Winchester City Homes for Sale

Winchester City Home Listings

$419,000
3 Beds 3 Baths VAWI2011614 MLS ACTIVE Status
Back on Market!!! A full bathroom was added to the property and it appraised for $435k when it had 2.5 bathrooms and now it has 3 full bathrooms. This exquisite Cape Cod residence, originally built in 1929 and set to undergo a stunning renovation in 2026, seamlessly blends timeless charm with modern luxury. Nestled in a desirable neighborhood, this home invites you into a warm and inviting atmosphere, perfect for creating cherished memories. Step inside to discover an open floor plan adorned with rich hardwood and luxury vinyl plank flooring, enhancing the home's elegance. The spacious dining area flows effortlessly into a beautifully appointed kitchen, featuring upgraded countertops and stainless steel appliances, including a dishwasher, microwave, and electric oven/range. Enjoy casual meals in the cozy kitchen table space, where culinary delights come to life. The living area boasts a charming fireplace, perfect for cozy evenings, while built-ins and crown moldings add a touch of sophistication. With three well-sized bedrooms and three bathrooms, including a luxurious tub shower, this home offers ample space for relaxation and rejuvenation. The partially finished basement, complete with a walkout level, provides endless possibilities for customization, whether as a home gym, office, or entertainment space. Outside, the driveway offers access to the basement, while the low-maintenance lot allows for easy enjoyment of your surroundings. Experience a lifestyle of comfort and elegance in this beautifully renovated home, where every detail has been thoughtfully designed for modern living.

131 Shirley St, Winchester

$499,900
3 Beds 3 Baths VAWI2011602 MLS COMING SOON Status
Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds.

510 S Cameron St, Winchester

$409,000
4 Beds 1 Baths VAWI2011520 MLS ACTIVE Status
Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

322 E Piccadilly, Winchester

$699,000
7 Beds 5 Baths VAWI2011542 MLS ACTIVE Status
Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester

$350,000
3 Beds 2 Baths VAWI2010942 MLS ACTIVE Status
Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal retreat for anyone seeking a warm and inviting atmosphere. As you step inside, you'll be greeted by a spacious layout that encourages both relaxation and entertaining. The partially finished basement offers endless possibilities-whether you envision a cozy family room, a home office, or a play area, the choice is yours! The main living areas are bathed in natural light, creating a welcoming ambiance that feels like home. The exterior of the property is equally inviting, with a classic brick façade that stands the test of time. Enjoy the convenience of on-street parking, ensuring that you and your guests always have a place to park. The surrounding neighborhood is a tapestry of tree-lined streets and friendly faces, fostering a sense of community that is hard to find. Location is key, and this home does not disappoint. Situated in a vibrant area, you'll find an array of local amenities just a stone's throw away. Explore nearby parks for leisurely strolls or picnics, and take advantage of local shops and eateries that add character to the community. Whether you're grabbing a morning coffee or enjoying a weekend brunch, the neighborhood offers a delightful selection of options to satisfy your cravings. For those who appreciate the outdoors, the proximity to parks and recreational areas provides ample opportunities for hiking, biking, and enjoying nature. The community is well-connected, making it easy to access nearby attractions and essential services. This charming ranch-style home is more than just a property; it's a place where memories are made and cherished. With its inviting atmosphere, convenient location, and potential for personalization, this residence is ready to welcome you home. Don't miss the chance to make this delightful space your own!

1048 Woodland Ave, Winchester

$615,000
5 Beds 4 Baths VAWI2011344 MLS ACTIVE Status
Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the main and upper levels, and meaningful improvements come together across three finished levels. The main level is designed for connection and comfort, beginning with a two-story foyer that opens into an airy, open-concept layout. The kitchen flows seamlessly into the main living area, creating an ideal space for everyday living and entertaining, while offering defined rooms for flexibility. Just off the kitchen, the mudroom connects to the garage and provides ample storage and seating when entering and exiting the home. A dedicated office provides a quiet place to work, and the formal dining room—enhanced with beautiful moldings—offers an elegant setting for gatherings. A separate music room adds space to relax or unwind. Throughout the main level, new crown molding, freshly painted walls and ceilings, and bamboo flooring create a cohesive feel, while brushed nickel finishes add a modern touch. The fireplace with new gas logs serves as an inviting focal point for the living area. From the main level, step through one of the new sliding glass doors onto the newly built deck, with stairs leading directly to the yard. This outdoor space is ideal for morning coffee, summer dinners, or entertaining friends. Upstairs, new oak hardwood flooring enhances the main stairs, landing, hallway, and primary suite, including a large double-sided walk-in closet. The entire upper level has freshly painted walls and ceilings, while new crown molding extends from the two-story foyer into the hallway. The primary bathroom has been updated and features heated flooring with app control for added comfort. The additional upstairs bathroom has also been updated, and the other three upstairs bedrooms feature new carpeting, giving the entire level a fresh, cohesive feel. One of the most convenient features of the upper level is the dedicated laundry room—no more carrying baskets between floors. Finished with waterproof LVT flooring, cabinetry, a countertop, walk-in closet shelving, and included Consumer Reports top-rated high efficiency washer and dryer, it is both practical and well-appointed. The lower level expands the home even further with nearly 1,000 additional finished square feet. Fresh paint and new carpeting throughout give this level a clean, updated feel. This space includes a large recreation room with a separate entry, offering excellent flexibility for entertaining or everyday living. It also features a fifth bedroom (non-legal egress) and a full bathroom, and an additional washer and dryer hookup - making it ideal for guests, extended stays, or multi-use living arrangements. Behind the scenes, the home has been carefully maintained and upgraded for long-term comfort and efficiency. The roof, washer and dryer, and HVAC system are all approximately four years old. The HVAC system is a Carrier air handler paired with a Carrier air-conditioning unit featuring a variable-speed inverter compressor, providing exceptional efficiency and helping keep energy costs low. Additional improvements include upgraded R-52 attic insulation, Honeywell Home app controls, and a Tamko Titan architectural shingle roof rated for 50 years. The attached 2-car garage has also been enhanced with highly insulated Lewin-Yount doors and Aladdin Connect smartphone control. With approximately 2,700 square feet above grade plus nearly 1,000 finished square feet in the basement, this 5-bedroom, 3½-bath Winchester City home offers a rare combination of space, versatility, and move-in-ready convenience. From its open and functional floor plan to its hardwood and bamboo flooring, updated systems, flexible living spaces, and thoughtful upgrades throughout, this is a home designed for both everyday living and memorable gatherings. Come inside, take your time, and imagine making it yours. Welcome HOME!

