Niles Harrison Pfeiffer

Niles Harrison Pfeiffer Central Florida REALTOR®

$1,660,000.00
311 8TH AVENUE, WINDERMERE, FL - 34786
5 beds
4 baths
3,805 sqft
$1,660,000.00
311 8TH AVENUE, WINDERMERE, FL - 34786
Niles Harrison Pfeiffer
$1,660,000.00
5 beds
4 baths
3,805 sqft
311 8TH AVENUE, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 1913
  • $436.27/sqft
  • Lot size: 10,000 sqft
  • 177 days on market

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.

  • 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

Features

Financial

Let's get in touch!

Niles Harrison Pfeiffer

Niles Harrison Pfeiffer

Central Florida REALTOR®

See also

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9146 GREAT HERON CIRCLE, ORLANDO, FL - 32836
$1,699,000.00
5 bds
4 ba
4,614 sqft
9146 GREAT HERON CIRCLE, ORLANDO, FL - 32836
For Sale
5701 TARAWOOD DRIVE, ORLANDO, FL - 32819
$1,590,000.00
5 bds
4 ba
3,288 sqft
5701 TARAWOOD DRIVE, ORLANDO, FL - 32819
For Sale
8273 WILSON TERRACE, ORLANDO, FL - 32819
$1,550,000.00
6 bds
6 ba
4,500 sqft
8273 WILSON TERRACE, ORLANDO, FL - 32819
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6333319
Listing updated: January 31, 2026 at 3:49PM
Listing provided by: Karen O'Neil, COLDWELL BANKER RESIDENTIAL RE
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