Date
Details
Price
Change
Source
1/15/2026
Listed
$590,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$590,000 Just Listed
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Property Description
Welcome home to 157 Oak Dr. in Winchester, VA-an inviting property offering comfort, thoughtful updates, and a peaceful setting. This home has been refreshed with luxury vinyl plank flooring throughout most of the home and fresh paint, creating a clean, move-in-ready feel. Be Sure to Watch The Video to Experience Even More of This Home! The primary suite has been remodeled, including an updated bathroom and walk-in closet, creating a comfortable retreat. A large bonus room over the 2-car garage offers endless possibilities-home office, playroom, gym, or guest space. The home features dual-zoned heating and cooling for added comfort, with the upper-level heat pump replaced in 2021, as well as a new water filtration system installed in 2022. Surrounded by trees for privacy, this property offers a serene setting while remaining just minutes from Winchester's medical facilities, restaurants, and shopping. Convenient access to I-81 makes commuting easy. Do Not Miss Your Opportunity to Tour This Home! Call Your Agent or The Listing Agent Today
Full Property Details
Full Property Details for 157 Oak Dr
General
- Price: $590,000
- HOA FEE: $25/month
- HOA FEE FREQ.: Annually
- Taxes: $1,848 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: VAFV2038906
- Updated: Today (1/15/2026)
- Added to Site: Today
Interior
- Number of Rooms: 12
- Rooms/Areas: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Sun/Florida Room, Office, Bathroom 2, Bonus Room, Primary Bathroom, Half Bath
- Interior Features: Additional Stairway, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Ceiling Fan(s), Central Vacuum, Breakfast Area, Dining Area, Family Room Off Kitchen, Pantry, Primary Bath(s), Walk-in Closet(s), Water Treat System, Wood Floors
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Wood
- Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer, Oven/Range - Electric, Refrigerator, Washer, Extra Refrigerator/Freezer
- Flooring: Hardwood, Luxury Vinyl Plank
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
- Upper Floor Baths: 2
- Upper - Full Baths: 2
- Main Floor Baths: 1
- Main - 1/2 Baths: 1
Bedrooms
- Total Bedrooms: 4
- Bedrooms Upper: 4
Other Rooms
- Laundry: Main Floor
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Features: Paved Driveway
- Parking Type: Attached Garage, Driveway
- Garage Description: Additional Storage Area, Garage - Front Entry, Inside Access, Garage Door Opener
Location
- County: FREDERICK
- Subdivision: WESTWOOD TERRACE
- Driving Directions: From Route 50 West turn right onto Pinehill Dr, Turn left on to Oak Dr. Home on Left. GPS also works
School Information
- School District: Frederick County Public Schools
Community
- Association: Yes
- Assoc. Fees Include: Road Maintenance, Snow Removal
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s), Zoned
- Heating Fuel: Electric
- Water Heater: Electric
Utilities
- Sewer: On Site Septic, Septic < # of BR
- Water: Well
Structural Information
- Architectural Style: Colonial
- Structure Type: Detached
- Construction: Vinyl Siding
- Foundation: Crawl Space
- Windows: Bay/Bow, Vinyl Clad
- Stories Description: Main, Upper 1
- Square Feet: 2,280
- Sq. Ft. Source: Estimated
- Living Area: 2,280 Sq. Ft.
- Finished Above Grnd: 2,280 Sq. Ft.
- Year Built: 1989
- Year Built Source: Estimated
- Property Condition: Excellent
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 5
- Lot Size (Sq. Ft.): 217,800
- Lot Size Source: Estimated
- Street/Road Desc.: Paved
- Zoning: RA
- Lot Description: Backs to Trees, Landscaping, Trees/Wooded
- Fencing (Description): Invisible
Financial Considerations
- Price Per Sq. Ft.: $258.77
- Association Fee: $300
- Assoc Fee Freq.: Annually
- Assessment Year: 2025
- County Tax: $1,848
- County Tax Freq: Annually
- Tax w/Assessment: $384,900
- Tax Amount: $1,848
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 2280
Disclosures and Reports
- Ownership: Fee Simple
- Inclusions: Refrigerator, Dishwasher, Built-in Microwave, Stove, Disposal, Washer, Dryer, Garage Refrigerator (as is), whole house vacuum (as is)
- Section: 7
- Lot Number: 4
Listed by Keller Williams Realty, Phyllis Guthrie and Keller Williams Realty, Richard L Guthrie
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 157 Oak Dr —
Phyllis Guthrie
Keller Williams Realty
Richard L Guthrie
Keller Williams Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 157 Oak Dr
School District:Frederick County Public Schools, Winchester, VA
| Name | Grades | Distance |
|---|---|---|
Indian Hollow Elementary School 1548 North Hayfield Road, Winchester, VA 22603 | PK-5 | 1.3 mi |
Frederick County Middle School 4661 North Frederick Pike, Winchester, VA 22603 | 6-8 | 3.2 mi |
James Wood High School 161 Apple Pie Ridge Road, Winchester, VA 22603 | 9-12 | 4.9 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 157 Oak Dr
Tax History
Tax History for 157 Oak Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$822
—
$384,900
19%
2024
$822
-50%
$322,500
—
2023
$1,645
-1%
$322,500
18%
2022
$1,668
—
$273,500
—
2021
$1,668
8%
$273,500
8%
2020
$1,548
—
$253,800
—
2019
$1,548
6%
$253,800
6%
2018
$1,463
2%
$239,800
—
2017
$1,439
13%
$239,800
13%
2016
$1,276
7%
$212,600
—
2015
$1,191
—
$212,600
4%
2014
$1,194
—
$204,100
—
2013
$1,194
—
$204,100
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 157 Oak Dr
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- Single Family
- Active
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- Single Family
- Closed
- Updated 4 hours ago
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- 4Total Baths
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157 Oak Drive, Winchester, VA 22603 (MLS# VAFV2038906) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 157 Oak Drive is currently listed for $590,000 and was received on January 15, 2026. Want to learn more about 157 Oak 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.