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101 Lee St

Windermere FL 34786

5
4
2
5791 sq. ft.
18138 sq. ft.
Single-Family
Currently for sale - view listing

Overview

Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere’s weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location.

Features

5 bedrooms
4 bathrooms
2 carspaces
2 garage spaces
5791 sq. ft. floor area
18138 sq. ft. lot size
Single-Family

Property history for 101 Lee St

2026
Rented
Undisclosed
23 Feb 2026 by ISLEWORTH REALTY LLC
2019
Sold
$765,000
15 Aug 2019 by Melissa Tyrcha, of LAKESIDE REALTY WINDERMERE INC
2013
Sold
$375,000
06 Sep 2013 by Judy Black, of BHHS FLORIDA REALTY

Happy sellers in Windermere

76%
76% of sellers in Windermere reported that their sale price either exceeded or met their price expectations.

Windermere stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 15 reviews in Windermere over the last 12 months.

Local market activity for 5 bedroom single-family properties in Windermere

In the last 12 months, 139 five-bedroom single-family properties similar to 101 Lee St, have been sold.

This represents a 17% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

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