Winchester City County Real Estate

Winchester City County Real Estate

Welcome to Winchester City, Virginia, a charming destination steeped in history and brimming with modern amenities! Nestled in the picturesque Shenandoah Valley, Winchester is not just a city; it's a vibrant community that beautifully blends its rich past with a bright future.

As the county seat of Frederick County, Winchester boasts a captivating history that dates back to its founding in 1744. The city played a significant role during the Civil War, making it a focal point for history enthusiasts. You can explore this heritage through the well-preserved architecture of the Old Town, where cobblestone streets are lined with delightful boutiques, restaurants, and galleries. The iconic Handley Regional Library and the historic George Washington’s Office Museum are must-visit spots for those looking to soak in the local culture.

Winchester is also known for its stunning natural surroundings. With the Blue Ridge Mountains to the west and the Allegheny Mountains to the north, outdoor enthusiasts will find a plethora of activities, from hiking and biking to scenic drives. The nearby Shenandoah National Park offers breathtaking views and vibrant wildlife, making it a perfect escape for nature lovers.

For families, Winchester City provides excellent schools, community parks, and recreational facilities, ensuring a high quality of life. The city also hosts various events throughout the year, including the Shenandoah Apple Blossom Festival, which draws visitors from all over.

Whether you are looking to buy a home, invest in property, or simply explore, Winchester City welcomes you with open arms and a promise of delightful experiences!

Newest Listings in Winchester City County

$650,000
4 Beds ⋅ 4 Baths
Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including elegant formal living and dining rooms ideal for entertaining. The heart of the home features an inviting open-concept kitchen and family room, creating the perfect space for everyday living and gathering with family and friends. A bright and airy sunroom provides the perfect spot to relax while overlooking the backyard. The finished basement offers exceptional flexibility with abundant space for a recreation room, home theater, fitness area, office, or guest suite. A spacious 2-car garage provides plenty of storage and convenience. Ideally situated in a prime location close to shopping, dining, schools, commuter routes, and all that Winchester has to offer, this impressive home combines space, convenience, and timeless appeal. If you're searching for a move-in-ready home with generous living areas and an unbeatable location, 1529 Dalton Place is one you won't want to miss. All sizes are approximate.

1529 Dalton Pl, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$1,495,000
Great Warehouse in the City of Winchester, approximately 13,000 sq. ft. will be vacant by end of October

567 N Cameron St, Winchester

Listing courtesy of Compass. Contact: (703) 310-6111
$375,000
3 Beds ⋅ 2 Baths
Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

1004 Pennsylvania Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$180,000
3 Beds ⋅ 1 Baths
Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to transform it into a distinctive home while building meaningful sweat equity. The level backyard provides plenty of usable outdoor space, and the rear alley creates the possibility of adding a gated entrance for convenient off-street parking behind the home. A rare opportunity to reimagine a well-located Winchester property and make it entirely your own.

309 Liberty Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$1,395,000
Legacy Investment Opportunity: Prime, Turn-Key Asset in Downtown Historic District! 7500 SF over four floors, located on the celebrated Walking Mall, Winchester, VA, the fastest-growing metro area in Virginia! This historic building has been fully modernized and is 100% occupied with a strong leasing history. List Price: $1,395,000. CAP Rate: 7.5%. Annual Net Rent: $106K. The property features a strategic mix of four stabilized leases, including prime ground-floor retail and Class A office suites across the second, third, and fourth floors. This is a very rare income opportunity!

