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$1,660,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 3,805 Sq. Ft.
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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.

Full Property Details for 311 E 8th Ave

General

  • Price: $1,660,000
  • Taxes: $15,684 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6333319
  • Updated: 10/21/2025
  • Added to Site: 191 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Family Room, Gas
  • Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer, Water Softener, Wine Refrigerator
  • Flooring: Carpet, Ceramic Tile, Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside

Exterior

  • Exterior Features: French Doors, Garden, Irrigation System, Lighting, Rain Gutters

Parking

  • Carports: Yes
  • Carport: 2
  • Carport Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Assigned, Covered, Driveway, Off Street

Location

  • Area: 34786 - Windermere
  • County: Orange
  • Development Name: 34786 - Windermere
  • Subdivision: WINDERMERE TOWN
  • Driving Directions: Head West on 6th Avenue from Conroy Windermere Road, Left on Bessie Street, Home is on the Right.
  • Direction Faces: Southeast

School Information

  • Elementary School: Windermere Elem
  • Middle School: Gotha Middle
  • High School: Olympia High

Community

  • Community Name: 34786 - Windermere
  • Community Features: Community Boat Ramp, Fishing, Lake, Water Access, Waterfront, Golf Carts OK

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water District: LAKE BESSIE
  • Water: Well
  • Utility Description: BB/HS Internet Available, Electricity Connected, Natural Gas Available, Natural Gas Connected

Structural Information

  • Exterior Const.: Wood Frame, Wood Siding
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,805
  • Sq. Ft. Source: Public Records
  • Year Built: 1913

Lot Features

  • Lot Size (Acres): 0.23
  • Lot Size (Sq. Ft.): 10,000
  • Lot Size: 10000
  • Street/Road Desc.: Dirt, Gravel
  • Fencing (Description): Wood

Water Features

  • Water Front: Yes
  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Extras: Yes
  • Water Front Name: LAKE BESSIE
  • Water Front Desc.: Lake, Waterfront, Lake Front

Financial Considerations

  • Tax Amount: $15,684
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: PLAT OF WINDERMERE G/36 THE E 100 FT OFLOT 164
  • Flood Zone Info: X
  • APN: 172328933601641
  • Property ID: 172328933601641
  • Block/Lot/Section: 1
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 311 E 8th Ave —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 311 E 8th Ave

School District:Orange County School District
NameGradesDistance
Windermere Elementary School
11125 Park Avenue, Windermere, FL 34786
K-51.3 mi
Gotha Middle School
9155 Gotha Road, Windermere, FL 34786
6-82.5 mi
Olympia High School
4301 South Apopka Vineland Road, Orlando, FL 32835
9-121.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 311 E 8th Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/21/2025
Price Reduced
$1,660,000
-5.14%
MLS
8/07/2025
Listed
$1,750,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 311 E 8th Ave

Year
Property Taxes
Change
Tax Assessment
Change
2024
$15,684
—
$946,690
3%
2024
$15,684
13%
$918,873
5%
2023
$13,826
59%
$877,045
80%
2021
$8,715
-26%
$488,273
-30%
2022
$11,792
35%
$694,270
52%
2021
$8,715
3%
$457,289
-1%
2019
$8,464
5%
$462,344
7%
2018
$8,068
3%
$433,978
1%
2017
$7,855
2%
$430,528
1%
2016
$7,680
5%
$426,126
16%
2015
$7,324
16%
$366,857
10%
2014
$6,337
2%
$333,506
2%
2013
$6,204
—
$327,885
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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311 E 8th Avenue, Windermere, FL 34786 (MLS# O6333319) is a Single Family property with 5 bedrooms and 4 full bathrooms. 311 E 8th Avenue is currently listed for $1,660,000 and was received on August 07, 2025. This property is listed by Karen O'Neil from our Winter Park Office.Want to learn more about 311 E 8th Avenue? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

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