City Of Winchester Real Estate

City Of Winchester Real Estate

Welcome to the City of Winchester, Virginia, a vibrant and historic community that seamlessly blends small-town charm with modern amenities. Nestled in the picturesque Shenandoah Valley, Winchester offers a unique lifestyle enriched by its rich history, beautiful landscapes, and a warm, welcoming atmosphere.

As one of the oldest cities in the United States, Winchester boasts a captivating heritage that is reflected in its well-preserved architecture and numerous historical landmarks. Stroll through the charming streets of Old Town, where you’ll find an array of boutique shops, delightful cafes, and art galleries that showcase local talent. The city's vibrant cultural scene is further enhanced by events throughout the year, including festivals, farmers' markets, and live music performances that bring the community together.

For those who appreciate the great outdoors, Winchester is surrounded by stunning natural beauty. The nearby Shenandoah National Park offers hiking, biking, and breathtaking views, while the area's parks and recreational facilities provide ample opportunities for family fun and relaxation. Whether you enjoy a leisurely stroll along the scenic trails or an afternoon picnic in one of the many parks, there’s something for everyone to enjoy.

Families will find an excellent selection of schools and educational programs, making Winchester an ideal place to raise children. The community is known for its friendly residents who take pride in their neighborhoods, creating a sense of belonging that is hard to find elsewhere.

In the City of Winchester, you’ll discover a perfect balance of history, culture, and community spirit. Come explore the possibilities and make this enchanting city your new home!

Newest Listings in City Of Winchester

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:

621 Watson Ave, Winchester
$273,500
3 Beds ⋅ 2 Baths
Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas. The updated kitchen features new cabinetry and stainless steel appliances, creating a clean, contemporary space perfect for everyday living and entertaining. Both bathrooms have also been thoughtfully updated, adding to the home’s fresh and modern appeal. Enjoy your morning coffee or unwind at the end of the day on the covered front porch. The partially fenced yard provides space to enjoy the outdoors, while the storage shed offers convenient additional space for tools, lawn equipment, and seasonal items. Convenient rear-entry parking provides easy access to the home, with additional street parking available in front. The unfinished basement provides valuable additional storage and utility space. With its attractive updates, functional floor plan, outdoor space, storage shed, and convenient parking, 621 Watson Avenue is a standout opportunity in Winchester! Whether you're searching for a comfortable place to call home or a great investment property, this beautifully refreshed duplex is ready for its next owner. Schedule your tour on ShowingTime today and see why 621 Watson Avenue stands out!

621 Watson Ave, Winchester

Listing courtesy of Samson Properties. 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:

Start Your Search

How much is your home worth?

Get instant property value now!