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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. Schedule your private showing today. One or more photos have been virtually staged.
| DAYS ON MARKET | 225 | LAST UPDATED | 2/24/2026 |
|---|---|---|---|
| TRACT | WINDERMERE TOWN | YEAR BUILT | 1913 |
| COMMUNITY | 34786 - Windermere | COUNTY | Orange |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| Elementary School | Windermere Elem |
|---|---|
| Jr. High School | Gotha Middle |
| High School | Olympia High |
| PRICE HISTORY | |
| Prior to Oct 21, '25 | $1,750,000 |
|---|---|
| Oct 21, '25 - Feb 24, '26 | $1,660,000 |
| Feb 24, '26 - Today | $1,549,000 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer, Water Softener, Wine Refrigerator |
| AREA | 34786 - Windermere |
| BASEMENT | Crawl Space |
| CONSTRUCTION | Frame, Wood Siding |
| EXTERIOR | Garden, Lighting, Rain Gutters |
| FIREPLACE | Yes |
| HEAT | Central |
| INTERIOR | Built-in Features, Crown Molding, Eat-in Kitchen, Open Floorplan, Walk-In Closet(s) |
| LOT | 10019 sq ft |
| LOT DESCRIPTION | Waterfront |
| PARKING | Assigned, Covered, Driveway, Off Street |
| SEWER | Septic Tank |
| STORIES | 2 |
| SUBDIVISION | WINDERMERE TOWN |
| TAXES | 15684 |
| UTILITIES | Natural Gas Available, Electricity Connected, Natural Gas Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Lake, Water |
| WATER | Private, Well |
| WATER ACCESS | LAKE BESSIE |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Lake Privileges, Lake Front |
MORTGAGE CALCULATOR
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Listing provided by Karen O'Neil, COLDWELL BANKER RESIDENTIAL RE, 407-647-1211
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 3/17/26 1:49 PM PDT.
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