311 E 8th Ave
Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,805 sqft
5 Beds
4 Baths
3,805 sqft
Local Information
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Description
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.
Application fee $50 / tenant over the age of 18. Additional fees - Cleaning Fee $1250. Pond Use and Maintenance at Tenants discretion and costs. Lease Terms - First month and Security Deposit. 12month Lease Term.
Sewer, Water, Landscaping included in Rent
Application fee $50 / tenant over the age of 18. Additional fees - Cleaning Fee $1250. Pond Use and Maintenance at Tenants discretion and costs. Lease Terms - First month and Security Deposit. 12month Lease Term.
Sewer, Water, Landscaping included in Rent
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from April 18, 2026
Home Highlights
Parking
No Info
Outdoor
No Info
View
No Info
HOA
None
Price/Sqft
No Info
Listed
66 days ago
Home Details for 311 E 8th Ave
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Heating & Cooling Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
Levels, Entrance, & Accessibility Floors: Carpet, Hardwood |
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Property Type / Style Property Type: Single Family Home |
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Lease Term: 1 Year |
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Price History for 311 E 8th Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 05/18/2026 | $6,000 | ListingRemoved | Zillow Rentals |
| 04/01/2026 | $1,549,000 | ListingRemoved | Stellar MLS #O6333319 |
| 03/17/2026 | $6,000 | Listed For Rent | Zillow Rentals |
| 03/17/2026 | $6,000 | ListingRemoved | Stellar MLS #O6364016 |
| 03/17/2026 | $6,000 | PriceChange | Stellar MLS #O6364016 |
| 02/24/2026 | $1,549,000 | PriceChange | Stellar MLS #O6333319 |
| 01/14/2026 | $6,500 | PriceChange | Stellar MLS #O6364016 |
| 12/01/2025 | $6,750 | Listed For Rent | Stellar MLS #O6364016 |
| 10/21/2025 | $1,660,000 | PriceChange | Stellar MLS #O6333319 |
| 08/07/2025 | $1,750,000 | Listed For Sale | Stellar MLS #O6333319 |
| 08/05/2025 | $6,750 | ListingRemoved | Stellar MLS #O6302814 |
| 06/16/2025 | $6,750 | PriceChange | Stellar MLS #O6302814 |
| 05/01/2025 | $7,500 | Listed For Rent | Stellar MLS #O6302814 |
| 07/12/2024 | $850,000 | ListingRemoved | Stellar MLS #O5926994 |
| 10/29/2023 | ListingRemoved | Stellar MLS #O6141867 | |
| 09/19/2023 | $1,850,000 | Listed For Sale | Stellar MLS #O6141867 |
| 09/05/2023 | ListingRemoved | Zillow Rentals | |
| 06/07/2023 | $6,500 | Listed For Rent | Zillow Rentals |
| 10/01/2022 | ListingRemoved | Zillow Rental Manager | |
| 09/15/2022 | $7,000 | Listed For Rent | Zillow Rental Manager |
| 05/20/2021 | $800,000 | Sold | N/A |
| 03/31/2021 | $850,000 | Pending | Stellar MLS #O5926994 |
| 03/04/2021 | $850,000 | Listed For Sale | Stellar MLS #O5926994 |
| 07/04/2020 | $5,000 | ListingRemoved | Agent Provided |
| 07/03/2020 | $799,000 | ListingRemoved | Agent Provided |
| 05/18/2020 | $5,000 | Listed For Rent | Agent Provided |
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $15,684 |
| Assessment | $918,873 |
Home facts updated by county records
Comparable Sales for 311 E 8th Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.15 | Single-Family Home | $2,065,000 | 07/14/25 | 5 | 4 | 3,950 | |
0.08 | Single-Family Home | $910,000 | 05/09/26 | 3 | 2.5 | 2,475 | |
0.14 | Single-Family Home | $1,700,000 | 10/10/25 | 4 | 4.5 | 3,670 | |
0.13 | Single-Family Home | $830,000 | 10/27/25 | 4 | 2 | 2,582 | |
0.26 | Single-Family Home | $1,850,000 | 05/30/25 | 4 | 3.5 | 3,650 | |
0.22 | Single-Family Home | $1,050,000 | 05/21/26 | 4 | 3 | 2,412 | |
0.26 | Single-Family Home | $2,171,470 | 04/29/26 | 5 | 4.5 | 3,994 | |
0.20 | Single-Family Home | $850,000 | 10/21/25 | 3 | 2 | 2,778 | |
0.11 | Single-Family Home | $752,500 | 01/28/26 | 3 | 2 | 1,664 | |
0.20 | Single-Family Home | $2,350,000 | 10/14/25 | 6 | 5.5 | 4,599 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 311 E 8th Ave.
What Locals Say about Windermere
At least 270 Trulia users voted on each feature.
93 % Say it's dog friendly
92 % Say there are sidewalks
87 % Say car is needed
87 % Say parking is easy
81 % Say people would walk alone at night
80 % Say it's quiet
79 % Say there's holiday spirit
78 % Say kids play outside
75 % Say streets are well-lit
64 % Say yards are well-kept
60 % Say they plan to stay for at least 5 years
59 % Say it's walkable to grocery stores
56 % Say there's wildlife
55 % Say it's walkable to restaurants
54 % Say neighbors are friendly
40 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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311 E 8th Ave, Windermere, FL 34786 is a 5 bedroom, 4 bathroom, 3,805 sqft single-family home. This property is not currently available for sale. 311 E 8th Ave was last sold on May 20, 2021 for $800,000 (13,233% higher than the asking price of $6,000). The current Trulia Estimate for 311 E 8th Ave is $1,452,300.

