Isleworth
Homes for Sale in Windermere, FL
All 258 homes for sale in Windermere, FL · median $1,100,000 · 228 homes for sale in 34786 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Photo via Stellar MLS
As of November 2026, Isleworth in Windermere, FL has 21 homes for sale, asking from $2,800,000 to $11,900,000 (median $4,395,000). Over the 12 months ending 2026-11-13, 5 recorded sales closed at a median of $3,725,000, $702 per square foot, a median 20 days on market, sellers accepting 89% of original asking. Homes listed or recently sold were built 1987 - 2026 with 2 new construction; 33 of 33 report an HOA (median $1,224/mo); 1 of the 33 geocoded homes sit in a FEMA special flood hazard zone (median elevation 124 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $62,110 ($61,440 with the full homestead exemption).
Last 30 days in Isleworth: 1 new listing (median asking $3,600,000), 3 closed sales (median $3,337,000). As of November 13, 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 · 232 daysTop listing
Active · 32 days
Active · 291 days
Active · 55 days
Active · 94 days
Active · 119 days
Active · 126 days
Active · 304 days
Active · 159 days
Active · 184 days
Active · 41 days
Active · 227 days
Active · 6 days
Active · 35 daysActive and pending Isleworth listings as of 2026-11-02, 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.
Price here is driven by scale and condition more than anything else. With a median living area north of 6,100 square feet and a median price of $3,850,000, you are paying for large custom homes behind a guarded gate on a golf course. The spread is wide and condition-driven: homes built between 1987 and 2024 sit side by side, so a renovated estate and a dated original command very different numbers even at similar footprints. The median of roughly $743 per square foot is a useful anchor, but it blurs that range.
The current posture leans toward buyers. Months of supply sits at 15.2 against just 19 active listings and 14 closings in the window, and prices are down 17.5% year over year. That combination gives a buyer room to negotiate and time to be selective. For a seller, it means pricing to the current market and to the home's actual condition matters more than the headline median; the 18-day median days-on-market reflects well-prepared, correctly priced homes, not the whole field.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
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 November 14, 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), 261 homes closed in the last 12 months at a median of $602K ($242/sq ft), down 3.0% year over year, with a median 41 days on market. Right now 73 active and 11 pending listings put supply at about 3.4 months - a balanced market. See the live ZIP 34786 housing market and the Orange County market.
County records show 23 qualified sales in Isleworth across 2024 - 2025 (13 in 2024, 10 in 2025), median $3.70M - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Isleworth: of 12 listing addresses checked against the FEMA National Flood Hazard Layer, 92% sit outside the FEMA Special Flood Hazard Area (Zone X); 8% are in an A-series high-risk zone where flood insurance is required with a federally backed mortgage. Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Windermere.
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).
Isleworth is a guarded, golf-oriented gated community in Windermere where large custom estates set the tone. With 151 homes and only 19 active, inventory is thin in absolute terms even as the supply math leans buyer-friendly.
The setting & the homes.
Aerial and on-site photos of Isleworth. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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IsleworthPhotos from Stellar MLS listings in Isleworth; content deemed reliable but not guaranteed.
Who Isleworth is best for.
Best for
- Buying a large custom home and willing to compare condition carefully against the median
- Seeking a guarded, gated setting with golf, clubhouse, fitness, and pool access
- Buyers who value negotiating leverage in a market with ample supply
Probably not for
- Needing a fast close without a buyer-approval and HOA review step
- Looking for a smaller or lower-maintenance home than the 6,100-plus-square-foot norm here
- Expecting a tight, competitive market where listings move in days across the board
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.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
0% 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 (2026-11-14).
Isleworth Market Scorecard
Isleworth is currently a strong buyer's market. About 21.0 months of supply, a median asking price of $4,395,000, and homes go under contract in about 136 days.
Typical home value in the 34786 ZIP is $704,680, about 10.3% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · 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.
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 contributors.
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.
