$6,500/month
311 E 8th Avenue Windermere, FL 34786 - LAKE BESSIE
For Rent MLS# O6364016
5 beds 4 baths 3,805 sq ft Single Family
Details for 311 E 8th Avenue
MLS# O6364016
Description for 311 E 8th Avenue, Windermere, FL, 34786 - LAKE BESSIE
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.
Listing Information
Property Type: Rental, Single Family Residence
Status: Active
Bedrooms: 5
Bathrooms: 4
Lot Size: 0.23 Acres
Square Feet: 3,805 sq ft
Year Built: 1913
Stories: 2 Story
Date Available: 12/1/2025
Subdivision: Windermere Town
County: Orange
School Information
Elementary: Windermere Elem
Middle: Gotha Middle
High: Olympia High
Room Information
Main Floor
Bathroom 4:
Bathroom 3:
Bedroom 2:
Living Room:
Kitchen:
Upper Floor
Bedroom 1:
Primary Bedroom:
Bathrooms
Full Baths: 4
Additonal Room Information
Laundry: Inside
Interior Features
Appliances: Water Softener, Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Additional Interior Features: Ceiling Fan(s), Eat-In Kitchen, Walk-In Closet(s), Upper Level Primary, Kitchen/Family Room Combo, Open Floorplan
Utilities
Cooling: Central Air, Ceiling Fan(s)
Heating: Electric, Central
Exterior / Lot Features
Lot View: Lake,Water
Waterfront Details
Standard Water Body: LAKE BESSIE
Water Front Features: Lake Privileges
Community Features
Security Deposit: 6500
Driving Directions
Head West on 6th Avenue from Conroy Windermere Road, Left on Bessie Street, Home is on the Right.
Financial Considerations
Tenant Pays: Gas,Janitorial Service
Owner Pays: Sewer,Water
Tax/Property ID: 17-23-28-9336-01-641
A broker reciprocity listing courtesy: COLDWELL BANKER RESIDENTIAL RE
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Sales History & Tax Summary for 311 E 8th Avenue
Sales History
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Tax Summary
| Tax Year | Estimated Market Value | Total Tax |
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| Currently not available. | ||
Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 311 E 8th Avenue
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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