922 Wayne Dr, Winchester

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Winchester City, VA, Homes for Sale

Winchester City, located in the northern Shenandoah Valley of Virginia, is a historic and vibrant community with a rich past and a promising future. With a population of around 27,000, the city offers a small-town feel with all the amenities of a larger city. The Winchester City real estate market is welcoming and friendly, with a strong sense of community. The downtown area is filled with charming shops, cafes and restaurants, and residents of Winchester City homes can enjoy events like the annual Apple Blossom Festival and the First Friday Night Live concert series.

One of the biggest draws of living in Winchester City homes is their location. Nestled in the heart of the Shenandoah Valley, residents have easy access to various outdoor activities, including hiking, biking and fishing. The area is also home to several parks and nature preserves, including the Shenandoah National Park and the Sky Meadows State Park.

Winchester City has a rich history dating back to the colonial era, and the area played a significant role in both the Revolutionary and Civil Wars. Visitors can learn about the city's past by visiting historic sites like Stonewall Jackson's Headquarters Museum and the George Washington's Office Museum.

Residents of Winchester City homes can also enjoy a variety of amenities, including excellent schools, healthcare facilities, and cultural institutions. The city is home to Shenandoah University, which offers a range of academic programs and cultural events, including theater productions and music concerts. The Museum of the Shenandoah Valley is another popular cultural attraction featuring exhibits on local history and art.

Public Transportation Options

The Winchester City real estate market offers several public transportation options for residents and visitors to get around the city and the surrounding area. Whether you prefer to take the bus, train or a ride-sharing service, options are available to meet your needs.

Winchester Transit: The city operates a public bus service called Winchester Transit, which provides fixed-route and paratransit services within the city limits. The bus routes cover most of the city, including major shopping areas, medical facilities, and government offices. The paratransit service is available for eligible individuals who cannot use fixed-route buses due to a disability.

Virginia Regional Transit: Virginia Regional Transit (VRT) is a regional public transportation system that serves Winchester City homes and the surrounding counties. VRT operates several bus routes that connect Winchester City to other cities and towns in the area, including Front Royal, Stephens City, and Berryville. The bus routes are designed to meet the needs of commuters, students and other passengers traveling to work, school or other destinations.

Amtrak: Winchester City is served by Amtrak's Capitol Limited and Cardinal train services, which connect the city to major cities on the east coast, including Washington D.C., Baltimore, Pittsburgh and Chicago. The city's Amtrak station is downtown and offers daily departures and arrivals.

Taxi and Ride-Sharing Services: The Winchester City real estate market also has several taxi and ride-sharing services, including Uber and Lyft, which provide on-demand transportation services within the city and the surrounding area. Taxis can be hailed on the street or by a local taxi company.

Shopping Centers

Residents of Winchester City homes can visit a variety of shopping centers that cater to the needs and preferences of different shoppers. There is something for everyone in this vibrant city, from small boutiques to large shopping malls. Whether you're looking for the latest fashion trends, home decor, or a bite to eat, there is sure to be a shopping center in Winchester that suits your needs. Here are some of the notable shopping centers near Winchester City homes for sale:

Apple Blossom Mall: Located at 1850 Apple Blossom Dr, Winchester, VA, Apple Blossom Mall is one of the largest shopping centers in the area. The mall features more than 80 stores, including Macy's, JCPenney and Belk, as well as a food court and a cinema.

Creekside Station: Creekside Station is a shopping center at 3103 Valley Ave, Winchester, VA. It features several retailers, including Target, Bed Bath & Beyond, and Michaels, as well as various restaurants and services.

Downtown Winchester: The downtown area of the Winchester City real estate market offers a unique shopping experience with a mix of small boutiques, antique shops, and specialty stores. Visitors can stroll through the pedestrian-friendly streets and discover hidden gems, such as the Shenandoah Valley Discovery Museum and the Old Court House Civil War Museum.

Winchester Gateway: Winchester Gateway is a shopping center at 1900 S Pleasant Valley Rd, Winchester, VA. The shopping center features several retailers, including Walmart, Marshalls, Ross Dress for Less, and restaurants and services.

Jubal Square Shopping Center: Jubal Square Shopping Center is at 2144 S. Pleasant Valley Rd, Winchester, VA. It features a variety of stores, including Kohl's, Petco and Dollar Tree, as well as several restaurants and services.

Summary

The Winchester City real estate market is a vibrant and welcoming community that offers a small-town feel with all the amenities of a larger city. With its stunning natural beauty, rich history, and cultural attractions, homes for sale in Winchester City are a great choice. Whether you're interested in outdoor activities, cultural events, or simply soaking up the local atmosphere, there is something for everyone in this charming community of Winchester City homes.

Set Up a Time to View a Winchester City Home!

Call us at 703-462-0700 or email us at DarrenRobertsonHomes@gmail.com to schedule a time to see an available property in this Shenandoah Valley community.

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