Isleworth
Homes for Sale in Windermere, FL
All 244 homes for sale in WINDERMERE, FL · median $966,750 · 230 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, Isleworth in Windermere, FL has 19 homes for sale. Over the 12 months ending 2026-09-20, 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 (-18% 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).
| Location | WINDERMERE, Orange County, FL · ZIP 34786 |
|---|---|
| Homes in the community | 151 (FL DOR 2025 assessment roll) |
| Years built | 1987–2024 (median 1997) |
| Typical living area | 6,118 sq ft (median) |
| Home types (current listings and sales) | single-family 97% |
| Amenities listed by sellers | Gated Community - Guard, Playground, Golf, Golf Carts OK, Community Mailbox, Gated |
| Sale prices, last 12 months | $3,850,000 median across 14 closed sales · $743 per sq ft · -17.5% vs the prior 12 months |
| Days on market (closed sales) | 18 median |
| For sale right now | 19 active, 3 pending · median asking $4,999,500 · 15.2 months of supply |
| Owner-occupied (homestead) share | 52% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Isleworth key facts,” movewithmomentum.com/neighborhoods/isleworth-windermere, data as of September 20, 2026.
Last 30 days in Isleworth: 11 new listings (median asking $4,395,000), 3 under contract right now. As of October 5, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Homes For Sale Right Now in Isleworth
Live MLS inventory for Isleworth. 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 and pending Isleworth listings as of 2026-10-04, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026. Tap any home to ask about it.
Every Home for Sale in Isleworth Windermere Right Now (22)
All 22 active and pending Isleworth Windermere listings with a detail page, newest first, refreshed twice a day from the MLS.
- 4906 Aviva Garden Court · $3,850,000 · 4 bd / 4.5 ba · listed Sep 29, 2026 · listed by The Simon Simaan Group
- 5050 Isleworth Country Club Drive · $3,189,000 · 4 bd / 4.5 ba · listed Sep 19, 2026 · listed by Compass Florida Llc
- 5373 Isleworth Country Club Drive · $7,200,000 · 5 bd / 5.5 ba · listed Sep 19, 2026 · listed by Stockworth Realty Group
- 5036 Latrobe Drive · $18,750,000 · 6 bd / 8 ba · listed Sep 18, 2026 · listed by Isleworth Realty Llc
- 5237 Isleworth Country Club Drive · $3,600,000 · 5 bd / 5 ba · pending · listed Sep 12, 2026 · listed by Isleworth Realty Llc
- 5524 Worsham Court · $3,500,000 · 4 bd / 6 ba · listed Sep 11, 2026 · listed by Atlis Realty Group Llc
- 9921 Lake Louise Drive · $6,650,000 · 5 bd / 6 ba · listed Sep 5, 2026 · listed by Isleworth Realty Llc
- 5379 Isleworth Country Club Drive · $2,900,000 · 4 bd / 3.5 ba · pending · listed Sep 5, 2026 · listed by Lokation
- 9316 Gladys Garden Ct · $6,500,000 · 5 bd / 6.5 ba · listed Aug 27, 2026 · listed by Isleworth Realty Llc
- 5151 Latrobe Dr · $3,800,000 · 4 bd / 4.5 ba · listed Jul 26, 2026 · listed by Isleworth Realty Llc
- 5073 Latrobe Dr · $2,800,000 · 4 bd / 5 ba · listed Jul 18, 2026 · listed by Isleworth Realty Llc
- 5199 Latrobe Dr · $5,300,000 · 6 bd / 6.5 ba · listed Jul 15, 2026 · listed by Isleworth Realty Llc
- 6462 Deacon Cir · $6,595,000 · 5 bd / 5 ba · listed Jul 7, 2026 · listed by Isleworth Realty Llc
- 9832 Laurel Valley Drive · $11,750,000 · 6 bd / 8.5 ba · listed Jul 6, 2026 · listed by Real Broker, Llc
- 5138 Fairway Oaks Dr · $4,999,500 · 4 bd / 5 ba · listed by Isleworth Realty Llc
- 9144 Isleworth Gardens Drive · $4,100,000 · 3 bd / 4 ba · listed by Megan Dowdy Realty, Llc
- 9323 Gladys Garden Court · $11,900,000 · 6 bd / 8 ba · listed by Corcoran Premier Realty
- 5074 Isleworth Country Club Drive · $7,250,000 · 5 bd / 6.5 ba · listed by Mem Realty Group
- 5145 Latrobe Drive · $2,949,000 · 4 bd / 4.5 ba · listed by Southern Realty Group Llc
- 9648 Mccormick Place · $3,800,000 · 3 bd / 3.5 ba · pending · listed by Isleworth Realty Llc
- 9725 Chestnut Ridge Drive · $5,975,000 · 7 bd / 6 ba · listed by Douglas Elliman
- 4819 Alexandra Garden Court · $3,200,000 · 4 bd / 4.5 ba · listed by Isleworth Realty Llc
Isleworth right now
🟢 Buyer-leaning market. 15.2 months of supply and 14% 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 September 20, 2026. Confidence: Very High (22 active and pending listings, 14 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($3.85M) is down 17.5% from the prior 12 months ($4.67M) 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 20. Confidence: Medium (14 and 12 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 5, 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
