Invitation-only · 600 acres
Isleworth
Arnold Palmer-designed championship golf, 24-hour security, and trophy lakefront on Lakes Butler, Chase, and Louise. Central Florida's most exclusive address.
$4.9M – $30M+Explore
Orange County · 34786 · The Butler Chain of Lakes
Windermere
Florida's most coveted lakefront address. Thirteen interconnected lakes, four flagship gates, and the lifestyle that defines Central Florida luxury.
Estate$1.5M – $5M+Lakefront$5M – $20M+
- $1.5M–$5M+
- $5M–$20M+
- 13
- ~30%
Median Estate Sale
Lakefront Range
Interconnected Lakes
Off-market closings
The Brief
Quiet, gated, and on the water.
Windermere is a 2.3-square-mile incorporated town of about 3,030 residents on the western edge of Orange County — historic main street, a few hundred homes, a post office. The address that shows up on closing statements is much larger: four flagship gated communities — Isleworth, Keene's Pointe, Reserve at Lake Butler Sound, and the Town of Windermere itself — anchored by 5,000 acres of navigable Butler Chain water.
What separates this market from Dr. Phillips, Bay Hill, or Lake Nona isn't the price tag. It's the dock. Most waterfront lots here are dockable, the chain is fully navigable top-to-bottom without trailering, and the daily rhythm is boat-first. Owners commute by water to the club, to dinner, to neighbors. That's the lifestyle the Live MLS below is pricing.
Live · Updated every 5 minutes
Active Windermere Listings
Direct from Stellar MLS — every active home in 34786, filtered to the four flagship communities. Click into any listing for full photos, history, and a same-day showing through Ryan.
Every active home currently on MLS in 34786
Live · Stellar MLS
$2.6M
6219 Tiroco Way
Windermere, Florida
7 BD · 6 BA · 5,221 SF · 0.45 AC
New
$670K
4819 Indian Deer Road
Windermere, Florida
4 BD · 4 BA · 3,049 SF · 0.3 AC
New
$430K
8866 Herencia Aly
Windermere, Florida
3 BD · 3 BA · 1,577 SF · 0.15 AC
New
$950K
8355 Torcello Isle Drive
Windermere, Florida
5 BD · 4 BA · 4,202 SF · 0.2 AC
New
$6.95M
6462 Deacon Cir
Windermere, Florida
5 BD · 6 BA · 7,178 SF · 0.64 AC
New
$889K
111 Main Street
Windermere, Florida
3 BD · 2 BA · 2,272 SF · 0.39 AC
New
$3.25M
8340 Lake Burden Circle
Windermere, Florida
6 BD · 7 BA · 6,848 SF · 0.65 AC
New
$27M
5603 Marleon Drive
Windermere, Florida
7 BD · 10 BA · 22,108 SF · 11.58 AC
New
$1.57M
33 Main Street
Windermere, Florida
4 BD · 2 BA · 2,130 SF · 0.37 AC
New
$1.24M
8409 Vivaro Isle Way
Windermere, Florida
6 BD · 5 BA · 4,176 SF · 0.21 AC
New
$975K
1317 Glenheather Drive
Windermere, Florida
4 BD · 3 BA · 2,811 SF · 0.24 AC
New
$625K
8632 Abbotsbury Drive
Windermere, Florida
4 BD · 4 BA · 2,720 SF · 0.14 AC
New
$1.45M
11617 Camden Park Drive
Windermere, Florida
6 BD · 5 BA · 3,463 SF · 0.26 AC
New
$2.7M
9222 Tibet Pointe Circle
Windermere, Florida
5 BD · 6 BA · 5,323 SF · 0.47 AC
New
$1.4M
1554 Lake Rhea Drive
Windermere, Florida
4 BD · 3 BA · 3,427 SF · 0.28 AC
New
$1.43M
1125 Kelso Boulevard
Windermere, Florida
4 BD · 4 BA · 3,660 SF · 1 AC
New
$575K
12533 Cragside Lane
Windermere, Florida
4 BD · 2 BA · 2,151 SF · 0.17 AC
New
$2.5M
105 Pine Street
Windermere, Florida
5 BD · 6 BA · 5,696 SF · 0.57 AC
New
$1.46M
2509 Ridgewind Way
Windermere, Florida
4 BD · 4 BA · 3,844 SF · 0.75 AC
$440K
7612 Fairgrove Avenue
Windermere, Florida
3 BD · 3 BA · 1,742 SF · 0.15 AC
$2.29M
1136 Lake Whitney Drive
Windermere, Florida
4 BD · 6 BA · 5,722 SF · 0.53 AC
$2.89M
5061 Sawyer Cove Way
Windermere, Florida
4 BD · 5 BA · 3,888 SF · 0.46 AC
$445K
7560 Bentonshire Avenue
Windermere, Florida
4 BD · 4 BA · 1,905 SF · 0.07 AC
$573K
9072 Woodbreeze Boulevard
Windermere, Florida
3 BD · 2 BA · 1,721 SF · 0.32 AC
Showing the first 24 of 233 active listings · browse the full search →
Listings courtesy of Stellar MLS. All information deemed reliable but not guaranteed. Equal Housing Opportunity. Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351.
Off-market access
Roughly 30% of luxury closings in Windermere never appear on Zillow.
Especially in Isleworth and the Reserve at Lake Butler Sound, the highest-quality inventory moves through relationships, not MLS. The MaxLife VIP list is how serious buyers see those homes first — pocket listings, estate sales, and pre-MLS opportunities, hand-curated by Ryan.
