Windermere Town
Homes for Sale in Windermere, FL
All 236 homes for sale in Windermere, FL · median $949,995 · 206 homes for sale in 34786 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of October 2026, Windermere Town in Windermere, FL has 6 homes for sale and 1 pending, asking from $1,089,000 to $3,300,000 (median $1,446,500). Over the 12 months ending 2026-09-20, 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 - 2025 with 1 new construction; 7 listings state no HOA; 2 of the 19 geocoded homes sit in a FEMA special flood hazard zone (median elevation 109 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).
Last 30 days in Windermere Town: 3 new listings (median asking $1,395,000), 1 under contract right now, 2 closed sales (median $770,000). As of October 15, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
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 · 7 daysTop listing
Active · 307 days
Active · 59 days
Active · 12 days
Active · 10 days
Active · 155 days
Pending · 24 daysActive and pending Windermere Town listings as of 2026-10-15, 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 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 September 20, 2026. Confidence: High (8 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 20. Confidence: High (20 and 15 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 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 20, 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), 788 homes closed in the last 12 months at a median of $640K ($261/sq ft), down 0.6% year over year, with a median 40 days on market. Right now 131 active and 43 pending listings put supply at about 3.7 months - a balanced market. See the live ZIP 34786 housing market and the Orange County market.
County records show 19 qualified sales in Windermere Town across 2024 - 2025 (10 in 2024, 9 in 2025), median $1.01M - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Windermere Town: of 14 listing addresses checked against the FEMA National Flood Hazard Layer, 86% sit outside the FEMA Special Flood Hazard Area (Zone X); 14% 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 203 homes in Windermere, Orange County, built between 1913 and 2024 (median 1978), with a median living area of about 2,331 square feet. 65% 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
Windermere TownWindermere TownWindermere TownWindermere TownWindermere TownWindermere TownWindermere Town
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 20 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.
20% of homes for sale in ZIP 34786 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-15).
Windermere Market Scorecard
Windermere is currently a seller's market. About 3.1 months of supply, a median asking price of $1,446,500, and homes go under contract in about 36 days.
Typical home value in the 34786 ZIP is $702,439, about 7.9% 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.
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 contributors.
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
Recent Developments in Windermere Town
Development, infrastructure, retail, and school activity affecting Windermere Town, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection. The developer projects thousands of jobs at full build-out.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 10 miles southeast of Windermere Town.
Source: Spectrum News 13 - September 2026Development
Lake County approves 2,241-acre Panther Run rezoning for up to 2,624 homes near Clermont
The Lake County Commission voted 3-1 on Sept. 1 to rezone about 2,241 acres in the Wellness Way area, north of Sawgrass Bay Boulevard, for GT Homes. The planned unit development allows up to 2,624 residential units and more than 1 million square feet of non-residential space, with sites reserved for a future public high school and public safety facilities. Plans include extending County Road 455 and about 11 miles of public trails.
What it may mean for the marketThe plan adds long-term housing supply, employment space and new connector roads in south Lake County, with infrastructure planned ahead of residential growth. The site is about 8 miles southwest of Windermere Town.
Source: Clermont Sun - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 7 miles southeast of Windermere Town.
Source: FOX 35 Orlando - July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The project is about 11 miles east of Windermere Town, elsewhere in Orange County.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 9 miles northeast of Windermere Town, elsewhere in Orange County.
Source: Orange County Newsroom - June 2026Development
Mixed-use high-rise redesigned for 924 and 934 North Magnolia Avenue
A redesigned 17-story mixed-use high-rise was proposed for 924 and 934 North Magnolia Avenue in Orlando's North Quarter district by Acram Group. The project would include 350 residential units, about 3,300 square feet of ground-floor commercial space, and a parking garage with 510 spaces, replacing two 1972 office buildings. A public plaza is planned at the corner of Magnolia and Weber Street.
What it may mean for the marketWould replace two aging office buildings with 350 residences, ground floor retail, and structured parking, adding housing density and a public plaza along the Orlando Urban Trail. The project is about 13 miles east of Windermere Town, elsewhere in Orange County.
Source: Florida YIMBY
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
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 203 homes built between 1913 and 2024, and 65% 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 (4.7). Basis: Recent Direction -28.7% year-over-year; Liquidity & Demand 3.3 months of supply; Owner Commitment 65% 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.
