Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, Virginia—a charming city steeped in history and surrounded by breathtaking natural beauty. Nestled in the scenic Shenandoah Valley, Winchester is known for its rich heritage, vibrant community, and picturesque landscapes. As one of the oldest towns in the United States, it boasts a captivating blend of historic architecture and modern amenities, making it an ideal place for both families and individuals alike.

The heart of Winchester is its beautifully preserved Old Town, where cobblestone streets lead you past delightful boutiques, artisanal shops, and cozy cafes. Here, you can savor local flavors at farm-to-table restaurants or enjoy a leisurely stroll while admiring the stunning historic buildings that date back to the 18th century. The city also hosts a variety of annual events, including the popular Shenandoah Apple Blossom Festival, which brings together residents and visitors for a celebration of spring, community, and local culture.

Nature enthusiasts will find plenty to love about Winchester, as the surrounding area offers numerous parks, hiking trails, and outdoor recreational opportunities. The nearby Blue Ridge Mountains provide a stunning backdrop for activities such as hiking, biking, and even wine tasting at local vineyards.

With a strong sense of community and a commitment to preserving its historical roots, Winchester is not just a place to live—it's a place to thrive. Whether you're looking for a quaint starter home or a spacious family residence, Winchester has something to offer everyone. Come explore the charm and character of this delightful Virginia city, and discover why so many have chosen to call it home.

Newest Listings in Winchester

164 Brookland Court, Unit 11, Winchester
$240,000
2 Beds ⋅ 2 Baths
Welcome to this move in ready, 2-bedroom, 2-bathroom condominium located on the east side of Winchester. The vaulted family room is inviting with a gas fireplace, sky lights and sliding glass door to the balcony. Luxury vinyl plank flooring can be foundout throughout the unit, while bathrooms are tiled. The primary suite showcases an updated bathroom and walk-in closet. Bedroom two has a bay window and the hall bathroom is updated as well. Private balcony overlooks a peaceful lawn/park area. Condo fee covers exterior maintenance, trash, and water. Owner recently installed a brand new HVAC system, complete with UV air filter. Top floor level living means no footsteps above! Easy access to the DMV. Low maintenance for owners and investors!

164 Brookland Court, Unit 11, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

2025 Senseny Rd, Winchester
$340,000
3 Beds ⋅ 2 Baths
Welcome to 2025 Senseny Road! This home offers a comfortable layout with a welcoming front porch, recently refreshed with a fresh coat of paint. Inside, you’ll find an inviting main living area with an open-concept flow between the living room and kitchen. The kitchen overlooks the backyard, where you’ll find a storage shed offering additional space for your outdoor needs. Just off the main living area, a hallway provides access to a full bathroom, a closet, and a convenient laundry area with washer and dryer. The home features three bedrooms, including a primary bedroom with an adjoining half bath. Installed frost proof water faucets front and back Oct 2026.The roof was replaced April 2018. Whether you’re looking for a place to call home or an opportunity to add your own personal touches, this property offers a functional layout and a welcoming place to make your own!

2025 Senseny Rd, Winchester

Listing courtesy of Keller Williams Realty. Contact:

1915 Wayland Dr, Winchester
$464,900
4 Beds ⋅ 3 Baths
There's a lot to love about 1915 Wayland Drive, starting with the location! Tucked into an established Winchester neighborhood, this well-maintained Colonial is just minutes from Winchester Medical Center, shopping, restaurants, and Routes 37, 50, and 81. Inside, you'll find a home that's comfortable, welcoming, and has plenty of room to spread out. Hardwood floors run through much of the main level, and the 9-foot ceilings give everything a nice, open feel. The family room, with its gas fireplace, is the perfect place to settle in after a long day. There's also a separate living room with French doors that would make a great home office, reading room, or a quiet spot to get away for a bit. The kitchen has plenty of cabinet and counter space, stainless steel appliances, and a breakfast area for everyday meals. When the weather is nice, open the French doors and head out to the patio for dinner outside or just a little time to relax. The separate dining room is ready for holiday dinners or having friends over. Upstairs are four spacious bedrooms, including a primary bedroom with its own private bath, plus another full bath for the remaining bedrooms. And you'll appreciate the little things that make daily life easier, like the main-level laundry room that connects directly to the two-car garage. The backyard has mature trees and room to enjoy being outside. Whether you're curled up by the fireplace on a chilly evening, enjoying coffee on the patio, or heading out for a quick trip across town, this is a home that makes everyday living easy. Come take a look and see how it feels to you! *Three rooms have been virtually staged so you can imagine the possibilities.