The Four Flagships
One zip code. Four very different addresses.
Windermere's reputation is built on four distinct gated communities, each with its own price tier, club structure, and buyer profile. We negotiate in all four.
Nicklaus Signature · 250 acres
Keene's Pointe
The Golden Bear Club — Jack Nicklaus Signature course, tennis, and dining. Lake Tibet-Butler waterfront. Fastest-moving luxury community in Central Florida (36-day median DOM).
$1.8M – $8M
48 estates · 1–10 acres
Reserve at Lake Butler Sound
Ultra-luxury custom estates on Lakes Tibet-Butler, Pocket, and Fish. Premium privacy without a mandatory club. Currently the leverage tier — softer 89% sold-to-list.
$2M – $10M+
Gated waterfront · Lake Down
Lake Butler Sound · Casabella
Lake Butler Sound (larger-lot, higher-end) and Casabella (European-inspired) — gated waterfront with the most accessible direct boat-from-home Butler Chain entry.
$900K – $4M
Living on the chain
Thirteen lakes. Thirty-two canals. One private dock.
The Butler Chain of Lakes is why Windermere exists. 5,000+ acres of interconnected water, 11+ navigable miles top-to-bottom — and Florida's very first “Outstanding Florida Waters” designation, awarded in 1985 and held since.
- Total water surface
- 5,000+ acres
- Navigable canals
- 32
- Connected lakes
- 13
- Public ramp
- R.D. Keene Park
Insider knowledge
The details a Zillow profile won't tell you.
Lake speed limits aren't uniform.
Wauseon Bay is 100% no-wake to protect Bird Island's Audubon rookery. Most main bodies allow unlimited HP; canals and shoreline zones are idle-speed. Knowing this matters when you're trying a boat at a showing.
Dock permits go through SJRWMD — and can be denied.
Existing-dock grandfathering and rebuild rights vary lot-to-lot. We verify the permit chain in due diligence, not after closing. New-dock cost runs $8K–$20K with permits.
Windermere Prep has a private walking gate.
The K–12 IB campus shares a back gate with Waterstone and The Enclave. Two communities; one short walk to school. Drives premium for those subdivisions.
OCPS school assignment is street-by-street.
Two homes 400 feet apart can feed different middle schools. Always cross-check with OCPS Find My School before writing an offer — listing-sheet info is often outdated.
Septic still exists near downtown.
Older Windermere-village-adjacent homes haven't all been connected to municipal sewer. Affects insurance, expansion plans, and resale. Always pull the utility map.
~30% of luxury closings here never hit Zillow.
Especially Isleworth and the Reserve at Lake Butler Sound. The relationship-driven off-market network is real here. The VIP list is how you see them first.
The Concierge Desk
Tell me what you're looking for in Windermere.
The lake. The gate. The boat draft. The school assignment. The budget. Whatever the search criteria, give me the picture and I'll come back with three options worth your time — including anything currently off-market.
Ryan answers personally — typically within the hour
Common questions
Windermere, answered.
What makes the Butler Chain of Lakes special?
The Butler Chain consists of 13 interconnected freshwater lakes — Lake Down, Wauseon Bay, Lake Butler, Lake Tibet-Butler, Lake Chase, Lake Isleworth, Lake Louise, Lake Sheen, and more — connected by 32 navigable canals spanning 11+ miles. Residents can boat from any lake to any other without trucking a vessel. The system has carried Florida's 'Outstanding Florida Waters' designation since 1985, the highest environmental classification in the state. It's a 24-hour boat-first lifestyle unique to Central Florida.
How does Windermere compare to Dr. Phillips?
Windermere is the lake-first, quiet-retreat choice — the Butler Chain, small-town Windermere, Isleworth, and Keene's Pointe, with a community centered on boating and golf. Dr. Phillips is the urban-suburban-luxury choice — Restaurant Row, the Marketplace, fast MCO commute, and strong school choice including the VPA Magnet. Windermere prices run roughly 43% higher than Dr. Phillips for comparable tiers. Buyers who want exclusivity and a dock lifestyle lean Windermere; buyers who want luxury plus daily-life convenience lean Dr. Phillips.
Is Isleworth membership required to live there?
No, membership in the Isleworth Golf & Country Club is optional for homeowners. About 70–80% of estate owners join. Initiation fees run $25,000–$200,000 depending on membership tier, with annual dues of $24,000–$36,000+. There is typically a 2–5-year waiting list. Non-members can play only by booking a stay at the Lodge. Membership includes the 18-hole Arnold Palmer course, fine dining, spa, tennis, and boat dock access to the Butler Chain.
What are the schools like in Windermere?
Public schools in 34786 are among Orange County's strongest: Windermere Elementary, Bridgewater Middle (STEM-focused), and Windermere High (opened 2017). School assignment depends on your specific street — always verify with OCPS Find My School before closing. For private school, Windermere Preparatory School is the top option — the only IB school in Central Florida, with MIT, Juilliard, and UNICEF partnerships.
Can I access the Butler Chain without living on the water?
Yes. R.D. Keene Park on Conroy-Windermere Road provides public boat ramp access to Lake Tibet-Butler (and thus the full chain) for $5/day or $150/annual pass. Hours are 6:30 a.m.–8 p.m. in summer, 6:30 a.m.–6 p.m. in winter; the gate closes when the 49 vehicle/trailer spaces fill. Many Windermere area residents who don't have waterfront homes use the park regularly for recreational access to the chain.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · All information deemed reliable but not guaranteed · Equal Housing Opportunity · MLS data courtesy of Stellar MLS · Full disclaimer