Set on 21.5 acres just minutes from downtown Winchester, this 5-bedroom home offers over 5,800 finished square feet with a blend of space, functionality, and outdoor living in a highly convenient location. Combining usable land, thoughtful improvements, and indoor and outdoor entertaining spaces, this property offers a rare opportunity close to town amenities. The main living areas feature an open flow between the kitchen and living room, highlighted by a fireplace and a custom kitchen with Mennonite-built cabinetry, stainless steel appliances, gas cooking, and a generous pantry. A fully finished basement with a second fireplace provides additional space for recreation, guests, or multi-generational living. Outdoor living includes an in-ground pool with hot tub, a 16'x27' covered patio with outdoor kitchen featuring a sink, grill, and refrigerator, a 16'x12' pergola, outdoor fireplace, detached pool house, and an additional covered hot tub area. The property also features a private stocked pond and a 24'x36' barn equipped with two stalls, wash bay, tack room, second-story hay loft, hot/cold water, and electric, making it suitable for equestrian or hobby use. An 18'x20' wood shed with outdoor wood stove adds additional utility. Additional features include a 1,270 sq ft three-car garage with 10'x8' doors, propane heat on the main level, heat pump on the upper level, outdoor wood stove capable of heating the entire home, gas water heater, and a new water heater installed in 2026. Conveniently located within approximately 5 miles of downtown Winchester, enjoy nearby shopping, dining, entertainment, Jim Barnett Park, Trails at the Museum of the Shenandoah Valley, and Rose Hill Park within walking distance. Above-ground hot tub, propane tank, and outbuildings convey AS-IS. *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer's decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.