311 E 8TH AVENUE WINDERMERE FL 34786 MLS #O6333319 | Gary Kusher | Florida Real Estate

311 E 8TH AVENUE
WINDERMERE, FL, 34786
$1,549,000
5 Beds
4 Baths
3,805 SqFt
0.23 Acres
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MLS #O6333319 image #0
Luxury Lakefront Home in Downtown Windermere. New Price – No HOA – Private Lake Bessie.
Now offered at a newly adjusted price, this exceptional luxury lakefront home in Windermere, Florida presents one of the most compelling waterfront opportunities currently available in Downtown Windermere.If you have been searching for a no HOA lakefront property in Windermere with private shoreline access, 311 E 8th Avenue delivers true waterfront living on Lake Bessie, a rare find in today’s Central Florida luxury market.This Downtown Windermere lakefront residence offers. Panoramic water views from multiple rooms, Golf-cart-friendly access to the historic town center, No HOA restrictions, Significant recent system upgrades. Lakefront inventory in Downtown Windermere remains extremely limited. With this meaningful price improvement, the home now represents exceptional value for buyers seeking privacy, location, and long-term appreciation in one of Orange County’s most established luxury communities.Inside, the open-concept floor plan is designed to maximize natural light and capture lake views throughout the main living areas. The chef’s kitchen features stainless steel appliances, a natural gas range, custom cabinetry, and seamless flow into lakefront gathering spaces. A fireplace anchors the dining area, framed by tranquil views of the koi pond and rock waterfall.The flexible layout supports multigenerational living with two main-floor ensuite bedrooms. Upstairs, the private primary suite showcases elevated views of Lake Bessie and toward the grounds of Isleworth Golf & Country Club, along with a spa-inspired bath and spacious walk-in closet.Recent capital improvements provide confidence for today’s buyers navigating Florida insurance and ownership considerations, including: 50-year architectural roof, Carrier HVAC systems, Updated drain field, Water softener, New flooring. Outdoor features include a firepit, screened front porch, peaceful water frontage, and lake access for paddleboarding, kayaking, fishing, and sunset entertaining. Located minutes from Winter Garden, Dr. Phillips Restaurant Row, and Walt Disney World, this property combines luxury lakefront living with everyday convenience. New price. Rare Downtown Windermere lakefront opportunity. No HOA.
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Property Details

Price:
$1,549,000
MLS #:
O6333319
Status:
Active
Beds:
5
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDERMERE TOWN
Neighborhood:
34786windermere
Listed Date:
Aug 7, 2025
Finished Sq Ft:
3,805
Total Sq Ft:
3,805
Lot Size:
10,000 sqft / 0.23 acres (approx)
Year Built:
1913
WaterfrontLakefront34786 – Windermere34786windermereWindermere TownWindermere ElemGotha MiddleOlympia HighLake BessieBuyer To Conduct Due Diligence With Town And County Rules And Regulations8-12 Months

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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 OK
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

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Single Family in WINDERMERE as of Mar 19, 2026
257
Single Family Listed
101
Avg DOM
462
Avg $ / SqFt
$2,229,890
Avg List Price

Property Summary

    Located in the WINDERMERE TOWN subdivision, 311 E 8TH AVENUE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $1,549,000 and features 5 beds, 4 baths, and has approximately 3,805 square feet of living space, and was originally constructed in 1913. The current price per square foot is $407. The average price per square foot for Single Family listings in WINDERMERE is $462. The average listing price for Single Family in WINDERMERE is $2,229,890. To schedule a showing of MLS#o6333319 at 311 E 8TH AVENUE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 2392986550.

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311 E 8TH AVENUE
WINDERMERE, FL