Oak Hill Homes with Paved Driveway Parking features

Oak Hill Homes with Paved Driveway Parking features

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Newest Oak Hill Homes with Paved Driveway Parking features

199 Oak Hill Dr, Stephens City
$1,490,000
6 Beds ⋅ 7 Baths
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.

199 Oak Hill Dr, Stephens City

Listing courtesy of Re/Max Roots. Contact:

1009 Oak Hill Ave, Hagerstown
$585,000
6 Beds ⋅ 4 Baths
A rare opportunity on beautiful Oak Hill Avenue! Offering 6 bedrooms, 4 full baths, dual-zone central air, a detached 2-car garage, exceptional off-street parking and an incredibly flexible finished third floor, this remarkable home blends the character and craftsmanship buyers love with the modern comforts they want. The massive, deep wraparound porch creates an unforgettable first impression and offers an incredible outdoor living space for morning coffee, evening conversations and entertaining. Step inside to soaring 10+ foot ceilings, gorgeous hardwood floors, beautiful moldings, curved windows, leaded and stained glass, abundant natural light and architectural details that give this home warmth and personality at every turn. The beautifully remodeled kitchen is designed for both everyday living and entertaining with custom cabinetry, stainless steel appliances, tile backsplash, breakfast nook and an additional wet bar/coffee station. Multiple living and gathering spaces provide tremendous flexibility, while beautifully renovated bathrooms bring a fresh, modern feel to the home's timeless surroundings. The primary suite is truly a retreat, with generous proportions, wonderful natural light, convenient adjacent laundry and an exquisite spa-inspired bath featuring a freestanding soaking tub, double vanity and oversized custom shower. The second level offers additional spacious bedrooms and baths, while the finished third floor expands the possibilities even further with two additional bedrooms, a kitchenette, full bath and dedicated mini-split heating and cooling. It's an ideal setup for guests, multi-generational living, home offices, creative space or a private upper-level retreat. Outdoor living continues on the huge rear deck overlooking the backyard, and parking is exceptional with a large newer concrete parking pad plus a detached 2-car garage—room for multiple vehicles without relying on street parking. Important improvements add confidence to all of the character: the wraparound porch was completely rebuilt in 2023, the roof was replaced in 2017, gutters are brand new in 2026, and the home also features updated plumbing, an updated electrical panel and dual-zone central air conditioning. Beautifully preserved, thoughtfully updated and incredibly versatile, 1009 Oak Hill Avenue offers a combination of space, character, modern amenities and functionality that is difficult to duplicate. Come experience everything this special home has to offer.

1009 Oak Hill Ave, Hagerstown

Listing courtesy of Samson Properties. Contact:

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