Seller's Agent in 2026
Mike Webber
EXP Realty, LLC
(703) 728-7574
4 in this area
75 Total Sales
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.
Last Agent to Sell the Property
(866) 825-7169 va.broker@exprealty.net EXP Realty, LLC Brokerage Phone: 8668257169 Listed on: 11/20/2025
Last Buyer's Agent
(571) 386-1075 shannon@carterbraxtonproperties.com Pearson Smith Realty, LLC License #0225264366
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $350,000 | Chicago Title | |
| Deed | $136,750 | None Listed On Document |
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $339,500 | New Conventional | |
| Previous Owner | $300,000 | New Conventional |
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 03/04/2026 03/04/26 | Sold | $350,000 | -5.4% | $190 / Sq Ft |
| 02/15/2026 02/15/26 | Pending | -- | -- | -- |
| 01/22/2026 01/22/26 | Price Changed | $369,900 | 0.0% | $201 / Sq Ft |
| 01/22/2026 01/22/26 | For Sale | $369,900 | -1.3% | $201 / Sq Ft |
| 01/14/2026 01/14/26 | Pending | -- | -- | -- |
| 01/12/2026 01/12/26 | For Sale | $374,900 | 0.0% | $204 / Sq Ft |
| 12/31/2025 12/31/25 | Pending | -- | -- | -- |
| 11/20/2025 11/20/25 | For Sale | $374,900 | -- | $204 / Sq Ft |
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $993 | $206,924 | $58,200 | $148,724 |
| 2024 | $742 | $161,400 | $39,700 | $121,700 |
| 2023 | $823 | $161,400 | $39,700 | $121,700 |
| 2022 | $817 | $133,900 | $33,700 | $100,200 |
| 2021 | $1,477 | $133,900 | $33,700 | $100,200 |
| 2020 | $1,417 | $124,100 | $33,700 | $90,400 |
| 2019 | $1,417 | $124,100 | $33,700 | $90,400 |
| 2018 | $1,232 | $110,200 | $33,500 | $76,700 |
| 2017 | $1,221 | $110,200 | $33,500 | $76,700 |
| 2016 | $1,186 | $104,300 | $31,000 | $73,300 |
| 2015 | $584 | $104,300 | $31,000 | $73,300 |
| 2014 | $594 | $100,300 | $31,000 | $69,300 |
Seller's Agent in 2026
Mike Webber
EXP Realty, LLC
(703) 728-7574
4 in this area
75 Total Sales
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Buyer's Agent in 2026
Shannon Spiliotopoulos
Pearson Smith Realty, LLC
(703) 447-7878
1 in this area
5 Total Sales
Source: Bright MLS
MLS Number: VAFV2038002
APN: 49A021-13-12
Ask me questions while you tour the home.