1915 Wayland Dr, Winchester

Listing courtesy of Samson Properties. Contact:

609 Quartzite Cir, Winchester
$489,900
4 Beds ⋅ 3 Baths
Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides a generous recreation room, an additional bedroom, and a full bath, offering flexible space for guests, a home office, or everyday living. Enjoy the fully fenced backyard with a patio, perfect for relaxing or entertaining, along with the convenience of an attached 2-car garage. Ideally located near shopping, dining, schools, parks, and major commuter routes, this home combines comfort, versatility, and a convenient Winchester location.

609 Quartzite Cir, Winchester

Listing courtesy of Samson Properties. Contact:

119 Gravenstein Ct, Winchester
$1,399,000
5 Beds ⋅ 5 Baths
AN EXTRAORDINARY OPPORTUNITY Coming Soon 119 Gravenstein Court, a spacious, beautifully maintained home where exceptional quality meets an unforgettable setting. Enjoy expansive, open-concept floor plan, high-end finishes, and thoughtfully designed living spaces that make everyday living exceptional. Over 5600 SF of finished living space with teasers that include a double height stone fireplace, open living and dining areas with french doors opening to a huge enclosed porch, overlooking the private backyard. A main-level primary suite with magnificent en suite bathroom, and an expansive walk-out lower level provides incredible additional living and entertaining space, perfect for hosting family and friends! But the true showstopper Views that are simply once in a lifetime. Sweeping, unobstructed vistas of rolling open farmland and majestic mountains create a backdrop that is increasingly hard to find. A rare combination of space, quality, condition, and breathtaking scenery. 119 Gravenstein is more than a home—it's a privilege and lifestyle worth waiting for! Stay tuned. This one is special!

119 Gravenstein Ct, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

425 Crow Dr, Winchester
$355,000
3 Beds ⋅ 2 Baths
Nestled in the serene Wilde Acres community, this charming split foyer home is a canvas awaiting your personal touch. With construction set to be completed in 2026, you have the unique opportunity to customize your dream space from the ground up. Imagine the possibilities with three spacious bedrooms and two full bathrooms, perfect for creating a cozy retreat for you and your loved ones. The property boasts a generous 0.24-acre lot, providing ample outdoor space for relaxation and recreation. The unfinished basement presents an exciting opportunity for additional living space, whether you envision a home theater, a playroom, or a personal gym. With an attached two-car garage and driveway parking, convenience is at your fingertips. Embrace the tranquility of lakeside living while being part of a vibrant neighborhood. This home is not just a property; it's a place where you can create lasting memories. Don't miss your chance to make this house your home! Images are computer-generated renderings for illustrative purposes only and may not reflect the final product. Features, finishes, dimensions, and other details are subject to change. Information is deemed reliable but not guaranteed; buyers should independently verify all details. Check out the construction timelapse video attached to this listing!

