101 Lee StreetWindermere, FL 34786

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.

Property Information

Property type

Residential

Sub-type

Single Family Residence

Year built

1978

Living area

4,186 Sq Ft

Lot size

0.42 acres

Garage spaces

2

Ownership

Fee Simple

Zoning

WND-SFR

Days on market

23

MLS^® Listing#

O6437573

Property Features

Interior

Eat-in Kitchen · High Ceilings · Walk-In Closet(s) · Wet Bar · In-Law Floorplan

Exterior

Balcony · Lighting · Private Entrance · Rain Gutters

Appliances

Bar Fridge · Cooktop · Dishwasher · Disposal · Dryer · Gas Water Heater · Microwave · Refrigerator · Washer

Cooling

Central Air · Zoned

Heating

Central · Electric

Flooring

Tile · Wood

Fireplace

Family Room · Gas

Pool

Gunite · In Ground · Screen Enclosure · Private

Parking

Driveway · Garage Door Opener · Garage Faces Side · Attached

Laundry

Inside · Laundry Room

Patio

Covered · Patio · Screened

Lot features

Landscaped

Construction

Stucco · Frame

Foundation

Slab

Roof

Shingle

Security

Smoke Detector(s)

Community

Park · Tennis Court(s)

Utilities

Natural Gas Available · Cable Available · Electricity Connected · Natural Gas Connected · Water Connected

Sewer

Septic Tank

Water source

Public

Rooms

Schools

Elementary

Windermere Elem

Middle

Gotha Middle

High

Olympia High

Financial Details

HOA

None

Annual taxes

$11,693Tax year 2025

Parcel number

07-23-28-9332-01-760

Directions

CONROY-WINDERMERE RD...TURNS INTO 6TH AVE...TURN RIGHT ONTO LEE STREET. HOME IS ON THE LEFT.