185 Loudoun St N, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$719,000
7 Beds ⋅ 5 Baths
Situated on a prominent corner lot in an exclusive cul-de-sac enclave of distinguished homes, this impressive stone-front residence offers exceptional space, comfort, and timeless appeal in one of the area’s most desirable neighborhoods. Ideally located near fine dining, shopping, banks, and everyday conveniences, the home combines luxury living with unmatched accessibility. Built in 2011 and meticulously maintained, freshly painted, with new wall to wall carpet, this expansive residence features 7 bedrooms and 5 full bathrooms thoughtfully designed for both elegant entertaining and comfortable everyday living. A dramatic two-story foyer creates a grand first impression, flanked by formal living and dining rooms that add sophistication and charm. The upper level includes a luxurious owner’s suite with a spacious bedroom and spa-inspired bath, along with generously sized secondary bedrooms, including a Jack-and-Jill bath and an additional hall bath arrangement designed for convenience and privacy. The main level offers a desirable guest suite with a full bath, ideal for multigenerational living or visiting guests. At the heart of the home is a beautifully appointed gourmet kitchen featuring upgraded cabinetry, granite countertops, a center island, breakfast area, and seamless flow into the expansive family room. The finished lower level provides exceptional versatility with a large recreation/family room, an additional suite, and three flexible rooms perfectly suited for guest accommodations, home offices, fitness space, or playrooms. Step outside to the inviting deck overlooking the gently rolling backyard — an ideal setting for relaxing mornings, outdoor dining, and entertaining in a peaceful, private setting. House blueprints provided in this listing are for reference only and may not accurately reflect the current structure. Call your real estate agent and schedule a showing today!

2700 Loyalty Ct, Winchester

Listing courtesy of Elcy & Co. Realty, LLC.. Contact: 5403230675
$429,000
4 Beds ⋅ 2 Baths
Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a charming community park, this home is ideally located just minutes from Winchester Medical Center, the Museum of the Shenandoah Valley, and Old Town Winchester's restaurants, shops, and entertainment.

1310 Whittier Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$500,900
4 Beds ⋅ 3 Baths
Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides a generous recreation room, an additional bedroom, and a full bath, offering flexible space for guests, a home office, or everyday living. Enjoy the fully fenced backyard with a patio, perfect for relaxing or entertaining, along with the convenience of an attached 2-car garage. Ideally located near shopping, dining, schools, parks, and major commuter routes, this home combines comfort, versatility, and a convenient Winchester location.

609 Quartzite Cir, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$379,000
3 Beds ⋅ 4 Baths
Welcome home to this beautifully maintained 3-bedroom, 2-full-bath/2 half bath, end-of-row townhouse! Perfectly situated in a highly desirable, family-friendly neighborhood, step inside to find gleaming hardwood floors and large, sunlit rooms that offer plenty of space to live and entertain. The heart of the home features a spacious kitchen that flows seamlessly onto a private rear deck—perfect for morning coffee or weekend barbecues. Outside features a private backyard with lovely patio and shed. Cozy up by one of the two beautiful fireplaces, located on both the main level and in the fully finished basement. The lower level provides excellent flexible space for a family room, home office, or gym. This move-in-ready property comes complete with all appliances and boasts a newer roof for ultimate peace of mind. Enjoy the convenience of dedicated off-street parking and a location that can't be beat. You are just minutes away from beautiful downtown shopping, vibrant restaurants, and houses of worship. Don't miss your chance to own this turnkey gem in an ideal community. See list of improvements in Documents.

2055 Cidermill Ln, Winchester

Listing courtesy of Colony Realty. Contact:

$360,000
3 Beds ⋅ 3 Baths
Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water heater, 2025 - new sewer line under driveway & from driveway to street, new LVP in kitchen, 2026 - replaced / leveled living room floor & subfloor, new LVP. Schedule your tour today!

117 E Pall Mall St, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$334,900
3 Beds ⋅ 3 Baths
New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter thoroughfares. No HOA.

913 Orchard Hill Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$449,000
4 Beds ⋅ 2 Baths
Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a true gem—a finished attic with an exposed brick wall, providing a unique, flexible space ideal for a home office, a creative studio, or a quiet retreat. Step outside and discover the large covered front porch. Adorned with a stylish wooden ceiling, it's the perfect spot to relax and enjoy the neighborhood. The rear deck and fully-fenced backyard offer a private oasis for outdoor gatherings. Situated on a desirable corner lot, the home's prime location puts you just moments away from Winchester's best shopping, dining, and schools. Parking is a breeze with a detached garage and a private driveway, providing abundant off-street parking—a valuable convenience in this downtown neighborhood. Offering recently updated HVAC on 3 levels.

420 W Cork St, Winchester

Listing courtesy of Colony Realty. Contact:

Start Your Search