Isleworth homes for sale: Guard-gated golf and lakefront estates in Windermere, FL
Every Isleworth home on the market, straight from the MLS feed, with what homes here actually sold for, what the HOA costs by enclave and how a purchase behind the gate works.
Isleworth homes for sale now.
Homes for sale inside Isleworth, including Isleworth West and the Gardens of Isleworth. They come straight from the MLS feed, update on their own and show homes for sale only, no rentals.
Current Isleworth listings appear here.
See Isleworth homes for saleListings courtesy of Stellar MLS as distributed by MLS GRID. Some IDX listings have been excluded from this website. IDX information is provided for consumers' personal, non-commercial use, is deemed reliable but is not guaranteed by MLS GRID, and each listing shows its listing brokerage, MLS number and status. Presented by Andy Neal, REALTOR®, The Agency FL, (407) 619-3517.
What do Isleworth homes cost?
How much do homes in Isleworth sell for?
Mostly between about $2.7 million and $11.5 million. The 10 recorded Isleworth sales we checked from September 2025 to August 2026 ran from $2,745,000 to $11,500,000. Garden villas and Isleworth West homes sat at the lower end; golf-front estates on Isleworth Country Club Drive at the top.
Isleworth at a glance
- Address
- Windermere, FL 34786, in unincorporated Orange CountyNot inside the Town of Windermere
- Gate
- Guard-staffed around the clock; Isleworth West and the Gardens use either Isleworth gateMLS listings; Andy Neal, October 2026
- Homes
- Single-family estates and garden villas; no condos or townhomes found
- Lots
- About half an acre to 2.3 acresRecent sales and listings, 2025–26
- Club
- Private and optional, by invitation, separate from the homeHow the club works
What Isleworth homes actually sold for.
Asking prices are only half the story. These are closed sales from county records, each one reported by the local paper. It isn't every sale, so read it as a range, not an average.
Recorded Isleworth sales, September 2025 to August 2026
10 sales we checked, from $2.745M to $11.5M. Hover or tap a dot for the street and date.
Show the numbers
| Street (section) | Recorded | Sale price | Built | Living sq ft |
|---|---|---|---|---|
| Louise Cove Dr (Isleworth West) | Mar 31, 2026 | $2,745,000 | 2002 | — |
| Louise Cove Dr (Isleworth West) | Mar 19, 2026 | $2,900,000 | 2002 | — |
| Joanna Garden Ct (Gardens) | Feb 20, 2026 | $2,950,000 | 2007 | 4,089 |
| Isleworth Gardens Dr (Gardens) | Nov 26, 2025 | $3,550,000 | 2006 | 4,333 |
| Alexandra Garden Ct (Gardens) | Aug 20, 2026 | $3,900,000 | 2008 | 5,695 |
| Latrobe Dr | Dec 30, 2025 | $4,400,000 | 1989 | 5,721 |
| Deacon Cir | Mar 25, 2026 | $4,475,000 | 1989 | 5,853 |
| Louise Cove Dr (on Lake Louise) | Jul 2, 2026 | $4,898,000 | 2002 | 5,752 |
| Isleworth Country Club Dr (golf views) | Sep 5, 2025 | $8,500,000 | 2013 | 11,403 |
| Isleworth Country Club Dr (golf-front) | May 15, 2026 | $11,500,000 | 1999 | 9,511 |
Orange Observer weekly Windermere sales reports from county records, September 11, 2025 to August 27, 2026; the March 31, 2026 Isleworth West sale from its MLS record (Bex Realty). The Observer reports only each week's top sales, so this isn't a complete list. Living area for the two Isleworth West sales is left out because the sources disagree.
Ranges from the table above. An MLS-based tracker counts 14 Isleworth closings in the 12 months to September 20, 2026, at a median of 92.3% of the original asking price (movewithmomentum.com, Stellar MLS data); it may count only the main "Isleworth" subdivision.
Four kinds of Isleworth home.
On October 13, 2026, 21 Isleworth homes were listed for sale, from $2.8 million to $18.75 million, with about 2,850 to 15,300 square feet of living area. Most fall into one of these groups.
Golf-front estates
Along Isleworth Country Club Drive and the course. The two highest recorded sales in the past year were here.
Lots about 0.5 to 1.2 acres in recent salesLakefront estates
On Lake Louise, Lake Chase and the other chain lakes around the community, some with private docks.
Dock permits: Orange County EPDGarden villas
Smaller homes on Isleworth Gardens Drive and the Garden Courts. A second fee covers the landscaping, irrigation and landscape lighting.
Built mostly 2006 to 2008; new builds listed for 2027Louise Cove Drive
Homes off Louise Cove Drive, near Lake Louise, built around 2002, with the same HOA fee as the main community and use of either gate.
One quarterly HOA fee on recent listingsSnapshot of Andy's Isleworth listings page, October 13, 2026 (21 for sale; rentals left out). New builds: a six-bedroom Gardens of Isleworth home listed at $7,999,000 with a 2027 completion year (MLS data, August 11, 2026) and a pre-construction lakefront estate on Latrobe Drive listed at $18,750,000 (October 2026). Lots: listing records, 2025–26. Gates and the Gardens fee: Andy Neal, October 2026.
