311 E 8th Ave
Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,805 sqft
5 Beds
4 Baths
3,805 sqft
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Living Area
3,805 sqft
Price/Sqft
$381
About this House
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
311 E 8th Ave, Windermere, FL 34786 is a 5 bedroom, 4 bathroom, 3,805 sqft single-family home. It last sold for $800,000 on May 20, 2021 (13,233% above the $6,000 asking price). More recently, it was listed as a rental in March 2026 with an asking price of $6,000 per month. That rental listing was removed on May 18, 2026. It is currently off market. The Trulia Estimate is $1,448,200, with a rent estimate of $5,875/month.
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 |
Market trends in Windermere
Last updated June 2026
Avg. sale price
$722K
$50KMoM
Sale-to-List Price
97.3%
0.2%MoM
Price per sq ft
$273
$11MoM
Available listings
285
6MoM
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 |
|---|---|---|---|---|---|---|---|
0.08 | 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 | |
0.22 | Single-Family Home | $1,050,000 | 05/21/26 | 4 | 3 | 2,412 | |
0.16 | Single-Family Home | $2,175,000 | 06/18/26 | 4 | 4.5 | 4,471 | |
0.26 | Single-Family Home | $2,171,470 | 04/29/26 | 5 | 4.5 | 3,994 | |
0.41 | Single-Family Home | $765,000 | 07/30/26 | 5 | 2.5 | 2,539 | |
0.20 | Single-Family Home | $850,000 | 10/21/25 | 3 | 2 | 2,778 | |
0.11 | Single-Family Home | $770,000 | 06/11/26 | 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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
Homes for sale near 311 E 8th Ave
Off Market Homes Near 311 E 8th Ave
Frequently asked questions about 311 E 8th Ave
- What is 311 E 8th Ave estimated to be worth?Trulia's estimated value for 311 E 8th Ave in Windermere, FL is $1,448,200.
- What is the price history for 311 E 8th Ave?311 E 8th Ave in Windermere, FL last sold for $800,000 in May 2021.
- Is Windermere a buyer's or seller's market?Windermere is currently a balanced market, based on recent for-sale activity.
- What's the median sale price in Windermere?The median sale price in Windermere is $722K. That is up $50K from the prior month.
- Does 311 E 8th Ave have air conditioning?Yes, 311 E 8th Ave in Windermere, FL has air conditioning.
- Does 311 E 8th Ave have laundry facilities?Yes, 311 E 8th Ave in Windermere, FL has in-unit laundry.

