Winchester City Homes with Colonial Style

Winchester City Homes with Colonial Style

Welcome to Winchester City, Virginia, a charming locale steeped in rich history and vibrant culture. Nestled in the picturesque Shenandoah Valley, Winchester is renowned for its stunning landscapes, historic architecture, and a warm community spirit. With a population that embraces both tradition and modernity, this city has something for everyone—from bustling downtown shops and delightful eateries to serene parks and outdoor recreational opportunities.

One of the most captivating features of Winchester is its architectural heritage, particularly the prevalence of Colonial-style homes. These stately residences exude timeless elegance, showcasing classic features such as symmetrical facades, gabled roofs, and inviting front porches. The Colonial homes in Winchester often boast intricate woodwork, spacious layouts, and expansive gardens, making them perfect for families and those seeking a slice of historic charm.

Living in a Colonial-style home in Winchester means more than just enjoying beautiful architecture; it’s about becoming part of a community that values its history while looking towards the future. Residents can partake in numerous local events, explore historical sites such as the Museum of the Shenandoah Valley, or take leisurely strolls through the scenic Old Town, where cobblestone streets and quaint boutiques await.

Whether you’re searching for a family-friendly neighborhood or a serene retreat, Winchester City offers an array of Colonial-style homes that cater to diverse tastes and lifestyles. Discover the perfect blend of history and modern living in this enchanting Virginia city, where every home tells a story and every street invites exploration.

Newest Winchester City Homes with Colonial Style

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

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

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:

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

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

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:

3 Beds ⋅ 4 Baths

Situated in the charming Orchard Hill subdivision, this delightful twin home offers a perfect blend of comfort and functionality. Built in 1987, this Colonial-style residence boasts a classic brick exterior that exudes warmth and character. With over 2,000 square feet of thoughtfully designed living space, this home is ideal for those seeking a cozy retreat. As you approach the property, you'll appreciate the inviting sidewalks that lead you to the entrance, enhancing the neighborhood's friendly atmosphere. The well-maintained lot, spanning 0.1 acres, provides a manageable outdoor space, perfect for gardening or enjoying a quiet afternoon in the sun. An outbuilding adds extra storage or workspace, catering to your organizational needs. Step inside to discover a fully finished walkout basement, offering versatile space that can be transformed into a recreation room, home office, or guest suite. The interior features a harmonious blend of carpet, luxury vinyl plank, and vinyl flooring, ensuring both style and comfort throughout the home. The heart of the home is the spacious kitchen, equipped with modern appliances including a dishwasher, smooth top range, refrigerator, microwave, and range hood. The adjoining dining area flows seamlessly into the living space, where a fireplace creates a cozy ambiance for those chilly evenings. With three generous bedrooms and three full bathrooms plus an additional half bath, this home provides ample space for relaxation and privacy. The convenience of upper-floor laundry adds to the home's appeal, making daily chores a breeze. Parking is easy with a driveway accommodating two vehicles, ensuring you and your guests have easy access. This property is not just a house; it's a place where memories are made. Whether you're hosting friends for a barbecue in the backyard or enjoying a quiet evening on the incredible screened in porch this home offers the perfect backdrop for your lifestyle. Experience the charm and comfort of Orchard Hill living-your new home awaits!

2104 Stoneleigh Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

3 Beds ⋅ 2 Baths

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

Listing courtesy of MarketPlace REALTY. Contact:

4 Beds ⋅ 2 Baths

Seller offering closing cost assistance on select offers—contact the listing agent for details. Welcome to this beautifully renovated historic home in the heart of Old Town Winchester, where timeless charm meets modern living. This move-in-ready 4-bedroom, 2-bath home has been thoughtfully updated throughout, featuring a stunning kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and designer finishes. Enjoy new flooring, fresh paint, updated lighting, and renovated bathrooms. Outside, relax on the inviting covered front porch or entertain on the rear patio overlooking the spacious fenced backyard. Just minutes away from the Winchester Walking Mall, restaurants, shopping, breweries, parks, and local events, this turnkey home offers the perfect blend of historic character, modern updates, and an unbeatable location. Schedule your private tour today!

