Winchester Real Estate

2 Beds ⋅ 2 Baths ⋅ VAFV2044858 MLS

102 Buckwood Ln, Winchester

3 Beds ⋅ 1 Baths ⋅ VAFV2044782 MLS

Charming home tucked away in the woods! This 3-bedroom, 1-bath home in Shawneeland is located just 20 minutes from Winchester City. Set on a partially wooded lot, the property offers peaceful surroundings and inviting outdoor spaces, including a front deck and a private rear deck. A storage shed is located in the backyard for convenience. The open-concept main level features a kitchen with upgraded quartz countertops and stainless steel appliances, a living room with a stone wood-burning fireplace, and a dining area. Also on the main level is a spacious bedroom, a full bathroom, and a dedicated laundry area. Upstairs, a spiral staircase leads to two additional bedrooms, creating a cozy and flexible layout. Enjoy the privacy and natural beauty of a wooded setting while remaining conveniently close to Winchester. Approximate updates include new roof in 2023,new water heater in 2022, new water softener in 2022, septic pumped in 2026, new pressure tank in 2024, new microwave in 2026.

132 Dogwood Trl, Winchester

$4,990,000

VAFV2044864 MLS

Rutherford Crossing is a two-tenant NNN retail strip center at 105-109 Market Street in Winchester, VA, anchored by corporate Starbucks (S&P: BBB+) with 10% rent step-ups every five years, alongside V Nails & Spas on a lease running through 2035. The offering delivers approximately $330,000 in stabilized NOI with true triple net structure and minimal landlord responsibilities, making it a clean, passive addition to any retail investment portfolio. The property sits within Rutherford Crossing, an approximately 600,000 SF power center along the growing I-81 corridor, surrounded by national credit anchors and steady daily traffic that drive consistent consumer draw. Winchester continues to see strong population and retail growth, giving this asset the location fundamentals and co-tenancy strength that long-term investors look for.

105 Market St, Winchester

$384,990

3 Beds ⋅ 4 Baths ⋅ VAWI2011622 MLS

The most affordable townhomes in Winchester City! END OF ROW Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room ***OFFERING UP TO $5K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free deck overlooking mature trees. Attached 1-car garage provides additional storage and convenience. New luxury townhomes in Winchester are selling quickly; schedule your tour today before this opportunity is gone!*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 126 Monteith Dr, Winchester

$635,000

4 Beds ⋅ 3 Baths ⋅ VAFV2044652 MLS

Welcome to 104 Yarrow Court, a spacious 4 bedroom, 2.5 bath Colonial tucked away on a quiet cul-de-sac in Briarwood Estates. Offering 3,437 finished square feet above grade, this home provides generous living spaces and a flexible layout with room to spread out. The main level features hardwood flooring, a formal dining room, family room off the kitchen, and a gourmet kitchen with granite countertops, stainless steel appliances, maple cabinetry, and a center island. Two fireplaces, including a double-sided gas fireplace, add warmth and character, while the sunroom offers additional space to relax or entertain. Upstairs, you will find four bedrooms, including a spacious primary suite with a walk-in closet and private bath with a soaking tub. Recent improvements include fresh interior paint, new carpet, exterior door repairs and paint, replacement window screens, and refreshed landscaping with rubber mulch. The full unfinished basement offers nearly 2,000 additional square feet for storage or future finishing. Additional features include a patio, attached 2 car garage, .27 acre lot, and convenient access to Route 7, shopping, dining, and everyday amenities.

104 Yarrow Ct, Winchester

$419,000

3 Beds ⋅ 3 Baths ⋅ VAWI2011614 MLS

Back on Market!!! A full bathroom was added to the property and it appraised for $435k when it had 2.5 bathrooms and now it has 3 full bathrooms. This exquisite Cape Cod residence, originally built in 1929 and set to undergo a stunning renovation in 2026, seamlessly blends timeless charm with modern luxury. Nestled in a desirable neighborhood, this home invites you into a warm and inviting atmosphere, perfect for creating cherished memories. Step inside to discover an open floor plan adorned with rich hardwood and luxury vinyl plank flooring, enhancing the home's elegance. The spacious dining area flows effortlessly into a beautifully appointed kitchen, featuring upgraded countertops and stainless steel appliances, including a dishwasher, microwave, and electric oven/range. Enjoy casual meals in the cozy kitchen table space, where culinary delights come to life. The living area boasts a charming fireplace, perfect for cozy evenings, while built-ins and crown moldings add a touch of sophistication. With three well-sized bedrooms and three bathrooms, including a luxurious tub shower, this home offers ample space for relaxation and rejuvenation. The partially finished basement, complete with a walkout level, provides endless possibilities for customization, whether as a home gym, office, or entertainment space. Outside, the driveway offers access to the basement, while the low-maintenance lot allows for easy enjoyment of your surroundings. Experience a lifestyle of comfort and elegance in this beautifully renovated home, where every detail has been thoughtfully designed for modern living.

