Twitter
Facebook
Email
|
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.
| DAYS ON MARKET | 123 | LAST UPDATED | 10/21/2025 |
|---|---|---|---|
| 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 - Today | $1,660,000 |
| 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
TOTAL MONTHLY PAYMENT
0
P
I
*Estimate only
| SATELLITE VIEW |
| / | |
We respect your online privacy and will never spam you. By submitting this form with your telephone number
you are consenting for Lee
Valdes to contact you even if your name is on a Federal or State
"Do not call List".
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 12/5/25 5:34 PM PST.
This IDX solution is (c) Diverse Solutions 2025.