199 Oak Hill Dr, Stephens City, VA 22655
What's special
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.
- 14 days
- 1,089
- 80
Likely to sell faster than
Travel times
Family Room
Kitchen
Primary Bedroom
Zillow last checked:
Listing updated:
Leah Clowser 540-247-1941,
RE/MAX Roots (540) 686-7362
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 7
- Full bathrooms: 5
- 1/2 bathrooms: 2
- Main level bathrooms: 7
- Main level bedrooms: 6
Basement
- Area: 4405
Heating
- Heat Pump, Electric
Cooling
- Ceiling Fan(s), Central Air, Electric
Appliances
- Included: Microwave, Built-In Range, Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Stainless Steel Appliance(s), Washer, Washer/Dryer Stacked, Water Conditioner - Owned, Water Heater, Electric Water Heater
- Laundry: Lower Level, Main Level
Features
- 2nd Kitchen, Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-in Features, Ceiling Fan(s), Crown Molding, Entry Level Bedroom, Exposed Beams, Family Room Off Kitchen, Open Floorplan, Formal/Separate Dining Room, Kitchen - Gourmet, Kitchen Island, Pantry, Primary Bath(s), 9'+ Ceilings, Beamed Ceilings, High Ceilings, Vaulted Ceiling(s)
- Flooring: Hardwood, Luxury Vinyl
- Doors: Double Entry
- Basement: Connecting Stairway,Partial,Finished,Garage Access,Heated,Improved,Interior Entry,Exterior Entry,Rear Entrance,Walk-Out Access,Windows,Workshop
- Number of fireplaces: 2
- Fireplace features: Gas/Propane, Mantel(s), Stone
Interior area
- Total structure area: 9,421
- Total interior livable area: 7,508 sqft
- Finished area above ground: 5,016
- Finished area below ground: 2,492
Video & virtual tour
Property
Parking
- Total spaces: 9
- Parking features: Storage, Built In, Garage Faces Front, Garage Door Opener, Inside Entrance, Oversized, Underground, Driveway, Attached
- Attached garage spaces: 3
- Uncovered spaces: 6
Accessibility
- Accessibility features: Accessible Entrance
Features
- Levels: Three
- Stories: 3
- Patio & porch: Deck, Patio
- Exterior features: Extensive Hardscape, Lighting, Play Equipment, Satellite Dish, Storage, Rain Gutters
- Has private pool: Yes
- Pool features: Heated, In Ground, Salt Water, Vinyl, Private
- Has view: Yes
- View description: Mountain(s)
Lot
- Size: 5.02 Acres
- Features: Backs to Trees, Front Yard, Landscaped, Level, Private, Rear Yard, SideYard(s), Sloped, Wooded
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 734F
- Zoning: RA
- Zoning description: RESIDENTIAL AGRICULTURE
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch/Rambler
- Property subtype: Single Family Residence
Materials
- Brick
- Foundation: Slab
- Roof: Shingle
Condition
- Excellent
- New construction: No
- Year built: 1984
- Major remodel year: 2026
Utilities & green energy
- Sewer: Septic < # of BR
- Water: Well
- Utilities for property: Satellite Internet Service
Community & HOA
Community
- Subdivision: Oak Hill
HOA
- Has HOA: Yes
- Services included: Road Maintenance
- HOA fee: $125 annually
- HOA name: OAK HILL HOA
Location
- Region: Stephens City
Financial & listing details
- Price per square foot: $198/sqft
- Tax assessed value: $1,113,250
- Annual tax amount: $5,344
- Date on market: 10/9/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
- Road surface type: Black Top
Price history
| Date | Event | Price |
|---|---|---|
| 10/9/2026 | Listed for sale | $1,490,000+49%$198/sqft |
Source:  Bright MLS #VAFV2042214 Report a problem | ||
| 10/6/2023 | Sold | $1,000,000$133/sqft |
Source: Bright MLS #VAFV2013724 Report a problem | ||
| 9/10/2023 | Contingent | $1,000,000$133/sqft |
Source: Bright MLS #VAFV2013724 Report a problem | ||
| 9/6/2023 | Listed for sale | $1,000,000+117.4%$133/sqft |
Source: Bright MLS #VAFV2013724 Report a problem | ||
| 2/28/2017 | Sold | $459,900-1.1%$61/sqft |
Source: Public Record Report a problem | ||
| 1/30/2017 | Pending sale | $464,900$62/sqft |
Source: Colony Realty #FV9835988 Report a problem | ||
| 1/6/2017 | Listed for sale | $464,900+7.1%$62/sqft |
Source: Colony Realty #FV9835988 Report a problem | ||
| 7/15/2013 | Sold | $434,000-3.3%$58/sqft |
Source: Public Record Report a problem | ||
| 6/6/2013 | Pending sale | $449,000$60/sqft |
Source: Colony Realty #FV8092790 Report a problem | ||
| 5/30/2013 | Listed for sale | $449,000$60/sqft |
Source: Colony Realty #FV8092790 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,344 +58.4% | $1,113,250 +68.3% |
| 2024 | $3,373 | $661,400 |
| 2023 | $3,373 +104.9% | $661,400 +22.5% |
| 2022 | $1,646 | $539,800 |
| 2021 | $1,646 -45% | $539,800 +9.9% |
| 2020 | $2,996 -50% | $491,100 |
| 2019 | $5,991 +355.7% | $491,100 +6.5% |
| 2018 | $1,315 -49.2% | $461,000 +6.9% |
| 2017 | $2,587 +7% | $431,100 +7% |
| 2016 | $2,417 +7.1% | $402,900 |
| 2015 | $2,256 +99.7% | $402,900 +5.1% |
| 2014 | $1,130 | $383,200 |
| 2013 | -- | $383,200 -0.8% |
| 2012 | -- | $386,200 |
| 2011 | -- | $386,200 -8.6% |
| 2010 | -- | $422,500 |
| 2009 | -- | $422,500 +3.2% |
| 2008 | -- | $409,400 |
| 2007 | -- | $409,400 |
| 2006 | -- | $409,400 |
| 2005 | -- | $409,400 +41.6% |
| 2003 | -- | $289,200 |
| 2002 | -- | $289,200 |
| 2001 | -- | $289,200 |
Monthly payment
Estimated market value
$1,416,200
$1.35M - $1.49M
$4,497/mo
Climate risks
Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.