Westchester
Mostly one-story single-family homes · Built 1987 to 1990 · about 1,490 to 2,000 sq ft
One-story homes with British street names and two ponds.
Westchester at a glance
Location: Haughton Lane off South Hiawassee Road, with Piccadilly Lane and Grosvenor Lane inside
Builder: Custom and individual builders
Built: 1987 to 1990
Homes: About 160 homes
Home types: Mostly one-story single-family homes
Size: About 1,490 to 2,000 sq ft
Bedrooms: 3 to 4 bedrooms
Area: North MetroWest & Hiawassee
What Westchester has
What is close to Westchester
- Winn-Dixie on South Hiawassee ~1 mi
- MetroWest Golf Club ~1 mi
- Publix at MetroWest Village ~1.5 mi
- Valencia College West ~1.5 mi
Approximate distances from the community entrance. Walt Disney World is roughly 20 to 25 minutes away off-peak. Kirkman Road, Hiawassee Road and I-4 back up at rush hour, especially around Universal, so send me your work address and I will map your real commute.
Schools
🏫 MetroWest Elementary
🏫 Chain of Lakes Middle
🏫 Olympia High
Orange County Public Schools. Zoning changes, so verify every address.
Westchester market snapshot
Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 15, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.
Westchester homes for sale right now
Straight from Stellar MLS. Save the search and get new Westchester listings the day they hit.
Buying or selling in Westchester?
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🏡 Buyer Guide
How buying in Westchester works, from new construction versus resale to what to verify on HOA, CDD and school zoning.
🔑 Seller Guide
Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.
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Next step: book a 30 minute call and we will walk through it together for Westchester.
Westchester FAQ
Where is Westchester in MetroWest?
Westchester is in north MetroWest along Westgate Drive, Raleigh Street and South Hiawassee Road, at Haughton Lane off South Hiawassee Road, with Piccadilly Lane and Grosvenor Lane inside.
How far is Westchester from Walt Disney World?
Roughly 20 to 25 minutes off-peak from this part of MetroWest. I will map the exact drive from the entrance before you choose.
When were homes in Westchester built?
1987 to 1990. Most homes were built by individual or custom builders.
What amenities does Westchester have?
Two ponds with about 20 waterfront homesites, Quarter-acre homesites, No CDD.
Is Westchester a gated community?
Westchester is not listed as gated. Ask me about gated options nearby.
What schools serve Westchester?
Schools commonly listed for this community: MetroWest Elementary, Chain of Lakes Middle, Olympia High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.
Is Westchester in the City of Orlando or unincorporated Orange County?
Every MetroWest home has an Orlando mailing address, but the mailing address does not settle jurisdiction. Parts of MetroWest sit inside the City of Orlando and the community also appears in Orange County commission districts, so I confirm city or county for every address on the Property Appraiser site. Taxes, utilities and services follow that answer.
Does Westchester pay a master association fee and a neighborhood HOA fee?
Every home in MetroWest belongs to the MetroWest Master Association, which maintains the boulevards, common areas and community-wide standards. Most neighborhoods, including Westchester, also have their own association with its own dues and rules. Ask for both amounts and exactly what each covers before you write an offer, and I will pull them for any home you like.
Can I rent out a home in Westchester?
MetroWest Master Association leasing rules (Feb 2026) require a first lease of at least 7 months, ban short-term rentals like Airbnb and VRBO, and require tenant screening and a crime-free lease addendum. Westchester's own association can add stricter rules, so I check both sets of documents before you buy a rental.
What do homes in Westchester sell for?
Per Stellar MLS, the median sale price in Westchester was $378,750 across 8 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.
Thinking about Westchester?
Give me 30 minutes and tell me your timeline. I will send back:
- Recent closed sales in Westchester, straight from Stellar MLS
- City or county, master and neighborhood HOA dues, and rental rules for the homes that fit
- Your real commute, mapped from the entrance
No pressure. If you are selling a home somewhere else first, we will plan both sides together.
Semper Fi to your real estate needs. Jorge Martinez, REALTOR®
Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify city or county jurisdiction, master and neighborhood association dues, rental rules, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.