101 LEE STREET, WINDERMERE, FL 34786

  • Open House
  • New Listing
  • Virtual Tour
  • Price Reduced$95,000
  • Active

$1,300,000

  • 5 BedroomBedrooms
  • 4 BathroomBathrooms
  • 4,186 Sq.Ft.
  • Single Family
  • Active
  • MLS# O6437573
  • Floor Plan
  • Sold on 
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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 Windermeres 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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Property Details 101 LEE STREET, WINDERMERE, FL 34786

Facts & Features

  • MLS #: O6437573
  • Status: Active
  • Date Listed: 09/16/2026
  • Type: Single Family
  • Sub Type: Single Family Residence
  • Year Built: 1978
  • Price: $1,300,000
  • Acres: 0.42
  • Area: 34786 - Windermere
  • County: Orange
  • Subdivision: TOWN OF WINDERMERE
  • Bedrooms: 5
  • Bathrooms: 4
  • Full Baths: 4
  • Total SqFt: 4,186

Amenities

  • Parking: Driveway, Garage Door Opener, Garage Faces Side
  • # of Garages: 2
  • Features: Golf Carts OK, Park, Tennis Court(s)
  • Waterfront: Yes
  • Waterfront Type: Public
  • Pool: Yes
  • Pool Type: Gunite, In Ground, Lighting, Screen Enclosure

Interior

  • Interior Features: Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Thermostat, Walk-In Closet(s), Wet Bar
  • Flooring: Tile, Wood
  • Appliances: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Refrigerator, Washer
  • Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Water Connected
  • Heating: Central, Electric
  • Cooling: Central Air, Zoned

Exterior

  • Exterior Features: Balcony, Lighting, Private Entrance, Private Mailbox, Rain Gutters
  • Lot Description: Landscaped
  • Roof: Shingle
  • Construction: Stucco, Frame

Schools

  • Elementary: Windermere Elem
  • Middle: Gotha Middle
  • High: Olympia High

Additional Information

  • Zoning: WND-SFR

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