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Property Description
Build Your Dream Lakefront Home in the Town of Windermere! Opportunity is knocking in one of Central Florida's most desirable areas! This exceptional one-acre lakefront homesite on Oakdale Street in the town offers a rare opportunity to bring your vision to life and build the custom home you have always dreamed of. With an impressive 105 feet of direct frontage on beautiful Lake Bessie, this property provides the space, privacy, and waterfront setting to create something truly special. One of the biggest advantages of this property is NO HOA. Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a stunning custom estate, a spacious family home, or a private lakeside retreat, this property gives you the opportunity to create a home that is uniquely yours. The expansive one-acre lot provides plenty of room to design the lifestyle you want. Imagine a beautiful custom residence with expansive living spaces, a resort-style pool, outdoor entertaining areas, lush landscaping, a private garden, oversized garage, and breathtaking views of Lake Bessie. With 105 feet of lake frontage, you can take full advantage of the waterfront setting and enjoy the beauty and tranquility of lakefront living right in the heart of Windermere. Instead of settling for someone else's floor plan, start with a blank canvas and create a home designed around the way you live. Bring your architect, builder, and ideas and transform this exceptional homesite into your own private sanctuary. Location is everything, and this property offers the best of the Old Windermere lifestyle. Ideally located within a short distance of the Windermere Farmers Market, local shops, restaurants, and more, while beautiful Lake Butler is just blocks away. Town residents also have access to a boat ramp on Lake Butler and Lake Bessie, along with tennis courts, providing even more opportunities to enjoy the outdoors and the unique lifestyle that makes Windermere so desirable. Windermere is known for its beautiful lakes, charming community atmosphere, desirable residential neighborhoods, and convenient proximity to everything that makes Central Florida such a sought-after place to live. Opportunities to own a large lakefront homesite with no HOA and 105 feet of Lake Bessie frontage are truly special. This is your opportunity to stop dreaming about the perfect home and start building it. Make your vision come to life. Make this exceptional Windermere lakefront property the place you call home. Don't miss this rare opportunity!
Full Property Details
Full Property Details for 1221 Oakdale St
General
- Price: $1,250,000
- Taxes: $14,735 (2026)
- Status: Active
- Type: Lots/Land
- Source: MidFloridaRegionalMLS
- MLS ID: O6446547
- Updated: 10/1/2026
- Added to Site: 1 day(s) ago
Additional Information
- Shared Amenities: Basketball Court, Park, Pickleball Court(s), Playground, Tennis Court(s), Trail(s)
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: WINDERMERE TOWN
- Driving Directions: Head South on Main Street from 6th Avenue, Left on 12th Avenue, Lot is on the corner by the lake.
- Direction Faces: West
School Information
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
Community
- Community Name: 34786 - Windermere
- Community Features: Fishing, Private Boat Ramp, Water Access, Waterfront, Golf Carts OK, Park, Playground, Sidewalks
- Optional Amenities: Basketball Court, Park, Pickleball Court(s), Playground, Tennis Court(s), Trail(s)
Utilities
- Sewer: Septic Needed
- Water District: LAKE BESSIE
- Water: Well Required
- Utility Description: Cable TV Available, Electricity Available, Water Available
Structural Information
- Current Bldg. Use: Unimproved
Lot Features
- Property View: Golf Course, Water
- Lot Size (Acres): 1
- Lot Size (Sq. Ft.): 43,480
- Lot Size: 43480
- Lot Dimensions: 100 x 419 x 105 x 451
- Frontage: City Street
- Street/Road Desc.: Dirt
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake, Lake - Chain of Lakes
- Water Extras: Yes
- Water Front Name: LAKE BESSIE
- Water Front Desc.: Waterfront, Lake Front
Financial Considerations
- Price Per Acre: $1,250,000
- Assoc Fee Desc.: None
- Tax Amount: $14,735.79
- Tax Year: 2026
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: PLAT OF WINDERMERE G/36 LOT 6 & N 20 FTOF LOT 5 & BEG NE COR LOT 6 RUN NELY ALONG PROJECTED N LINE OF LOT 6 TO E LINE OF SW1/4 OF NE1/4 S TO A PT OF PROJECTEDLINE OF S LINE OF N 20 FT OF LOT 5 NLY TO POB
- Flood Zone Info: AE
- APN: 172328933600060
- Property ID: 172328933600060
- Block/Lot/Section: 36/6
Listed by The Simon Simaan Group
Get Pre-Approved Today
Schools
Schools serving 1221 Oakdale St
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Windermere Elementary School 11125 Park Avenue, Windermere, FL 34786 | K-5 | 1.6 mi |
Gotha Middle School 9155 Gotha Road, Windermere, FL 34786 | 6-8 | 2.9 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 1.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1221 Oakdale St
Date
Details
Price
Change
Source
10/01/2026
Listed
$1,250,000
47.06%
MLS
6/09/2021
Sold
$850,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 1221 Oakdale St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,831
—
$900,000
—
2024
$14,845
3%
$900,000
—
2023
$14,468
20%
$900,000
24%
2021
$12,065
-8%
$725,000
-9%
2022
$13,136
9%
$800,000
28%
2021
$12,065
12%
$625,000
—
2019
$10,769
9%
$625,000
11%
2018
$9,859
2%
$565,000
—
2017
$9,686
-2%
$565,000
—
2016
$9,834
2%
$565,000
5%
2015
$9,622
3%
$540,000
3%
2014
$9,314
—
$522,500
—
2013
$9,270
—
$522,500
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1221 Oakdale St
1221 Oakdale Street, Windermere, FL 34786 (MLS# O6446547) is a Lots/Land property with a lot size of 1 acre. 1221 Oakdale Street is currently listed for $1,250,000 and was received on October 01, 2026. Want to learn more about 1221 Oakdale Street? Do you have questions about finding other Lots/Land real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

