Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
2008 to 2012Years built
1,080 to 3,450 sq ftHome size
2 to 5 bedroomsBedrooms
Lakes of Windermere & Lake BurdenArea
Why people move here

Townhomes and homes next to the Lake Burden Shops.

Preston Square mixes 68 townhomes and 75 single-family homes from 2008 to 2012 at SR 535 and Overstreet Road. Some homes on the west side back to a blueberry farm.
The Lake Burden Shops are right next door and Publix is under a mile away.
First-time buyers and downsizers who want convenience over square footage.

Preston Square at a glance

Location: Winter Garden Vineland Road (SR 535) at Overstreet Road

Builder: Meritage Homes and Centerline Homes

Built: 2008 to 2012

Homes: 143 homes (68 townhomes, 75 single-family)

Home types: Townhomes and single-family homes

Size: About 1,080 to 3,450 sq ft

Bedrooms: 2 to 5 bedrooms

Area: Lakes of Windermere & Lake Burden

Life here

What Preston Square has

🏊Community pool
🏀Basketball court
🛠Playground
🌳Park
Proximity

What is close to Preston Square

  • Lake Burden Shops ~0.1 mi
  • Lakeside Village (Publix) ~0.8 mi
  • Restaurant Row ~4.1 mi
  • Winter Garden Village ~4.2 mi

Approximate distances from the community entrance. Walt Disney World is roughly 10 to 15 minutes away off-peak. Two-lane roads around the lakes and SR 535 slow down at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Sunset Park Elementary

🏫 Horizon West Middle

🏫 Windermere High

Orange County Public Schools. Zoning changes, so verify every address.

OCPS school locator
The numbers

Preston Square market snapshot

$582,500Median sale priceLast 12 months.
76 daysDays on marketMedian cumulative days on market.
12Closed sales2 the year before.
99%Sale-to-list price ratioMedian for the last 12 months.

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.

Live MLS listings

Preston Square homes for sale right now

Straight from Stellar MLS. Save the search and get new Preston Square listings the day they hit.

Start of list of properties

Active, 6828 HELMSLEY CIRCLE, , ,press enter for more details, To favorite this property press control+s.
$575,000
$279
Active
6828 HELMSLEY CIRCLE
Windermere, FL 34786
4
Beds
,
3
Baths
,
2,064
square feet,
Welcome to this beautifully fully renovated Windermere home, where every room has been thoughtfully updated to create a fresh, modern, move-in-ready living experience. Located in the desirable Preston Square community, this 4-bedroom, 3-bath home offers a convenient location near Sunset Park Elementary, Horizon West Middle and Windermere High, along with easy access to shopping, dining, entertainment and the growing Horizon West area. With stylish updates throughout and an excellent Windermere location, this is a home you won’t want to miss!
Residential
MLS# O6435655 Lpt Realty, LLC
More Details
Active, 7060 VENTNOR DRIVE, , ,press enter for more details, To favorite this property press control+s.
$444,900
$271
Active
7060 VENTNOR DRIVE
Windermere, FL 34786
3
Beds
,
3
Baths
,
1,642
square feet,
BEST VALUE TOWNHOUSE IN WINDERMERE! OUTSTANDING HOME AND LOCATION in the desirable community of Preston Square in Windermere FL. This amazingly unique 3 bedroom, 2, 5 bath feels like a single family home with its large kitchen and attached 2-car garage. When you enter, you will be welcomed by the beautiful columns, hardwood floors, separate dining room, separate living room and a great paved private courtyard. Wonderful front porch overlooks the park, community pool and basketball areas. Other awesome features include crown molding, sliding door with built-in blinds, retractable ceiling fans, plantation shutters and curved archways. Expansive kitchen has plenty of 42" wood cabinets and granite countertops with backsplash and an additional eat-in-kitchen space. Master suite has large walk-in closet, tray ceiling and spacious master bath with double sink, granite countertops, wood cabinets, jetted tub and shower. Wonderfully kept community maintains ground maintenance. Close to Disney, Publix, restaurants, retail stores, major roads and excellent Windermere schools. MOVE-IN-READY. Room measurements are approximate. Must see!
Residential
MLS# S5153025 Agent Trust Realty Corporation
More Details
See all Preston Square homes for sale
Free guides

Buying or selling in Preston Square?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Preston Square 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.

Questions buyers ask

Preston Square FAQ

Where is Preston Square in Windermere?

Preston Square is in the Lakes of Windermere and Lake Burden area off SR 535, at Winter Garden Vineland Road (SR 535) at Overstreet Road.

How far is Preston Square from Walt Disney World?

Roughly 10 to 15 minutes off-peak from this part of Windermere. I will map the exact drive from the entrance before you choose.

When were homes in Preston Square built?

2008 to 2012, by Meritage Homes and Centerline Homes.

What amenities does Preston Square have?

Community pool, Basketball court, Playground, Park.

Is Preston Square a gated community?

Preston Square is not listed as gated. Ask me about gated options nearby.

What schools serve Preston Square?

Schools commonly listed for this community: Sunset Park Elementary, Horizon West Middle, Windermere High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Preston Square in the Town of Windermere?

Many Windermere addresses are in unincorporated Orange County, not the Town. Taxes, rules and services differ, so I confirm the jurisdiction for every address.

What do homes in Preston Square sell for?

Per Stellar MLS, the median sale price in Preston Square was $582,500 across 12 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.

Your next step

Thinking about Preston Square?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Preston Square, straight from Stellar MLS
  • Town or county, HOA and lake access 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®

Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719
More in Lakes of Windermere & Lake BurdenAshlin ParkBerkshire ParkCasa Del LagoEnclave at Windermere LandingLake BurdenLakes of WindermereAll Windermere communities
Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge

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 Town or county jurisdiction, 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.