WINDERMERE TOWN
Homes for Sale in WINDERMERE, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
WINDERMERE TOWN right now
🟡 Balanced market. 3.4 months of supply and 25% 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 August 2, 2026. Confidence: High (8 active and pending listings, 16 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($881K) is down 36.6% from the prior 12 months ($1.39M). With about a dozen 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: High (16 and 18 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
WINDERMERE TOWN market snapshot (as of August 2, 2026): the median sale price is about $881K ($449 per sq ft over the trailing 12 months of closed sales), a median 32 days on market for closed sales, and 3.4 months of supply, a balanced market. The trailing-12-month median is down 37% from the prior 12 months, computed from record-level Stellar MLS closed sales (16 closings in the current window).
WINDERMERE TOWN is a community of 508 homes in WINDERMERE, Orange County, built between 1910 and 2024 (median 1978.0), with a median living area of about 2,682 square feet. 70% 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 WINDERMERE TOWN. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WINDERMERE TOWNPrice 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 ($881K) IS the median in the snapshot above, and the move from 2025 ($1.39M) IS the -36.6% one-year change.
Windows contain 0 to 18 sales each (16 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.
Windermere Market Scorecard
Windermere is currently a balanced market. About 4.2 months of supply, a median asking price of $1,198,000, and homes go under contract in about 18 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 WINDERMERE TOWN, 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 WINDERMERE TOWN
Live MLS inventory for WINDERMERE TOWN. 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 · 23 daysTop listing
Active · 307 days
Active · 1 days
Active · 102 days
Pending · 113 days
Pending · 11 days
Pending · 53 daysActive and pending WINDERMERE TOWN 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.
WINDERMERE TOWN 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 WINDERMERE TOWN
- Playground · reported on 9 of 10 listings
- Tennis Court(s) · reported on 8 of 10 listings
- Golf Carts OK · reported on 8 of 10 listings
- Park · reported on 7 of 10 listings
- Restaurant · reported on 2 of 10 listings
- Security Lights · reported on 1 of 10 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
- Windermere Elem · Elementary
- Gotha Middle · Middle
- Olympia High · High
Zoned schools reflect the assignments reported on recent WINDERMERE TOWN 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 WINDERMERE TOWN address.
The WINDERMERE TOWN buying strategy.
If we were buying in WINDERMERE TOWN 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.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
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 WINDERMERE TOWN.
A closer look at the WINDERMERE TOWN market
At a median of $449 per square foot, WINDERMERE TOWN 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 3.4 months of supply, a balanced market and the trailing-12-month median down 37% year over year. Homes that do trade take a median 32 days on market, useful leverage on any listing that has lingered.
The housing stock is 508 homes built between 1910 and 2024, and 70% 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 WINDERMERE TOWN. 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 WINDERMERE TOWN 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 (5.0). Basis: Recent Direction -36.6% year-over-year; Liquidity & Demand 3.4 months of supply; Owner Commitment 70% owner-occupied; Pricing Power 94.4% 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 WINDERMERE TOWN 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 WINDERMERE TOWN sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WINDERMERE TOWN, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your WINDERMERE TOWN home worth?
Get a no-obligation home value based on real comparable sales in WINDERMERE TOWN, 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 WINDERMERE TOWN on the map →
Frequently Asked Questions
What is the median home price in WINDERMERE TOWN?
How long do homes in WINDERMERE TOWN take to sell?
Is WINDERMERE TOWN a buyer's or seller's market right now?
How many homes are in WINDERMERE TOWN?
What share of WINDERMERE TOWN is owner-occupied?
When were the homes in WINDERMERE TOWN built?
Do cash buyers compete in WINDERMERE TOWN?
Who is the best real estate agent for WINDERMERE TOWN?
How do I find a top WINDERMERE real estate agent who knows WINDERMERE TOWN?
Can Momentum Realty connect me with an agent for WINDERMERE TOWN?
Nearby Communities
Explore more neighborhoods near WINDERMERE TOWN 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 (street-list match (17 streets, ZIP 34786)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2014 (122 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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