PRESTON SQUARE
Homes for Sale in WINDERMERE, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
PRESTON SQUARE right now
🔴 Seller-leaning market. 0.9 months of supply and 0% of the inventory already under contract give sellers the pressure advantage.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 August 2, 2026. Confidence: Medium (1 active and pending listings, 11 closed sales in 12 months).
🟡 Still climbing. The trailing-12-month median ($620K) is up 0.0% from the prior 12 months ($620K). With about 5 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Low (11 and 3 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
PRESTON SQUARE market snapshot (as of August 2, 2026): the median sale price is about $620K ($243 per sq ft over the trailing 12 months of closed sales), a median 28 days on market for closed sales, and 0.9 months of supply, a seller-leaning market. The trailing-12-month median is up 0% from the prior 12 months, computed from record-level Stellar MLS closed sales (11 closings in the current window).
PRESTON SQUARE is a community of 142 homes in WINDERMERE, Orange County, built between 2008 and 2012 (median 2008), with a median living area of about 2,016 square feet. 63% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of PRESTON SQUARE. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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PRESTON SQUAREPrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($620K) IS the median in the snapshot above, and the move from 2025 ($620K) IS the +0.0% one-year change.
Windows contain 0 to 13 sales each (11 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026. Deemed reliable but not guaranteed.
PRESTON SQUARE Market Scorecard
PRESTON SQUARE is currently a strong seller's market. About 1.1 months of supply, a median asking price of $630,000, and homes go under contract in about 20 days.
Go deeper: county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in PRESTON SQUARE, WINDERMERE
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 August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in PRESTON SQUARE
Live MLS inventory for PRESTON SQUARE. 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 PRESTON SQUARE listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026. Tap any home to ask about it.
PRESTON SQUARE on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at PRESTON SQUARE
- Pool · reported on 14 of 14 listings
- Playground · reported on 12 of 14 listings
- Basketball Court · reported on 7 of 14 listings
- Park · reported on 6 of 14 listings
- Clubhouse · reported on 5 of 14 listings
- Deed Restrictions · reported on 4 of 14 listings
- Community Mailbox · reported on 3 of 14 listings
- Recreation Facilities · reported on 2 of 14 listings
- Maintenance · reported on 1 of 14 listings
- Tennis Court(s) · reported on 1 of 14 listings
- Trail(s) · reported on 1 of 14 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
- Sunset Park Elem · Elementary
- Horizon West Middle School · Middle
- Windermere High School · High
Zoned schools reflect the assignments reported on recent PRESTON SQUARE 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 PRESTON SQUARE address.
The PRESTON SQUARE buying strategy.
If we were buying in PRESTON SQUARE 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.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
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 PRESTON SQUARE.
A closer look at the PRESTON SQUARE market
At a median of $243 per square foot, PRESTON SQUARE prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 0.9 months of supply, a seller-leaning market. Homes that do trade take a median 28 days on market, useful leverage on any listing that has lingered.
The housing stock is 142 homes built between 2008 and 2012, and 63% 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 PRESTON SQUARE. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in PRESTON SQUARE buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (7.2). Basis: Recent Direction +0.0% year-over-year; Liquidity & Demand 0.9 months of supply; Owner Commitment 63% owner-occupied; Pricing Power 96.2% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- 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.
Tools for a PRESTON SQUARE 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 PRESTON SQUARE sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in PRESTON SQUARE, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your PRESTON SQUARE home worth?
Get a no-obligation home value based on real comparable sales in PRESTON SQUARE, 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 homes for sale in PRESTON SQUARE on the map →
Frequently Asked Questions
What is the median home price in PRESTON SQUARE?
How long do homes in PRESTON SQUARE take to sell?
Is PRESTON SQUARE a buyer's or seller's market right now?
How many homes are in PRESTON SQUARE?
What share of PRESTON SQUARE is owner-occupied?
When were the homes in PRESTON SQUARE built?
Do cash buyers compete in PRESTON SQUARE?
Who is the best real estate agent for PRESTON SQUARE?
How do I find a top WINDERMERE real estate agent who knows PRESTON SQUARE?
Can Momentum Realty connect me with an agent for PRESTON SQUARE?
Nearby Communities
Explore more neighborhoods near PRESTON SQUARE with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2014 (69 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 your area comps.
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