425 Crow Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

102 Duke, Winchester
$700,000
4 Beds ⋅ 5 Baths
**QUICK DELIVERY – DECEMBER 2026!** Welcome to Abrams Pointe, a beautiful new single-family home community featuring spacious homesites in Winchester, Virginia! **Why wait to build when you can move into this stunning Carlisle home by Maronda Homes this December?** This beautifully designed, brand-new home offers the perfect combination of spacious living, modern comfort, and stylish finishes throughout. From the moment you step inside, you'll appreciate the inviting open-concept layout. The chef-inspired kitchen features beautiful quartz countertops, upgraded cabinetry, a spacious center island, and a pantry. It flows seamlessly into the breakfast area and expansive great room, creating the perfect setting for everyday living and entertaining. Upstairs, the luxurious owner's suite offers a spacious en-suite bathroom and oversized walk-in closet. Additional generously sized bedrooms, a Jack-and-Jill bathroom, another full hall bathroom, and a versatile loft provide plenty of room for everyone. The convenient upper-level laundry room includes a laundry sink. The **fully finished lower level** adds even more living and entertaining space, featuring an expansive recreation room, an additional full bathroom, and a walk-out to the beautiful wooded backyard, offering both convenience and a peaceful natural setting. Additional highlights include a two-car garage, beautiful designer selections, and thoughtfully chosen upgrades throughout. Conveniently located near Historic Downtown Winchester, shopping, dining, Shenandoah University, and major commuter routes, Abrams Pointe offers the perfect balance of peaceful suburban living and everyday convenience. **Ready for delivery in December 2026!** Don't miss this opportunity to own a beautifully appointed, brand-new Carlisle home on a desirable walk-out homesite backing to trees, without the wait of building from the ground up! *Exterior rendering is for illustrative purposes.*

102 Duke, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

0000 Light Rd Ne, Winchester
$122,500
Hurry! Don't miss this wooded lot opportunity, in the perfect location on peaceful Light Rd.. No restrictions! Large lot available! WELL ON SITE! Over 8 acres for sale in northern Frederick County VA! This property is just 22 minutes from the city limits of Winchester. Winchester and Frederick County is the fastest growing area currently, in the state! Lot could be your weekend get-away, hunting lot, possible building lot. Bring your Builder or build your firepit and pitch tents/bring your RV! Don't miss this amazing price and views! The location is everything! 10 minutes to 522 N., 25 minutes to Berkeley Springs, WV. where you'll discover quaint shops and delicious dining options. 25 mintues from Old Town Winchester, featuring wonderful entertainment, a wide variety of shops and dining options. Within 20-30 minutes you have fantastic recreational opportunities - Rock Harbor Golf course, Cacapon State Park, canoeing and fishing on the Potomac and Cacapon Rivers. Additionally, there are a significant number of large employers in the Winchester area if you're still in your working years. And finally, close to major commuter routes, 522, I-81, I-66, Rts. 7, 9 and 50! Broker and Agent make no representations as to the accuracy of these statements and information included. Buyers are advised to do their research on anything pertinent to their purchasing decision.

0000 Light Rd Ne, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

250 Monteith Dr, Winchester
$374,990
3 Beds ⋅ 4 Baths
***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* Don't miss your opportunity to own a beautifully upgraded, 3-level luxury townhome in the heart of Winchester! As part of Phase 1, this home offers an exceptional opportunity to secure premium finishes and thoughtful upgrades at an incredible value. Featuring 3 bedrooms, a 1-car garage, and an impressive collection of upgrades already included in the price, this home delivers the elevated style and functionality today's buyers are looking for. The stunning upgraded kitchen serves as the heart of the home, featuring an oversized island with seating for four, stylish finishes, and an open-concept layout ideal for entertaining and everyday living. The finished lower level adds even more versatility, complete with a private full bathroom and walk-in shower—perfect for a guest retreat, home office, recreation room, or potential fourth bedroom. Outside 10' x 16' maintenance-free deck, overlooking mature trees for a peaceful setting and added privacy. Upstairs, enjoy three well-appointed bedrooms and the convenience of a dedicated laundry area. An attached 1-car garage provides additional convenience and storage. Premium upgrades. Exceptional design. Phase 1 opportunity. With a finished lower level, upgraded kitchen, spacious deck, and so much more already included in the price, this home offers a level of value that's hard to overlook. Phase 1 opportunities won't last forever! Schedule your tour today and discover everything this exceptional home has to offer.

