Windermere Rep
Homes for Sale in Windermere, FL
True comps, carrying-cost math, and listings before the portals.
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.
The 60-Second Overview
Windermere Rep market snapshot (as of July 15, 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.
Windermere Rep is a community of 173 homes in Windermere, Orange County, built between 1913 and 2024 (median 1977), with a median living area of about 2,436 square feet. 70% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
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 Rep 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 July 15 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 %s through %s. Deemed reliable but not guaranteed.
The Windermere Rep buying strategy.
If we were buying in Windermere Rep 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 Rep.
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 Rep. 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 Rep in 15 seconds.
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 Rep 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 Rep sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windermere Rep, 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 Rep home worth?
Get a no-obligation home value based on real comparable sales in Windermere Rep, 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 Rep?
How long do homes in Windermere Rep take to sell?
How many homes are in Windermere Rep?
What share of Windermere Rep is owner-occupied?
When were the homes in Windermere Rep built?
Do cash buyers compete in Windermere Rep?
Who is the best real estate agent for Windermere Rep?
How do I find a top Windermere real estate agent who knows Windermere Rep?
Can Momentum Realty connect me with an agent for Windermere Rep?
Should you buy in Windermere Rep?
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 July 15, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (4 streets, ZIP 34786)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| 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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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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