What it costs to own, beyond the price.
Every Isleworth home pays the community association. The Gardens of Isleworth adds a second fee for its grounds. Club membership is optional, with its own fees, which the club doesn't publish.
| Section | Per quarter | Per year |
|---|---|---|
| Main community | $3,672 | $14,688 |
| Isleworth West | $3,672 | $14,688 |
| Gardens of Isleworth, Unit 2 | $3,438 | $13,752 |
| Gardens of Isleworth (two fees) | $3,297 + $3,129 | $25,704 |
One listing's figures for each row: main community July 30, 2026 (MLS O6427447); Isleworth West Mar and Oct 2026; Gardens Unit 2 October 2026; Gardens sales November 2025 and February 2026; the second fee is for the grounds (Andy Neal, Oct 2026). Dues cover a 24-hour guard, private roads, security, reserves and management; most also list cable and internet. Confirm each home's figures on its estoppel certificate.
- Property tax rate
- About 15.98 mills for FY 2026-27, the unincorporated Orange County rate, before any lake district levy and non-ad valorem chargesAbout $1,598 per $100,000 of taxable value; see the tax table in our Windermere guide
- Tax example
- $45,808 in 2025 taxes on a 5,972 sq ft home on Isleworth Country Club DriveListing record, July 2026; your bill depends on value and homestead
- Club
- Isleworth Golf & Country Club is optional and by invitation, with a waiting list; the club doesn't disclose its length or its feesClub and HOA, explained in the Isleworth guide
- Homestead
- Live in the home on January 1 and file by March 1 for up to $50,000 off the assessed valueF.S. 196.031; Amendment 3, approved November 3, 2026, raises the non-school exemption from 2027
How an Isleworth purchase works.
The steps are the usual Florida ones, with a few that matter more here: gate access, the association's paperwork and, for lakefront homes, the dock and seawall.
- Book every showing ahead
Visitors enter on a resident's guest list or a scheduled appointment, so your agent arranges each visit with the listing agent.
Isleworth Community Association gate system - Read the HOA disclosure summary before you sign
If it isn't given before the contract, you can cancel within 3 days of getting it, or before closing.
F.S. 720.401 - Inspect for the home's age and setting
Many homes date from 1989 on: insurers ask for a 4-point inspection on homes over 20 years old, and the wind-mitigation form changed in April 2026.
Citizens Property Insurance; form OIR-B1-1802 (Rev. 04/26) - Order the estoppel certificate
The association issues it within 10 business days. It shows the dues and anything else owed to the association.
F.S. 720.30851 - Decide on the club separately
Membership is optional and by invitation, through the club's membership office, and isn't part of buying the home.
isleworth.com, membership page; Andy Neal, October 2026
On a lakefront home, also check
-
The parcel's flood zoneFEMA Flood Map Service Center or Orange County InfoMap
-
Permits for the dock and any seawallA new dock needs an Orange County EPD permit; the application fee is $965.50 from October 1, 2026
-
Which lake the home is onThe lakes around Isleworth are all on the Butler Chain; see the lake map in the guide
-
The county's proposed boating zonesSlow-speed zones in nearby canals go to a county vote on December 1, 2026
F.S. 720.401 and 720.30851 (2026); Citizens Property Insurance inspections page and March 19, 2026 bulletin; Orange County EPD dock permit page (read October 22, 2026); Orange County boating code update page (hearings October 28 and December 1, 2026). Closing costs and tax rules for all of Windermere: before you buy in Windermere.
More on Isleworth.
More on Isleworth
- The Isleworth guide: history, the lakes, the club and the HOA in detail.
- Golden Oak homes for sale, with a side-by-side comparison with Isleworth.
- Windermere's gated communities, compared gate by gate.
- How Andy works with luxury buyers and sellers.
- Andy's blog: Isleworth vs Golden Oak.
Thinking about Isleworth?
The Isleworth guide
The club, the lakes, the HOA and the history, in one place.
Read the guideGet a free home valuation
Andy's opinion of your Isleworth home's value and what you could move with. Not an appraisal.
Start hereSell your Isleworth home
How Andy prices, markets and negotiates a sale behind a staffed gate.
How Andy sellsBuying in Isleworth, answered.
01How much do homes in Isleworth cost?
Recorded Isleworth sales we checked from September 2025 to August 2026 ranged from $2,745,000 to $11,500,000. On October 13, 2026, homes listed for sale ran from $2.8 million to $18.75 million. The listings on this page update on their own; the sales table shows dated closings.
02What are the HOA fees in Isleworth?
2025–26 listings show association dues of $3,672 a quarter in the main community and Isleworth West, covering a 24-hour guard, private roads, security, reserves and management. Gardens of Isleworth homes show $3,297 to $3,438 a quarter, and some carry a second fee of $3,129 a quarter for landscaping, irrigation and landscape lighting (Andy Neal). Check the estoppel certificate for the home you choose.
