About This Home

This 6-bedroom, 7-bathroom single family at 199 OAK HILL Drive in Stephens City, VA is listed for $1,490,000 ($198 per sqft). Built in 1984, the home offers 7,508 sqft of living space on a 5.02 acres lot.

Key Features

  • Built in 1984
  • 5.02 acre lot
  • 3 stories
  • 9 parking spaces
  • Private pool
  • Fireplace

Property Details

3 stories
5 full, 2 half
3-car garage
1984

Amenities

PoolFireplaceA/C
Listing Description

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 replace

d 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.

Monthly Cost Estimate

$8,094/mo

20% down · 6.5% · 30 years

Principal$1,078
Interest$6,457
Insurance$435
HOA$125

Estimates only. Actual payments may vary.

Location

199 OAK HILL Drive

Stephens City, VA 22655

OAK HILL

Features & Amenities

Interior Features

2nd KitchenBathroom - Soaking TubBathroom - Stall ShowerBathroom - Tub ShowerBathroom - Walk-In ShowerBreakfast AreaBuilt-InsCeiling Fan(s)Crown MoldingsEntry Level BedroomExposed BeamsFamily Room Off KitchenFloor Plan - OpenFormal/Separate Dining RoomKitchen - GourmetKitchen - IslandPantryPrimary Bath(s)

Property Details

Construction

Brick

Pool Features

Pool

Parking

Garage - AttachedDriveway

Heating

Heat Pump (Heating)

Cooling

Central AirCeiling Fan(s)

Appliances

Built-In MicrowaveBuilt-In RangeDishwasherDisposalDryerRange HoodRefrigeratorStainless Steel AppliancesWasherWasher/Dryer StackedWater Conditioner - OwnedWaterHeater

Questions & Answers

This 6-bedroom, 7-bathroom single family at 199 OAK HILL Drive is listed at $1,490,000 ($198/sqft). The estimated monthly payment is $8,094 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance, HOA fees.

HOA fees are $125/month.

Key features include: Built in 1984, 5.02 acre lot, 3 stories, 9 parking spaces, Private pool, Fireplace. Interior Features: 2nd Kitchen, Bathroom - Soaking Tub, Bathroom - Stall Shower.

This property is listed by Leah R REALTOR.

LR

Leah R REALTOR

License 0225048720

Agent at Top of VA, LLC

Listed by Top of VA, LLC · Broker phone: (540) 955-0911 · View on Broker Site

MLS# VAFV2042214· Source: Bright MLS· 20 days on PropertySimple

Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

199 OAK HILL Drive, Stephens City, VA 22655

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