Recently Viewed Properties
See This Home
Save This Listing
Close

$5,500

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 3,805 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 311 E 8th Ave

General

  • Rent: $5,500
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6364016
  • Added to Site: 228 day(s) ago

Rental Information

  • Lease/Rent Term: 12 Months
  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 7
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Kitchen and Family Room Combination, Open Floorplan, PrimaryBedroom Upstairs, Walk-In Closet(s)
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Water Softener
  • Furnishings: Unfurnished

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside

Parking

  • Carports: Yes
  • Carport: 2
  • Carport Spaces: 2
  • Covered Spaces: 2

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.

School Information

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

Community

  • Community Name: 34786 - Windermere
  • Pet Restrictions: Pet application will be considered

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Water District: LAKE BESSIE

Structural Information

  • Stories/Levels: Two
  • Square Feet: 3,805
  • Living Area: 3,805 Sq. Ft.
  • Year Built: 1913

Lot Features

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

Water Features

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

Financial Considerations

  • Lease Price: $6,000
  • Application Fee: $50
  • Security Deposit: $6,000

Disclosures and Reports

  • APN: 172328933601641
  • Property ID: 172328933601641

Meet the listing and selling agent

Meet the listing and selling agent
— 311 E 8th Ave —

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 ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price History for 311 E 8th Ave

Date
Details
Price
Change
Source
6/15/2026
Sold
$5,500
-8.33%
MLS
3/17/2026
Price Reduced
$6,000
-7.69%
MLS
1/14/2026
Price Reduced
$6,500
-3.7%
MLS
12/01/2025
Listed
$6,750
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Just Listed near 311 E 8th Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

9415 Daney St, Gotha, FL 34734 - Photo 1 Just Listed
$315,000

9415 Daney St  Gotha, FL 34734

  • Single Family
  • Active
  • Updated 2 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 985
    Sq. Ft.
Listed by Watson Realty Corp
5014 Sawdust Cir, Ocoee, FL 34761 - Photo 1 Just Listed
$445,000
Open House

5014 Sawdust Cir  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 19 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,732
    Sq. Ft.
Listed by Century 21 Carioti
464 New Meadows Ct, Ocoee, FL 34761 - Photo 1 Just Listed
$312,000

464 New Meadows Ct  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,024
    Sq. Ft.
Listed by C Brenner Inc
1980 Erving Cir, Ocoee, FL 34761 - Photo 1 Just Listed
$169,999

1980 Erving Cir  #107  Ocoee, FL 34761

  • Condo
  • Active
  • Updated 8 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,074
    Sq. Ft.
Listed by Premium Realty Advisors Llc

Price Reduced near 311 E 8th Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1643 Shonnora Dr, Gotha, FL 34734 - Photo 1 Price Reduced
-$24,900 (-4.74%)
$499,900

1643 Shonnora Dr  Gotha, FL 34734

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,896
    Sq. Ft.
Listed by Southern Prestige Realty Inc
9467 Lake Lotta Cir, Gotha, FL 34734 - Photo 1 Price Reduced
-$10,000 (-3.75%)
$257,000

9467 Lake Lotta Cir  Gotha, FL 34734

  • Townhouse
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,072
    Sq. Ft.
Listed by Watson Realty Corp
300 E Geneva St, Ocoee, FL 34761 - Photo 1 Price Reduced
-$10,900 (-2.13%)
$500,000

300 E Geneva St  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,138
    Sq. Ft.
Listed by David Plasencia, Esq. (407) 579-9369
1855 Black Maple Pl, Ocoee, FL 34761 - Photo 1 Price Reduced
-$20,099 (-3.53%)
$549,900

1855 Black Maple Pl  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,936
    Sq. Ft.
Listed by Metropolis R.E. Solutions, Llc

Recent Sales near 311 E 8th Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

812 East Blvd, Windermere, FL 34786 - Photo 1 Sold
$5,500

812 East Blvd  Windermere, FL 34786

  • Single Family
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,680
    Sq. Ft.
Listed by The Simon Simaan Group
Sold by Stellar Non-Member Office
820 East Blvd, Windermere, FL 34786 - Photo 1 Sold
$6,000

820 East Blvd  Windermere, FL 34786

  • Single Family
  • Closed
  • Updated 10 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,713
    Sq. Ft.
Listed by The Simon Simaan Group
Sold by Stellar Non-Member Office
307 W 4th Ave, Windermere, FL 34786 - Photo 1 Sold
$5,475

307 W 4th Ave  Windermere, FL 34786

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,190
    Sq. Ft.
Listed and Sold by Mainframe Real Estate
1917 Pamlynne Pl, Windermere, FL 34786 - Photo 1 Sold
$6,000

1917 Pamlynne Pl  Windermere, FL 34786

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,534
    Sq. Ft.
Listed by Capital Homes Inc
Sold by Stellar Non-Member Office

311 E 8th Avenue, Windermere, FL 34786 (MLS# O6364016) is a Single Family property that was sold at $5,500 on June 15, 2026. This property was 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 real estate for sale or rent in Windermere? You can browse all Windermere rentals or contact a Coldwell Banker agent to request more information.