101 Lee Street, Windermere, FL 34786
$1,300,000 - For Sale
Property Details
Price: $1,300,000
Sq Ft: 4,186
($311 per sqft)
Bedrooms: 5
Bathrooms: 4
City:Windermere
County:Orange
Type:Single Family
Development:Town Of Windermere
Subdivision:Town Of Windermere
Acres:0.4200
Virtual Tour/Floorplan:View
Year Built:1978
Listing Number:O6437573
Status Code:A-Active
Taxes:$11,692.57
Tax Year: 2025
Garage: 2
/ Y
Furnishings: Unfurnished
Pets Allowed: Yes
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Equipment:
Bar Fridge
Built-In Oven
Cooktop
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Refrigerator
Washer
Interior Features:
Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
Thermostat
Walk-In Closet(s)
Wet Bar
Exterior Features:
Balcony
Lighting
Private Entrance
Private Mailbox
Rain Gutters
Financial Information:
Taxes: $11,692.57
Tax Year: 2025
Room Dimensions:
Laundry: Inside, Laundry Room
School Information:
Elementary School: Windermere Elem
Middle School: Gotha Middle
Junior High: Gotha Middle
High School: Olympia High
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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.
MLS Area: 34786 - Windermere
Total Square Footage: 5,791
Price per Square Feet: $310.56
Water: Public
Construction: Stucco, Frame
Date Listed: 2026-09-16 00:00:00
Pool: Y
Pool Description: Gunite, In Ground, Lighting, Screen Enclosure
Furnished: Unfurnished
Windows: Shades
Parking: Driveway, Garage Door Opener, Garage Faces Side
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Tile, Wood
Roof: Shingle
Heating: Central, Electric
Cooling: Central Air, Zoned
Fireplace: Y
Security: Smoke Detector(S)
Laundry: Inside, Laundry Room
Pets: Yes
Sewer: Septic Tank
Lot Desc.: Landscaped
Parcel ID: 07-23-28-9332-0
Listing Courtesy Of: Stockworth Realty Group
jbettosini@stockworth.com
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.
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Additional Information:
MLS Area: 34786 - Windermere
Total Square Footage: 5,791
Price per Square Feet: $310.56
Water: Public
Construction: Stucco, Frame
Date Listed: 2026-09-16 00:00:00
Pool: Y
Pool Description: Gunite, In Ground, Lighting, Screen Enclosure
Furnished: Unfurnished
Windows: Shades
Parking: Driveway, Garage Door Opener, Garage Faces Side
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Tile, Wood
Roof: Shingle
Heating: Central, Electric
Cooling: Central Air, Zoned
Fireplace: Y
Security: Smoke Detector(S)
Laundry: Inside, Laundry Room
Pets: Yes
Sewer: Septic Tank
Lot Desc.: Landscaped
Parcel ID: 07-23-28-9332-0
Map of 101 Lee Street, Windermere, FL 34786
Listing Courtesy Of: Stockworth Realty Group
jbettosini@stockworth.com
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