311 E 8TH AVENUE
WINDERMERE, FL, 34786
$1,660,000
5 Beds
4 Baths
3,805 SqFt
0.23 Acres
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$1,660,000
311 E 8TH AVENUE
WINDERMERE, FL, 34786
Luxury Lakefront Living in Downtown Windermere | Fresh Opportunity on Lake Bessie.
Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid-back charm in the heart of Downtown Windermere. Imagine waking up to shimmering water views, paddle-boarding before breakfast, and ending each day with sunsets that paint the sky—this is everyday life at 311 E 8th Avenue.
Tucked within one of Central Florida’s most desirable communities, this home offers unmatched privacy, no HOA, and timeless design with modern updates. A screened front porch sets a relaxed tone, leading into an open floor plan that blends comfort and sophistication. The chef’s kitchen with stainless steel appliances, natural gas range, and custom cabinetry opens to sunlit gathering spaces that overlook the lake, creating an effortless flow for entertaining.
A cozy fireplace anchors the dining area, framed by windows with views of the koi pond and rock waterfall. Two main-floor ensuite bedrooms provide convenience for family or guests, while the upstairs primary suite feels like a private sanctuary with panoramic views of Lake Bessie and Isleworth Golf Course, a spa-inspired bath, and a spacious walk-in closet.
Outside, life slows down. Start your mornings lakeside with coffee and birdsong, spend afternoons fishing or paddle-boarding from your own shoreline, and wind down by the firepit under the stars. Recent updates—50-year architectural roof, Carrier AC units, new flooring, water softener, updated drain field, and fresh paint inside and out—offer peace of mind for years to come.
Here, every day feels like a getaway. Windermere’s golf cart-friendly lifestyle puts you steps from weekly farmers markets, local cafés, food truck Fridays, and the Butler Chain of Lakes. Zoned for top-rated schools and only minutes from Winter Garden, Dr. Phillips, and Disney, this rare property blends luxury, lifestyle, and lakefront living in one unforgettable home.
Your lakefront story begins here. Schedule your private tour today. One or more pictures are virtually staged.

Property Details

Price:
$1,660,000
MLS #:
O6333319
Status:
Active
Beds:
5
Baths:
4
Address:
311 E 8TH AVENUE
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDERMERE TOWN
Neighborhood:
34786windermere
City:
WINDERMERE
Listed Date:
Aug 7, 2025
State:
FL
Finished Sq Ft:
3,805
Total Sq Ft:
3,805
ZIP:
34786
Lot Size:
10,000 sqft / 0.23 acres (approx)
Year Built:
1913

Schools

Elementary School:
Windermere Elem
Middle School:
Gotha Middle
High School:
Olympia High

Interior

Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer, Water Softener, Wine Refrigerator
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile, Vinyl
Heating
Central
Laundry Features
Inside

Exterior

Community Features
Community Boat Ramp, Fishing, Lake, Water Access, Waterfront, Golf Carts O K
Construction Materials
Wood Frame, Wood Siding
Exterior Features
French Doors, Garden, Irrigation System, Lighting, Rain Gutters
Parking Features
Assigned, Covered, Driveway, Off Street
Roof
Shingle

Financial

Tax Year
2024
Taxes
$15,684
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311 E 8TH AVENUE
WINDERMERE, FL