Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$6,000.00/month
311 E 8TH AVENUE, WINDERMERE, FL - 34786
5 beds
4.0 baths
3,805 sqft
$6,000.00/month
311 E 8TH AVENUE, WINDERMERE, FL - 34786
Gabriella Massaro
$6,000.00/month
5 beds
4.0 baths
3,805 sqft
311 E 8TH AVENUE, WINDERMERE, FL - 34786
For Rent
Photo 1
  • Built in 1913
  • Lot size: 10,000 sqft
  • 196 days on market

Virtually Staged. Luxury Lakefront Executive Rental in Downtown Windermere on Lake Bessie. Now offered at a newly adjusted price, this rare 5-bedroom lakefront home presents one of the most compelling rental opportunities in Windermere.Set on Lake Bessie, this renovated residence offers panoramic water views, flexible living spaces, and true indoor-outdoor Florida living, a feature not commonly found in the current rental inventory. Many competing properties offer limited outdoor space or no water access; this home provides a lakefront setting with room to relax and entertain. The open-concept floor plan features a chef’s kitchen with gas range, custom cabinetry, and premium finishes, flowing into spacious living and dining areas. Two first-floor ensuite bedrooms offer ideal flexibility for guests, home office, or multigenerational living. The second-floor primary suite provides a private retreat with elevated lake views. Outdoor features include a screened porch, landscaped yard, fire-pit area, and koi pond, creating a peaceful setting for everyday living or entertaining. Located in Downtown Windermere, this home offers golf-cart-friendly access to local shops, weekly farmers markets, and community events, with convenient proximity to Orlando’s major employment centers, top-rated schools, and world-class attractions including Disney and Universal. Rarely available as a rental, this lakeview property combines location, space, and lifestyle in one of Central Florida’s most sought-after communities. Schedule your private showing today.

  • 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!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

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4,598 sqft
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For Rent
353 LAKE AMBERLEIGH DRIVE, WINTER GARDEN, FL - 34787
$5,500.00
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2.5 ba
2,762 sqft
353 LAKE AMBERLEIGH DRIVE, WINTER GARDEN, FL - 34787
For Rent
706 CANOPY ESTATES DRIVE, WINTER GARDEN, FL - 34787
$6,000.00
5 bds
6.0 ba
4,019 sqft
706 CANOPY ESTATES DRIVE, WINTER GARDEN, FL - 34787
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6364016
Listing updated: June 15, 2026 at 5:41PM
Listing provided by: Karen O'Neil, COLDWELL BANKER RESIDENTIAL RE
Last checked 2 months ago
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