Flood & Insurance Context
Of 15 sampled listing addresses in this community: 87% outside the FEMA Special Flood Hazard Area (Zone X/B/C); 13% in an A-series Special Flood Hazard Area zone.
Address-sampled; individual parcels vary - verify any specific address at msc.fema.gov. Check any address at FEMA's Flood Map Service Center, and see average home-insurance costs by Florida county.
Source: FEMA National Flood Hazard Layer, address-level lookups (n=15) · as of 2026-10
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. 5 on record.
- 1002 Oakdale Street · off market
- 109 E 12Th Avenue · off market
- 725 Oakdale Street · off market
- 728 Forest Street · off market
- 811 Main Street · off market
| Location | Windermere, Orange County, FL · ZIP 34786 |
|---|---|
| Homes in the community | 203 (FL DOR 2025 assessment roll) |
| Years built | 1913–2024 (median 1978) |
| Typical living area | 2,331 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Park, Playground, Tennis Court(s), Golf Carts OK, Trail(s), Pickleball Court(s) |
| Sale prices, last 12 months | $895,000 median across 20 closed sales · $400 per sq ft · -28.7% vs the prior 12 months |
| Days on market (closed sales) | 31 median |
| For sale right now | 6 active, 2 pending · median asking $1,747,500 · 3.3 months of supply |
| Owner-occupied (homestead) share | 65% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Windermere Town key facts,” movewithmomentum.com/neighborhoods/windermere-town-windermere, data as of September 20, 2026.
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 October 2026 through October 2026. Deemed reliable but not guaranteed.
Just listed in Windermere Town
The newest homes for sale in Windermere Town right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 104 E 1St Avenue $1,280,000 · 4 bd · 2.5 ba · 2,441 sq ft · 10 days on market Courtesy of NOVA REAL ESTATE SERVICES INC
- 101 Lee Street $1,395,000 · 5 bd · 4 ba · 4,186 sq ft · 12 days on market Courtesy of STOCKWORTH REALTY GROUP
- 212 W 1St Avenue $1,498,000 · 4 bd · 2 ba · 2,627 sq ft · 59 days on market Courtesy of HOME WISE REALTY GROUP, INC.
- 715 Magnolia Street $1,089,000 · 4 bd · 3 ba · 3,390 sq ft · 155 days on market Courtesy of IRIS INTERNATIONAL
- 436 E 7Th Avenue $2,175,000 · 4 bd · 5 ba · 3,136 sq ft · 307 days on market Courtesy of TALENT REALTY SOLUTIONS
Checked against the MLS Oct 15, 2026. All new listings in this market.
Every Home for Sale in Windermere Town Windermere Right Now (6)
All 6 active and pending Windermere Town Windermere listings with a detail page, newest first, refreshed twice a day from the MLS.
- 104 E 1st Avenue · $1,280,000 · 4 bd / 2.5 ba · listed Oct 3, 2026 · listed by Nova Real Estate Services Inc
- 101 Lee Street · $1,395,000 · 5 bd / 4 ba · listed Sep 16, 2026 · listed by Stockworth Realty Group
- 212 W 1st Avenue · $1,498,000 · 4 bd / 2 ba · listed Sep 10, 2026 · listed by Home Wise Realty Group, Inc.
- 930 East Boulevard · $1,895,000 · 4 bd / 4.5 ba · pending · listed Aug 31, 2026 · listed by Corcoran Premier Realty
- 715 Magnolia Street · $1,089,000 · 4 bd / 3 ba · listed Jul 16, 2026 · listed by Iris International
- 436 E 7th Avenue · $2,175,000 · 4 bd / 5 ba · listed Jul 16, 2026 · listed by Talent Realty Solutions
Recently sold in Windermere Town Windermere
- 706 Oakdale Street · sold $850,000
- 811 Main Street · sold $690,000
- 725 Oakdale Street · sold $1,000,000
- 109 E 12Th Avenue · sold $1,150,000
- 1002 Oakdale Street · sold $890,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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- Windermere home values: what is my house worth?
- ZIP 34786 housing scorecard
Email me new listings in Windermere Town
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Windermere Town
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windermere Town will answer, and the answer is published on this page for the next buyer.
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?
Where is Windermere Town, and what county is it in?
Is Windermere Town in a flood zone?
Is Windermere Town a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 15, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 34786)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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.
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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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Nearby Communities
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More on Windermere Town
- Home values · What homes in Windermere Town actually sell for