WINDERMERE ISLE
Homes for Sale in WINDERMERE, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
WINDERMERE ISLE right now
🟢 Buyer-leaning market. 8.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.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: Medium (6 active and pending listings, 8 closed sales in 12 months).
🟢 Still climbing. The trailing-12-month median ($1M) is up 16.1% from the prior 12 months ($861K). With about 6 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: Medium (8 and 6 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 ISLE market snapshot (as of August 2, 2026): the median sale price is about $1M ($282 per sq ft over the trailing 12 months of closed sales), a median 29 days on market for closed sales, and 8.0 months of supply, a buyer-leaning market. The trailing-12-month median is up 16% from the prior 12 months, computed from record-level Stellar MLS closed sales (8 closings in the current window).
WINDERMERE ISLE is a community of 122 homes in WINDERMERE, Orange County, built between 2017 and 2020 (median 2019), with a median living area of about 3,336 square feet. 68% 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 ISLE. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WINDERMERE ISLEPrice 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 ($1M) IS the median in the snapshot above, and the move from 2025 ($861K) IS the +16.1% one-year change.
Windows contain 0 to 18 sales each (8 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 2017 through 2026. Deemed reliable but not guaranteed.
WINDERMERE ISLE Market Scorecard
WINDERMERE ISLE is currently a buyer's market. About 6.0 months of supply, a median asking price of $1,080,000, and homes go under contract in about 111 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 ISLE, 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 ISLE
Live MLS inventory for WINDERMERE ISLE. 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 · 50 daysTop listing
Active · 187 days
Active · 184 days
Active · 1 days
Active · 143 days
Pending · 22 days
Pending · 83 daysActive and pending WINDERMERE ISLE listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2017 through 2026. Tap any home to ask about it.
WINDERMERE ISLE 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 ISLE
- Pool · reported on 12 of 13 listings
- Playground · reported on 11 of 13 listings
- Park · reported on 8 of 13 listings
- Deed Restrictions · reported on 8 of 13 listings
- Community Mailbox · reported on 6 of 13 listings
- Trail(s) · reported on 4 of 13 listings
- Association Recreation - Owned · reported on 3 of 13 listings
- Irrigation-Reclaimed Water · reported on 3 of 13 listings
- Cable TV · reported on 2 of 13 listings
- Maintenance · reported on 2 of 13 listings
- No Truck/RV/Motorcycle Parking · reported on 1 of 13 listings
- Secured Garage/Parking · reported on 1 of 13 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
- Castleview Elementary · Elementary
- Horizon West Middle School · Middle
- Horizon High School · High
Zoned schools reflect the assignments reported on recent WINDERMERE ISLE 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 ISLE address.
The WINDERMERE ISLE buying strategy.
If we were buying in WINDERMERE ISLE 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 ISLE.
A closer look at the WINDERMERE ISLE market
At a median of $282 per square foot, WINDERMERE ISLE 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 8.0 months of supply, a buyer-leaning market and the trailing-12-month median up 16% year over year. Homes that do trade take a median 29 days on market, useful leverage on any listing that has lingered.
The housing stock is 122 homes built between 2017 and 2020, and 68% 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 ISLE. 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 ISLE 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 (6.5). Basis: Recent Direction +16.1% year-over-year; Liquidity & Demand 8.0 months of supply; Owner Commitment 68% owner-occupied; Pricing Power 95.6% 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 ISLE 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 ISLE sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WINDERMERE ISLE, 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 ISLE home worth?
Get a no-obligation home value based on real comparable sales in WINDERMERE ISLE, 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 ISLE on the map →
Frequently Asked Questions
What is the median home price in WINDERMERE ISLE?
How long do homes in WINDERMERE ISLE take to sell?
Is WINDERMERE ISLE a buyer's or seller's market right now?
How many homes are in WINDERMERE ISLE?
What share of WINDERMERE ISLE is owner-occupied?
When were the homes in WINDERMERE ISLE built?
Do cash buyers compete in WINDERMERE ISLE?
Who is the best real estate agent for WINDERMERE ISLE?
How do I find a top WINDERMERE real estate agent who knows WINDERMERE ISLE?
Can Momentum Realty connect me with an agent for WINDERMERE ISLE?
Nearby Communities
Explore more neighborhoods near WINDERMERE ISLE 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 (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2017 (59 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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