Rolling Hills Homes For Sale In Winchester City

7 Beds ⋅ 5 Baths ⋅ VAWI2011542 MLS ⋅ ACTIVE Status

Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester

$525,000

4 Beds ⋅ 4 Baths ⋅ VAWI2009012 MLS ⋅ CLOSED Status

HUGE PRICE IMPROVEMENT! Welcome to this beautiful "picture perfect" brick front 4-bedroom, 3.5-bath home in the desirable Rolling Hills community of Winchester, VA. Perfectly located at the end of a cul-de-sac in an established (and sought after) neighborhood, this one-owner property has been meticulously maintained and is ready for its next chapter. Inside, you’ll find a spacious and inviting layout that includes a bright living room with a beautiful fireplace, perfect for relaxing or entertaining. High ceilings (9 foot!) on BOTH the main and top level makes the space feel even larger! The kitchen has been thoughtfully upgraded and is truly a chef’s dream, featuring a gas stove, double oven, and high-quality finishes. Upstairs, generous bedrooms provide comfort and privacy, while the primary suite (with a tray ceiling!) offers a relaxing retreat. The home also boasts a mostly finished basement, providing flexible space for a recreation room, home office, or gym. There is a full bathroom down there too! Recent updates include a NEW roof and a newer deck, ideal for enjoying the outdoors. The pride of ownership extends beyond the interior, with a beautifully landscaped yard enhanced by hand selected trees and thoughtful plantings, offering both curb appeal and a peaceful setting. Centrally located to shopping, dining, schools, and major commuter routes, yet tucked away in a quiet neighborhood, this property provides the perfect balance of convenience and tranquility. Don’t miss this opportunity to own a truly special home in one of Winchester’s most sought-after communities.

2812 Ridgetop Court, Winchester

$635,000

5 Beds ⋅ 4 Baths ⋅ VAWI2007660 MLS ⋅ CLOSED Status

Welcome to 800 Kennedy Drive, a spacious Colonial by Richmond American Homes located in the desirable Rolling Hills Estates. This home offers three finished levels with a smart, open layout—perfect for everyday living and entertaining. The main level flows seamlessly from room to room, featuring beautiful hardwood floors and fresh new carpet throughout. The large family room, featuring a stone fireplace, is a warm and inviting space and serves as a beautiful focal point of the home. The kitchen is well-equipped with extensive counter space, a walk-in pantry, new refrigerator, double wall ovens, and a gas cooktop. A sunroom off the kitchen adds valuable living space on the main floor and structurally extends to the basement, increasing usable square footage below. Originally designed by the builder as an office, the main-level bedroom was upgraded during construction to include a closet and a full bath, offering excellent flexibility for office space, guests or multi-generational living. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with a large sitting room—an ideal space to read and relax—and an en suite bath. The walk-up lower level features an expansive recreation room, a den, a full bath, and generous storage areas, offering a flexible footprint for future customization. This home is located just 1.5 miles from the future Ward’s Plaza Redevelopment Project, which includes a 50,325-square-foot Publix supermarket expected to open in late 2026, bringing approximately 150 jobs to the area. The project also features planned infrastructure improvements such as new streets, upgraded stormwater, water, and sewer systems. A portion of Hope Drive is also proposed for vacation to create green space or a linear park. Located in the sought-after Handley School District and with easy access to Routes 37, I-66, and I-81, this move-in-ready home offers comfort, functionality, and long-term value. You can view the marketing brochure here: https://buy800kennedy.my.canva.site/

800 Kennedy Drive, Winchester

$825,000

3 Beds ⋅ 4 Baths ⋅ VAWI2007182 MLS ⋅ CLOSED Status

Custom built home by Owner. This spacious home will fill all of your entertaining needs both inside and outside, Open Kitchen and family room, built in wet bar, sunroom and a Florida room to take you outside to a beautiful inground pool.. Covered area for your pool equipment and entertain at your tiki bar with a full bath. Want to entertain inside , you can do it in the formal dinning room and spacious sunken formal living room. 3 Bedrooms with a 4th that could be used as a bedroom or office. 3 1/2 Baths. Master suit has his and her bathrooms and closets. Large Laundry room. And don't forget the 4 car heated garage with plenty of extra space. Call and schedule your appointment to view this fabulous home.

707 Kennedy Drive, Winchester

$414,000

3 Beds ⋅ 2 Baths ⋅ VAWI2006804 MLS ⋅ CLOSED Status

605 Dulles Circle, Winchester

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Rolling Hills Homes For Sale In Winchester City