Colonial Homes for Sale in Winchester County VA

Check out the Virtual Tour! Rich with character and steeped in history, this spacious vintage home sits proudly on a corner lot, offering timeless appeal with many original features still intact. From the moment you enter, you’ll appreciate the craftsmanship of a bygone era—complete with built-in bookshelves, a charming upper-level sleeping porch, and a traditional canning storage area in the

Jennifer Egen Samson Properties

THIS IS A MUST SEE! Wonderful location, 3 years new property, located in short drive to everything, Winchester. This is an offering you don't want to miss out on. Its not often that a nearly new construction home with all the best of everything comes on the market. For starters theres No HOA .All the appliances and operating systems are still under warranty and the interior is in blank canvas new

Dave Milburn Coldwell Banker Realty

Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and

Dan Whitacre Colony Realty

Welcome to this spacious and well-maintained home in the desirable Meadow Branch South community. Offering over 3,300 square feet, this 4-bedroom, 2.5-bath home provides the perfect blend of space, comfort, and thoughtful updates. The main level features an updated kitchen, ideal for both everyday living and entertaining, along with multiple living areas that offer flexibility for today’s

Kira Grubb Realty ONE Group Old Towne

Back and better than EVER! New Sales Price!! Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly $20,000 under appraisal value!! Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready

VAIBHAV AGARWAL Realty FC, LLC

Welcome to 1300 Caroline Street—where timeless design meets everyday functionality in one of Winchester’s most convenient locations. Perfectly positioned on a spacious 0.31-acre corner lot, this beautifully maintained residence offers 4 bedrooms, 3.5 bathrooms, a finished basement, and a desirable 2-car side-load garage. The main level showcases a thoughtfully renovated kitchen featuring updated

Lisa Behr Hunt Country Sotheby's International Realty

Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Check. Endless possibilities? Check!!! This amazing property, located within the Historic Winchester District, presents a one-of-a-kind opportunity to own a piece of history - all just minutes from the Old Town mall. The front of the main home dates back to 1856! You will surely fall in love with the wood

Kristin Crosby Samson Properties

The perfect old town Winchester location and ready for you to move in......Classic brick “American Foursquare” house in Winchester’s historic district. . This well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front

Roger Lamborne MarketPlace REALTY

Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot.The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to

Sineenat Sirimas Pearson Smith Realty, LLC

Beautiful brick-front Colonial in a prime location! Nestled in a quiet neighborhood yet just minutes from I-81 and local amenities, this stunning home offers the perfect blend of convenience and tranquility.Brand new LVP flooring was just installed on both levels. Step into the grand two-story foyer, flanked by a formal living room and dining room accented with elegant columns and a cozy

Elizabeth Flood Keller Williams Realty

Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and

Gillian Greenfield Coldwell Banker Premier

OPEN HOUSE SATURDAY MAY 9th 1 - 3 PM!Located in The Old Town Winchester area but on a quiet street, we are happy to list this nicely remodeled 2 level home. Since the purchase of this center hall Circa 1930s home, the owners have totally resurfaced and painted the metal roof, installed windows,installed all new plumbing and electrical services, a dual zoned HVAC system, sanded the gleaming

Lisette Turner Century 21 Redwood Realty

Incredible location, incredible home! Relax on the elevated front porch overlooking Leicester St, or retreat to the private back yard. Inside, gleaming wood floors and original trim compliment the new kitchen and bathrooms. HVAC, wiring, plumbing, windows, roofing, and siding have been lovingly replaced/updated in the last 5 years. This home is walkable to everything, and sits on a calm side

William Steinmetz RE/MAX Roots

An amazing totally renovated 1820 home in the heart of downtown/historic district!! This home features: 4bedrooms, 3 full baths, remodeled gourmet kitchen, refinished hardwood floors, barn style doors, deluxeprimary bath, and so much more.

