Landlord's Agent in 2026
Karen O'Neil
COLDWELL BANKER REALTY
(407) 789-5565
25 Total Sales
311 E 8th Ave Windermere, FL 34786
Windermere AreaEstimated Value: $1,364,106 - $2,132,000
5
Beds
4
Baths
3,805
Sq Ft
$425/Sq Ft
Est. Value
Highlights
- Boat Ramp
- Access To Lake
- Open Floorplan
- Windermere Elementary School Rated A
- Lake View
- No HOA
About This Home
As of June 2026Virtually 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.
Last Agent to Rent the Property
COLDWELL BANKER REALTY Brokerage Phone: 407-647-1211 License #3511091 Listed on: 12/01/2025
Last Renter's Agent
COLDWELL BANKER REALTY Brokerage Phone: 407-647-1211 License #3511091 Listed on: 12/01/2025
Home Details
Home Type
- Single Family
Year Built
- Built in 1913
Lot Details
- 10,000 Sq Ft Lot
Parking
- 2 Carport Spaces
Home Design
- Bi-Level Home
Interior Spaces
- 3,805 Sq Ft Home
- Open Floorplan
- Ceiling Fan
- Family Room Off Kitchen
- Living Room
- Lake Views
Kitchen
- Eat-In Kitchen
- Range
- Microwave
- Dishwasher
Flooring
- Carpet
- Laminate
Bedrooms and Bathrooms
- 5 Bedrooms
- Primary Bedroom Upstairs
- En-Suite Bathroom
- Walk-In Closet
- 4 Full Bathrooms
Laundry
- Laundry in unit
- Dryer
- Washer
Outdoor Features
- Access To Lake
- Boat Ramp
Schools
- Windermere Elementary School
- Gotha Middle School
- Olympia High School
Utilities
- Central Heating and Cooling System
- Water Softener
Community Details
- No Home Owners Association
- Windermere Town Subdivision
Listing and Financial Details
- Residential Lease
- Security Deposit $6,000
- Property Available on 12/1/25
- Tenant pays for cleaning fee, gas
- The owner pays for grounds care, sewer, water
- 12-Month Minimum Lease Term
- Available 6/14/26
- $50 Application Fee
- 7-Month Minimum Lease Term
- Assessor Parcel Number 17-23-28-9336-01-641
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Closed on
May 8, 2023
Sold by
Bought by
Current Estimated Value
Purchase Details
Listed on
Mar 4, 2021
Closed on
May 13, 2021
Sold by
Bought by
Seller's Agent
Simon Simaan
THE SIMON SIMAAN GROUP
Buyer's Agent
Simon Simaan
THE SIMON SIMAAN GROUP
List Price
$850,000
Sold Price
$800,000
Premium/Discount to List
-$50,000
-5.88%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
14.50%
Original Mortgage
$600,000
Interest Rate
0.031%
Mortgage Type
New Conventional
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Home Values in the Area
Average Home Value in this Area
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $100 | None Listed On Document | ||
| $800,000 | First American Title |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Previous Owner | $600,000 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 06/15/2026 06/15/26 | Rented | $5,500 | -8.3% | -- | |
| 06/14/2026 06/14/26 | Under Contract | -- | -- | -- | |
| 03/17/2026 03/17/26 | Price Changed | $6,000 | -7.7% | $2 / Sq Ft | |
| 01/14/2026 01/14/26 | Price Changed | $6,500 | -3.7% | $2 / Sq Ft | |
| 12/01/2025 12/01/25 | For Rent | $6,750 | +8.0% | -- | |
| 11/03/2023 11/03/23 | Rented | $6,250 | 0.0% | -- | |
| 10/12/2023 10/12/23 | Price Changed | $6,250 | -0.8% | $2 / Sq Ft | |
| 09/28/2023 09/28/23 | For Rent | $6,300 | -16.0% | -- | |
| 09/30/2022 09/30/22 | Rented | $7,500 | +7.1% | -- | |
| 09/28/2022 09/28/22 | Under Contract | -- | -- | -- | |
| 09/15/2022 09/15/22 | For Rent | $7,000 | 0.0% | -- | |
| 05/13/2021 05/13/21 | Sold | $800,000 | -5.9% | $210 / Sq Ft | View Prior Sale |
| 03/31/2021 03/31/21 | Pending | -- | -- | -- | |
| 03/04/2021 03/04/21 | For Sale | $850,000 | +24185.7% | $223 / Sq Ft | |
| 07/03/2020 07/03/20 | Sold | $3,500 | 0.0% | $1 / Sq Ft | View Prior Sale |
| 07/03/2020 07/03/20 | Rented | $3,500 | -30.0% | -- | |
| 05/18/2020 05/18/20 | Price Changed | $5,000 | +11.1% | $1 / Sq Ft | |
| 02/15/2020 02/15/20 | Price Changed | $4,500 | +12.5% | $1 / Sq Ft | |
| 02/04/2020 02/04/20 | Price Changed | $4,000 | -20.0% | $1 / Sq Ft | |
| 12/11/2019 12/11/19 | For Rent | $5,000 | 0.0% | -- | |
| 10/26/2019 10/26/19 | For Sale | $799,000 | -- | $210 / Sq Ft |
Source: Stellar MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $16,156 | $936,440 | $350,000 | $586,440 |
| 2025 | $16,156 | $946,690 | $350,000 | $596,690 |
| 2024 | $13,826 | $918,720 | $350,000 | $568,720 |
| 2023 | $13,826 | $877,045 | $350,000 | $527,045 |
| 2022 | $11,792 | $694,270 | $250,000 | $444,270 |
| 2021 | $8,715 | $488,273 | $250,000 | $238,273 |
| 2020 | $7,927 | $457,289 | $210,000 | $247,289 |
| 2019 | $8,464 | $462,344 | $210,000 | $252,344 |
| 2018 | $8,068 | $433,978 | $185,000 | $248,978 |
| 2017 | $7,855 | $430,528 | $185,000 | $245,528 |
| 2016 | $7,680 | $426,126 | $185,000 | $241,126 |
| 2015 | $7,324 | $406,092 | $165,000 | $241,092 |
| 2014 | $6,337 | $333,506 | $165,000 | $168,506 |
Source: Public Records
Agents Affiliated with this Home
-
Karen O'Neil
-
Milton James
Seller's Agent in 2023
Milton James
COLDWELL BANKER REALTY
(407) 572-4458
229 Total Sales
-
Simon Simaan
Seller's Agent in 2022
Simon Simaan
THE SIMON SIMAAN GROUP
(407) 558-1396
159 Total Sales
-
Matthew Burks
M
Seller's Agent in 2020
Matthew Burks
CORCORAN PREMIER REALTY
(407) 257-5347
50 Total Sales
-
Chocky Burks
Seller's Agent in 2020
Chocky Burks
CORCORAN PREMIER REALTY
(407) 749-6200
33 Total Sales
-
Steve Healy
Seller Co-Listing Agent in 2020
Steve Healy
CORCORAN PREMIER REALTY
(407) 230-1441
128 Total Sales
Map
Source: Stellar MLS
MLS Number: O6364016
APN: 17-2328-9336-01-641
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All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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