101 Lee Street, Windermere, FL 34786

$1,395,000
5
BD
4
BA
4,186
SqFt

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List Price
$1,395,000
MLS#
O6437573
Type
Single Family Residential
Property Style
Single Family
Bedrooms
5
Bathrooms
4
Living Area
4,186
Lot Size
18,138
Subdivision
Town Of Windermere
Year Built
1978

Property Description

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.

Additional Information

Community Features
Golf Carts OK, Park, Tennis Court(s), No Deed Restriction
Exterior Construction
Stucco, Frame
Style
Three+ Story
Interior
Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Thermostat, Walk-In Closet(s), Wet Bar
Interior Features
Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Thermostat, Walk-In Closet(s), Wet Bar
Appliances
Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Refrigerator, Washer
Exterior
Balcony, Lighting, Private Entrance, Private Mailbox, Rain Gutters
Roof
Shingle
High School
Olympia High
Middle School
Gotha Middle
Elementary School
Windermere Elem
Extra Rooms
Interior In-Law Suite w/Private Entry
Located Near
Landscaped
Utilities
BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Water Connected
Fireplace
Yes
Garage
Driveway, Garage Door Opener, Garage Faces Side
Floor
Tile, Wood
Heating
Central, Electric
Cooling
Central Air, Zoned
Pool
Yes
Pool Type
Private
Water
Boatable Water, Lake Front

Listing courtesy of STOCKWORTH REALTY GROUP.

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