Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, Virginia—a charming city steeped in history and surrounded by the breathtaking beauty of the Shenandoah Valley. Known for its rich heritage and vibrant community, Winchester offers an idyllic blend of small-town charm and modern conveniences, making it a perfect place to call home.

Founded in 1744, Winchester is one of the oldest towns in the Shenandoah Valley, with a historic downtown that showcases beautifully preserved architecture and a variety of local shops, restaurants, and cultural attractions. Stroll along the picturesque streets and discover the charm of the Handley Regional Library, the historic Old Court House, and the vibrant arts scene that includes galleries and theaters showcasing local talent.

Winchester is also a hub for outdoor enthusiasts, with nearby parks, hiking trails, and the stunning natural landscapes of the Blue Ridge Mountains. Whether you’re exploring the scenic trails of the Appalachian Trail or enjoying a leisurely day at Jim Barnett Park, there’s no shortage of outdoor activities to keep you engaged and active.

Families will appreciate the excellent school system, numerous recreational programs, and a strong sense of community that makes Winchester a welcoming place for all ages. With a variety of housing options—from historic homes to modern developments—there’s something for everyone in Winchester.

Experience the unique blend of history, culture, and natural beauty that makes Winchester, Virginia, a wonderful place to live, work, and play. Come and discover your new home in this vibrant city, where every day brings new adventures and lasting memories.

Newest Listings in Winchester

$349,900
2 Beds ⋅ 1 Baths ⋅ VAFV2043734 MLS
The Perfect Starter or downsize Home Awaits! Current Shawneeland Inventory 208 Beaver Trail 101 Tonto Trail 212 Falcon Trail 211 Inca Trail 107 Pinto Trail 123 Killbuck Trail Comcast/Xfinity available on this street. New plan on almost 1/3 of acre! Affordable new home close to town with full unfinished basement (ruff in future bath) for future needs. Upgrades include: Hardwood floors throughout, tile in bath floors, granite countertops kitchen, upgraded cabinets. Builder upgrade full front covered porch and to be Timbertech. Why buy a townhome when you can have your own home! Discover an incredible opportunity to own a brand-new, single-family home on over 1/3 of an acre, offering unparalleled privacy on short street with little traffic and flat lot. This affordable new construction provides the space and freedom you won't find in a townhome. Key Features & Upgrades: Premium Location: Private, expansive lot (1/3+ acre) located low within a desirable community. Quality Finishes: Enjoy hardwood flooring throughout the main living areas, elegant tile in all bathroom floors, granite countertops in the kitchen, and upgraded cabinetry. Outdoor Living: Relax on the stunning, full front covered porch, upgraded with durable, low-maintenance Timbertech decking. Future Potential: A full, unfinished basement provides a blank canvas for future expansion, storage, or customization to meet your evolving needs. Convenience: Just minutes from town, offering easy access to amenities while maintaining a peaceful residential setting. This home is designed for modern living and exceptional value.

101 Tonto, Winchester
$325,000
3 Beds ⋅ 3 Baths ⋅ VAFV2043712 MLS
Rare end-unit townhome situated on one of the community's desirable homesites, backing to mature trees for exceptional privacy. This spacious three-level home offers an open-concept main level featuring a bright living room, an expansive kitchen with center island, stainless steel appliances, abundant cabinetry, and a dining area with direct access to an oversized composite deck overlooking the wooded backyard. Upstairs you'll find a generous primary suite with walk-in closet and private bath, two additional bedrooms, a full hall bath, and convenient bedroom-level laundry. The entry level includes an attached garage, ample storage, and walkout access to a covered patio. Enjoy the perfect combination of indoor and outdoor living with peaceful wooded views—all just minutes from shopping, dining, schools, and major commuter routes.

280 Sage Cir, Winchester
$525,000
5 Beds ⋅ 4 Baths ⋅ VAFV2043592 MLS
Nestled in the charming Apple Ridge community, this stunning Colonial-style home offers a perfect blend of comfort and elegance. Set on a generous 0.4-acre lot, the property backs onto serene open common areas and lush trees, providing a tranquil retreat right in your backyard. Enjoy the luxury of multiple balconies, a spacious deck, and a welcoming porch, ideal for relaxing or entertaining while soaking in the peaceful views of nature. With five spacious bedrooms and four full bathrooms, this home is designed for both relaxation and functionality. The fully finished basement with Kitchen adds extra living space. The main floor laundry adds convenience to your daily routine, while the attached front-entry garage ensures easy access and ample parking. The Apple Ridge neighborhood is known for its friendly atmosphere and community spirit. Excellent local schools are just a short drive away, making this location ideal for those seeking a nurturing environment. With a personal in-ground pool, this home invites you to create lasting memories during warm summer days. Experience the best of suburban living, where comfort meets community, and make this beautiful property your new home.