Clark Smith Samson Properties

Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

Mafe Zambrano Inmobiliaria De Las Casas LLC

**Motivated sellers!! Now offering to pay buyers closing costs!!** TONS OF UPGRADES! This home has been updated top to bottom. From the roof, windows, kitchen, bathrooms, light fixtures, HVAC, and so on. Located just 1 block from Handley High School, this home and all of its high end improvements make it a treasure waiting to be discovered. As you walk through this home you'll notice that a ton

Michael Sprague Samson Properties

Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for

Laura White ERA Oakcrest Realty, Inc.

This diamond in the rough has solid bones and plenty of potential for the right buyer. The HVAC system is only two years old, the water heater is brand new, and both full bathrooms have already been updated. The home could use some fresh paint, and the dishwasher is currently not working, but the major systems are in great shape—making this an excellent opportunity for a starter home or

Jamie Cook Treck Realty LLC

Beautiful, just like brand new, 3 bedroom 2.5 bath end unit townhome located in The Lofts at Creekside! Walking distance to local restaurants and shopping here in Creekside. Home features large kitchen island, stainless steel appliances, and luxury vinyl plank flooring, private balcony, surrounded by open floor plan which provides for great entertainment. Nice upgrades all throughout the house!

Christopher Hild Realty FC, LLC

Claim your spot in the heart of the city with this authentic 1866 gem, perfectly positioned to enjoy everything downtown Winchester has to offer. Proudly displaying its Winchester Historic Building plaque, this home is just steps from the vibrant local dining scene, boutique shopping, parks, and schools. It’s a rare find that pairs 19th-century soul with modern reliability, featuring the coveted

Dan Whitacre Colony Realty

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

Dana Cloud Realty ONE Group Old Towne

ATTENTION ALL INVESTORS OR FUTURE LANDLORDS COME CHECKOUT THIS MULTI FAMILY 3 UNIT PROPERTY. IT CONSIST OF 2 HOUSES. EACH UNIT IS A 2 BED 1BATH EACH HAVE STOVE REFRIGERATOR MICROWAVE WASHER DRYER. CURRENTLY FULLY RENTED. SO NOW IS YOUR CHANCE TO OWN A TURNKEY RENTAL PROPERTY ALL WELL MAINTAINED WITH OFF STREET PARKING. CLOSE TO DOWNTOWN & SHOPPINGRESTRICTED SHOWINGS. NEW PIC'S COMING SOON.

Richard Kozlowski Long & Foster Real Estate, Inc.

Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Winchester’s historic downtown walking mall, offering easy access to restaurants, bars, boutiques, and entertainment. Originally built in the 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural charm, and

Janet Flaherty Keller Williams Realty

Distinctive home on the historic register, Winchester walking tour, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester; restaurants, festivals, shopping! Gorgeous inside and out. Fully renovated, 4 levels with a two-story log cabin (the blue building) likely built with timber from Fort Loudoun) , gourmet emodeled kitchen with gas cooking,

Roxanne Watts Coldwell Banker Realty

This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

Marco Novillo Spring Hill Real Estate, LLC.

Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking

Lawrence Lessin Homes By Owner, Inc.

A Stunning Brick Colonial residence graced by meticulously manicured gardens and lush vegetation, cocooning the property in a tranquil and private ambiance. Offering an array of amenities, each of its three immaculately finished floors mirrors the care bestowed upon the surrounding gardens. Generously proportioned rooms bathed in natural light enhance the spacious open plan living areas,

Kathryn Hallett Long & Foster Real Estate, Inc.

Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to everything while still offering the privacy and feel of a standalone home. Inside, you’ll find a

Mr. Nate Crandell HoneyWay

Step into this meticulously maintained colonial home, a testament to quality craftsmanship and thoughtful design by Richmond American Homes. Situated in the desirable Meadow Branch South neighborhood, this residence offers an exceptional living experience with a perfect balance of formal and casual spaces This home is situated in a vibrant community with easy access to major roads, shopping, and

Kim Kroner Washington Dulles Real Estate Group