250 Monteith Dr, Winchester

Listing courtesy of DRB Group Realty, LLC. Contact:

Homesite 1 Monteith Dr, Winchester
$384,990
3 Beds ⋅ 4 Baths
***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE! ** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* Don't miss your opportunity to own a beautifully upgraded, 3-level luxury townhome in the heart of Winchester! As part of Phase 1, this home offers an exceptional opportunity to secure premium finishes and thoughtful upgrades at an incredible value. Featuring 3 bedrooms, a 1-car garage, and an impressive collection of upgrades already included in the price, this home delivers the elevated style and functionality today's buyers are looking for. The stunning upgraded kitchen serves as the heart of the home, featuring an oversized island with seating for four, stylish finishes, and an open-concept layout ideal for entertaining and everyday living. The finished lower level adds even more versatility, complete with a private full bathroom and walk-in shower—perfect for a guest retreat, home office, recreation room, or potential fourth bedroom. Outside 10' x 16' maintenance-free deck, overlooking mature trees for a peaceful setting and added privacy. Upstairs, enjoy three well-appointed bedrooms and the convenience of a dedicated laundry area. An attached 1-car garage provides additional convenience and storage. Premium upgrades. Exceptional design. Phase 1 opportunity. With a finished lower level, upgraded kitchen, spacious deck, and so much more already included in the price, this home offers a level of value that's hard to overlook.**Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

Homesite 1 Monteith Dr, Winchester

Listing courtesy of DRB Group Realty, LLC. Contact:

112 Killaney Ct, Winchester
$620,000
4 Beds ⋅ 4 Baths
Pride of ownership exudes from this cul-de-sac Colonial in Raven Pointe. From the moment you walk up to the brick porch to start your tour imagine relaxing in your rocking chair or loveseat during quiet mornings or evenings. Enter the home to find hardwood floors, soft paint decor, and perfectly sized rooms, including the formal living room with a double-sided fireplace leading into the family room, and a dining room capable of hosting all your holiday parties, which opens into a kitchen with ample cabinetry and updated SS appliances. The dual-zone HVAC, upgraded in 2021, will keep you comfortable even on the hottest days and coldest nights. The large capacity hot water heater means you can shower while the dishwasher is running with no worries. Exit the kitchen to the maintenance-free composite decking and the fully fenced backyard oasis, which includes a patio off the basement, a shed for gardening tools, yard equipment, or essential toys, and a quaint second patio ideally situated for a fire pit. Upstairs you again find wood floors, appropriately sized bedrooms, and a nook area—added by the owner—that could serve as a studio, nursery, or office off the primary bedroom. If this home didn't have enough to offer, WAIT: there is still the finished basement with a bar area, a rec area for entertaining, a walkout to the patio, plenty of windows for natural light, and a full bath. Enjoy this fine home and make time to visit; you will be elated at what you see!

112 Killaney Ct, Winchester

Listing courtesy of RE/MAX Roots. Contact:

694 Round Hill Rd, Winchester
$300,000
3 Beds ⋅ 1 Baths
The moment you step inside, you’re enveloped by the unmistakable feeling of HOME. Nestled on an expansive double lot totaling over half an acre, this charming 1950s residence perfectly blends serene country living with modern town convenience. The main level boasts a bright, open floor plan that seamlessly connects the inviting family room to a classic country kitchen—complete with stainless steel appliances and a cozy dining area. Upstairs, delightful architectural details like angled ceilings showcase the home's original character. With 3 bedrooms and two distinct enclosed porches, the layout feels remarkably spacious. Step outside onto your private, naturally shaded deck—ideal for morning coffee or hosting evening gatherings. A detached garage and a separate carport offer ample parking and storage, completing this picturesque property. Don't miss the chance to embrace a lifestyle where comfort, community, and peace meet!

694 Round Hill Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

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