City Of Winchester Real Estate

City Of Winchester Real Estate

Welcome to the City of Winchester, Virginia, a charming and vibrant community nestled in the heart of the Shenandoah Valley. Known for its rich history and picturesque landscapes, Winchester offers a unique blend of small-town charm and modern amenities, making it an ideal place for families, professionals, and retirees alike.

As a subdivision within Winchester City, residents enjoy the benefits of a close-knit community while being just a stone’s throw away from the bustling activities of downtown. The area boasts a rich tapestry of historical landmarks, including the iconic Old Court House and the serene Museum of the Shenandoah Valley, which showcases the region's cultural heritage. Nature enthusiasts will appreciate the abundance of parks and outdoor recreational opportunities, with the nearby Shenandoah National Park offering stunning views and hiking trails.

Winchester's vibrant downtown area is filled with charming boutiques, delightful cafes, and a variety of dining options, catering to every palate. The city also hosts numerous annual events, including the renowned Shenandoah Apple Blossom Festival, which brings together locals and visitors for a celebration of community spirit and seasonal beauty.

Families will be pleased to find a range of educational options, from top-rated public schools to private institutions, ensuring a quality education for children of all ages. With a strong sense of community, welcoming neighborhoods, and a rich array of amenities, the City of Winchester is not just a place to live but a place to thrive. Discover your dream home in this enchanting city, where history meets hospitality.

Newest Listings in City Of Winchester

$629,000
4 Beds ⋅ 3 Baths ⋅ VAWI2011638 MLS
If you've been waiting for a home that offers both character and modern convenience, this one deserves a close look. This all-brick, charming Cape Cod is located on a beautiful tree-lined street in the heart of Winchester with more space & versatility than meets the eye. Cross the threshold into the large, welcoming foyer and let your gaze take it all in...Large living room, large dining room, gorgeous staircase and center hall that draws you toward the beautifull, newly installed gourmet kitchen with butlers pantry. With 3 finished levels this home delivers space, comfort, and an unbeatable location in highly desired Downtown Winchester. Thoughtfully maintained and recently refreshed, this home features 4 bedrooms, 2 full baths, and a half bath, beautiful refinished wood floors and a newly remodeled kitchen that is sure to impress. Completed in September 2026, the kitchen dazzles with ample gorgeous cabinetry, extra-depth quartz counter tops, stunning center island with modern pendant lighting, pantry cabinets, stainless appliances, new flooring, built-in shelves, under cabinet lighting & butlers pantry. Additionally, the main level offers a primary bedroom/flex space with full bath. This home was originally built with a primary bedroom & bathroom on the main level. The present owners converted bedroom to use as a den. Use as you wish AND with little effort, the primary bedroom could easily be restored for those who desire "primary on the main". The main level is rounded out with mudroom with radiant heat in floors, dedicated office space and easy access to rear yard with patio. Upstairs, three additional bedrooms and another full bath provide plenty of room for family, guests, or a home office. The space on the upper level will take you by surprise with 2 rooms being quite large with charming built-in's and large closets. The walk-up basement adds valuable flexibility with large recreation room, a laundry area, workshop, and bonus room currently used as an office, plus a half bath. Outside, enjoy a detached one-car garage, fully fence rear yard, city sidewalks and a convenient location where so much is within easy reach. Walk to the Downtown Walking Mall, John Handley High School campus, restaurants, and more. Winchester Medical Center is just 2 miles away. The vibrant neighborhood offers a welcoming mix of households while remaining peaceful in the evenings. With the roof replaced in 2024 (includes garage), kitchen remodeled in 2026, upper wood floors refinished in 2026, and exterior trim freshly painted in 2026, this special home is ready for its next chapter. A place to with warmth, memories, and plenty of room to do so. All you have to do is move in.

507 S Stewart St, Winchester
$299,500
3 Beds ⋅ 2 Baths ⋅ VAWI2011582 MLS
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
$325,000
4 Beds ⋅ 2 Baths ⋅ VAWI2011592 MLS
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
$308,000
2 Beds ⋅ 2 Baths ⋅ VAWI2011408 MLS
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
$289,900
2 Beds ⋅ 2 Baths ⋅ VAWI2011406 MLS
Nestled in the charming City of Winchester, this exquisite end-of-row townhouse has undergone a remarkable transformation, with major renovations completed in 2026 that elevate it to a new standard of luxury living. The timeless Colonial architectural style, complemented by a classic brick exterior, exudes elegance and warmth, inviting you to experience a lifestyle of comfort and sophistication. Step inside to discover a thoughtfully designed interior that seamlessly blends modern amenities with classic charm. The spacious layout features two well-appointed bedrooms and one and a half beautifully updated bathrooms, providing ample space for relaxation and privacy. The renovations have introduced high-end finishes throughout, ensuring that every corner of this home reflects quality and style. T. The open-concept living area is bathed in natural light, creating an inviting atmosphere perfect for entertaining or unwinding after a long day. Outside, the property boasts a generous lot size of three acres, offering a serene retreat from the hustle and bustle of everyday life. While there is no pool, the expansive outdoor space provides endless possibilities for gardening, outdoor gatherings, or simply enjoying the tranquility of nature. Parking is a breeze with two dedicated spaces in the parking lot, ensuring convenience for you and your guests. The location is ideal, providing easy access to local amenities, parks, and vibrant community life, all while maintaining a sense of privacy and seclusion. This home is not just a place to live; it's a lifestyle choice that embodies luxury, comfort, and a sense of belonging. Experience the perfect blend of modern living and classic elegance in this beautifully renovated townhouse, where every detail has been meticulously crafted to create a warm and inviting atmosphere. Embrace the opportunity to make this exceptional property your new home.

2640 Limestone Ct, Winchester
$425,000
3 Beds ⋅ 3 Baths ⋅ VAWI2011380 MLS
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
$369,999
3 Beds ⋅ 2 Baths ⋅ VAWI2011384 MLS
Home Warranty for the Buyer + Bonus for the Buyer’s Agent with a Ratified Contract in September! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom upstairs. Enjoy the peace of mind that comes with numerous recent updates and renovations completed in 2024, including architectural shingles, carport soffit, central heating and air conditioning with a dual-zone electric heat pump, crawl space sump pump and poly, and fresh paint throughout. Inside, you’ll find refinished real hardwood floors in the living areas and bedrooms, updated flooring in the kitchen and bathrooms, and numerous updated plumbing and light fixtures, vanities, outlets and switches. The Kitchen and primary bathroom feature a quartz countertop, an undermount sink with beautiful tiled shower with a glass door. This home offers a wonderful opportunity to move right in and enjoy.

2919 S Pleasant Valley Rd, Winchester
$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
$268,000
2 Beds ⋅ 1 Baths ⋅ VAWI2010796 MLS
**PRICE REDUCTION** This charming house in the heart of the City of Winchester has already been 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. 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, 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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