03Do I have to join Isleworth Country Club to buy a home?
No. Club membership is optional (Andy Neal, October 2026) and billed separately from the HOA. The club says memberships are by invitation only, with a waiting list; it doesn't disclose how long the list is. The Isleworth guide covers the club in detail.
04Can I tour an Isleworth home without an appointment?
No. Isleworth's gate is staffed, and visitors enter on a resident's guest list or a scheduled appointment. To see a home, your agent books the showing with the listing agent, who arranges gate access.
05Are there lakefront homes for sale in Isleworth?
Yes, when they come up. Isleworth has over seven miles of Butler Chain shoreline, and a Lake Louise home on Louise Cove Drive closed at $4,898,000 in July 2026. Check the dock permits and the flood zone on any lakefront home.
06Is Isleworth in the Town of Windermere?
No. Isleworth has a Windermere 34786 address but is in unincorporated Orange County, so homes pay the county's fire and sheriff millage instead of the Town's rate: about 15.98 mills in total for FY 2026-27, before any lake district levy and non-ad valorem charges.
07What does an HOA estoppel certificate cost in Florida?
The statute sets a $250 fee, plus $100 for delivery within three business days and $150 if the account is delinquent. The state adjusts these for inflation every five years; the 2022 adjustment raised them to $299, $119 and $179. The association must issue the certificate within 10 business days.
08Are new homes being built in Isleworth?
Yes, on a small scale. In August 2026 a six-bedroom new build in the Gardens of Isleworth was listed at $7,999,000 with a 2027 completion year, and a pre-construction lakefront estate on Latrobe Drive was listed at $18,750,000 in October 2026.
09Which homes does this page show?
Homes for sale in every Isleworth plat, including Isleworth West and the Gardens of Isleworth, at $350,000 and up, with no rentals. Listings come from Stellar MLS and update automatically. Some other sites mix in rentals or homes from nearby communities with similar names.
See an Isleworth home.
Tell Andy what you're looking for: golf-front, on the lake, a garden villa or a new build. He'll arrange showings at the gate and get you the HOA figures for each home.
Book a private showing
A short note is enough. Andy replies personally.
Andy Neal, Realtor · The Agency FL · (407) 619-3517
Sources and how we compiled this page Updated November 2026 · 15 sources
How we compiled it
Sale prices come from county records as reported by the Orange Observer, each report opened and checked; HOA figures come from dated MLS listing records. Listing data comes live from Stellar MLS. Streets are given without house numbers. Rates and rules change; confirm anything you rely on with the source or with Andy.
- Orange Observer, weekly Windermere home sales reports: September 11 and December 4, 2025; January 8, February 26, March 26, April 1, May 21, July 9 and August 27, 2026
- Bex Realty MLS records: Louise Cove Dr (sold March 19 and March 31, 2026); Gardens of Isleworth (sold November 26, 2025 and February 20, 2026)
- Coldwell Banker, Isleworth Country Club Dr listing, MLS O6427447 (July 30, 2026)
- Realgeeks IDX records, Isleworth West (MLS O6430931) and Gardens of Isleworth Unit 2 (MLS O6397842), read October 22, 2026
- Andy Neal, Isleworth listings page snapshot (October 13, 2026)
- movewithmomentum.com, Isleworth and Gardens of Isleworth home values (Stellar MLS data to September 20 and August 11, 2026)
- Isleworth Golf & Country Club: About, Amenities and Membership pages (read October 22, 2026)
- Isleworth Community Association resident site, public page (read October 22, 2026)
- Florida Statutes 720.401, 720.30851 and 196.031 (2026); DBPR 2022 estoppel fee adjustment (Shumaker client alert, July 25, 2022)
- Orange County FY 2026-27 adopted millage (September 24, 2026) and Orange County Public Schools (September 9, 2026)
- Citizens Property Insurance, inspections page and March 19, 2026 bulletin on form OIR-B1-1802
- Orange County Environmental Protection Division, dock permit page (read October 22, 2026)
- Orange County, Chapter 8 boating code update page and draft ordinance (May 19, 2026)
- Florida Division of Elections, 2026 constitutional amendments, Ballot No. 3
- Andy Neal, The Agency FL: club membership optional, gate use for Isleworth West and the Gardens, what the Gardens' second fee covers (October 2026)
Andy Neal, Realtor, The Agency FL · 4757 The Grove Dr, Suite 124, Windermere, FL 34786 · (407) 619-3517 · Florida Sales Associate, Lic. SL3396613.
The Agency FL (H2 Collective LLC d/b/a The Agency FL), a Florida-licensed real estate brokerage, Lic. CQ1073923. Equal Housing Opportunity.
Information on this page is for general guidance and was checked in October 2026; it isn't legal, tax or insurance advice. Andy Neal and The Agency FL are not affiliated with Isleworth Golf & Country Club or the Isleworth Community Association.
