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

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 75-gallon 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:

104 Mountain Ldg, Winchester
$345,000
3 Beds ⋅ 3 Baths
Peaceful Wooded Views & Numerous Recent Updates! Welcome home to this inviting Colonial built in 2009, offering 1,912 finished sq. ft. across two finished levels. Enjoy hardwood floors, a relaxing wooded backdrop, rear deck, fenced backyard, storage shed, and plenty of parking with the gravel driveway and additional parking space. The Primary bedroom features custom made drapes and an ensuite bathroom. The dining room and the living room both feature custom made cornice's. Numerous improvements include a newer central air system (2024, under warranty), new well pump and new water lines (2026), and completely updated crawl space with new insulation and vapor barrier (2026). Additional 2024 updates include sliding glass doors with internal blinds, Nest thermostat, ADT alarm panel, water-protected outdoor GFCI outlets, and an insulated storage room with windows on the deck. Enjoy the comfort of a thoughtfully maintained home and the tranquility of its peaceful setting!

104 Mountain Ldg, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

134 Wilkins Dr, Winchester
$399,900
4 Beds ⋅ 2 Baths
Welcome to this spacious 4-bedroom, 2-full-bath split-level home in Winchester! Offering 2,556 square feet of living space, there's plenty of room to spread out and enjoy. The versatile layout features a comfortable living room, family room with gas fireplace, large recreation room, and an oversized sunroom that's perfect for relaxing or entertaining. Step outside to enjoy the fenced backyard, complete with an above-ground pool (last opened in 2025), storage shed, and established landscaping. Conveniently located just minutes from Old Town Winchester, Jim Barnett Park, Shenandoah University, and major commuter routes, this home offers a great combination of space, outdoor enjoyment, and convenience! New architectural shingle roof 2024. Property sold as-is

134 Wilkins Dr, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

15 W Germain St, Winchester
$219,000
4 Beds ⋅ 2 Baths
Single family house half a mile from down town walking mall, Apple Blossom parade route, restaurants, court house, and conveniences! Interior fully renovated in 2022. Four bedrooms, one full bath, one half bath, and a fenced-in level backyard. Property is zoned RB1 with allowable uses such as hair salon, barber shop, restaurant, etc--please consult with City Zoning Office. Please see attached document for additional information.

15 W Germain St, Winchester

Listing courtesy of Levi Clarke, LLC. Contact:

15 W Germain St, Winchester
$219,000
Single family house half a mile from down town walking mall, Apple Blossom parade route, restaurants, court house, and conveniences! Interior fully renovated in 2022. Four bedrooms, one full bath, one half bath, and a fenced-in level backyard. Property is zoned RB1 with allowable uses such as hair salon, barber shop, restaurant, etc--please consult with the City Zoning Office. Please see attached document for additional information.

15 W Germain St, Winchester

Listing courtesy of Levi Clarke, LLC. Contact:

135 Mascouten St, Winchester
$600,000
6 Beds ⋅ 5 Baths
Welcome home to 135 Mascouten St!!! Walk in to find a lovely foyer and flex space, proceeding to an large open and welcoming floor plan with living/dining and kitchen with sizeable island. In this spacious home you'll find that it has not one, but two primary suites, one on the first floor with a beautiful walk in shower, walk in closet and large double vanity, the second located upstairs with a cozy bathroom and tub shower with another walk in closet. With six total bedrooms; the second floor primary and three on the second floor, the first floor primary, and an additional bedroom in the basement, there is no shortage for flexible living, sleeping, hobbies, office space, etc. Add the large finished basement and work room, and you have over 3500 square feet of living space for all of your dreams. This home was built for entertainment, enjoyment and memories. While nestled on a quiet street and backing to common space, you can enjoy your fenced yard and tree views. ***///*** 3D Tour Available on Zillow!

135 Mascouten St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

2631 Jones Rd, Winchester
$352,000
3 Beds ⋅ 2 Baths
Nestled in Jackson Woods Estates, this charming ranch-style home offers a perfect blend of comfort and functionality. You will love all the large windows allowing tons of natural light! Built in 2010, this well-maintained residence features three inviting bedrooms with large closets, double windows and two full bathrooms, making it a perfect home for those seeking a cozy atmosphere yet full sized bedrooms. Step inside to discover a warm and welcoming interior, highlighted by beautiful LVP flooring and ceiling fans with a view through the living area to the private backyard. The combination dining and living area creates a seamless flow, perfect for entertaining or enjoying quiet evenings at home. The eat-in kitchen, complete with country-style charm and ample table space, is a delightful spot for casual meals and gatherings. Modern appliances, including a built-in microwave, dishwasher, electric oven, and refrigerator complete the open kitchen design. The main floor laundry adds convenience to your daily routine, while the entry-level bedrooms offers flexibility for guests or a home office. Outside, the generous half-acre lot provides plenty of space for outdoor dining - the Sellers loved their private, treed backyard and you will too! Located in Jackson Estates and very close to Middle Road it is an easy distance to downtown and to local parks, schools, and public services. Explore nearby walking trails at Rose Hill Park, Stonebrook Country Club and a quick ride to all the great local restaurants and entertainment in Winchester City! Septic pumped in October.

2631 Jones Rd, Winchester

Listing courtesy of Colony Realty. Contact:

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