Property Search

Save
Ask
Tour
Hide
Share
$1,490,000
2 Days On Site

199 OAK HILL DRIVE
STEPHENS CITY, VA 22655

Single Family Residence|Coming Soon
6
Beds
7
Total Baths
5
Full Baths
2
Partial Baths
7,508
SqFt
$198
/SqFt
1984
Built
Subdivision:
OAK HILL
County:
FREDERICK
Listing courtesy of Re/Max Roots
Call Now: (703) 898-3565
Is this the listing for you? We can help make it yours.
(703) 898-3565
Upcoming Open Houses
Sat, Oct 10, 11:00 AM - 2:00 PM
199 OAK HILL DRIVE199 OAK HILL DRIVE199 OAK HILL DRIVE199 OAK HILL DRIVE
Save
Ask
Tour
Hide
Share

Mortgage Calculator

Monthly Payment (Est.)

Enter an interest rate to see your estimated monthly payment.
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

Save
Ask
Tour
Hide
Share
Listing Snapshot
Price 
$1,490,000
Days On Site 
2 Days
Bedrooms 
6
Inside Area (SqFt) 
7,508 sqft
Total Baths 
7
Full Baths 
5
Partial Baths 
2
Lot Size 
5.02 Acres
Year Built 
1984
MLS® Number 
VAFV2042214
Status 
Coming Soon
Property Tax 
$5,344
HOA/Condo/Coop Fees 
$10.42 monthly
Sq Ft Source 
Estimated
Friends & Family
Recent Activity
2 days agoListing updated with changes from the MLS®
2 days agoListing first seen on site
General Features
Acres 
5.02
Attached Garage 
Yes
Foundation 
Slab
Garage 
Yes
Garage Spaces 
3
Levels 
Three Or More
Parking 
OversizedGarage Door OpenerGarageDrivewayUndergroundInside EntranceAttached
Parking Spaces 
9
Property Sub Type 
Single Family Residence
Special Circumstances 
Standard
SqFt Above 
5016
SqFt Below 
2492
SqFt Total 
9421
Style 
Ranch/Rambler
Water Source 
Well
Zoning 
RA
Interior Features
Appliances 
RangeWater PurifierElectric Water HeaterBuilt-In RangeDishwasherDisposalDryerRange HoodRefrigeratorStainless Steel Appliance(s)WasherWasher/Dryer StackedWater HeaterMicrowave
Basement 
FinishedExterior EntryWalk-Out AccessDaylightPartialInterior Entry
Cooling 
Central AirCeiling Fan(s)Electric
Fireplace 
Yes
Fireplace Features 
GasStone
Fireplaces 
2
Flooring 
HardwoodVinyl
Heating 
ElectricHeat Pump
Interior 
Ceiling Fan(s)Kitchen IslandPantryVaulted Ceiling(s)High CeilingsBeamed CeilingsBuilt-in FeaturesCrown MoldingOpen FloorplanSoaking Tub
Laundry Features 
Main LevelLower Level
Main Level Bedrooms 
6
Save
Ask
Tour
Hide
Share
Exterior Features
Construction Details 
Brick
Exterior 
LightingRain GuttersStorage
Lot Features 
SlopedWoodedFront YardLevelPrivateBack Yard
Other Structures 
Workshop
Patio And Porch 
DeckPatio
Pool Features 
HeatedIn GroundSalt WaterVinylPrivate
Private Pool 
Yes
Roof 
Shingle
View 
Mountain(s)
Waterview 
Mountain(s)
Community Features
Association Fee 
$125.0
Association Fee Frequency 
Annually
School District 
FREDERICK COUNTY PUBLIC SCHOOLS
Schools
School District
FREDERICK COUNTY PUBLIC SCHOOLS
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of Re/Max Roots



The real estate listing information is provided by Bright MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
Save
Ask
Tour
Hide
Share
Popular areas we serve

Northern Virginia Communities

  1. Aldie
  2. Alexandria
  3. Annandale
  4. Arlington
  5. Ashburn
  6. Bluemont
  7. Brambleton
  8. Bristow
  9. Broadlands
  10. Burke
  11. Centreville
  12. Chantilly
  13. Fairfax
  14. Falls Church
  15. Gainesville
  16. Great Falls
  17. Herndon
  18. Leesburg
  19. Manassas
  20. Manassas Park
  21. McLean
  22. Middleburg
  23. Oakton
  24. Reston
  25. South Riding
  26. Springfield
  27. Sterling
  28. Stone Ridge
  29. Vienna
  30. Winchester
  31. Woodbridge

Browse by Area

Start A Custom Search