Windermere Town
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.
Market Heat
As of September 2026, Windermere Town in Windermere, FL has 6 homes for sale and 1 pending, asking from $1,099,000 to $10,200,000 (median $2,035,000). Over the 12 months ending 2026-09-12, 20 recorded sales closed at a median of $895,000, $400 per square foot, a median 31 days on market, sellers accepting 94% of original asking (-29% versus the prior year). Homes listed or recently sold were built 1935 - 2026 with 3 new construction; 7 listings state no HOA; 3 of the 17 geocoded homes sit in a FEMA special flood hazard zone (median elevation 113 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $14,920 ($14,250 with the full homestead exemption).
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 · 7 days
Active · 307 days
Active · 16 days
Active · 35 days
Active · 134 days
Pending · 53 daysActive and pending Windermere Town 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.
Windermere Town right now
🟡 Balanced market. 3.3 months of supply and 14% 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 September 12, 2026. Confidence: High (7 active and pending listings, 20 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($895K) is down 28.7% from the prior 12 months ($1.26M). 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 September 12. Confidence: High (20 and 15 sales in the two windows).
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
Windermere Town market snapshot (as of September 12, 2026): the median sale price is about $895K ($400 per sq ft over the trailing 12 months of closed sales), a median 32 days on market for closed sales, and 3.3 months of supply, a balanced market. The trailing-12-month median is down 29% from the prior 12 months, computed from record-level Stellar MLS closed sales (20 closings in the current window).
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 Windermere Town: of 17 listing addresses checked against the FEMA National Flood Hazard Layer, 82% sit outside the FEMA Special Flood Hazard Area (Zone X); 18% are in an A-series high-risk zone where flood insurance is required with a federally backed mortgage. Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Windermere.
Windermere Town is a community of 234 homes in Windermere, Orange County, built between 1910 and 2024 (median 1978.0), with a median living area of about 2,334 square feet. 66% 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 TownPhotos from Stellar MLS listings in Windermere Town; 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 ($895K) IS the median in the snapshot above, and the move from 2025 ($1.26M) IS the -28.7% one-year change.
Windows contain 0 to 20 sales each (20 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 seller's market. About 3.3 months of supply, a median asking price of $2,035,000, and homes go under contract in about 29 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 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 September 2026 through September 2026. Deemed reliable but not guaranteed.
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.
Shop the zone: Homes zoned for Olympia High High School
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 $400 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 3.3 months of supply, a balanced market and the trailing-12-month median down 29% 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 234 homes built between 1910 and 2024, and 66% 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 (4.8). Basis: Recent Direction -28.7% year-over-year; Liquidity & Demand 3.3 months of supply; Owner Commitment 66% owner-occupied; Pricing Power 93.6% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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 all homes for sale in Windermere →
Recently off market in Windermere Town
Homes in Windermere Town that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 2 on record.
- 109 E 12Th Avenue · off market
- 725 Oakdale Street · off market
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?
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?
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 (4 streets, ZIP 34786)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2014 (126 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 Windermere Town fits the bigger picture — live prices, inventory, and Momentum Scores:
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