144 Morning Glory, Winchester
$375,000
3 Beds ⋅ 1 Baths ⋅ VAFV2043688 MLS
Enjoy one-level living with 6.44 partly wooded acres. All-brick 3-bedroom, 1-bath home offering a peaceful country setting with plenty of room to enjoy the outdoors. Relax on the covered rear porch overlooking the property. The home features a paved driveway and a full unfinished basement, providing excellent storage or future expansion potential. New water heater installed in 2022. A wonderful opportunity for those seeking privacy, acreage, and the durability of an all-brick home. Be sure to check out our 3-D tour attached to this listing!

1480 Chestnut Grove Rd, Winchester
$290,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043682 MLS
Be the first to introduce your buyers to this well-maintained end-unit townhome in one of Winchester’s most convenient commuter locations. Situated at 316 Copperfield Lane, this 3-bedroom, 1.5-bath home, built in 2002, offers comfortable, low-maintenance living just minutes from Valley Mill Road, Route 7, and I-81. Ideal for first-time homebuyers, downsizers, or investors, this property is truly move-in and rental ready. The main level offers a functional, open flow between the living room, dining area, and kitchen, creating a comfortable space for everyday living and entertaining. A conveniently located laundry closet sits just off the kitchen, while a half bath completes the main level. Upstairs, you’ll find all three bedrooms, including a spacious primary bedroom featuring a walk-in closet. A full bathroom serves the upper level, providing a practical layout for families, guests, or roommates. Recent improvements include a recently replaced water heater, refrigerator, and a newly fenced backyard (scheduled for August 13), creating an inviting outdoor space complete with an existing deck and exterior storage shed. The sale includes all major appliances: washer, dryer, refrigerator, dishwasher, microwave, garbage disposal, and gas range, making for a seamless transition for its next owner or tenant. Parking is a standout feature, with two assigned parking spaces directly in front of the home plus two adjacent guest spaces, offering convenience that’s hard to find in many townhome communities. The HOA fee includes water, sewer, and trash service, helping keep monthly ownership costs predictable and affordable. If you have buyers looking for an affordable home in a prime commuter location or an investor searching for a turnkey long-term rental opportunity, be sure to schedule your tour now - this one won’t last long!

316 Copperfield Ln, Winchester
$219,900
1 Beds ⋅ 1 Baths ⋅ VAFV2043646 MLS
MUST SEE TO APPRECIATE THIS OFFBEAT RAISED FLAT, 1 BEDROOM 1 BATH, 4 ROOMS FRESHLY PAINTED. EAT IN KITCHEN COMES WITH A STOVE, REFRIGERATOR, MICROWAVE, LOTS OF CABINET SPACE. UPDATED HVAC & NEW ROOF FRESH PAINT. WASHER & DRYER IN THE LOWER-LEVEL GARAGE AREA WITH PLENTY OF ROOM FOR STORAGE. FENCED YARD FOR GARDENING OR PETS, OFF STREET PARKING. PRIVATE, CLOSE TO SHOPPING, DOWNTOWN & RT.37. " INVESTORS TAKE NOTICE THE HOME HAS BEEN PREVIOUSLY RENTED" OWNER IS A VIRGINIA LICENSED REALTOR

1057 Foreman Ln, Winchester
$879,900
5 Beds ⋅ 5 Baths ⋅ VAFV2043702 MLS
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
$300,000
VAFV2043700 MLS
Discover the possibilities with this beautiful 20.2-acre property offering the perfect blend of privacy, natural beauty, and opportunity. Featuring a mix of mature woods and a spacious open field, this versatile parcel is ideal for outdoor recreation, hunting, or creating your own private retreat. With a recorded dominant easement for ingress and egress, you’ll enjoy convenient access while maintaining the peaceful seclusion that makes this property so special. Whether you’re dreaming of building your custom home surrounded by nature or looking for a weekend getaway to enjoy the outdoors, this land provides the perfect canvas to bring your vision to life. Don’t miss the chance to own a slice of the countryside where you can create the lifestyle you’ve always imagined.

