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$485,500 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,200 Sq. Ft.
  • 2 Car Garage
  • Updated 5 days ago
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*Pictures coming soon 10/23* Welcome to 104 Stuart Drive! This charming brick ranch offers the ease of one-level living with approximately 2,200 square feet of thoughtfully designed space. Featuring three spacious bedrooms, two full bathrooms, a welcoming living room, a separate dining room, and a versatile bonus space perfect for a home office, gym, hobby room, or whatever suits your needs, this home offers flexibility to fit your lifestyle. French doors open to a freshly painted, covered rear porch overlooking a level backyard with a beautiful tree-lined backdrop, creating a peaceful setting to relax or entertain. Inside, two gas fireplaces add warmth and character, with one featuring newly upgraded logs in 2026. Enjoy peace of mind with numerous recent improvements, including a new roof and gutters with guards, water system, septic tank and distribution box, fencing, workshop/building wiring and electrical panel, washer and dryer, smart oven, and an additional building, all completed in 2024. Additional enhancements include a new concrete sidewalk from the driveway to the front door in 2025 and thoughtfully refreshed landscaping in 2026. Enjoy privacy, room to spread out, and the freedom of no HOA, all just minutes from town, shopping, dining, and everyday conveniences. With its blend of classic charm, practical updates, and a convenient location, this home is ready to welcome its next owner!

Full Property Details for 104 Stuart Dr

General

  • Price: $485,500
  • Taxes: $1,888 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAFV2045516
  • Updated: 10/16/2026
  • Added to Site: 6 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: Bathroom - Jetted Tub, Bathroom - Stall Shower, Bathroom - Walk-In Shower, Chair Railings, Crown Moldings, Dining Area, Kitchen - Island, Kitchen - Table Space, Pantry, Recessed Lighting, Water Treat System, Wood Floors, Attic, Carpet, Ceiling Fan(s), Combination Kitchen/Dining
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Brick, Gas/Propane, Screen
  • Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer - Electric, Icemaker, Oven - Self Cleaning, Oven/Range - Electric, Refrigerator, Washer
  • Flooring: Hardwood, Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Main & Up: 3

Other Rooms

  • Laundry: Main Floor, Has Laundry

Additional Information

  • Security/Safety: Exterior Cameras, Smoke Detector, Carbon Monoxide Detector(s), Doorman, Motion Detectors

Exterior

  • Exterior Features: Exterior Lighting, Gutter System, Outbuilding(s), Sidewalks
  • Porch/Patio/Deck: Patio(s)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Asphalt Driveway
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Side Entry, Oversized, Built In

Location

  • County: FREDERICK
  • Subdivision: JACKSON WOODS ESTATES
  • Driving Directions: From Valley Avenue in Winchester, take Middle Road 3-4 miles. Jackson Wood Estates is on the right shortly after Fellowship Bible Church.
  • Location Details: Rural

School Information

  • School District: Frederick County Public Schools

Community

  • Pets Allowed: Yes
  • Pets: No Pet Restrictions

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Septic Exists
  • Water: Well, Filter
  • Utility Description: Cable TV, Electric Available, Propane

Structural Information

  • Architectural Style: Ranch/Rambler
  • Structure Type: Detached
  • Construction: Brick, Concrete
  • Foundation: Crawl Space, Concrete Perimeter
  • Roof: Architectural Shingle
  • Walls/Ceilings: Dry Wall
  • Windows: Screens
  • Doors: French, Storm, Double Entry
  • Stories Description: Main
  • Square Feet: 2,200
  • Sq. Ft. Source: Estimated
  • Living Area: 2,200 Sq. Ft.
  • Finished Above Grnd: 2,200 Sq. Ft.
  • Year Built: 1971
  • Year Built Source: Estimated
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Shed, Shed Shop

Lot Features

  • Property View: Mountain, Trees/Woods
  • Lot Size (Acres): 0.56
  • Lot Size (Sq. Ft.): 24,393
  • Lot Size Source: Estimated
  • Street/Road Desc.: Black Top
  • Zoning: RP
  • Lot Description: Backs to Trees, Cleared, Landscaping, Level, Rear Yard, Sloping, Front Yard
  • Fencing (Description): Board, Wire, Wood

Financial Considerations

  • Price Per Sq. Ft.: $220.68
  • Tax w/Assessment: $393,428
  • Tax Amount: $1,888
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 37

Listed by Realty ONE Group Old Towne, Gerald Lee Owens Jr.

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Listing agent

— 104 Stuart Dr —

  • Gerald Lee Owens Jr.

    Realty ONE Group Old Towne

Listing Office Email: admin@realtyonegroupoldtowne.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 104 Stuart Dr

School District:Frederick County Public Schools, Winchester, VA
NameGradesDistance
Orchard View Elementary School
4275 Middle Road, Winchester, VA 22602
K-51.7 mi
James Wood Middle School
1313 Amherst Street, Winchester, VA 22601
6-83.7 mi
Sherando High School
185 South Warrior Drive, Stephens City, VA 22655
9-124.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 104 Stuart Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/16/2026
Listed
$485,500
11.61%
MLS
4/30/2024
Sold
$435,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 104 Stuart Dr

Year
Property Taxes
Change
Tax Assessment
Change
2026
$2,085
151%
$393,428
—
2024
$832
—
$393,428
21%
2024
$832
-50%
$326,200
—
2023
$1,664
6%
$326,200
27%
2022
$1,566
—
$256,700
—
2021
$1,566
2%
$256,700
2%
2020
$1,539
—
$252,300
—
2019
$1,539
9%
$252,300
9%
2018
$1,413
2%
$231,600
—
2017
$1,390
10%
$231,600
10%
2016
$1,263
7%
$210,500
—
2015
$1,179
-2%
$210,500
2%
2014
$1,202
—
$205,400
—
2013
$1,202
—
$205,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Realty ONE Group Old Towne, Gerald Lee Owens Jr.

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104 Stuart Drive, Winchester, VA 22602 (MLS# VAFV2045516) is a Single Family property with 3 bedrooms and 2 full bathrooms. 104 Stuart Drive is currently listed for $485,500 and was received on October 16, 2026. Want to learn more about 104 Stuart Drive? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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