Date
Details
Price
Change
Source
11/20/2025
Listed
$374,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$374,900 Sale Pending
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Property Description
Welcome to 166 Graywolf Trail, a stunningly renovated 4-bedroom, 3-bath home nestled on nearly a half acre of peaceful woodland in beautiful Winchester, VA. This move-in ready retreat blends modern comfort with a cozy family feel - the kind of home where memories are made. Step inside and discover an entirely new interior from top to bottom. Every inch has been thoughtfully updated: brand-new kitchen and bathrooms, all-new appliances, energy-efficient mini-split system, and contemporary finishes throughout. Located just minutes from Old Town Winchester, you're close to charming shops, cafés, and local favorites. Families love being near Jim Barnett Park, local schools, and scenic walking trails, offering the ideal mix of convenience and nature.
Full Property Details
Full Property Details for 166 Graywolf Trail
General
- Price: $374,900
- Taxes: $993 (2025)
- Status: Pending
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: VAFV2038002
- Updated: 1/14/2026
- Added to Site: 58 day(s) ago
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
- Upper Floor Baths: 1
- Upper - Full Baths: 1
- Main Floor Baths: 2
- Main - Full Baths: 2
Bedrooms
- Total Bedrooms: 4
- Bedrooms Upper: 2
- Bedrooms Main & Up: 2
Parking
- Parking Type: Driveway
Location
- County: FREDERICK
- Subdivision: SHAWNEELAND
- Driving Directions: GPS
School Information
- School District: Frederick County Public Schools
Heating & Cooling
- Cooling Type: Ductless/Mini-Split
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Water Heater: Electric
Utilities
- Sewer: Private Septic Tank
- Water: Well
Structural Information
- Architectural Style: Ranch/Rambler
- Structure Type: Detached
- Construction: Brick
- Foundation: Crawl Space
- Roof: Metal
- Stories Description: Main, Upper 1
- Square Feet: 1,840
- Sq. Ft. Source: Assessor
- Living Area: 1,840 Sq. Ft.
- Finished Above Grnd: 1,840 Sq. Ft.
- Year Built: 1965
- Year Built Source: Assessor
- Property Condition: Excellent
Lot Features
- Lot Size (Acres): 0.43
- Lot Size (Sq. Ft.): 18,730
- Lot Size Source: Estimated
- Zoning: R5
Financial Considerations
- Price Per Sq. Ft.: $203.75
- Other Fee: $330
- Other Fee Freq.: Semi-Annually
- Assessment Year: 2025
- City/TownTax Freq: Annually
- County Tax: $993
- County Tax Freq: Annually
- Tax w/Assessment: $206,924
- Tax Amount: $993
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 1840
Disclosures and Reports
- Ownership: Fee Simple
- Lot Number: 12
Listed by EXP Realty, LLC, James Michael Webber
We Value Your Privacy
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Listing agent
— 166 Graywolf Trail —
James Michael Webber
EXP Realty, LLC
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 166 Graywolf Trail
School District:Frederick County Public Schools, Winchester, VA
| Name | Grades | Distance |
|---|---|---|
Indian Hollow Elementary School 1548 North Hayfield Road, Winchester, VA 22603 | PK-5 | 3.6 mi |
Frederick County Middle School 4661 North Frederick Pike, Winchester, VA 22603 | 6-8 | 6.3 mi |
James Wood High School 161 Apple Pie Ridge Road, Winchester, VA 22603 | 9-12 | 8.3 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 166 Graywolf Trail
Tax History
Tax History for 166 Graywolf Trail
Year
Property Taxes
Change
Tax Assessment
Change
2024
$742
—
$206,924
28%
2024
$742
-50%
$161,400
—
2023
$1,483
—
$161,400
21%
2022
$1,477
—
$133,900
—
2021
$1,477
4%
$133,900
8%
2020
$1,417
—
$124,100
—
2019
$1,417
15%
$124,100
13%
2018
$1,232
1%
$110,200
—
2017
$1,221
3%
$110,200
6%
2016
$1,186
4%
$104,300
—
2015
$1,144
2%
$104,300
4%
2014
$1,117
—
$100,300
—
2013
$1,117
—
$100,300
—
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 166 Graywolf Trail
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- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 2Total Baths
- 2,428Sq. Ft.
- Single Family
- Active
- Updated 6 days ago
- 3Beds
- 3Total Baths
- 2,490Sq. Ft.
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- Single Family
- Active
- Updated 6 days ago
- 3Beds
- 3Total Baths
- 1,690Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 2Total Baths
- 3,192Sq. Ft.
- Townhouse
- Active
- Updated 4 days ago
- 3Beds
- 3Total Baths
- 1,500Sq. Ft.
- Single Family
- Active
- Updated 22 hours ago
- 4Beds
- 3Total Baths
- 2,248Sq. Ft.
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- Single Family
- Active
- Updated 4 days ago
- 3Beds
- 2Total Baths
- 1,682Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 4Beds
- 3Total Baths
- 2,184Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 4Beds
- 2Total Baths
- 2,400Sq. Ft.
- Farm Single-Family
- Active
- Updated 3 days ago
- 4Beds
- 2Total Baths
- 2,400Sq. Ft.
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166 Graywolf Trail, Winchester, VA 22602 (MLS# VAFV2038002) is a Single Family property with 4 bedrooms and 3 full bathrooms. 166 Graywolf Trail is currently listed for $374,900 and was received on November 20, 2025. Want to learn more about 166 Graywolf Trail? 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.