What the spread is really telling you
This is a mature, built-out community with a long construction history and a median year built of 1997. That age range is the key to the pricing picture: some homes have been taken down to the studs and rebuilt to current tastes, while others still wear their original finishes. Two homes of comparable size can trade far apart, which is why the per-square-foot median around $743 should be treated as a starting point for your own comparison, not a verdict on any single property.
Roughly half the homes here carry a homestead exemption, pointing to a mix of primary residences and seasonal or investment ownership. The amenity set is extensive on paper - guarded gate, golf, clubhouse, fitness center, pool, playground - and the community requires buyer approval, so budget time for that process. Verify current amenities, access, and fees directly with the HOA before you write an offer.
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.
Why work with Momentum here
In a buyer-leaning market with a wide, condition-driven price spread, the value is in the comparison work. We help you read past the median to what a specific home's finishes, footprint, and position are actually worth, navigate the buyer-approval and HOA requirements, and price or negotiate against the real field of 19 actives rather than the headline number.
Isleworth in 15 seconds.
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.
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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. 6 on record.
- 4806 Alexandra Garden Ct · off market
- 4812 Alexandra Garden Court · off market
- 5036 Latrobe Drive · off market
- 5379 Isleworth Country Club Drive · off market
- 9648 Mccormick Place · off market
- 9832 Laurel Valley Drive · off market
| Location | Windermere, Orange County, FL · ZIP 34786 |
|---|---|
| Homes in the community | 174 (FL DOR 2025 assessment roll) |
| Years built | 1987–2024 (median 1996.0) |
| Typical living area | 6,136 sq ft (median) |
| Home types (current listings and sales) | single-family 97% |
| Amenities listed by sellers | Gated Community - Guard, Playground, Golf, Community Mailbox, Golf Carts OK, Gated |
| Sale prices, last 12 months | $3,725,000 median across 5 closed sales · $702 per sq ft |
| Days on market (closed sales) | 20 median |
| For sale right now | 21 active, 0 pending · median asking $4,395,000 · 18.0 months of supply |
| Owner-occupied (homestead) share | 51% |
Data as of November 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2026 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 November 13, 2026.
Just listed in Isleworth
The newest homes for sale in Isleworth right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 5237 Isleworth Country Club Drive $3,600,000 · 5 bd · 5 ba · 5,972 sq ft · listed Oct 29, 2026 Courtesy of ISLEWORTH REALTY LLC
- 5092 Isleworth Country Club Drive $8,500,000 · 4 bd · 5 ba · 7,100 sq ft · listed Oct 3, 2026 Courtesy of ISLEWORTH REALTY LLC
- 9310 Isleworth Gardens Drive $3,595,000 · 3 bd · 4 ba · 4,333 sq ft · listed Sep 30, 2026 Courtesy of ISLEWORTH REALTY LLC
- 6126 Payne Stewart Drive $3,250,000 · 3 bd · 3.5 ba · 2,848 sq ft · listed Sep 26, 2026 Courtesy of IRWIN REALTY GROUP LLC
- 5186 Vardon Drive $4,395,000 · 6 bd · 6 ba · 4,739 sq ft · listed Sep 24, 2026 Courtesy of ISLEWORTH REALTY LLC
- 5373 Isleworth Country Club Drive $7,200,000 · 5 bd · 5.5 ba · 5,993 sq ft · listed Sep 10, 2026 Courtesy of STOCKWORTH REALTY GROUP
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Isleworth Right Now (21)
All 21 active and pending Isleworth listings with a detail page, newest first, refreshed twice a day from the MLS.
