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

$359,900
3 Beds ⋅ 1 Baths ⋅ VAWI2011258 MLS
Welcome to this beautifully updated brick home offering the perfect blend of charm and modern updates. Major improvements completed in 2021 include a new roof, windows, HVAC system, kitchen cabinets with granite countertops, and a renovated main-level bathroom. A new water heater was installed in 2024. In 2026, a city-permitted addition created a spacious new primary bedroom and bathroom, along with new roof framing, siding, and plumbing. Conveniently located close to shopping, dining, and commuter routes, this move-in-ready home is ready for its next owner. *Agent is related to landlord* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

236 Shawnee Ave, Winchester
$349,000
3 Beds ⋅ 3 Baths ⋅ VAFV2043742 MLS
Nestled in the serene Wilde Acres/Mtn Falls community, this exquisite split foyer home, built in 2020, offers a harmonious blend of modern luxury and natural beauty. Spanning a generous 0.78 acres, the property is enveloped by lush trees, providing a tranquil backdrop that enhances the sense of privacy and peace. Step inside to discover a warm and inviting interior, where laminated flooring flows seamlessly throughout the main living areas. The heart of the home features a spacious living room that effortlessly connects to a well-appointed kitchen, complete with ENERGY STAR appliances, including a built-in microwave, refrigerator, and stove. The pantry offers ample storage, ensuring that your culinary adventures are always well-equipped. With three thoughtfully designed bedrooms and two and a half bathrooms, this residence caters to both comfort and functionality. The master suite is a true retreat, boasting an en-suite bathroom that exudes elegance. The additional bedrooms are versatile, perfect for guests, a home office, or creative spaces. The partially finished basement, accessible via a side entrance, presents endless possibilities-whether you envision a cozy family room, a home gym, or additional storage. The attached two-car garage, featuring a side entry and built-in access, adds convenience to your daily routine. Outside, the expansive lot invites you to embrace the outdoors. Imagine sipping your morning coffee on a private patio, surrounded by the soothing sounds of nature, or hosting gatherings under the shade of towering trees. The level yard is perfect for gardening, play, or simply enjoying the picturesque mountain views that stretch beyond your property. This home is not just a residence; it's a lifestyle. With road maintenance and snow removal included in the association fee, you can enjoy the beauty of the changing seasons without the hassle of upkeep. The surrounding area offers a wealth of outdoor activities, from hiking to exploring nearby parks, making it an ideal setting for those who appreciate an active lifestyle. Experience the perfect blend of luxury, comfort, and nature in this stunning home, where every detail has been thoughtfully curated to create a sanctuary you'll be proud to call your own.

204 Cougar Trl, Winchester
$700,000
4 Beds ⋅ 4 Baths ⋅ VAFV2043616 MLS
Welcome home to this gorgeous custom-designed residence offering exceptional one-level living with quality craftsmanship and thoughtful details throughout. A welcoming foyer with an elegant tray ceiling sets the stage for the beautiful interior. The stunning gourmet kitchen is the heart of the home, featuring a large center island with leathered granite countertops, abundant soft-close cabinetry and drawers, Café-style stainless steel appliances, and generous counter space for cooking and entertaining. The spacious dining area showcases a tray ceiling and sliding glass doors that open to a screened-in covered porch, creating the perfect setting for relaxing or entertaining. The impressive living room features a soaring vaulted ceiling with exposed wood beams, a beautiful fireplace with a custom mantel, and large tinted windows that flood the space with natural light while enhancing energy efficiency and privacy. The private owner's suite is a luxurious retreat featuring a tray ceiling, two walk-in closets, and a spa-inspired en-suite bath with a double-sink vanity, linen closet, and a custom-designed tiled walk-in shower with a built-in seat. The desirable split-bedroom floor plan offers two additional generously sized bedrooms and a well-appointed hall bath with a tub/shower combination, providing comfort and privacy for family and guests. The walk-out lower level is truly in a class of its own and showcases the same exceptional craftsmanship and attention to detail found throughout the home. Filled with abundant natural light, this incredible space features a spacious family room, an attractive wet bar, a private bedroom, a full bath, dedicated office space, and a versatile bonus room currently used as a music room with a full-size window. A large unfinished storage area provides ample room for all your storage needs. Step outside to the concrete patio and unwind while listening to the peaceful sounds of the beautifully designed waterfall nestled within the professionally landscaped backyard. Gorgeous natural stone, thoughtfully planned landscaping, and mature plantings create a tranquil outdoor oasis that perfectly complements this remarkable home. While the photographs beautifully capture this home's stunning features, they simply cannot convey the warmth, quality, and craftsmanship you'll experience in person. This is a home that must be seen to be fully appreciated.

151 Feed Mill Ct, Winchester
$399,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043114 MLS
This charming ranch-style home, built in 1971, offers a perfect blend of comfort and functionality. With 1,916 sq. ft. of thoughtfully designed space, this residence features three inviting bedrooms and two full bathrooms, ideal for relaxation and privacy. The traditional floor plan is enhanced by beautiful hardwood and ceramic tile flooring, creating a warm and welcoming atmosphere throughout. The heart of the home is the eat-in kitchen, including a built-in microwave, dishwasher, and electric oven/range. Enjoy cozy meals at the kitchen table or gather around the wood-burning fireplace in the living area, perfect for creating lasting memories. Additional features include built-ins, ceiling fans, and a convenient main floor laundry area. Step outside to discover a generous 0.74-acre lot, beautifully landscaped and backing to serene trees, providing a peaceful retreat. The exterior boasts several porches and ample parking with an oversized attached 4-bay garage and paved driveway, which is fantastic for car enthusiasts. Located in a rural setting, this home offers picturesque views of the garden and surrounding woods, making it an ideal escape from the hustle and bustle. With its combination of comfort, space, and natural beauty, this property is ready to welcome you home. This is a Special Warranty Deed sale.

820 Cedar Grove Rd, 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
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