Brush Creek Rd, Winchester
$619,900
4 Beds ⋅ 5 Baths ⋅ VAFV2043500 MLS
No HOA! Settled at the end of the cul-de-sac and pushed back from the street to give additional privacy and comfort. This home has received several improvements since 2020. Including a whole new kitchen (Dec 2025), soft close cabinets, quartz countertop and backsplash, Stainless Steel appliances, the kitchen island was enlarged for more countertop space and additional storage, seats 2-3 people comfortably. Kitchen includes a large pantry with upgraded doors (2025). Both HVAC Systems were replaced and a humidifier was added (Spring 2026). Ducts were professionally cleaned (2020). Custom Blinds (2025). The spacious back yard has an aluminum 5ft fence with 2 single gates and 1 double gate (2024). Trex Deck 12x16ft with gate at top of stairs (2021). Custom built 10x12ft swing for 3 people or a hammock. Trees and bushes and fencing makes the back yard feel very private. Interior and exterior professionally painted (2020/21). Large 12x16ft shed added (2023). New carpet in basement and upper level (2020). Updated both half bathrooms (2022-23). Primary bathroom has a heated tile floor, walk-in shower with rain fall shower head and 4 body sprayers, large jacuzzi tub, double vanity, chandelier, and linen closet. Primary bedroom has two walk-in closets. One with a chandelier and upgraded closet system. Garage has a Mini Split heating/cooling system as well as its own attic with flooring for storage. All interior and exterior light fixtures have been updated. Both gas fireplaces were professionally serviced (2023). Basement is wired for surround sound, has upgraded dry bar with soft close cabinets, quartz countertop to match kitchen, and floating shelves, the basement also has two windows for natural light, and walk-up basement stairs. Upstairs bedrooms have a Jack-n-Jill bathroom between them with an updated double vanity (2025). The rear bedroom has a walk-in closet with a laundry shoot. Professional landscaping in front of home (2021). Home is wired with ADT security but isn't currently in use. Location is excellent, almost everything you'd need is 5-10 minutes away including Winchester Country Club, Costco, Shopping Centers, Downtown walking mall, commuter routes like rt. 50, rt. 7, rt. 522, and Interstate 81.

308 Huntersridge Rd, Winchester
$625,000
5 Beds ⋅ 3 Baths ⋅ VAFV2043680 MLS
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
$389,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043670 MLS
Welcome to 120 Hawk Trail, a beautifully maintained home offering the perfect blend of modern comfort, peaceful surroundings, and the relaxed mountain lifestyle that makes Shawneeland such a special place to call home. Surrounded by mature trees and nature, this inviting retreat provides privacy and serenity while still being conveniently located near Winchester. Built in 2014, this thoughtfully designed home offers the benefits of newer construction with a warm and comfortable feel. Step inside to a spacious living room featuring a high tray ceiling that adds character and an open, airy feel. Hardwood flooring flows throughout the main living and dining areas while large double windows in both areas provide abundant natural light. The kitchen is designed for both functionality and everyday enjoyment, featuring stainless steel appliances, abundant cabinetry, and plenty of workspace for meal preparation. A comfortable breakfast area near the large sliding glass door provides the perfect spot for a kitchen table, morning coffee, casual meals, or simply relaxing while enjoying peaceful views of the backyard. The flexible floor plan includes two spacious bedrooms and a primary suite featuring its own private full bathroom. A second full bathroom is conveniently located near the living areas and bedrooms, providing easy access for family and guests. The unfinished basement with a rough-in bathroom offers endless possibilities for future expansion. Create a recreation room, home gym, workshop, office, guest area, or additional living space tailored to your needs. Until then, it provides exceptional storage and a great opportunity to customize the home over time. This move-in ready home has been lovingly cared for by its original owner with thoughtful features throughout, including updated lighting and bathroom fixtures, ceiling fans for added comfort, and an attached two-car garage offering convenience and additional storage. Outside, the backyard provides a peaceful setting with plenty of space for outdoor enjoyment. Whether you're firing up the grill, gardening, relaxing with a good book, or simply enjoying the sounds of nature, this private setting creates a wonderful place to unwind. Life in Shawneeland offers a unique mountain community experience with amenities that make everyday living feel like a getaway. Residents enjoy access to a spring-fed lake, private Cherokee Beach, fishing ponds, hiking trails, playgrounds, picnic areas, sports courts, and beautiful mountain scenery. The community is maintained through the Shawneeland Sanitary District rather than a traditional homeowners association, with fees supporting road maintenance, snow removal, and upkeep of shared amenities. Nature lovers will appreciate the nearby access to George Washington National Forest, while Winchester provides shopping, dining, medical services, entertainment, wineries, and historic charm just a short drive away. Commuters will appreciate convenient access to major routes connecting to the Washington, DC metro area. Whether you are looking for a new home, weekend getaway, or peaceful place to reconnect with nature, 120 Hawk Trail offers the opportunity to enjoy the best of mountain living while staying connected to modern conveniences. Here, fresh air, quiet evenings, and the beauty of the outdoors become part of your everyday lifestyle.

120 Hawk Trl, Winchester
$429,000
4 Beds ⋅ 2 Baths ⋅ VAWI2011230 MLS
Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a charming community park, this home is ideally located just minutes from Winchester Medical Center, the Museum of the Shenandoah Valley, and Old Town Winchester's restaurants, shops, and entertainment.

1310 Whittier Ave, Winchester
Start Your Search