There are multiple listings for this address:
311 E 8TH AVENUE
WINDERMERE, FL, 34786
$1,549,000
5 Beds
4 Baths
3,805 SqFt
0.23 Acres
Add
MLS #O6333319 image #0
One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental | Downtown Windermere | Lake Bessie.
Now offered at an exceptional value, this rare luxury lakefront rental in Downtown Windermere delivers the ultimate Florida lifestyle for relocating executives and discerning families. Set on the shores of Lake Bessie, this beautifully renovated residence blends refined comfort, privacy, and unmatched walkability in one of Central Florida’s most sought-after communities.
Wake up to panoramic lake and golf course views, unwind on the screened porch, or enjoy evenings by the fireplace and dedicated fire-pit area. The landscaped backyard oasis features a tranquil koi pond and access to lake activities including paddle-boarding and kayaking a true retreat rarely available as a rental.
Inside, the open-concept layout showcases a chef’s kitchen with gas range, custom cabinetry, and premium finishes ideal for entertaining or everyday living. Two first-floor ensuite bedrooms provide flexible options for guests or home offices, while the second-floor primary suite offers a private sanctuary with sweeping lake views.
Located in Windermere’s golf-cart-friendly downtown, residents enjoy weekly farmers markets, food truck nights, top-rated schools, and charming tree-lined streets, all just minutes from Orlando’s business districts and world-class Disney and Universal attractions.
Highlights Include: Prime Downtown Windermere location, Renovated luxury interiors, Exceptional outdoor living and entertaining spaces, Ideal executive and relocation rental. This is more than a rental it’s a lifestyle opportunity. Schedule your private showing today and experience why Windermere continues to attract executives seeking luxury, convenience, and community.

Property Details

Price:
$1,549,000
MLS #:
O6333319
Status:
Active
Beds:
5
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDERMERE TOWN
Neighborhood:
34786windermere
Listed Date:
Aug 7, 2025
Finished Sq Ft:
3,805
Total Sq Ft:
4,928
Lot Size:
10,000 sqft / 0.23 acres (approx)
Year Built:
1913
34786 – Windermere34786windermereWindermere TownWindermere ElemGotha MiddleOlympia HighLake Bessie7 MonthsPets Allowed

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Schools

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

Interior

Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Water Softener
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Heating
Central, Electric
Laundry Features
Inside

Exterior

Financial

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Single Family in WINDERMERE as of Mar 13, 2026
250
Single Family Listed
101
Avg DOM
462
Avg $ / SqFt
$2,140,155
Avg List Price

Property Summary

    Located in the WINDERMERE TOWN subdivision, 311 E 8TH AVENUE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $1,549,000 and features 5 beds, 4 baths, and has approximately 3,805 square feet of living space, and was originally constructed in 1913. The current price per square foot is $407. The average price per square foot for Single Family listings in WINDERMERE is $462. The average listing price for Single Family in WINDERMERE is $2,140,155. To schedule a showing of MLS#o6333319 at 311 E 8TH AVENUE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 2392986550.

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311 E 8TH AVENUE
WINDERMERE, FL
311 E 8TH AVENUE
WINDERMERE, FL, 34786
$6,500
5 Beds
4 Baths
3,805 SqFt
0.23 Acres
Add
MLS #O6364016 image #0
One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental | Downtown Windermere | Lake Bessie.
Now offered at an exceptional value, this rare luxury lakefront rental in Downtown Windermere delivers the ultimate Florida lifestyle for relocating executives and discerning families. Set on the shores of Lake Bessie, this beautifully renovated residence blends refined comfort, privacy, and unmatched walkability in one of Central Florida’s most sought-after communities.
Wake up to panoramic lake and golf course views, unwind on the screened porch, or enjoy evenings by the fireplace and dedicated fire-pit area. The landscaped backyard oasis features a tranquil koi pond and access to lake activities including paddle-boarding and kayaking a true retreat rarely available as a rental.
Inside, the open-concept layout showcases a chef’s kitchen with gas range, custom cabinetry, and premium finishes ideal for entertaining or everyday living. Two first-floor ensuite bedrooms provide flexible options for guests or home offices, while the second-floor primary suite offers a private sanctuary with sweeping lake views.
Located in Windermere’s golf-cart-friendly downtown, residents enjoy weekly farmers markets, food truck nights, top-rated schools, and charming tree-lined streets, all just minutes from Orlando’s business districts and world-class Disney and Universal attractions.
Highlights Include: Prime Downtown Windermere location, Renovated luxury interiors, Exceptional outdoor living and entertaining spaces, Ideal executive and relocation rental. This is more than a rental it’s a lifestyle opportunity. Schedule your private showing today and experience why Windermere continues to attract executives seeking luxury, convenience, and community.

Property Details

Price:
$6,500
MLS #:
O6364016
Status:
Active
Beds:
5
Baths:
4
Type:
Rental
Subtype:
Single Family Residence
Subdivision:
WINDERMERE TOWN
Neighborhood:
34786windermere
Listed Date:
Dec 1, 2025
Finished Sq Ft:
3,805
Total Sq Ft:
4,928
Lot Size:
10,000 sqft / 0.23 acres (approx)
Year Built:
1913
34786 – Windermere34786windermereWindermere TownWindermere ElemGotha MiddleOlympia HighLake Bessie7 MonthsPets Allowed

Ask a Question

See this Listing

Send
  

Schools

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

Interior

Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Water Softener
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Heating
Central, Electric
Laundry Features
Inside

Exterior

Financial

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Rental in WINDERMERE as of Mar 13, 2026
250
Rental Listed
101
Avg DOM
462
Avg $ / SqFt
$2,140,155
Avg List Price

Property Summary

    Located in the WINDERMERE TOWN subdivision, 311 E 8TH AVENUE WINDERMERE FL is a Rental for sale in WINDERMERE, FL, 34786. It is listed for $6,500 To schedule a showing of MLS#o6364016 at 311 E 8TH AVENUE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 2392986550.

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