Isleworth market snapshot (as of September 20, 2026): the median sale price is about $3.85M ($743 per sq ft over the trailing 12 months of closed sales), a median 18 days on market for closed sales, and 15.2 months of supply, a buyer-leaning market. The trailing-12-month median is down 18% 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), 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 Isleworth across 2024 - 2025 (10 in 2024, 9 in 2025), median $3.80M - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Isleworth is a community of 151 homes in Windermere, Orange County, built between 1987 and 2024 (median 1997), with a median living area of about 6,118 square feet. 52% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
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 ($3.85M) IS the median in the snapshot above, and the move from 2025 ($4.67M) IS the -17.5% one-year change.
Windows contain 2 to 16 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.
12% of homes for sale in Isleworth 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 (2026-10-05).
Isleworth Market Scorecard
Isleworth is currently a buyer-leaning market. About 15.2 months of supply, a median asking price of $4,999,500, and homes go under contract in about 57 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Isleworth 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 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.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Windermere Elem · Elementary
- Chain of Lakes Middle · Middle
- Olympia High · High
Zoned schools reflect the assignments reported on recent Isleworth 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 Isleworth address.
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.
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 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.
Inventory runs at 15.2 months of supply, a buyer-leaning market and the trailing-12-month median down 18% year over year. Homes that do trade take a median 18 days on market, useful leverage on any listing that has lingered.
The housing stock is 151 homes built between 1987 and 2024, and 52% 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 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 5 factors (4.3). Basis: Long-Term Appreciation +174% since 2012; Recent Direction -17.5% year-over-year; Liquidity & Demand 15.2 months of supply; Owner Commitment 52% owner-occupied; Pricing Power 92.3% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $1,224/month (about $14,688/yr) · median of 35 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $1,224 per month ($14,688 a year) - the median AssociationFee across 35 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
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. 23 on record.
- 4806 Alexandra Garden Ct · off market
- 4812 Alexandra Garden Court · off market
- 4819 Alexandra Garden Court · off market
- 5036 Latrobe Drive · off market
- 5050 Isleworth Country Club Drive · off market
- 5073 Latrobe Dr · off market
- 5074 Isleworth Country Club Drive · off market
- 5138 Fairway Oaks Dr · off market
Frequently Asked Questions
What is the median home price in Isleworth?
How long do homes in Isleworth take to sell?
Is Isleworth a buyer's or seller's market right now?
How many homes are in Isleworth?
What share of Isleworth is owner-occupied?
When were the homes in Isleworth built?
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?
Where is Isleworth, and what county is it in?
Is Isleworth a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 4, 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 (6 streets, ZIP 34786)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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?
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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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See how Isleworth fits the bigger picture — live prices, inventory, and Momentum Scores:
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More on Isleworth
- Home values · What homes in Isleworth actually sell for