Downtown Winchester Homes for Sale

Welcome home to this charming, light filled Dutch Colonial in the heart of downtown Winchester. With four livable levels, this three bedroom, 2 bath home has been lovingly updated and renovated over the years embracing the charm of a bygone era and offering modern conveniences. Updates include the addition of a dual zone heat pump system (2019) providing cooling and heating to all four levels of

Dana Cloud Realty ONE Group Old Towne

Classic craftsman style bungalow featuring a covered front porch supported by Tuscan columns located in the historic district. Super location between Washington and Stewart streets, convenient to everything in Old Town and within feet of the parade route! Other features include tons of storage in three floors of living space with three or four bedrooms, one of which can be used as a library or

Kathrin Donovan Keller Williams Realty

It's all about spectacular mountain views! Built on one of the highest lots in Winchester by the area's premiere builder, Rhodes Brothers. Wake every morning to the fantastic views from the primary bedroom or enjoy your coffee while gazing at Great North Mountain. But this classic colonial home has a lot more to offer, including remodeled baths and kitchen, comfortable sunroom, five bedrooms, and

John Schroth Colony Realty

Multifamily, Professional Office, Historical Residence, or a combination of any of these opportunities! Even potential bed and breakfast or events center! Located in Historical Old Town Winchester, Holly House offers three floors, totaling over 7650 +/- SF, PLUS a HUGE outdoor English courtyard, ideal for urban gardening, building expansion, additional parking or pool! Iconic Federal Style

Gillian Greenfield Coldwell Banker Premier

Price Reduced! Welcome home to this beautifully renovated home in the heart of the City of Winchester. No detail was spared in bringing this home back to life. New roof, windows, hvac system, decks, electrical, plumbing, interior gutted and modernized. The stunning transformation includes the addition of a third level bedroom and bathroom making this a four bedroom, three and a half bath home.

Dana Cloud Realty ONE Group Old Towne

Rare and unique opportunity! Be just the second owner of this modern, custom, architect designed, home unlike any other! This one-of a kind contemporary home sits on the slope of one of the highest points in Winchester. It was designed by renowned local architects, Reader and Swartz, and built in 2006 by Ritter Construction. The Handley Heights location, next to an old Winchester neighborhood,

John Scully Colony Realty

Cherish Green Coldwell Banker Elite

Modern luxury meets timeless quality at 512 Miller Street! FAUVER & BROWNING Homes is offering this 3-bed + flex space on the main floor, 3-bath stunner loaded with Anderson windows and hardwood floors throughout.Love to cook? The GE Profile kitchen with granite counter tops and walk-in pantry delivers.Low-maintenance LP SmartSide keeps your curb appeal on

Mary Casselano Dream Real Estate

Enjoy the charm of this all-brick traditional home with lovely hardwood floors throughout. Nice size primary bedroom, all bedrooms have closets, and several recent updates in 2024 make this home absolutely move-in ready! You can decide if you prefer relaxing on your front or back porch or enjoying coffee on your rear balcony. There is also a back patio area if you want to grill your favorite

Pamela Foltz Realty ONE Group Old Towne

**OFFER DEADLINE MONDAY APRIL 21ST AT 2PM**Investor, builder, or renovation enthusiast—this is the opportunity you’ve been waiting for!This 2-bedroom, 1-bath home is a true fixer-upper with serious potential. Whether you’re looking to take on a full gut renovation or tear it down and start from scratch, this property is a blank canvas ready for your vision. With 882 square feet of

Chris Craddock EXP Realty, LLC

Charming Historic Home in Downtown Winchester – Move-In Ready!If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name!From the moment you step onto the inviting covered porch and through the front door, you’ll feel right at

Jeanne Mezzatesta Colony Realty

Charming Cape Cod in the Heart of Downtown Winchester! This beautifully maintained 3-bedroom home seamlessly blends timeless character with luxurious modern updates. Hardwood floors grace the main level, complementing a fully renovated kitchen featuring high-end finishes and ample table space. The bathrooms have been thoughtfully remodeled with upscale materials, new flooring and elegant touches

Holly Wilson Samson Properties

Historic Charm? Check!Modern Amenities? Check!Location? Check!Welcome to 320 S. Cameron Street! Built in 1773, this property will transport you back in time as soon as you arrive! The outside is host to 3 shops/outbuildings; some with power, an English garden, and original horse hitching posts! From the side porch, you will enter a newly renovated kitchen featuring stainless steel appliances and

Matt Leiva Keller Williams Realty

This charming classic brick ranch in Winchester, VA, features 3 bedrooms and 2 full bathrooms, with easy access to downtown Winchester. As you approach, the large covered front porch sets a welcoming tone. The basement, with a separate entrance and extra bedrooms, is large and very clean. It has a laundry area and one full bathroom, and the family room can be converted into a bedroom. Recent

Nathalie Acosta Spring Hill Real Estate, LLC.

