City Of Winchester Homes for Sale

City Of Winchester Homes for Sale

Welcome to the charming City of Winchester, Virginia, a vibrant community nestled in the heart of the Shenandoah Valley. Known for its rich history, stunning landscapes, and welcoming atmosphere, Winchester offers an exceptional quality of life for residents and visitors alike. The city is steeped in heritage, with beautifully preserved architecture and a quaint downtown area that features boutique shops, delightful eateries, and cultural attractions.

Winchester is also a hub for outdoor enthusiasts, boasting picturesque parks and trails that invite you to explore the natural beauty of the region. Whether you’re strolling along the historic Old Town or enjoying a picnic at Jim Barnett Park, the city provides a serene backdrop for relaxation and recreation.

For those considering a move to this idyllic locale, there are a variety of homes for sale that cater to diverse lifestyles and preferences. From charming single-family homes in established neighborhoods to modern townhouses and spacious estates, Winchester’s real estate market has something for everyone. Families will appreciate the top-rated schools and community amenities, while professionals can enjoy the convenience of nearby commuter routes.

With a strong sense of community and a plethora of local events and festivals throughout the year, Winchester is not just a place to live—it’s a place to thrive. Explore the homes for sale in the City of Winchester and discover the perfect setting for your next chapter. Your dream home awaits in this enchanting city!

Newest City Of Winchester Homes for Sale

$600,000
3 Beds ⋅ 2 Baths ⋅ VAWI2011162 MLS
Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The home spans approximately 3,480 square feet (1,844 main living areas + 804 sunroom + 832 basement). The traditional floor plan offers a formal dining room, perfect for hosting gatherings, while the butler's pantry adds a touch of convenience for entertaining. The kitchen is equipped with upgraded countertops and modern appliances, including a built-in microwave, cooktop, range hood, wall oven, dishwasher, and refrigerator, making meal preparation a joy. The home boasts three well-appointed bedrooms, each with ample closet space, including a walk-in closet in the master suite. The bathrooms are designed for comfort, featuring a full bath with a tub shower and a convenient half bath for guests. The property also includes a connecting stairway to the basement, where you'll find additional storage and laundry facilities. Outside, the extensive hardscape provides a relaxing outdoor space, perfect for enjoying the fresh air or hosting outdoor gatherings. A shed offers extra storage options for gardening tools or recreational equipment. Living in this vibrant community means enjoying the benefits of nearby parks, schools, and public services. The City of Winchester is known for its friendly atmosphere and active community life, with local events and activities that foster a sense of belonging. With on-street parking and a location that offers easy access to local amenities, this home is a perfect blend of comfort, style, and community spirit. Experience the charm of this Colonial residence and make it your own, where every corner feels like home. (See documents for improvements list)

1311 Handley Ave, Winchester
$325,000
4 Beds ⋅ 3 Baths ⋅ VAWI2011028 MLS
Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many visions, this property is the ideal project for someone ready to create something extraordinary. The home was once configured with an upper‑level apartment, complete with a private entrance, back stairway, and space for a second kitchen and bath—perfect for multi‑generational living, rental income, or reimagining the entire second floor into a spacious primary suite. Updated vinyl, energy‑efficient windows and a durable metal roof provide a strong start for renovation. A walk‑up attic offers excellent storage and the potential to be finished for additional living space. The upper level could accommodate three full bathrooms, allowing for a highly functional and modern second floor once renovated. An unfinished basement with both interior access and a walk‑up exit is even more space for storage. New electrical and plumbing updates are needed giving the next owner the opportunity to modernize the home exactly to their taste. With its architectural pedigree, adaptable layout, and solid structural foundation, this property is a rare chance to bring a historic home back to life and create something truly special.

719 National Ave, Winchester
$274,000
2 Beds ⋅ 1 Baths ⋅ VAWI2010796 MLS
This charming bungalow in the heart of the City of Winchester has already been beautifully renovated, offering the perfect blend of classic charm and modern living. Featuring 2 cozy bedrooms and a full bathroom, the home is designed with comfort and functionality in mind. Enjoy an updated kitchen and bathrooms, new appliances, and central A/C for a fresh, modern feel. The newly added front deck and patio provide great spaces to relax or entertain. Situated on a 0.17-acre lot with driveway parking, this home offers both indoor comfort and outdoor potential, all in a prime Winchester location. Don’t miss your chance to make it yours!

580 York Ave, Winchester
$459,999
5 Beds ⋅ 3 Baths ⋅ VAWI2010632 MLS
Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious bedrooms and 3 full bathrooms, there’s room for everyone. Situated on a quarter-acre lot with no HOA, you'll enjoy privacy and freedom. The large deck and screened-in porch are perfect for outdoor dining, entertaining, or simply unwinding. Conveniently located close to shopping centers and restaurants — everything you need is just minutes away!

419 Summit Ave, Winchester
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