101 Lee St

Windermere, FL 34786

$1,485,000
Price
5
Beds
4,186 Sq. Ft.
$355 / Sq. Ft.
4,186
Sq. Ft.
$355
per Sq. Ft.
a front view of a house with a yard
a front view of house with yard
an aerial view of a house with a garden and lake view
a living room with furniture and a potted plant
a living room with furniture and a dining table with kitchen view
a living room with furniture and a large window
a bathroom with a sink toilet and mirror
a living room with furniture fireplace and a large window
a living room with furniture and a fireplace
a living room with furniture and a flat screen tv
a living room with furniture and a window
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances granite countertop a stove and refrigerator
a view of a dining room with furniture window and outside view
a view of a dining room with furniture a kitchen and chandelier
a kitchen with a sink and stove
a kitchen with stainless steel appliances a sink a stove and white cabinets with wooden floor
a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher and cabinets with wooden floor
a kitchen with sink refrigerator and cabinets
a living room with furniture and a window
a living room with furniture and a large window
a living room with furniture
a view of a balcony with wooden floor
a view of a house with a yard
a bathroom with a double vanity sink and a mirror
a bathroom with a granite countertop shower and a sink
a white bath tub sitting in a bathroom
a living room with furniture and a wooden floor
a living room with furniture and a flat screen tv
a living room with furniture a rug and a flat screen tv
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove top oven
a living room with furniture and a flat screen tv
a bathroom with a sink toilet and shower
a bedroom with a bed and a chandelier
a bedroom with a bed and a chandelier
a bathroom with a double vanity sink toilet and shower
a view of a hallway with wooden floor and a living room
a view of balcony with couch
a view of a balcony with furniture and wooden floor
a view of a swimming pool with a patio
a front view of a house with a yard and trees
a view of a patio with a table and chairs
a view of swimming pool with a patio
a front view of a house with a garden
a front view of a house with a garden and plants
a front view of a house with a yard
a front view of house with yard and green space
a view of a swimming pool with a patio and a yard
a front view of a house with garden
a front view of a house with garden

Description

A new long elegantly paved driveway leads up to this beautifully updated 5-bedroom, 4,200 sq. ft. home in the charming Town of Windermere. With lush views of established landscaping & surrounding trees, this home combines comfort, style, and plenty of space for family and friends. The bright, open kitchen is the heart of the home, featuring granite countertops, stainless steel appliances, and windows that fill the space with natural light. The kitchen flows into the dining area and great room, where...A new long elegantly paved driveway leads up to this beautifully updated 5-bedroom, 4,200 sq. ft. home in the charming Town of Windermere. With lush views of established landscaping & surrounding trees, this home combines comfort, style, and plenty of space for family and friends. The bright, open kitchen is the heart of the home, featuring granite countertops, stainless steel appliances, and windows that fill the space with natural light. The kitchen flows into the dining area and great room, where vaulted ceilings, a cozy gas fireplace, and warm accent lighting make it the perfect place to gather. Step through the French doors to an oversized balcony overlooking the pool and privacy landscaping. The private master suite sits on its own level with a large sitting/dressing area and a personal balcony—a true retreat at the end of the day. On the main floor, you’ll find two more bedrooms, a full bath, and a convenient laundry room. The lower level offers a spacious entertainment area, an en-suite bedroom, an additional full bath, and a fifth bedroom which is currently serving as a stylish home gym. All open directly to the pool deck and fenced backyard, creating an easy flow for family fun and entertaining. Modern updates include Control4 home automation, Nest thermostats for all three AC units, energy-efficient new windows & doors and abundant landscaping. The home has recently been thoroughly redecorated throughout so is move in ready. Living in Windermere means more than just owning a home—you’ll enjoy access to town boat ramps, parks, and scenic docks. Plus, it’s just a short walk to the weekly Farmer’s Market and monthly Food Truck nights, where neighbors come together to enjoy the best of small-town living. This home has it all: space, comfort, and a welcoming community. Come see it for yourself—you’ll feel right at home the moment you arrive.
  1. Listed by Carey Sheffield • Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
    P: (407)-961-2979 C: (407)-961-2979 she@careysheffield.com
  2. Listed by Wayne Sheffield • Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
    P: (407)-274-2256 C: (407)-274-2256 WSheffield@Isleworth.com