21 E Germain St, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810

4 Beds ⋅ 4 Baths

Exceptional opportunity to own this beautifully crafted custom all-brick home on Winchester's desirable east side, nestled in an established neighborhood just minutes from Route 7, downtown Winchester, schools, shopping, dining, hospitals, and major commuter routes. Designed for both everyday living and entertaining, this impressive residence features an open-concept floor plan with gleaming hardwood floors, abundant natural light, custom built-ins, and a cozy gas fireplace. The contemporary gourmet kitchen showcases granite countertops, stainless steel appliances, a spacious pantry, and a generous breakfast area, flowing seamlessly into the Large dining and living spaces. The thoughtfully designed layout offers four spacious bedrooms, each with access to a full bathroom. On the main level, you'll find a welcoming guest bedroom with a nearby full bath, along with the luxurious primary suite featuring a private ensuite bath with a tub/shower combination and walk-in closet. A convenient laundry room with utility sink is located just off the kitchen and provides access to a covered carport and outdoor sitting area. A private upper-level suite includes its own entrance on main level with a connected living room, two upper level bedrooms, and full bath, and sitting area making it ideal for an in-law suite, au pair quarters, or private guest accommodations. Adding even more versatility, the detached two-car garage is topped by a fully equipped apartment complete with a bedroom, full bath, and kitchen/living area—perfect for rental income, multigenerational living, a home office, or long-term guests. Parking is abundant with front and rear driveways, the detached two-car garage, and additional street parking. Combining timeless craftsmanship, flexible living spaces, income-producing potential, and an unbeatable location, this one-of-a-kind property truly offers something for everyone. Don't miss the opportunity to make this exceptional home yours!

687 Woodland Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

3 Beds ⋅ 2 Baths

Welcome to this charming historic home in Old Town. A spacious 3-bedroom Colonial, where timeless character meets modern comfort in the heart of Winchester. Thoughtfully updated with today's buyer in mind, this charming residence offers upgraded amenities while preserving its classic appeal. Inside, you'll find generous living spaces filled with natural light, along with a walk-up attic offering abundant storage or future expansion potential. The full basement is ready to be finished, providing the perfect opportunity to create additional living space, a home gym, recreation room, or workshop. Outside, the detached garage offers exceptional versatility for parking, storage, hobbies, or a workshop. Ideally situated just minutes from the heart of historic Old Town Winchester, you'll enjoy the convenience of walking to local restaurants, boutique shopping, entertainment, the Shenandoah Valley Museum, and Valley Health Winchester Medical Center. Whether you're looking for a primary residence or an investment in one of Winchester's most desirable locations, this move-in-ready home offers the perfect combination of historic charm, modern updates, and unbeatable convenience.

108 Morgan St, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

3 Beds ⋅ 4 Baths

Welcome to this beautifully maintained townhome in the desirable Meadowbranch Mews community, where comfort, style, and convenience come together. Featuring three bedrooms and three-and-a-half bathrooms, this brick-front home offers timeless curb appeal and thoughtfully designed living spaces throughout. Step inside to a welcoming foyer with tile flooring that leads to an open and inviting main level. Rich hardwood floors, abundant natural light, and a neutral color palette create a warm atmosphere in the spacious living and dining areas. The kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, and a large center island with seating. Elevated ceilings enhance the home's airy feel, while a conveniently located powder room completes the main level. Upstairs, the spacious primary suite provides a relaxing retreat with a walk-in closet and private en-suite bath. Two additional bedrooms and a full hall bathroom offer plenty of space for family, guests, or a home office. The finished lower level adds exceptional flexibility with a large recreation room that can easily accommodate a media room, fitness area, playroom, or hobby space. This level also includes a guest room, full bathroom, laundry area, and generous storage. Recent updates include a new roof and gutters for added peace of mind. A private garage provides secure parking and extra storage, while the home's prime location places you just minutes from Winchester Medical Center, shopping, dining, and the charm of historic downtown Winchester. Residents of Meadowbranch Mews enjoy a low-maintenance lifestyle with community amenities that include a swimming pool, pickleball courts, picnic areas, snow removal, road maintenance, and trash service.

1352 Ramseur Ln, Winchester

Listing courtesy of Redfin Corporation. Contact:

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