Windermere
Homes for Sale in Windermere, FL
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 3 recorded sales closed at a median of $1,050,000, $416 per square foot, a median 22 days on market, sellers accepting 95% of original asking. At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $17,510 ($16,840 with the full homestead exemption).
Price here is driven less by any single formula than by condition and lot. With a median around $1,050,000 and a housing stock that spans more than a century, from 1913 through 2024, you are buying into a market where two homes at the same square footage can trade very differently depending on how they have been kept and updated. The median living area sits near 2,436 square feet, and the median price per square foot runs in the low $400s, but treat those as midpoints of a wide spread, not a menu.
Current posture is balanced leaning brisk. A median of 22 days on market tells us well-presented listings are moving in roughly three weeks, so sellers who prep and price to the current median should not sit long. Buyers should come organized: at this price point and pace, the homes that photograph and inspect cleanly do not linger, and the negotiating room tends to open up on the dated or deferred-maintenance listings rather than the turnkey ones.
Nearby homes for sale
No active listings inside Windermere Rep right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Windermere market snapshot (as of September 12, 2026): the median sale price is about $1.05M ($417 per sq ft over the trailing 12 months of closed sales), and a median 22 days on market for closed sales.
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.
Stellar MLS sales records identify 87 homes in Windermere that have changed hands since 2004, built between 1917 and 2026 (median 1983), with a median living area of about 3,072 sq ft and a typical 4-bedroom, 3-bath layout; 98% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Windermere pairs an unusually deep age range in its housing — 1913 to 2024, with a median build year of 1977 — against a small, high-value inventory of 173 homes. The result is a market where you are choosing as much between eras of construction as between price points.
Who Windermere is best for.
Best for
- Buyers comfortable above the $1,050,000 median who value lot and character over turnkey uniformity
- Renovation-minded buyers willing to underwrite an older home for the payoff of a specific location
- Move-up buyers wanting roughly 2,400-plus square feet and a range of build years to choose from
Probably not for
- Budget-constrained buyers who need a home well under the median price
- Buyers who want a large pool of listings and fast comparison shopping
- Buyers unwilling to budget for updates on an older-vintage home
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 ($1.05M) IS the median in the snapshot above.
Windows contain 0 to 3 sales each (3 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 2012 through 2026. Deemed reliable but not guaranteed.
26% 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 (2026-09-08).
The Windermere buying strategy.
If we were buying in Windermere 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.
A market defined by condition and vintage
The single most useful fact about Windermere is the age spread. A median year built of 1977 sitting inside a 1913-to-2024 range means you will tour original older structures, mid-cycle homes, and new construction in the same search. That variety is why the price-per-square-foot figure, in the low $400s at the median, only tells part of the story: a renovated older home and an unimproved one of the same size can land far apart.
Inventory is thin at 173 homes, and homestead share is high at about 70 percent, which points to a market held largely by long-term owners rather than churned by investors. Thin supply plus owner-occupancy usually means fewer listings and less urgency to discount, so timing and preparation matter more than they would in a higher-turnover community.
The location and the amenities are priced into every listing in Windermere. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this small and this varied in vintage, the work is separating condition from price. We read each listing against the median rather than the asking number, flag which older homes carry real deferred-maintenance risk versus which have been genuinely updated, and pace your offer to a market that is clearing well-kept homes in about three weeks.
Windermere in 15 seconds.
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 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 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windermere, 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 home worth?
Get a no-obligation home value based on real comparable sales in Windermere, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Windermere?
How long do homes in Windermere take to sell?
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How do I find a top Windermere real estate agent who knows Windermere?
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Should you buy in Windermere?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2012 (11 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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