Timeless Charm in the Heart of Downtown Windermere. Nestled beneath a canopy of majestic oak trees on one of Windermere’s most picturesque streets, this beautifully maintained three bedroom, two and half bath residence offers the perfect blend of classic Florida charm and modern comfort. Situated on a spacious 0.38 acre fenced homesite, this exceptional property features 2,795 square feet of living space and 4,163 total square feet, providing plenty of room to live, work, and entertain. From the moment you arrive, you will appreciate the peaceful setting and inviting curb appeal that make Oakdale Street one of the town’s most desirable locations. Inside, thoughtful craftsmanship is evident throughout with custom trim work, rich stone and wood flooring, double pane windows and doors, and a warm family room centered around a natural gas fireplace. The well appointed kitchen features a natural gas range, while the expansive air conditioned Florida room offers the perfect place to relax year round as you overlook the private backyard. Car enthusiasts, hobbyists, and those needing extra space will love the 4 car garage along with the detached air conditioned building, ideal as a home office, fitness studio, art studio, workshop, guest retreat, or whatever your heart desires. Recent improvements provide peace of mind, including: Roof replaced in 2019, newer HVAC system and water heater (4 years old) and a newer well pump (9 months old). Living in the Town of Windermere is more than owning a home, it’s embracing a lifestyle. Enjoy the beloved weekly farmers market, monthly food truck nights, festive holiday celebrations, and a charming downtown just a short walk away featuring a new Italian restaurant, breakfast café, coffee shop, wine bar, tennis courts, and more. Residents also enjoy exclusive access to community boat ramps on both Lake Butler and Lake Bessie, making it easy to experience the renowned Butler Chain of Lakes. If you have been searching for a home that offers character, generous space, exceptional flexibility, and one of Central Florida’s most treasured small town lifestyles, this is an opportunity you won’t want to miss. Be sure to click on the virtual tour links.
Sold for $1,000,000
Zillow last checked:
Listing updated:
Bought with:
Simon Simaan, 3265503
THE SIMON SIMAAN GROUP
Source: Stellar MLS,MLS#: O6425946
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Price history
| Date | Event | Price |
|---|---|---|
| 8/28/2026 | Sold | $1,000,000-4.7%$358/sqft |
Source:  Stellar MLS #O6425946 Report a problem | ||
| 8/11/2026 | Listed for sale | $1,049,000$375/sqft |
Source: Stellar MLS #O6425946 Report a problem | ||
| 8/9/2026 | Contingent | $1,049,000$375/sqft |
Source: Stellar MLS #O6425946 Report a problem | ||
| 7/28/2026 | Listed for sale | $1,049,000+16.6%$375/sqft |
Source: Stellar MLS #O6425946 Report a problem | ||
| 8/26/2022 | Sold | $900,000-2.7%$322/sqft |
Source: Public Record Report a problem | ||
| 7/10/2022 | Pending sale | $924,900$331/sqft |
Source: Stellar MLS #O6034161 Report a problem | ||
| 6/15/2022 | Listed for sale | $924,900+120.2%$331/sqft |
Source: Stellar MLS #O6034161 Report a problem | ||
| 7/24/2014 | Sold | $420,000-4.3%$150/sqft |
Source: Stellar MLS #O5303348 Report a problem | ||
| 6/26/2014 | Listed for sale | $439,000+59.6%$157/sqft |
Source: Stockworth Realty Group LLC #O5303348 Report a problem | ||
| 8/7/2000 | Sold | $275,000+19.6%$98/sqft |
Source: Public Record Report a problem | ||
| 10/16/1998 | Sold | $230,000$82/sqft |
Source: Public Record Report a problem | ||
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Estimated market value
$999,900
