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6 Beds
7 Baths
7,508 sqft

$1,490,000

199 OAK HILL DRIVE, STEPHENS CITY VA, 22655

Price per sqft$198.45
Built in1984
Property size7,508 sqft
Property typeResidential

Overview

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Listed Oct 1, 2026

Updated 33h ago

Privately nestled on five wooded acres just minutes from historic Winchester, this extensively renovated modern farmhouse offers more than 7,500 square feet of finished living space across three distinct finished living areas, providing exceptional flexibility for multi-generational living, extended family, guests or those seeking dedicated private space. The main residence combines exposed wood beams, hardwood floors, abundant natural light and polished finishes with generous living and entertaining spaces. Expansive country and mountain views are framed from the upper deck and dining room through a wall of windows and exposed beams. The finished walk-out lower level creates a second private living area with its own full kitchen, offering additional flexibility and separation. Completed in 2025, the approximately 1,700-square-foot attached ADU provides a third fully finished living area with a separate entrance and its own living room, dining room, full kitchen, two bedrooms with en-suite baths and a half bath. Beneath the ADU, approximately 1,861 square feet of unfinished basement space provides substantial storage and future potential. A custom-designed office overlooks the pool and surrounding grounds, offering a dedicated work-from-home space with views of the property. Outdoor living is centered around the heated in-ground saltwater pool, large deck, patio and fire-pit area, complemented by extensive hardscaping for entertaining, dining and relaxing. The five-acre grounds combine mature woods, landscaped areas and open spaces with an established collection of fruit trees and berry bushes, including fig, cherry, pear, persimmon, peach, plum and blackberry. A finished 15' x 15' outbuilding with LVP flooring and a mini-split provides additional flexible space for an office, studio, gym or hobby room. The attached two-car garage features custom cabinetry, while the paved driveway offers ample parking. Major improvements include the 2025 ADU addition, Andersen replacement windows, main-level HVAC replaced in 2024, upper-level HVAC replaced in 2025, and updates to the roof, siding, pool equipment and more. With three finished living areas, substantial additional unfinished space, five private acres, mountain and country views, a heated saltwater pool and multiple flexible work and entertaining spaces, this distinctive property offers space and privacy while remaining conveniently located near Winchester and within walking distance of Valerie Hill Vineyard & Winery.

$9,913/mo

Est. mortgage payment based on a $1,490,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
VAFV2042214

Interior Features

Bedrooms
6
Bathrooms
7
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
5.02 Acres

Other Property Details

Taxes
$5,344
Tax Frequency
Annually
Association Fee Frequency
Yearly
Garage
Yes
View
Yes
55+/Senior Community
No
MLS provider logo

Listed by Re/Max Roots
Listing Contact: 5402471941 

The IDX display contains information sourced from the Bright MLS, Inc. as of 10/2/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 10/2/2026 at 4:19 AM UTC

 

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