6.0 months of supply
Owner-occupied (homestead) share39%

Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Westchester Place key facts,” movewithmomentum.com/neighborhoods/westchester-place-winter-garden, data as of September 20, 2026.

Last 30 days in Westchester Place: 1 new listing (median asking $342,000). As of September 28, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.

Live · Westchester Place Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
6.0mo
Supply
3 to 6 months is the balanced band
0%
Under contract
Orange: 23% (1,755 of 7,529)
1 · 0
For sale · pending
live counts, refreshed twice daily
2
Sold · last 12 mo
10-yr average: about 2 a year
Ownership and context
39%
Owner-occupied · Westchester Place
32 of 83 parcels homesteaded (FL DOR 2025)
61%
Non-owner-occupied · Westchester Place
incl. 10% trust or LLC-held · 100% out-of-state
76
Homes in the community
plus 7 vacant residential lots · 83 residential parcels (FL DOR 2025)
Track record · 20 years of records
3
Recorded sales · 2024-2024
median $400K · qualified sales on the county roll (FL DOR 2025)
Est. 1915
Community established
homes built 1915-2024, median 1957 (FL DOR 2025)
2.6%/yr
Turnover rate
about 2 of 76 homes trade a year
Westchester Place Housing Pulse · Momentum Research · as of September 20, 2026

Westchester Place right now

🟡 Balanced market. 6.0 months of supply and 0% of the inventory already under contract put buyers and sellers on roughly even footing.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, 2 closed sales in 12 months).

Jump to: Price history & scorecard · Homes for sale · Schools · FAQ

· Updated September 28, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness

The market around Westchester Place

Westchester Place is too small for its own price trend, so here is the market around it.

Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).

ZIP and county figures describe the wider market, not Westchester Place specifically. Momentum Research analysis of MLS records.

Housing distress & ownership in Westchester Place, WINTER GARDEN

Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.

Active inventory in distress
22.22%
2 of 9 listings · short sale 2
Distress share trend - 22.22% now (2026-08-12 → 2026-09-22)

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 Westchester Place

Live MLS inventory for Westchester Place. 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 Westchester Place listings as of 2026-09-26, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026. Tap any home to ask about it.

Every Home for Sale in Westchester Place Winter Garden Right Now (1)

All 1 active and pending Westchester Place Winter Garden listings with a detail page, newest first, refreshed twice a day from the MLS.

  • 636 Coke Avenue · $342,000 · 2 bd / 1 ba · listed Sep 7, 2026 · listed by Valstar Realty Llc

Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.

If we were buying in Westchester Place today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Westchester Place.

A closer look at the Westchester Place market

Inventory runs at 6.0 months of supply, a balanced market.

The housing stock is 76 homes built between 1915 and 2024, and 39% 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 Westchester Place. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Westchester Place homeowners association, its management company or its developer, and we cannot help with dues, gate access, violations, amenity bookings or association documents. To reach the association, check your closing package, the recorded declaration at the county clerk, or search the association’s name at sunbiz.org for its registered agent. Call or message us to buy or sell a home in Westchester Place.
In short
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Westchester Place sales matched to your home.

What is your Westchester Place home worth?

Get a no-obligation home value based on real comparable sales in Westchester Place, 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 Winter Garden →

Real comps, not an automated estimate.

Recently off market in Westchester Place

Homes in Westchester Place that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.

How much local inventory is already under contract

28% of homes for sale in ZIP 34787 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 (2026-09-25).

Frequently Asked Questions

Is Westchester Place a buyer's or seller's market right now?
As of September 20, 2026, Westchester Place is roughly balanced: 6.0 months of supply at the current sales pace (Stellar MLS live counts).
How many homes are in Westchester Place?
The Florida DOR 2025 assessment roll shows 76 homes plus 7 vacant residential lots in Westchester Place (public records).
What share of Westchester Place is owner-occupied?
39% of Westchester Place parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Westchester Place built?
Homes in Westchester Place were built between 1915 and 2024, with a median year built of 1956.5 (FL DOR 2025 roll).
Who is the best real estate agent for Westchester Place?
The best agent for Westchester Place is one who actively works Winter Garden and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Westchester Place.
How do I find a top Winter Garden real estate agent who knows Westchester Place?
Share a few details in the form on this page. Momentum Realty has 320+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Westchester Place and the wider Winter Garden area.
Can Momentum Realty connect me with an agent for Westchester Place?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Westchester Place purchase or sale - no call center and no pressure.
Where is Westchester Place, and what county is it in?
Westchester Place is in WINTER GARDEN, Orange County, FL, ZIP codes 34777, 34787. The community's center is about 9 miles north of the center of WINTER GARDEN (straight-line).

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: September 26, 2026)
Housing stock & ownershipFlorida DOR assessment roll (street-list match (3 streets, ZIP 34777/34787))
Under-contract sharesStellar MLS records, as of 2026-09-20
Historical depthClosed-sale records back to 2006 (24 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.

Looking to buy here? Search homes for sale →

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Nearby Communities

Explore more neighborhoods near Westchester Place with Momentum Realty’s local guides.

Burchshire0.2 mi away · 273 homes, built 1910–24, 1 for saleWTWestpoint Townhomes A B0.2 mi away · 32 homes, built 2006–07TOTownhomes Of Winter Garden Condo0.3 mi away · 93 homes, built 1984–89Winter Oaks0.3 mi away · median $640K, 5 sales/12 moTownhomes Winter Garden0.3 mi away · median $172K, 4 sales/12 moOPOak Park At0.3 mi away · 43 homes, built 1997–99PPPleasant Park0.3 mi away · median $550K, 3 sales/12 moManns First Add0.3 mi away · 1 for sale

Browse all neighborhood guides →

Thinking of selling in Westchester Place? 2 recorded closings (window ending 2026-09-20). See the Orange County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.
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