Property Details for 101 Lee Street

Architectural Style
Other
Subdivision Name
WINDERMERE TOWN REP
Township
23
Garage Spaces
2
View
Trees/Woods, Water
Waterfront
No
Water View
Lake - Chain of Lakes
Furnished
Negotiable
LISTING UPDATED: 01/04/2026 02:11 PM

Property Details for 101 Lee Street

StatusActive
MLS #O6344558
Days on Market108
Taxes$11,349 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1978
Lot Size0.42 AC / 18,138 SF
CountyOrange County

Location

Listing Courtesy of ISLEWORTH REALTY LLC, Carey Sheffield; ISLEWORTH REALTY LLC, Wayne Sheffield
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Building Information for 101 Lee Street

Stories3Year Built1978Building Size-Lot Size0.42 AC / 18,138 SF

Payment Calculator

$8,183 per month

30 year fixed, 6.15% Interest

Principal and Interest

$7,238

Property Taxes

$946

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 101 Lee Street

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 5791.0
  • Building Area Units: Square Feet
  • Building Name Number: 101
  • Direction Faces: East
  • Directions: FROM CONROY WINDERMERE RD, CONTINUE ONTO E 6TH AVE. TURN RIGHT ONTO LEE STREET. HOME IS ON THE LEFT.
  • Elementary School: Windermere Elem
  • Middle Or Junior School: Gotha Middle
  • High School: Windermere High School
  • Mls Major Change Type: Price Decrease
  • Listing Service: Full Service
  • Road Frontage Type: Street Unpaved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 101
  • Street Name: LEE
  • Street Suffix: STREET
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
Taxes and HOA Information
  • Association: No
  • CDD: No
  • Tax Block: 1
  • Tax Book Number: Q-39
  • Tax Legal Description: REPLAT OF TOWN OF WINDERMERE Q/39 LOT 176
  • Tax Lot: 176
  • Tax Year: 2024
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Corner Lot, City Lot
  • Parcel Number: 072328933201760
  • Total Acreage: 1/4 to less than 1/2
  • Water Access: Lake - Chain of Lakes
  • Water Access: Yes
  • Water Extras: Boat Ramp - Private
  • Water Extras: Yes
  • Water: Boat Ramp - Private
  • Zoning: SFR
  • Living Area: 4186
Property and Assessments
  • Year Built Numeric: 1978
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0385F
  • Home Warranty: No
  • Homestead: Yes
  • New Construction: No
  • Property Attached: No
  • Public Survey Range: 28
  • Public Survey Section: 07
Utilities
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected
  • Water Source: Public, Well Required
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco, Wood Frame
  • Exterior Features: Balcony, Garden, Irrigation System, Lighting, Private Mailbox
  • Foundation Details: Slab
  • Levels: Multi/Split
  • Patio And Porch Features: Front Porch, Other, Screened
  • Pool Features: In Ground, Lighting, Screen Enclosure, Tile
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shingle
  • Security Features: Security Fencing/Lighting/Alarms, Smoke Detector(s)
  • Spa: No
  • Vegetation: Mature Landscaping, Trees/Landscaped
  • Waterfront Feet Total: 0
  • Number Of Stories: 3
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 4
  • Additional Rooms: Formal Living Room Separate
  • Appliances: Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace Features: Gas, Stone
  • Fireplace: Yes
  • Flooring: Porcelain Tile, Hardwood
  • Heating: Central
  • Interior Features: Eating Space In Kitchen
  • Laundry Features: Electric Dryer Hookup, Inside, Washer Hookup
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 9.0
  • Water View: Yes
  • Window Features: Aluminum Frames, Blinds, Display Window(s), Drapes, ENERGY STAR Qualified Windows, Rods, Shades, Shutters, Window Treatments, Wood Frames
  • Bathrooms Half: 0

Property History for 101 Lee Street

DateEvent & SourcePriceAppreciation
Dec 7, 2025

Price Change

MFRMLS #O6344558

$1,485,000—
Nov 3, 2025

Price Change

MFRMLS #O6344558

$1,550,000—
Sep 23, 2025

Listed (Active)

MFRMLS #O6344558

$1,650,000—
Aug 15, 2019

Sold (Public Record)

