Winchester Homes with Colonial Style

Winchester Homes with Colonial Style

Welcome to Winchester, Virginia, a charming city steeped in rich history and vibrant culture. Nestled in the picturesque Shenandoah Valley, Winchester is known for its stunning landscapes, historic architecture, and a warm sense of community. With a population of around 28,000, this city offers a delightful blend of small-town charm and modern amenities, making it an ideal place to call home.

One of the most captivating features of Winchester is its array of beautiful homes, particularly those showcasing Colonial-style architecture. These homes, often characterized by their symmetrical facades, grand columns, and elegant gabled roofs, embody the timeless elegance of early American design. Many of these Colonial residences are situated in tree-lined neighborhoods, providing a serene and inviting atmosphere for families and individuals alike.

Living in Winchester means enjoying a lifestyle enriched by history and nature. The city boasts an array of parks, historical sites, and cultural events, ensuring there’s always something to explore. Take a stroll through the historic downtown area, where you’ll find boutique shops, delightful eateries, and local galleries that reflect the community’s artistic spirit.

For outdoor enthusiasts, the surrounding Shenandoah National Park offers breathtaking views and endless opportunities for hiking, biking, and wildlife observation. Whether you’re drawn to the allure of Colonial homes or the vibrant community spirit, Winchester, Virginia, is a place where history meets modern living, creating a perfect backdrop for your next chapter. Explore your dream home in this enchanting city today!

Newest Winchester Homes with Colonial Style

4 Beds ⋅ 3 Baths

Beautiful 4 bedroom, 2.5-bath brick-front home situated on 2 private acres, offering the perfect blend of space, comfort, and recent updates. Shower on the main floor in laudry room, bonus room being used as a main floor bedroom. Major updates provide peace of mind, including a new roof (2025), HVAC systems replaced in 2023, 2024, and 2025, a new pressure tank, water heater, sump pump, Culligan water softener, and updated light fixtures Enjoy outdoor living on the spacious deck and paver patio, ideal for entertaining or relaxing. Inside, the kitchen features hardwood flooring, Corian countertops, a pantry, and ample cabinet space. The main level showcases elegant crown molding, a convenient laundry room with a shower, and freshly painted rooms that give the home a bright, refreshed feel. The oversized primary suite includes a huge walk-in closet for exceptional storage. . Full, unfinished, walkout level basement. Enjoy the privacy of country living while still being conveniently located to nearby amenities.

175 Shields Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362

3 Beds ⋅ 3 Baths

Charming Country Farmhouse with Modern Updates & Unrestricted Property! Welcome to this charming 1940's farmhouse, thoughtfully renovated and expanded in 2006 to blend timeless character with modern convenience. Offering 3 bedrooms and 3 full bathrooms, this inviting home provides a flexible layout that's perfect for a variety of lifestyles. The main level features a kitchen that flows seamlessly into the living room, creating the perfect gathering space. Two bedrooms and two full bathrooms are conveniently located on the main floor, including a comfortable primary suite complete with a generously sized walk-in closet and private ensuite bath. Upstairs, you'll find a spacious landing area leading to the third bedroom, which boasts its own ensuite full bath and access to a private outdoor deck—an ideal spot to enjoy your morning coffee or unwind at the end of the day. The walk-up attic offers excellent potential to finish and create additional living space, whether you envision a home office, bonus room, or hobby area. Comfort is ensured year-round with a central HVAC system, supplemented by a mini-split system and propane heater for added flexibility. The home also includes both an interior-access cellar and a traditional exterior root cellar, providing abundant storage options. Situated on a quarter-acre lot, the property also features a 24' x 24' detached two-car garage with automatic door openers and 30-amp electrical service, making it ideal for vehicles, a workshop, or recreational equipment. With no restrictions, this property offers many possibilities. Whether you're looking for modern living in a peaceful rural setting, homestead living, or simply room to create your own, this unique property is ready to welcome you home.

2346 Welltown Rd, Winchester

Listing courtesy of Touchstone Realty, LLC. Contact:

