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Property Description
Charming Craftsman in West Whitlock Avenue - Walk to John Handley! Welcome to 257 Jefferson Street, a beautifully maintained 3-bedroom, 1 full and 2 half bath Craftsman-style home located in the highly desirable West Whitlock Avenue subdivision. This 2,285 sq ft gem offers timeless charm, modern updates, and a prime location within walking distance to the prestigious John Handley High School. Inside, you'll find gorgeous hardwood floors throughout, adding warmth and character to every room. The main level features spacious living and dining areas, a bright sunroom perfect for relaxing or working from home, and a well-appointed kitchen ready for your personal touch. The finished basement offers a versatile entertainment space complete with a cozy fireplace, ideal for movie nights or gatherings. You'll also find ample storage and a dedicated laundry area, keeping things practical and organized. Step outside to enjoy the beautifully landscaped yard, private garden, detached garage, and rear deck-perfect for summer barbecues or quiet evenings under the stars. Don't miss this opportunity to own a stunning Craftsman in one of Winchester's most sought-after neighborhoods!
Full Property Details
Full Property Details for 257 Jefferson St
General
- Sold For: $500,000
- Taxes: $3,165 (2025)
- Status: Closed
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: VAWI2008852
- Added to Site: 162 day(s) ago
Interior
- Number of Rooms: 10
- Rooms/Areas: Living Room, Dining Room, Bedroom 2, Bedroom 3, Kitchen, Basement, Bedroom 1, Storage Room, Bathroom 1, Bathroom 2
- Interior Features: Floor Plan - Traditional, Kitchen - Island, Wood Floors, Window Treatments, Bathroom - Stall Shower, Bathroom - Tub Shower, Wine Storage, Ceiling Fan(s), Attic, Dining Area
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Brick, Mantel(s), Wood, Brick, Mantel(s), Wood
- Appliances: Oven/Range - Electric, Water Heater, Washer, Washer - Front Loading, Dryer - Electric, Exhaust Fan, Microwave, Refrigerator, Dishwasher, Stove
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 1
- Half Bathrooms: 2
- Upper Floor Baths: 1
- Upper - Full Baths: 1
- Main Floor Baths: 1
- Main - 1/2 Baths: 1
- Lower Floor Baths: 1
- Lower - 1/2 Baths: 1
Bedrooms
- Total Bedrooms: 3
- Bedrooms Upper: 3
- Bedroom 1: Bedroom 2 - Flooring - HardWood, Window Treatments, Upper 1
- Bedroom 2: Bedroom 3 - Flooring - HardWood, Window Treatments, Upper 1
- Bedroom 3: Bedroom 1 - Flooring - HardWood, Window Treatments, Upper 1
Other Rooms
- Living Room: Living Room - Fireplace - Other, Flooring - HardWood, Window Treatments, Crown Molding, Main
- Kitchen: Kitchen - Ceiling Fan(s), Double Sink, Flooring - Tile/Brick, Island, Main
- Dining Room: Dining Room - Window Treatments, Flooring - HardWood, Crown Molding, Main
- Laundry: Has Laundry, Dryer In Unit, Washer In Unit, Lower Floor
- Storage: Storage Room, Lower 1
Exterior
- Exterior Features: Awning(s), Gutter System, Sidewalks
- Porch/Patio/Deck: Deck(s)
Parking
- Garage: Yes
- Garage Spaces: 1
- Total Spaces: 4
- Parking Features: Concrete Driveway, Paved Driveway, Private
- Parking Type: Detached Garage, Driveway
- Garage Description: Additional Storage Area, Garage - Front Entry, Garage Door Opener
Location
- County: Winchester City
- Development Name: West Whitlock Avenue
- Subdivision: West Whitlock Avenue
- Cross Streets: Valley Ave
- Driving Directions: follow GPS
- Direction Faces: North
- Location Details: Other
- City Limits: Yes
School Information
- School District: Winchester City Public Schools
- High School: John Handley
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 - Electric BackUp, Radiator
- Heating Fuel: Oil
- Water Heater: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Electric Available, Phone Available, Sewer Available, Water Available
Structural Information
- Architectural Info: Craftsman
- Architectural Style: Craftsman
- Structure Type: Detached
- Construction: Brick
- Basement: Yes
- Basement Desc.: Full
- Foundation: Concrete Perimeter
- Roof: Architectural Shingle
- Walls/Ceilings: 2 Story Ceilings, Masonry
- Windows: Wood Frame, Storm, Double Hung
- Stories/Levels: 0
- Stories Description: Lower 1, Main, Upper 1
- Square Feet: 2,761
- Sq. Ft. Source: Assessor
- Living Area: 2,285 Sq. Ft.
- Year Built: 1946
- Year Built Source: Assessor
- Property Condition: Excellent
Unit Information
Unit 1
- Bathrooms-Lower: 1
Additional Structures
- Other Structures: Garage(s)
Lot Features
- Lot Size (Acres): 0.21
- Lot Size (Sq. Ft.): 9,017
- Lot Size Source: Assessor
- Frontage Feet: 75
- Street/Road Desc.: Concrete
- Zoning: MR
- Fencing (Description): Masonry/Stone, Partially, Chain Link
Financial Considerations
- Price Per Sq. Ft.: $295.69
- Assessment Year: 2025
- City/TownTax: $3,165
- City/TownTax Freq: Annually
- County Tax Freq: Annually
- Tax w/Assessment: $398,140
- Tax Amount: $3,165
- Tax Year: 2025
- Terms: Standard Sale
- Tax Total Finished Sq. Ft.: 2285
Disclosures and Reports
- Ownership: Fee Simple
- Lot Number: 4A
Listed by Keller Williams Realty, Kathrin Donovan
Sold by Realty ONE Group Old Towne, Stephanie Ryall
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Schools
Schools serving 257 Jefferson St
School District:Winchester City Public Schools
| Name | Grades | Distance |
|---|---|---|
Daniel Morgan Middle School 48 South Purcell Avenue, Winchester, VA 22601 | 7-8 | 1.3 mi |
John Handley High School 425 Handley Boulevard, Winchester, VA 22601 | 9-12 | 0.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 257 Jefferson St
Date
Details
Price
Change
Source
9/12/2025
Sold
$500,000
-6.52%
MLS
8/08/2025
Listed
$534,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
257 Jefferson Street, Winchester, VA 22601 (MLS# VAWI2008852) is a Single Family property that was sold at $500,000 on September 12, 2025. Want to learn more about 257 Jefferson Street? 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.

