Under contract-accepting backup offers. Experience the pinnacle of lakefront luxury breathtaking acres in the heart of Windermere, offering an extraordinary 320 feet of pristine ski lake frontage and an unmatched resort-style lifestyle. This one-of-a-kind waterfront compound features a stunning 6-bedroom, 5-bathroom main residence encompassing 12,323 gross square feet with 7,000 heated square feet, thoughtfully designed to maximize comfort, elegance, and breathtaking water views from nearly every angle. Adding to the property’s exceptional versatility is a private 2-bedroom, 1-bathroom guest house and separate garage apartment, creating incredible multigenerational living potential or the ideal setup for extended guests, private offices, or luxury accommodations. The showstopping covered dock pavilion is truly in a class of its own, featuring an expansive over-water lounge, designer outdoor kitchen, bar seating, dining area, and private boat slip, creating the ultimate lakeside retreat. Every detail of this estate has been curated to deliver a private luxury resort experience unlike anything else on the market. The grounds are equally spectacular with a custom screened pool and heated spa overlooking the lake, a private sandy beach, mature canopy trees, waterfront firepit lounge, multiple entertaining spaces, and beautifully manicured landscaping that creates total serenity and privacy. The property’s incredible resort-style entertaining infrastructure makes it ideal for hosting intimate gatherings or large-scale events with ease. Perfectly positioned just minutes from charming downtown Windermere, and conveniently located near Horizon West and downtown Winter Garden, this extraordinary estate also offers easy access to Orlando’s world-renowned attractions — including approximately 25 minutes to Disney and Central Florida’s premier theme parks, and only 30 minutes to Orlando International Airport (MCO). Whether enjoying peaceful mornings on the water, sunset cruises from your private dock, or entertaining on a grand scale, this extraordinary Windermere estate offers a rare opportunity to own one of Central Florida’s most impressive waterfront compounds. A true WOW property that must be experienced in person to fully appreciate its scale, setting, and lifestyle.
Property Details
Price:
$4,700,000
MLS #:
O6408637
Status:
Pending
Beds:
8
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WEST LAKE BUTLER ESTATES
Neighborhood:
34786windermere
Listed Date:
May 18, 2026
Finished Sq Ft:
7,000
Total Sq Ft:
12,323
Lot Size:
233,833 sqft / 5.37 acres (approx)
Year Built:
1997
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Bridgewater Middle
High School:
Windermere High School
Interior
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Gas Water Heater, Ice Maker, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Bathrooms
6 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Luxury Vinyl, Porcelain Tile
Heating
Central, Electric, Zoned
Interior Features
Built-in Features, Ceiling Fan(s), Crown Molding, Dry Bar, Open Floorplan, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
Laundry Features
Electric Dryer Hookup, Gas Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
Two
Exterior
Architectural Style
Florida, Other
Attached Garage YN
1
Construction Materials
Block
Covered Spaces
3
Direction Faces
East
Exterior Features
Awning(s), Balcony, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Yard, Storage
Garage Spaces
3
Lot Features
Cleared, In County, Landscaped, Oversized Lot, Street Dead-End, Unincorporated
Open Parking YN
1
Other Structures
Boat House, Guest House, Outdoor Kitchen, Shed(s), Workshop
Parking Features
Driveway, Garage Door Opener, Garage Faces Side, Guest, Portico, Workshop in Garage
Patio And Porch Features
Covered, Deck, Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
Roof
Shingle
Security Features
Security Lights, Security System, Security System Owned, Smoke Detector(s)
Spa Features
Heated, In Ground
View
Pool, Trees/Woods, Water
Waterfront Features
Lake Front
Financial
Tax Year
2025
Taxes
$17,387
Map
Community
- Address5500 W LAKE BUTLER ROAD WINDERMERE FL
- SubdivisionWEST LAKE BUTLER ESTATES
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BELLA VITA ESTATES
- BELLARIA
- BELMERE VILLAGE
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G4 50 58
- BELMERE VLG G2
- BUTLER BAY
- BUTLER BAY / LAKE CRESCENT RESERVE
- BUTLER RIDGE
- CARRINGTON
- CASA DEL LAGO REP
- CASA DEL LAGO-REPLAT
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DOWN ACRES ESTATES
- DOWN POINT SUB
- DOWNS COVE CAMP SITES
- EDEN’S HAMMOCK
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT WINDERMERE LANDING
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTATES AT WINDERMERE
- FARMS
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- ISLEWORTH
- ISLEWORTH 01 AMD
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 03 46/104
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 7
- KEENES POINTE UNIT 9
- KEENES POINTE UT 06 50 95
- LAKE BURDEN
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #79/32 LOT 223
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE CRESENT RESERVE
- LAKE DAVIS ESTATES
- LAKE DOWN ESTATES
- LAKE DOWN RESERVE
- LAKE HANCOCK SHORES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 3
- LAKE SAWYER SOUTH PH 5
- LAKES
- LAKES OF WINDERMERE PH 1
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE PH 3
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE AT LAKES OF WINDERMERE CONDO PH 3
- LAKESIDE VILLAGE TWNHMS
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE CONDO
- LAKESIDE/LKS/WINDERMERE PH 10
- LAKESIDE/LKS/WINDERMERE PH 3
- LAKESIDE/LKS/WINDERMERE PH 4
- LAKESIDE/LKS/WINDERMERE PH 9
- LEGADO
- LES TERRACES
- MARINA BAY ESTATES
- METCALF PARK REP
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE
- OASIS COVE II/LAKESIDE VILLAGE PH
- OASIS COVE II/LAKESIDE VILLAGE UN
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- PROVIDENCE PH 2
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND 45/120
- RESERVE AT LAKE BUTLER SOUND UNIT 02
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- RESERVE/BELMERE PH 04
- ROBERTS LANDING
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SOUND
- SILVER WOODS PH 01
- SILVER WOODS PH 02
- SILVER WOODS PH 03A
- SILVER WOODS PH 04
- SOUTHBRIDGE VILLAGE
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT PH 02
- SUMMERPORT PH 03
- SUMMERPORT PH 04 C E F & G
- SUMMERPORT PH 05
- SUMMERPORT PH 5
- SUMMERPORT PHASE 1
- SUMMERPORT TRAIL PH 2
- SUMMERPORT TRL
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST LAKE BUTLER ESTATES
- WEST POINT COMMONS
- WESTOVER CLUB
- WESTOVER CLUB PH 02 REP
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WINDEMERE SOUND PH 2
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE DOWNS PH 03
- WINDERMERE GRANDE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE LNDGS PH 02
- WINDERMERE POINTE
- WINDERMERE POINTE AT LAKE ROPER
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PH 3B
- WINDERMERE TRAILS PHASE 1C 80/15 LOT 113
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH IA
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Jun 13, 2026
287
Single Family Listed
100
Avg DOM
478
Avg $ / SqFt
$2,439,553
Avg List Price
Property Summary
- Located in the WEST LAKE BUTLER ESTATES subdivision, 5500 W LAKE BUTLER ROAD WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $4,700,000 and features 8 beds, 6 baths, and has approximately 7,000 square feet of living space, and was originally constructed in 1997. The current price per square foot is $671. The average price per square foot for Single Family listings in WINDERMERE is $478. The average listing price for Single Family in WINDERMERE is $2,439,553. To schedule a showing of MLS#o6408637 at 5500 W LAKE BUTLER ROAD in WINDERMERE, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
Similar Listings Nearby
Courtesy of THE REAL ESTATE COLLECTION LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 5500 W LAKE BUTLER ROAD
WINDERMERE, FL

