Preston Square
Homes for Sale in Windermere, FL
All 255 homes for sale in WINDERMERE, FL · median $930,000 · 176 homes for sale in 34786 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Preston Square in Windermere, FL has 2 homes for sale. Over the 12 months ending 2026-09-12, 12 recorded sales closed at a median of $582,500, $240 per square foot, a median 33 days on market, sellers accepting 96% of original asking. Homes listed or recently sold were built 2008 - 2011; 14 of 14 report an HOA (median $128/mo); none of the 14 geocoded homes sit in a FEMA special flood hazard zone (median elevation 117 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $9,710 ($9,040 with the full homestead exemption).
Preston Square right now
🔴 Seller-leaning market. 1.7 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 September 12, 2026. Confidence: Medium (2 active and pending listings, 12 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 60-Second Overview
Preston Square market snapshot (as of September 12, 2026): the median sale price is about $582K ($240 per sq ft over the trailing 12 months of closed sales), a median 33 days on market for closed sales, and 1.7 months of supply, a seller-leaning market.
In ZIP 34786 (WINDERMERE), 784 homes closed in the last 12 months at a median of $622K ($262/sq ft), down 1.5% year over year, with a median 38 days on market. Right now 113 active and 37 pending listings put supply at about 3.0 months - a balanced market. See the live ZIP 34786 housing market and the Orange County market.
Flood zones in Preston Square: of 14 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Windermere.
Preston Square is a community of 135 homes in Windermere, Orange County, built between 2008 and 2012 (median 2009), with a median living area of about 2,105 square feet. 62% 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 SquarePhotos from Stellar MLS listings in Preston Square; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($582K) IS the median in the snapshot above.
Windows contain 0 to 14 sales each (12 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 1.7 months of supply, a median asking price of $509,950, and homes go under contract in about 37 days.
Typical home value in the 34786 ZIP is $706,166, about 7.6% above 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.
Housing distress & ownership in Preston Square Windermere, 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 September 2026 through September 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 2026-09-14, 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.
Shop the zone: Homes zoned for Windermere High School
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 $240 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 1.7 months of supply, a seller-leaning market. Homes that do trade take a median 33 days on market, useful leverage on any listing that has lingered.
The housing stock is 135 homes built between 2008 and 2012, and 62% 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 3 factors (7.3). Basis: Liquidity & Demand 1.7 months of supply; Owner Commitment 62% owner-occupied; Pricing Power 96.4% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $128/month (about $1,536/yr) · median of 42 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $128 per month ($1,536 a year) - the median AssociationFee across 42 MLS records, normalised to a monthly figure; most are billed monthly. 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 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 all homes for sale in Windermere →
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?
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?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34786)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2014 (70 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 Preston Square fits the bigger picture — live prices, inventory, and Momentum Scores:
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