City Of Winchester Homes for Sale

City Of Winchester Homes for Sale

Welcome to the enchanting City of Winchester, Virginia, where history meets modern living in a picturesque setting. Nestled in the heart of the Shenandoah Valley, Winchester is renowned for its charming downtown area, rich Civil War heritage, and vibrant community spirit. With a perfect blend of small-town charm and urban conveniences, this city is an ideal place for families, retirees, and everyone in between.

The City of Winchester boasts a variety of homes for sale, catering to diverse tastes and lifestyles. Whether you're seeking a quaint historic home with character, a spacious suburban residence, or a contemporary townhouse, you’ll find an array of options that fit your needs. Many properties in this delightful subdivision feature beautifully landscaped yards, modern amenities, and proximity to local parks and schools, making it easy to enjoy the great outdoors and community events.

Winchester's real estate market is thriving, offering opportunities for first-time homebuyers and seasoned investors alike. With its affordable housing options and a welcoming atmosphere, this city is not just a place to live; it’s a place to thrive. Explore the charming neighborhoods, each with its unique personality, and discover why so many are choosing to call Winchester home.

In addition to its stunning homes, Winchester offers a rich tapestry of culture, dining, and recreation. From local farmers' markets to historic sites and outdoor adventures, there is something for everyone. Don’t miss the chance to find your dream home in this vibrant city where community and comfort come together seamlessly. Start your journey in Winchester today!

Newest City Of Winchester Homes for Sale

805 S Kent St, Winchester
$319,900
4 Beds ⋅ 2 Baths
Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own!

805 S Kent St, Winchester

Listing courtesy of Weichert, REALTORS. Contact:

1802 Tilghman Ln, Winchester
$394,000
2 Beds ⋅ 2 Baths
Nestled in the charming CITY OF WINCHESTER, this exquisite cottage-style residence offers a serene retreat for those seeking a luxurious yet comfortable lifestyle. Spanning 1,642 square feet, this thoughtfully crafted detached home features two spacious bedrooms and two full bathrooms, providing ample space for relaxation and privacy. The inviting living area is enhanced by a cozy fireplace, perfect for those cooler evenings, creating a warm ambiance that feels just like home. The exterior showcases a delightful blend of vinyl siding and brick, exuding timeless charm while requiring minimal maintenance. The meticulously landscaped garden and lawn views offer a picturesque backdrop, inviting you to unwind and enjoy the beauty of nature right from your own backyard. The attached garage provides convenient access and additional storage space, ensuring that your belongings are neatly organized. The property is designed for ease of living, with a layout that promotes both comfort and accessibility. While this community does not feature a pool, the surrounding area is rich with opportunities for leisure and social engagement. Residents can enjoy leisurely strolls through the beautifully maintained grounds or participate in community events that foster connections and friendships. This home is not just a residence; it's a lifestyle choice that emphasizes comfort, community, and luxury. With its high-end features and inviting atmosphere, it's the perfect place to create lasting memories and enjoy the finer things in life. Experience the joy of living in a space that truly feels like home, where every detail has been considered for your comfort and enjoyment. Discover the perfect blend of elegance and tranquility in this remarkable property, where you can embrace a fulfilling lifestyle in a welcoming community. Lots to offer at the community center that is in walking distance. This is one of the largest units in Willow Lawn.

1802 Tilghman Ln, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

23 E Germain St, Winchester
$185,000
3 Beds ⋅ 2 Baths
Welcome to this 3-bedroom, 2-bath home in Winchester, VA! Offering plenty of potential, this property could be an excellent opportunity for a first-time homebuyer or investor. The property also features a shed and workshop, providing additional storage and space for hobbies or projects. The home is being sold AS IS, WHERE IS. Buyers are responsible for performing their own due diligence regarding the property's condition, square footage, lot boundaries, zoning, permits, utilities, and any other matters of importance to the buyer. Bring your vision and explore the possibilities this property has to offer!

23 E Germain St, Winchester

Listing courtesy of Exit Success Realty. Contact:

317 S Kent St, Winchester
$399,000
4 Beds ⋅ 2 Baths
Welcome to this charming brick home located in the heart of Winchester! Filled with historic character, this home features beautiful hardwood floors throughout, spacious living areas, and oversized bedrooms. Enjoy relaxing on the covered front porch or entertaining on the covered back porch overlooking the large backyard. The home's timeless charm and generous room sizes offer a wonderful opportunity to make it your own. Location is a highlight! Situated right next to Ruth Jackson Memorial Park, within walking distance of Patsy Cline Memorial Park, and directly across the street from the Green Circle Trail, you'll have easy access to walking, biking, and outdoor recreation. Plus, you're just a short stroll from local shops, restaurants, Shenandoah University, and all that downtown Winchester has to offer. Historic charm, spacious living, and a fantastic location make this home a wonderful opportunity!

317 S Kent St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

3 S Euclid Ave, Winchester
$305,500
3 Beds ⋅ 2 Baths
Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently located on the main level, along with a dedicated office that provides a great space for working from home, hobbies, or additional flex space. One of the two full bathrooms is brand new, adding a fresh modern touch to this classic home.

3 S Euclid Ave, Winchester

Listing courtesy of Main Street Realty. Contact:

2519 Hockman Ave, Winchester
$299,900
2 Beds ⋅ 2 Baths
This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey!

2519 Hockman Ave, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

422 S Loudoun St, Winchester
$409,000
3 Beds ⋅ 3 Baths
PRICED BELOW RECENT APPRAISED VALUE. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level washer/dryer. The second level of the home offers a sitting area, primary bedroom with its own half bath and two addtional bedrooms with a shared bathroom. Accessed by the third bedroom, the attic offers a blank canvas and could be easily transformed into a secondary living area, home office, or a recreation and fitness room. Wide plank pine flooring remains throughout most of the home along with many traditional fiixtures. Recent improvements include a new gourmet kitchen with SS appliances, hvac, water heater, exterior clapboard cedar siding replaced where needed and new tile floors in the kitchen, main level bath and utility room. Step outside to the quaint backyard which offers an oasis for relaxation, play and gardening. The location of the home can't be beat. Just a few blocks to the pedestrian mall, one can experience a plethora of dining options, coffee shops, boutique stores, galleries and local social activities.

422 S Loudoun St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

1311 Handley Ave, Winchester
$600,000
3 Beds ⋅ 2 Baths
This charming Colonial home, built in 1952, exudes warmth and character, making it a perfect retreat. Nestled in the heart of the City of Winchester, this residence features three spacious bedrooms and one and a half bathrooms, ideal for comfortable living. Step inside to discover beautiful hardwood floors that flow throughout, complemented by a traditional floor plan that invites gatherings in the formal dining room. The upgraded countertops and butler's pantry in the kitchen enhance functionality, while the cozy fireplace adds a touch of elegance to the living space. The home boasts a well-designed attic and a convenient basement laundry area, ensuring ample storage and practicality. Outside, the extensive hardscape and outbuilding provide versatile outdoor space for relaxation or hobbies. Located in a vibrant community, residents enjoy easy access to local parks, perfect for leisurely strolls or picnics. The neighborhood is known for its friendly atmosphere and community events, fostering a sense of belonging. Excellent schools are just a stone's throw away, making this location ideal for those seeking quality education options. With on-street parking and a generous lot size, this property balances convenience and comfort. Experience the charm of this delightful home and the welcoming community that surrounds it.

1311 Handley Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

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