4 Beds ⋅ 4 Baths

Welcome to an extraordinary custom-built all-brick estate nestled on five beautifully manicured acres in the highly sought-after Apple Pie Ridge area. This exceptional property blends timeless elegance, quality craftsmanship, and modern updates to create a truly one-of-a-kind retreat. From the moment you arrive, the winding approach and picturesque setting set the stage for what's inside. Designed for both grand entertaining and everyday comfort, the home features three spacious bedrooms, three full bathrooms, and two half baths, with flexible living spaces that can easily accommodate a bedroom, guest suite, or recreation room. The heart of the home is the spectacular gourmet kitchen, where culinary enthusiasts will appreciate granite countertops, a commercial-size refrigerator, two Wolf wall ovens, a cooktop with downdraft ventilation, an expansive multi-level island with prep sink, and instant hot water. The kitchen flows effortlessly into the inviting family room with custom built-ins and a cozy gas fireplace, while the adjoining sunroom fills the home with natural light and offers panoramic views of the backyard oasis. Outside, resort-style living awaits. The inground pool is the centerpiece of the backyard, creating the perfect setting for relaxing afternoons, gatherings, and unforgettable summer entertaining. A brick patio overlooks the beautifully landscaped grounds, offering a peaceful space to unwind and enjoy the privacy of your surroundings. The primary suite is a private sanctuary complete with its own gas fireplace, cedar-lined walk-in closets with custom built-ins, and an impressive spa-inspired bath featuring a jetted soaking tub and separate shower. Additional bedrooms are generously sized, while a spacious office with custom built-ins provides the ideal work-from-home space. A large bonus room with a full bath offers endless possibilities and the fourth-floor bedroom is an incredible private retreat that any teenager or overnight guest will love. Movie nights become an event in the dedicated theater room, while the expansive unfinished basement offers tremendous potential for additional finished living space, a home gym, workshop, or recreation area. Car collectors, hobbyists, and outdoor enthusiasts will appreciate the attached and detached garages with room for up to six vehicles. The detached heated and cooled three-bay garage includes a full bath, separate septic system, and unfinished space above offering endless possibilities. This meticulously maintained home has been thoughtfully updated with two new HVAC systems, a new hot water heater, a new water softener, a new dishwasher, and a new washer and dryer. The original portion of the home also features premium Andersen windows with upgraded screens, enhancing both energy efficiency and timeless appeal. Properties of this caliber rarely become available.

194 Glendobbin Ln, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

4 Beds ⋅ 4 Baths

Situated on nearly 3 acres of peaceful, private land, 4241 Cedar Creek Grade offers a truly remarkable retreat framed by sweeping, 360-degree views of rolling hills and lush greenery. The exterior commands immediate curb appeal, highlighted by an impressive covered front porch with pillars, a well-manicured lawn, a wide driveway, and an attached three-car garage. Inside, the main level features high-end finishes like pristine hardwood floors and detailed crown molding throughout. A stately formal living room boasts elegant lunette windows, while the separate formal dining room showcases classic wainscoting and tray ceilings. At the heart of the home, the gourmet kitchen shines with upgraded countertops, maple cabinetry, a breakfast bar for additional seating, and stainless steel appliances. It seamlessly flows into a light-filled family room anchored by built-in storage and a cozy gas fireplace, extending into a captivating sunroom where vaulted wooden ceilings and wall-to-wall windows frame uninterrupted, panoramic views of the countryside. A convenient half bath completes the main floor. Upstairs, the expansive primary suite serves as a restful haven, featuring morning views, tray ceiling, a large walk-in closet, and a spa-like ensuite bath equipped with double sinks, a walk-in steam shower, and a relaxing corner soaking tub. Two additional bedrooms share a full bath, while a massive bonus room with its own attached full bath provides endless possibilities as a spacious fourth bedroom, recreation room, playroom, home office or gym. A dedicated upper-level laundry room adds ultimate everyday convenience. Additionally, the full unfinished walkout basement includes rough-in plumbing offering the perfect blank canvas for future expansion, while Glofiber high-speed internet ensures seamless connectivity throughout the property. Beyond the interior, the property unfolds into an extraordinary outdoor oasis built for lavish entertaining. Unwind in the private hot tub on the deck, dine alfresco on the patio, or relax under the cool shade of the covered gazebo—all set against the backdrop of a level, sprawling yard and picturesque scenery. This is more than just a home; it is a private sanctuary offering a lifestyle of unmatched tranquility and effortless luxury just minutes from town.

4241 Cedar Creek Grade, Winchester

Listing courtesy of Colony Realty. Contact:

This beautifully maintained 3-bedroom, 1.5-bath townhome offers three finished levels of living space with even more potential in the basement to create an additional bedroom, office, or recreation room. Step inside to find numerous recent updates, including new LVP flooring, fresh paint, updated lighting, new carpet upstairs, updated interior door hardware, a new washer and dryer, and a new hot water heater with updated plumbing. The spacious living areas flow seamlessly to a large rear deck overlooking peaceful woods, providing the perfect spot to relax or entertain. The fully fenced backyard is ideal for pets, play, or gardening. The HOA makes maintenance easy by mowing the front lawn and offers excellent neighborhood amenities, including a community in-ground pool, playground, and dog park, giving you resort-style living close to home.

