Coming Soon Open Saturday 10/10 11 AM-2 PM

MLS: #VAFV2042214, Listed By: Leah REALTOR, Re/Max Roots, Source:Bright MLS

199 Oak Hill Drive

STEPHENS CITY, VA 22655
Mark as Favorite
Bed 6

Bed

Bath 7

Bath

SqFt7,508

Sqft

Acres5.02

Acres(Lot)

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 i n 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.

Read More Expand
Tour with a ByOwner Agent

Detail Ic Property Details

Property Type : Residential

Price : $1,490,000

AD Id : 91624572

MLS Id : VAFV2042214

Beds : 6

Lot Size : 5.02 Acres

Living Area Size : 7,508 Sq. Ft

Tax Amount : $5,344

Year Built : 1984

Garage : 3

County : FREDERICK

Subdivision: Oak Hill

Open House Open House

  • 10/10 11 AM-2 PM
  • Map Map

Map

Map What's Nearby

Map Nearby Areas

Feature Features

  • Bedroom Information

    Total beds: 6

    Bathroom Information

    Total Baths: 7 Full Baths: 5 Half Baths: 2

    Room Information

    Has Basement: Yes Basement: Finished, Exterior Entry, Walk-Out Access, Daylight, Partial, Interior Entry
  • Flooring Information

    Hardwood, Vinyl
  • Roofing Information

    Shingle
  • Interior Features

    Ceiling Fan(s), Kitchen Island, Pantry, Vaulted Ceiling(s), High Ceilings, Beamed Ceilings, Built-in Features, Crown Molding, Open Floorplan, Soaking Tub Roof: Shingle Appliances: Range, Water Purifier, Electric Water Heater, Built-In Range, Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Stainless Steel Appliance(s), Washer, Washer/Dryer Stacked, Water Heater, Microwave Laundry Features: Main Level, Lower Level
  • Heating & Cooling

    Has Heating: Yes Heating: Electric, Heat Pump Has Cooling: Yes Cooling: Central Air, Ceiling Fan(s), Electric

  • Building Information

    Year Built: 1984 Building Area Total: 9421 Construction Materials: Brick Patio And Porch Features: Deck, Patio Pool Features: Heated, In Ground, Salt Water, Vinyl, Private Private Pool: Yes View: Mountain(s) Association Fee Frequency: Annually
  • Exterior Features

    Exterior Features: Lighting, Rain Gutters, Storage

  • Lot Information

    Lot Size Acres: 5.02 Lot Size Source: Assessor Lot Size Square Feet: 218671 Lot Description: Sloped, Wooded, Front Yard, Level, Private, Back Yard

    Property Information

    Subdivision: OAK HILL Source Property Type: Residential Postal Code Plus 4: 5136 Zoning Description: RESIDENTIAL AGRICULTURE Property SubType: Single Family Residence Levels: Three Or More Property Age: 42

  • Listing Price Information

    Listing Price: $1490000

  • Tax Information

    Parcel Number: 73-4-F Tax Lot: F Tax Year: 2025 Annual Tax: $5344

  • Parking Information

    Parking Total: 9 Oversized, Garage Door Opener, Garage, Driveway, Underground, Inside Entrance, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 3
    Homeowners Association Information
    Has Association: Yes HOA: $125.00

  • Location Information

    Direction: From Winchester, take Middle Road to Marlboro Road. Turn left onto Marlboro Road, then left onto Oak Hill Road. Property is on the left with a sign in the yard. WaterSource: Well
Sell a home like this and save $88,901 Find out How

How much is this property worth?

Curious about this home's true market value? Use our free Home Evaluation Tool to instantly get a personalized Comparative Market Analysis (CMA) report. Make smarter, data-driven decisions before you buy.

Images
Loading, please wait...

Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
106 Bookers Crest Drive, Stephens City, VA, 22655 $545,990 6 4 3,127 0.15 Acre
108 Bookers Crest Drive, Stephens City, VA, 22655 $539,990 4 3 2,638 0.16 Acre
TBD Oak Hill Court, Stephens City, VA, 22655 $1,100,000 4 4 2,891 6.69 Acres
LOT 1B Double Church Road, Stephens City, VA, 22655 $814,900 3 4 2,368 4.87 Acres
109 Kabardin Court, Stephens City, VA, 22655 $469,900 4 3 2,100 0.35 Acre
207 Clydesdale Drive, Stephens City, VA, 22655 $560,000 4 4 2,847 0.32 Acre
114 Latigo Court, Stephens City, VA, 22655 $625,000 4 3 3,545 0.36 Acre
112 Welsh Court, Stephens City, VA, 22655 $440,000 4 3 1,666 0.51 Acre
103 Ivy Hill Court, Stephens City, VA, 22655 $549,900 4 3 3,382 0.28 Acre
444 Talamore Drive, Stephens City, VA, 22655 $525,000 3 2 1,999 0.28 Acre

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 10/03/2026 @ 09:41

MLS: VAFV2042214 LISTED BY: Leah REALTOR, Re/Max Roots 540-686-7362 SOURCE: Bright MLS

Homes around $1,490,000

Selling? Save $88,901 when you sell a home like this

Tour with a ByOwner Agent