- 5092 Isleworth Country Club Drive · $8,500,000 · 4 bd / 5 ba · listed Oct 1, 2026 · listed by Isleworth Realty Llc
- 9310 Isleworth Gardens Drive · $3,595,000 · 3 bd / 4 ba · listed Sep 28, 2026 · listed by Isleworth Realty Llc
- 6126 Payne Stewart Drive · $3,250,000 · 3 bd / 3.5 ba · listed Sep 24, 2026 · listed by Irwin Realty Group Llc
- 5186 Vardon Drive · $4,395,000 · 6 bd / 6 ba · listed Sep 22, 2026 · listed by Isleworth Realty Llc
- 5373 Isleworth Country Club Drive · $7,200,000 · 5 bd / 5.5 ba · listed Sep 19, 2026 · listed by Stockworth Realty Group
- 5050 Isleworth Country Club Drive · $3,189,000 · 4 bd / 4.5 ba · listed Sep 19, 2026 · listed by Compass Florida Llc
- 5237 Isleworth Country Club Drive · $3,600,000 · 5 bd / 5 ba · 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
- 9316 Gladys Garden Ct · $6,500,000 · 5 bd / 6.5 ba · listed Aug 27, 2026 · listed by Isleworth Realty Llc
- 6462 Deacon Cir · $6,595,000 · 5 bd / 5 ba · listed Aug 15, 2026 · listed by Isleworth Realty Llc
- 5073 Latrobe Dr · $2,800,000 · 4 bd / 5 ba · listed Aug 15, 2026 · listed by Isleworth Realty Llc
- 5199 Latrobe Dr · $5,300,000 · 6 bd / 6.5 ba · listed Aug 15, 2026 · listed by Isleworth Realty Llc
- 5138 Fairway Oaks Dr · $4,999,500 · 4 bd / 5 ba · listed Aug 15, 2026 · listed by Isleworth Realty Llc
- 9144 Isleworth Gardens Drive · $4,100,000 · 3 bd / 4 ba · listed Aug 15, 2026 · listed by Megan Dowdy Realty, Llc
- 5151 Latrobe Dr · $3,800,000 · 4 bd / 4.5 ba · listed Aug 15, 2026 · listed by Isleworth Realty Llc
- 9323 Gladys Garden Court · $11,900,000 · 6 bd / 8 ba · listed Aug 15, 2026 · listed by Corcoran Premier Realty
- 5145 Latrobe Drive · $2,899,000 · 4 bd / 5 ba · listed Aug 15, 2026 · listed by Southern Realty Group Llc
- 5074 Isleworth Country Club Drive · $7,250,000 · 5 bd / 6.5 ba · listed Aug 15, 2026 · listed by Mem Realty Group
- 9725 Chestnut Ridge Drive · $5,975,000 · 7 bd / 6 ba · listed Aug 15, 2026 · listed by Douglas Elliman
- 4819 Alexandra Garden Court · $3,200,000 · 4 bd / 4.5 ba · listed Aug 15, 2026 · listed by Isleworth Realty Llc
Recently sold in Isleworth Windermere
- 4906 Aviva Garden Court · sold $3,725,000
- 5379 Isleworth Country Club Drive · sold $2,750,000
- 9648 Mccormick Place · sold $3,337,000
- 4806 Alexandra Garden Ct · sold $3,900,000
- 5036 Latrobe Drive · sold $4,350,000
- 9310 Isleworth Gardens Drive · sold $3,550,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
More Windermere home searches
- All homes for sale in Windermere, FL
- Homes for sale in Orange County, FL
- Windermere waterfront homes for sale
- Gated communities in Windermere
- Windermere golf course homes
- Windermere home values: what is my house worth?
- ZIP 34786 housing scorecard
Windermere guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Orange County)
- Homestead exemption (Orange County)
- Home insurance cost
- New construction
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
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What it really costs to own in Isleworth
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $1,224/month across 37 MLS listings (most billed quarterly; 2026-11-14). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Orange County is $1,409/yr (4,204 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. Flood: of 12 listing addresses checked against the FEMA flood map, 92% sit outside the high-risk zone and 8% inside one, where flood insurance is required with a federally backed mortgage. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 1993 across 33 listings. An original roof here would be about 33 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Isleworth
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Isleworth
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Isleworth will answer, and the answer is published on this page for the next buyer.
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 in a flood zone?
Is Isleworth a good place to live?
Should you buy in Isleworth?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: November 2, 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.
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