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199 Oak Hill Drive Stephens City, VA $ 1,490,000
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$ 1,490,000 Get more info
199 Oak Hill Drive
$ 1,490,000
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199 Oak Hill Drive

Stephens City, VA, 22655
$ 1,490,000
Bedrooms6 Baths5.2 Sq 7,508

Monthly Estimate*

$ 9,408

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Single Family Home for sale in Stephens City, VA

for $1,490,000 with 6 bedrooms and 5 full baths, 2 half baths. This 7,508 square foot home was built in 1984 on a lot size of 5.02.

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.

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Single Family Coming Soon

Price

$ 1,490,000

Bedrooms

6

Full Bath

5

Half Bath

2

Property Type

Single Family

Taxes

$ 5,344

Style

Ranch/Rambler

Lot Size

5.02

Year Built

1984

Town/City

Stephens City

County/Region

Frederick

MLS | Web ID

VAFV2042214
Features
General
Living Area 7508
Sewer Septic < # of BR
Heating Heat Pump(s)
Cooling Ceiling Fan(s) Central A/C
Possession Settlement
Roof Shingle
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
Zoning RA
HOA Fee 125.00
Garage Spaces 3.00
Association Fee Includes Road Maintenance
Patio/Porch Features Deck(s) Patio(s)
Architectural Style Ranch/Rambler
Pool Features Heated In Ground Saltwater Vinyl
Construction Materials Brick
School District FREDERICK COUNTY PUBLIC SCHOOLS
Year Built 1984
View Mountain
Levels 3
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Accessibility Level Entry - Main
Assoc Fee Paid Per Annually
County FREDERICK
New Construction N
Property Type Residential
HOA Y
Subdivision Name OAK HILL
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 5
Status COMING SOON
Directions 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.
City STEPHENS CITY
Disclosures Subject to Condo/HOA Docs
Association Name OAK HILL HOA
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 218671.00
Tax Annual Amount 5344.0
Property Condition Excellent
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 5
Bathrooms Count Main Level 7.00
Price Per Sq Ft Total AG 297.05
Vacation Rental Y/N N
Standard Status Coming Soon
Year Built Source Assessor
Legal Subdivision OAK HILL
Tax Lot F
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Interior
Interior Amenities 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 Fam
Heating Fuel Electric
Basement Connecting Stairway Daylight Partial Fully Finished Garage Access Heated Improved Interior Access Outside Entrance Rear Entrance Walkout Level Windows Workshop
Flooring Hardwood Luxury Vinyl Plank
Total Fireplaces 2
Fireplace Features Gas/Propane Mantel(s) Stone
Hot Water Electric
Basement (Y/N) Y
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 5016
Half Baths 2
Central Air Y/N Y
Total Bedrooms 6
Below Grade Finished Area 2492
Main Level Bedrooms 6
Below Grade Finished Area Unit Type Square Feet
Laundry Type Lower Floor Main Floor
Below Grade Finished Area Source Estimated
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 7
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Exterior
Exterior Amenities Extensive Hardscape Exterior Lighting Play Equipment Satellite Dish Secure Storage Gutter System
Pool Yes - Personal
Parking Features Paved Driveway
Lot Features Backs to Trees Front Yard Landscaping Level Private Rear Yard SideYard(s) Sloping Trees/Wooded
Water Source Well
Garage Features Additional Storage Area Built In Garage - Front Entry Garage Door Opener Inside Access Oversized Underground
Type of Parking Attached Garage Driveway
Foundation Details Slab
Water View Y/N N
Lot Size Acres 5.02
Road Surface Type Black Top
Lot Size Source Assessor
Waterfront Y/N N
Door Features Double Entry
Land Assessed Value 133200.00
Navigable Water Y/N N
Water Oriented Y/N N
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Internal Only
Street Number 1 199
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* Excluded Features
List By
Re/Max Roots

Broker

leahcansell@gmail.com

Email

Affordability Calculator

$9,853
Per Month
95%
5%
0%
Monthly Principal & Interest
$9,408
Monthly Property Taxes
$445
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3533201 Elementary School
3533240 Middle School
Unknown High School High School
See complete school information
Pricing History
Date Price Price Change Description
10/1/2026 $1,490,000 Listed Price

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199 Oak Hill Drive, Stephens City, VA, 22655 is a Single Family Home for sale at $1,490,000 with 7,508 sqft and a lot size of 5.02. 199 Oak Hill Drive has 6 bedrooms, 5.2 baths, and was built in 1984. The property's zip code is 22655 which is in Stephens City, VA

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