Isleworth
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
Over the 12 months ending 2026-09-12, 14 recorded sales closed at a median of $3,850,000, $743 per square foot, a median 18 days on market, sellers accepting 92% of original asking (-11% versus the prior year). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $64,190 ($63,520 with the full homestead exemption).
Isleworth right now
🔴 Off the recent peak. The trailing-12-month median ($3.85M) is down 11.1% from the prior 12 months ($4.33M) and up 174% since 2012. 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: Medium (14 and 13 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
Nearby homes for sale
No active listings inside Isleworth 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
Isleworth market snapshot (as of September 12, 2026): the median sale price is about $3.85M ($743 per sq ft over the trailing 12 months of closed sales), and a median 18 days on market for closed sales. The trailing-12-month median is down 11% from the prior 12 months and up 174% since 2012, computed from record-level Stellar MLS closed sales (14 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.
Stellar MLS sales records identify 195 homes in Isleworth that have changed hands since 2005, built between 1986 and 2026 (median 1996), with a median living area of about 6,060 sq ft and a typical 5-bedroom, 5.5-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.
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 ($3.85M) IS the median in the snapshot above, and the move from 2025 ($4.33M) IS the -11.1% one-year change.
Windows contain 2 to 18 sales each (14 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 2004 through 2026. Deemed reliable but not guaranteed.
Isleworth Market Scorecard
Isleworth is currently a strong buyer's market. About 13.6 months of supply, a median asking price of $4,100,000, and homes go under contract in about 76 days.
Go deeper: 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.
Life at Isleworth
- Gated Community - Guard · reported on 23 of 26 listings
- Playground · reported on 22 of 26 listings
- Golf Carts OK · reported on 22 of 26 listings
- Golf · reported on 22 of 26 listings
- Community Mailbox · reported on 18 of 26 listings
- Gated Community · reported on 18 of 26 listings
- Gated · reported on 15 of 26 listings
- Buyer Approval Required · reported on 13 of 26 listings
- Cable TV · reported on 12 of 26 listings
- Security · reported on 12 of 26 listings
- Deed Restrictions · reported on 9 of 26 listings
- Clubhouse · reported on 8 of 26 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.
The Isleworth buying strategy.
If we were buying in Isleworth 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 Isleworth.
A closer look at the Isleworth market
At a median of $743 per square foot, Isleworth prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The trailing-12-month median down 11% year over year. Homes that do trade take a median 18 days on market, useful leverage on any listing that has lingered.
The location and the amenities are priced into every listing in Isleworth. 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 Isleworth 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 3 factors (6.0). Basis: Long-Term Appreciation +174% since 2012; Recent Direction -11.1% year-over-year; Pricing Power 92.3% 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 Isleworth 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 Isleworth sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Isleworth, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Isleworth home worth?
Get a no-obligation home value based on real comparable sales in Isleworth, 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 Isleworth
Homes in Isleworth 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. 14 on record.
- 4806 Alexandra Garden Ct · off market
- 4812 Alexandra Garden Court · off market
- 4819 Alexandra Garden Court · off market
- 5073 Latrobe Dr · off market
- 5138 Fairway Oaks Dr · off market
- 5145 Latrobe Drive · off market
- 5151 Latrobe Dr · off market
- 5199 Latrobe Dr · off market
Frequently Asked Questions
What is the median home price in Isleworth?
How long do homes in Isleworth take to sell?
Have Isleworth home prices gone up?
Who is the best real estate agent for Isleworth?
How do I find a top Windermere real estate agent who knows Isleworth?
Can Momentum Realty connect me with an agent for Isleworth?
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 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2004 (211 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 Isleworth fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Isleworth with Momentum Realty’s local guides.