
Land with Home for Sale in Stephens City, Virginia
199 Oak Hill Dr, Stephens City, VA 22655
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.
Location
- Street address
- 199 Oak Hill Dr
- County
- Frederick County
- Zip code
- 22655
- Community
- Oak Hill
- School district
- Frederick County Public Schools
- Elevation
- 868 feet
Property details
- Acreage
- 5.02 acres
- MLS #
- TREND VAFV2042214
- Posted
Property taxes
- Recent
- $5,344
Expenses
- Homeowner Association Fee
- $125 annually
Details and features
Listing
- Type
- Residential
Exterior
- Parking Spaces
- 9
- Parking
- Driveway, Garage-Attached
- Pool
- Private
Structure
- Style
- Rambler
- Stories
- 3
- Heating
- Heat Pump
- Cooling
- Ceiling Fan(s), Central Air
- Materials
- Brick
Interior
- Rooms
- Basement, Bathroom x 7, Bedroom x 6, Dining Room, Family Room
- Fireplaces
- Yes
- Appliances
- Built-In Microwave, Built-In Range, Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Washer/Dryer Stacked, Water Conditioner-Owned, Water Heater
- Features
- 2nd Kitchen, Bathroom-Soaking Tub, Bathroom-Stall Shower, Bathroom-Tub Shower, Bathroom-Walk-In Shower, Breakfast Area, Built-Ins, Ceiling Fan(s), Crown Moldings, Entry Level Bedroom, Exposed Beams, Family Room Off Kitchen, Floor Plan-Open, Formal/Separate Dining Room, Kitchen-Gourmet, Kitchen-Island, Pantry, Primary Bath(s)
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Oct 9, 2026 | New listing | $1,490,000 | — | TREND |






























































































































