# 199 OAK HILL Drive, Stephens City, VA 22655 > **TL;DR:** 6bd/7ba single family, $1,490,000 ($198/sqft), built 1984, 7,508 sqft. > Pool, Fireplace, A/C, 3-car garage. Est. $8,094/mo. Listed 25 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,490,000 | | Price/sqft | $198 | | Bedrooms | 6 | | Bathrooms | 5 full, 2 half | | Square Feet | 7,508 | | Year Built | 1984 | | Lot Size | 218,671 sqft (5.02 acres) | | Stories | 3 | | Garage | 3-car | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 25 | ## Why This Home Stands Out - **Pool** - Pool listed; type not specified - **Large Garage** - 3-car garage ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $7,534 | | Estimated Insurance | $435 | | HOA | $125 | | **Total** | **$8,094** | ## Key Amenities - Pool - Fireplace - A/C - 3-car garage ## Property Highlights - Built in 1984 - 5.02 acre lot - 3 stories - 9 parking spaces - Private pool - Fireplace ## Description ### Agent 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 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. ## Location - **Address:** 199 OAK HILL Drive, Stephens City, VA 22655 - **County:** FREDERICK - **Neighborhood:** OAK HILL - **Coordinates:** 39.09385, -78.26942 - **Google Maps:** https://www.google.com/maps?q=39.09385,-78.26942 ## Virtual Tour & Media - **Video Tour:** https://www.zillow.com/view-imx/2a9a2b92-dc14-46a3-9a1f-47f59b1c42f7?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard ## Listing Agent - **Name:** Leah R REALTOR · **License:** 0225048720 - **Brokerage:** Top of VA, LLC - **Broker Phone:** (540) 955-0911 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/199-Oak-Hill-Dr_Stephens-City_VA_22655_M57045-93233?f=listhub&s=TRENDPA&m=VAFV2042214&c=propsimple) ## Photos ![199 OAK HILL Drive - Photo 1](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f3055237304r.jpg) ![199 OAK HILL Drive - Photo 2](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2291397414r.jpg) ![199 OAK HILL Drive - Photo 3](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f3289080819r.jpg) ![199 OAK HILL Drive - Photo 4](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2531446910r.jpg) ![199 OAK HILL Drive - Photo 5](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f3202934890r.jpg) ![199 OAK HILL Drive - Photo 6](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f4190518140r.jpg) ![199 OAK HILL Drive - Photo 7](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2528836382r.jpg) ![199 OAK HILL Drive - Photo 8](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f1821883781r.jpg) ![199 OAK HILL Drive - Photo 9](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f659673001r.jpg) ![199 OAK HILL Drive - Photo 10](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2632569524r.jpg) ![199 OAK HILL Drive - 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Photo 121](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f16186899r.jpg) ![199 OAK HILL Drive - Photo 122](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f3520751135r.jpg) ![199 OAK HILL Drive - Photo 123](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f80090767r.jpg) ![199 OAK HILL Drive - Photo 124](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2127673309r.jpg) ![199 OAK HILL Drive - Photo 125](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f3503585366r.jpg) ![199 OAK HILL Drive - Photo 126](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f1093462153r.jpg) ![199 OAK HILL Drive - Photo 127](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2357995717r.jpg) ![199 OAK HILL Drive - Photo 128](http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2908331198r.jpg) --- **MLS#:** VAFV2042214 | **Updated:** 2026-10-27 **Source:** listhub *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.* [View on PropertySimple](https://staging.propertysimple.ai/listing/199-oak-hill-drive-stephens-city-va-22655-12069fa9647b4ed08c24e3f40d304508) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/199-oak-hill-drive-stephens-city-va-22655-12069fa9647b4ed08c24e3f40d304508#listing", "url": "https://staging.propertysimple.ai/listing/199-oak-hill-drive-stephens-city-va-22655-12069fa9647b4ed08c24e3f40d304508", "name": "199 OAK HILL Drive, Stephens City, VA 22655", "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 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.", "image": [ "http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f3055237304r.jpg", "http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2291397414r.jpg", "http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f3289080819r.jpg", "http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2531446910r.jpg", "http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f3202934890r.jpg", "http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f4190518140r.jpg", "http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f2528836382r.jpg", "http://lh.rdcpix.com/11189b183183f6f847817a2c4e21cd34l-f1821883781r.jpg", 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