$1,490,000

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… Read More 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. Read Less

Courtesy of Leah R REALTOR, Re/Max Roots 540-686-7362

Listing Snapshot

Days Online

Last Updated

Oct 9, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

7,508

Lot Size

5.02 Acres

Year Built

1984

MLS Number

VAFV2042214

Additional Details

Property Access

Road Surface: Black Top

Appliances & Equipment

Built-In Microwave, Built-In Range, Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Washer/Dryer Stacked, Water Conditioner - Owned, Water Heater

Basement

Connecting Stairway, Daylight, Partial, Fully Finished, Garage Access, Heated, Improved, Interior Access, Outside Entrance, Rear Entrance, Walkout Level, Windows, Workshop

Building

Built in 1984, Built in 2026 (effective), Living area: 7508, Levels: 3, Construction Materials: Brick

Cooling

Ceiling Fan(s), Central A/C

Doors

Double Entry

Accessibility Features

Level Entry - Main

Exterior Features

Patio/Porch Features: Deck(s), Patio(s), Extensive Hardscape, Exterior Lighting, Play Equipment, Satellite Dish, Secure Storage, Gutter System

Fireplaces

2 fireplaces, Gas/Propane, Mantel(s), Stone

Floors

Hardwood, Luxury Vinyl Plank

Foundation

Slab

Garage

3 spaces

Heating

Heat Pump(s)

Home Owner's Association

Association Fee: $125, Fee Frequency: Annually, Fee Includes: Road Maintenance

Interior Features

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, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Gourmet, Kitchen - Island, Pantry, Primary Bath(s)

Lot

5.02 acres, Backs to Trees, Front Yard, Landscaping, Level, Private, Rear Yard, SideYard(s), Sloping, Trees/Wooded

Parking

Paved Driveway

Pool

Heated, In Ground, Saltwater, Vinyl

Property

Excellent, Other structures: Above Grade, Below Grade, Mountain

Roof

Shingle

Sewer

Septic < # of BR

Taxes

Annual Amount: $5,344, Lot: F, Year: 2025, Zoning: RA, Zoning description: RESIDENTIAL AGRICULTURE

Utilities

Water Source: Well

Find The Perfect Home

'VIP' Listing Search

Whenever a listing hits the market that matches your criteria you will be immediately notified.

Join The List

Mortgage Calculator

Selling price

Down payment

Term (years)

Interest rate (%)

Monthly Payment

199 OAK HILL DRIVE

'VIP' Listing Search

Schools In The Area

Similar Listings

Find My Dream Home

1. Neighborhoods

2. Home Type

3. Send