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.
- Built in 1913
- $407.10/sqft
- Lot size: 10,000 sqft
- 219 days on market
- Directions: Head West on 6th Avenue from Conroy Windermere Road, Left on Bessie Street, Home is on the Right.
- County: Orange
- Geo subdivision: WINDERMERE TOWN
Nearby Schools
Windermere Elem
Gotha Middle
Olympia High
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Let's get in touch!
Let's get in touch!

Niles Harrison Pfeiffer
Central Florida REALTOR®
- Source: Stellar MLS
- MLS #: O6333319
Listing updated: March 14, 2026 at 6:05PM
Listing provided by: Karen O'Neil, COLDWELL BANKER RESIDENTIAL RE
Last checked 16 hours ago
Listing provided by: Karen O'Neil, COLDWELL BANKER RESIDENTIAL RE
Last checked 16 hours ago
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