Public Record #651374599

$765,000

+3.5% / yr

Aug 15, 2019

Sold

MFRMLS #O5785705

$765,000—
Jul 3, 2019

Pending

MFRMLS #O5785705

—
May 22, 2019

Listed (Active)

MFRMLS #O5785705

$825,000—
Oct 8, 2014

Sold (Public Record)

Public Record #462571676

$647,000

-46.6% / yr

Oct 8, 2014

Sold

MFRMLS #O5225703

$647,000—
Aug 26, 2014

Pending

MFRMLS #O5225703

—
Aug 1, 2014

Sold (Public Record)

Public Record #432113366

$727,175

+107.2% / yr

May 5, 2014

Listed (Active)

MFRMLS #O5225703

$764,900—
Sep 6, 2013

Sold

MFRMLS #O5169587

$375,000—
Sep 3, 2013

Sold (Public Record)

Public Record #368830243

$375,000

+1.3% / yr

Aug 16, 2013

Pending

MFRMLS #O5169587

—
Jul 3, 2013

Listed (Active)

MFRMLS #O5169587

$428,900—
Jul 21, 2008

Withdrawn

MFRMLS #O4815411

$849,000—
Nov 27, 2007

Listed (Active)

MFRMLS #O4815411

$849,000—
May 17, 2002

Sold (Public Record)

Public Record #93795841

$325,000—
DateEvent & SourcePrice
12/07/2025

Price Change

MFRMLS #O6344558

$1,485,000
11/03/2025

Price Change

MFRMLS #O6344558

$1,550,000
09/23/2025

Listed (Active)

MFRMLS #O6344558

$1,650,000
08/15/2019

Sold (Public Record)

Public Record #651374599

$765,000

+3.5% / yr

08/15/2019

Sold

MFRMLS #O5785705

$765,000
07/03/2019

Pending

MFRMLS #O5785705

—
05/22/2019

Listed (Active)

MFRMLS #O5785705

$825,000
10/08/2014

Sold (Public Record)

Public Record #462571676

$647,000

-46.6% / yr

10/08/2014

Sold

MFRMLS #O5225703

$647,000
08/26/2014

Pending

MFRMLS #O5225703

—
08/01/2014

Sold (Public Record)

Public Record #432113366

$727,175

+107.2% / yr

05/05/2014

Listed (Active)

MFRMLS #O5225703

$764,900
09/06/2013

Sold

MFRMLS #O5169587

$375,000
09/03/2013

Sold (Public Record)

Public Record #368830243

$375,000

+1.3% / yr

08/16/2013

Pending

MFRMLS #O5169587

—
07/03/2013

Listed (Active)

MFRMLS #O5169587

$428,900
07/21/2008

Withdrawn

MFRMLS #O4815411

$849,000
11/27/2007

Listed (Active)

MFRMLS #O4815411

$849,000
05/17/2002

Sold (Public Record)

Public Record #93795841

$325,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 101 Lee Street

Taxable ValueLand-Additions-Total-
Tax Record2024$11,349 ($946 / month)
Home Facts
Beds5Total Finished SqFt4,186 SqFtAbove Grade Finished SqFt4,186 SqFtStories2Lot Size18,138 SqFtStyleSingle Family ResidenceYear Built1978Year Renovated1994ZoningSFRCountyORANGEAPN07-23-28-9332-01-760Fireplace TypeHas Fireplace

Schools near 101 Lee Street

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Windermere Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Gotha Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Windermere Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Gotha Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 101 Lee Street, Windermere, FL 34786

101 Lee Street is a single family home for sale in Windermere, FL 34786. This property was listed for sale on September 23, 2025 by ISLEWORTH REALTY LLC, it's currently listed at $1,485,000. It has been on the market for a total of 108 days and was last sold on August 15, 2019. This listing's school district is Orange County Public Schools. Nearby schools include Windermere Elementary School, Cornerstone Academy Charter and Gotha Middle School. 101 Lee Street is a 5-bed, 4-bath, 4,186 sqft single family home built in 1978.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of ISLEWORTH REALTY LLC, Carey Sheffield; ISLEWORTH REALTY LLC, Wayne Sheffield

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 01/04/2026 02:11 PM