120 Scirocco Ln, Winchester

Listing courtesy of Mountains Edge Realty LLC. Contact: 5406831891

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

4 Beds ⋅ 4 Baths

Welcome to this exceptional 4-bedroom, 3.5-bath Colonial in the sought-after Raven Pointe subdivision, where luxury living extends well beyond the front door. The backyard is a true showstopper, featuring a one-year-old 20' x 40' heated Hayward OmniLogic saltwater pool with a tanning ledge, sunken spa, and Coverstar automatic safety cover. A covered Trex deck with a porch swing overlooks the private backyard, creating the perfect space for relaxing or entertaining. Inside, the main level offers a private home office with custom built-ins, a formal dining room, a spacious family room with a gas fireplace, and a beautifully appointed kitchen featuring a large center island, butler's pantry, stainless steel appliances, gas cooking, and a bright breakfast room. Upstairs, the spacious primary suite includes luxury vinyl plank flooring, a walk-in closet, and a spa-like bath with a jetted tub, walk-in shower, and dual vanities. Three additional bedrooms, a versatile bonus room, and an upper-level laundry room complete the second floor. The finished walk-up basement is made for entertaining with a large recreation room, wet bar with a built-in ice maker, full bath, storage room, and a flexible bonus room that can serve as a fifth bedroom, home gym, or office. Located in Raven Pointe with sidewalks and streetlights, this home is just minutes from shopping, dining, schools, and commuter routes. Offering an incredible combination of elegant living spaces and a resort-style backyard, this is a home you won't want to miss.

107 Cahille Dr, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

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

5 Beds ⋅ 5 Baths

Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room with 20-foot ceilings, custom built-ins, a gas fireplace, and high windows featuring remote-controlled custom shades. The gourmet kitchen boasts granite countertops, soft-close cabinets, stainless steel appliances, double wall ovens, a gas cooktop, and opens seamlessly to a second living area with a warm gas fireplace. Main-level primary suite offers tray ceilings, a custom walk-in closets one with a built-in makeup vanity, and a bathroom with dual vanities and a large walk-in shower. Upstairs, you will find two additional spacious bedrooms, a full bath, plus a private in-law suite with its own en-suite bathroom. The bright walk-out lower level features a spacious rec room, full bathroom, bedroom, and a dedicated office space with a window that can also serve as a versatile bonus room. Enjoy outdoor living from the expansive composite deck or relax on the lower covered patio with ceiling fans giving an outdoor living room feel overlooking a private yard supported by an underground irrigation system. Complete with an oversized 3-car garage and located just minutes from I-81, shopping, and downtown Winchester!

243 Summerfield Dr, Winchester

Listing courtesy of Colony Realty. Contact:

5 Beds ⋅ 3 Baths

COMING SOON! Being beautifully remodeled and updated, this home is getting a fresh new look inside and out! Enjoy relaxing times on the expansive front porch and entertain year-round on the covered rear deck in private back yard. More details, professional photos, and a full list of features are coming soon—stay tuned for this exciting opportunity in Winchester!

139 Darby Dr, Winchester

Listing courtesy of Coldwell Banker Realty. Contact: chrissi.chapman@cbmove.com

4 Beds ⋅ 4 Baths

Gorgeous 4-Bedroom Colonial in Sought-After Sovereign Village! This beautifully maintained home is nestled on a large cul-de-sac, offering privacy, space, and comfort both inside and out. This home boasts a well-designed layout perfect for everyday living and entertaining. The bright, open main level with shining hardwood floors creates a warm and inviting atmosphere. Cozy up by the gas fireplace in the living area or enjoy meals in the spacious bay window style dining area overlooking the backyard. The chef's kitchen with large island, granite countertops and stainless steel appliances (BRAND NEW REFRIGERATOR!) opens seamlessly to the living spaces and offers plenty of room for meal prep and gatherings. Step outside to the fantastic Private Deck, Patio and Backyard, ideal for outdoor entertaining, gardening, or simply relaxing in your own Peaceful Oasis. On the second level, the spacious primary suite has a large walk-in closet, ensuite with a jacuzzi tub, and recessed high ceilings that add so much character. The two additional bedrooms are bright, generously sized and share a full hallway bathroom. The laundry room is right outside of the large 4th bedroom with its own private bathroom and walk in closet. The mostly finished basement has new LVP (photos not updated), abundant storage space and the main area has so many possibilities! Additional highlights include: Brand New HVACS, Brand New Sump Pump, New Water Softener & New Water Heater. Community Pool Access (Pool membership for Sovereign Village residents is $210 as long as in good standing with the HOA. Senior Passes for those 55+ is $176.) Located on a Cul-De-Sac and Walking Distance to the Elementary School.

104 Murphy Ct, Winchester

Listing courtesy of Epic Realty, LLC.. Contact: (703) 328-3000

3 Beds ⋅ 4 Baths

PRICE ADJUSTMENT. 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:

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