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$1,395,000

5 Beds 4 Baths 4,186 SQFT 0.42 Acres
Type: Single Family

101 LEE STREET
WINDERMERE, FL 34786

MLS#: O6437573
Kim Androff
Kim Androff
The Real Estate Advantage
Agent
Phone: 952.465.7807
Office: 952.898.5800
Presented by: STOCKWORTH REALTY GROUP with 407-909-5900. - 407-909-5900

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.


 

Interior Features

Bedrooms

Total Bedrooms5

Bathrooms

Half Baths0
Total Baths4

Other Interior Features

LivingAreaSource0 sqft
Air Conditioning Y/NYes
Fireplace FeaturesFamily Room, Gas
Fireplace Y/NYes
FlooringTile, Hardwood
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesCeiling Fan(s), Eating Space In Kitchen, High Ceilings, Thermostat, Walk-In Closet(s), Wet Bar
Laundry FeaturesInside, Laundry Room
Window FeaturesShades

General

Additional Parcels Y/NNo
Additional RoomsInterior In-Law Suite w/Private Entry
AppliancesBar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Refrigerator, Washer
Attached Garage Yes
Building Area Units0 sqft
Carport Y/NNo
CityWINDERMERE
Community FeaturesPrivate Boat Ramp, Golf Carts OK, Park, Tennis Court(s)
Construction MaterialsStucco, Wood Frame
CoolingCentral Air, Zoned
CountyOrange
DirectionsCONROY-WINDERMERE RD...TURNS INTO 6TH AVE...TURN RIGHT ONTO LEE STREET. HOME IS ON THE LEFT.
Elementary SchoolWindermere Elem
Facing DirectionEast
Flood Zone CodeX
Flood Zone Code XY
Full Baths4
Garage Spaces2
Garage Y/NYes
HeatingCentral, Electric
High SchoolOlympia High
In Law Suite Description2+ Bathrooms, 2+ Bedrooms, Attached, Private Entrance
In Law Suite YNYes
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionREPLAT OF TOWN OF WINDERMERE Q/39 LOT 176
LevelsThree Or More
Listing TermsCash, Conventional, VA Loan
Living Area Units0 sqft
Lot Size Square Feet18,138 sqft
Lot Size UnitsSquare Feet
MLS Area34786 - Windermere
Middle/Junior High SchoolGotha Middle
Minimum Lease7 Months
New ConstructionNo
Occupancy TypeVacant
OwnershipFee Simple
Patio/Porch FeaturesCovered, Patio, Screened
Pets AllowedYes
Pool FeaturesGunite, In Ground, Lighting, Screen Enclosure
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
Security FeaturesSmoke Detector(s)
Senior Community Y/NNo
SewerSeptic Tank
Standard StatusActive
StatusActive
Subdivision NameTOWN OF WINDERMERE
Tax Annual Amount$11,693
Tax Lot176
Tax Year2025
Total Rooms7
UtilitiesBB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Water Connected
Virtual TourClick here
Water Access TypeLake - Chain of Lakes
Water Access Y/NYes
Water View Y/NNo
Year Built1978
ZoningWND-SFR

Exterior

Building Area Total5,791 sqft
Covered Spaces2
Exterior AmenitiesBalcony, French Doors, Irrigation System, Lighting, Private Entrance, Private Mailbox, Rain Gutters, Sliding Doors
Foundation DetailsSlab
Lot FeaturesLandscaped
Lot Size Acres0.42
Lot Size Area18,138 sqft
Parking FeaturesDriveway, Garage Door Opener, Garage Faces Side
Private PoolYes
Road Surface TypeDirt
VegetationMature Landscaping, Trees/Landscaped
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

  

Similar Properties

$1,395,000

5 Beds 4 Baths 4,186 SQFT 0.42 Acres
Type: Single Family

101 LEE STREET
WINDERMERE, FL 34786

MLS#: O6437573
Kim Androff
Kim Androff
The Real Estate Advantage
Agent
Phone: 952.465.7807
Office: 952.898.5800