Wooden construction, Alley side home ready for construction. Boarders Downton Winchester, blocks form Historic Old town, Walking Mall and restaurant Alley. 5 minutes drive to Shenandoah University. Winchester has been named fastest growing place in all of VA. Best place to retire by FORBS magazine. 15 hour outside of Washington DC excellent location for rental. City approved plans to

Carlos Beamon Samson Properties

Welcome to this centrally located home in the heart of Winchester. With easy access to I-81, this home is in a great commuter's location. Just a quick walk or drive away are the charming shops and restaurants of Historic Old Town Winchester. The main level features hardwood floors, a living room with wood-burning brick fireplace and a formal dining room, featuring a charming a built in China

Heloisa Amar Samson Properties

?? LOCATION, LOCATION, LOCATION! Charming Brick Bungalow in Prime Downtown Winchester!?? This delightful three-bedroom, two-bath brick one level home is brimming with charm and ideally located within walking distance of downtown Winchester, Handley High School, the Patsy Cline House, 2-blocks from the parade route, and the historic district. With gorgeous hardwood floors, fresh modern

Vanessa Couture ERA Oakcrest Realty, Inc.

Immaculate Renovation of 3 Bedroom and 1 Bath Single Family Home*New Kitchen Includes: New White Cabinets, New Quartz Countertop, New Stainless Steel Appliances, New Ceramic Tile Flooring*Refinished Hardwood Floors*New Windows*New HVAC*All New Bathroom*Newer Roof, Gutters and Downspouts*New Side Porch and Decking*New Exterior Doors*New Recessed Lights*New Washer and Dryer*Full Unfinished

Gary Green Samson Properties

This charming all-brick ranch is making its first appearance on the market since the 1970s! It's a fantastic opportunity for first-time homebuyers or investors looking to add their personal touch. The home features three bedrooms, with hardwood floors, carpet, and a full bath on the main level. The cozy family room and kitchen complete the main floor, with hardwood flooring said to be beneath

Jeff Boppe Long & Foster Real Estate, Inc.

PRICE REDUCED. A beautifully updated home in the perfect spot to enjoy all of the excitement of downtown living. A short walk brings you to the historic walking mall; amidst the shops, restaurants and entertainment. Take advantage of First Fridays, Apple Blossom festivities and Old Town events throughout the year. Enjoy the large front and back porches for relaxing with a nice drink and a good

Jimmy Biedrzycki CENTURY 21 New Millennium

Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lots are located within the Historic District of Winchester. Two parcels are included in this listing. Previously, the lots were

Kim Hurst MarketPlace REALTY

Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lot is located within the Historic District of Winchester. One parcels is included in this listing. Two lots are available for

Kim Hurst MarketPlace REALTY

Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lot is located within the Historic District of Winchester. One parcels is included in this listing. This lot includes a water and sewer

Kim Hurst MarketPlace REALTY

Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and Enterprise Zone.

Gillian Greenfield Coldwell Banker Premier

FOR SALE+PAD SITE APPROVED* (!) Pad site approved for 2000 SF professional office building on Pleasant Valley Road, Winchester City. Very rare opportunity! Will have direct access from Pleasant Valley Road. Excellent visibility and traffic count! Ideal for professional medical office building. Asking $299K. Contact Agent for more details!

Gillian Greenfield Coldwell Banker Premier

Ready to build your dream home or investment property in the City of Winchester? Now is your opportunity to purhcase a parcel in the heart of Winchester. HR1 Zoning-High density Residential. No water, sewer or electric to property.

Dana Cloud Realty ONE Group Old Towne

Roger Walker Crum Realty, Inc.

Rossum Crossing is Winchester's newest townhome community, which is located near shopping and dining. The St. Paul Townhome features 3 bedrooms, 2 1/2 baths, and a one-car garage. The main floor has an open-concept floorplan with a spacious family room that leads to a fully equipped kitchen. The kitchen has an island, pantry closet, and breakfast nook. This level also has a powder room. You can

Dick Bryan New Home Star Virginia, LLC

Welcome to Piccadilly Circle, a newly built luxury home community located in the heart of Old Town Winchester, VA. A great location within walking distance of over 30 restaurants, 60 shops, and numerous historical sites and museums. Circle residents can also take advantage of nearby community playgrounds and parks. This home is move-in ready!On the main entry level, find Luxury Vinyl

Jason Aikens RE/MAX Roots

This circa 1863 Italianate home is located in the heart of Winchester's historic district within a short walk to Handley Library and downtown. The home has been elegantly restored, blending timeless charm with modern comforts. The interior is restored to its original grandeur with high ceilings, hardwood floors, decorative moldings, and fireplaces in every room. Fully updated gourmet kitchen with

John Schroth Colony Realty