131 Shirley St, Winchester

$220,000

2 Beds ⋅ 1 Baths ⋅ VAFV2044850 MLS

Tucked away at the end of the neighborhood and surrounded by serene woods, 610 Puma Trl offers the perfect blend of privacy and charm. This adorable 2-bedroom, 1-bath rancher is a true retreat, featuring modern updates and a warm, inviting layout. Enjoy peaceful living with beautiful natural surroundings while still being conveniently located near town. A rare opportunity to own your own slice of quiet, comfortable living.

610 Puma Trl, Winchester

$350,000

3 Beds ⋅ 2 Baths ⋅ VAFV2044840 MLS

Charming 3-bedroom, 2-full-bath Cape Cod situated on .88 acres in a convenient location just minutes from Winchester City. This inviting home offers the flexibility of a main-level bedroom and full bath, along with a cozy wood-burning fireplace that adds warmth and character. Enjoy relaxing or entertaining on the welcoming front porch or side porch, with plenty of outdoor space to enjoy. A standout feature of this property is the large detached barn/garage offering 7 bays—an incredible amount of space for vehicles, equipment, storage, a workshop, hobbies, or recreational toys. With nearly an acre, a versatile floor plan, and exceptional outbuilding space, this property offers a unique combination of convenience, character, and functionality while being extremely close to Winchester.

144 Apple Valley Rd, Winchester

$375,000

3 Beds ⋅ 3 Baths ⋅ VAFV2044836 MLS

With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior boasts luxurious vinyl plank flooring and cozy carpet, creating a warm atmosphere throughout. An unfinished walkout basement provides endless possibilities for customization, whether you envision a home gym, a cozy den, or additional storage. Enjoy the convenience of upper-floor laundry and a driveway for easy parking. Nestled on a generous 0.27-acre level lot with possible option for expansion, this property invites you to create your own outdoor oasis. Imagine summer barbecues or quiet evenings on your future patio. With its thoughtful design, this home is waiting for your personal touch. Embrace the opportunity to make this house your dream home!

904 Panther Dr, Winchester

$370,000

3 Beds ⋅ 3 Baths ⋅ VAFV2044744 MLS

With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior boasts luxurious vinyl plank flooring and cozy carpet, creating a warm atmosphere throughout. An unfinished walkout basement provides endless possibilities for customization, whether you envision a home gym, a cozy den, or additional storage. Enjoy the convenience of upper-floor laundry and a driveway for easy parking. Nestled on a generous 0.27-acre level lot with possible option for expansion, this property invites you to create your own outdoor oasis. Imagine summer barbecues or quiet evenings on your future patio. With its thoughtful design, this home is waiting for your personal touch. Embrace the opportunity to make this house your dream home!

902 Panther Dr, Winchester

$499,900

3 Beds ⋅ 3 Baths ⋅ VAWI2011602 MLS

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds.

510 S Cameron St, Winchester

$634,900

5 Beds ⋅ 4 Baths ⋅ VAFV2044776 MLS

Your Next Chapter Starts Here! Space, style, flexibility, and a backyard made for entertaining — all tucked away on a quiet cul-de-sac in desirable Oakdale Crossing. This impressive 5-bedroom, 4-bathroom, three-level Colonial, with new roof (2026), delivers the kind of versatile space today’s buyers are looking for, with room to work from home, host friends, grow your household, or create the ultimate hangout zone. Start with the front wraparound porch, the perfect spot for morning coffee or winding down at the end of the day. Out back, the fun really begins: multiple composite decks with a pergola overlook a private, fully fenced yard backed by mature trees, creating your own outdoor retreat. The 20' x 30' saltwater above-ground pool takes summer entertaining to the next level. Inside, beautiful hardwood floors run throughout the main and upper levels. The main level offers an easy-flowing layout with a welcoming family room featuring a gas fireplace, separate dining and living rooms, plus a spacious kitchen with upgraded countertops, breakfast bar, and breakfast room. The first floor also includes a bedroom and full bathroom — ideal for guests, a home office, or flexible living arrangements. Upstairs, the spacious primary suite feels like a private escape, complete with double sinks, jetted tub, walk-in shower, and walk-in closet. Three additional bedrooms, a full bathroom, and conveniently located laundry complete the upper level. And then there’s the lower level — a huge bonus space ready for whatever your lifestyle demands. The large family room with wet bar is made for movie nights, game days, parties, or a dedicated entertainment space. An additional room plus a full bathroom offers incredible flexibility for a home gym, office, guest suite, teen hangout, or potential in-law setup. Outside your front door, you're conveniently located near Winchester Country Club, shopping, restaurants, and schools, giving you the best of both convenience and neighborhood living. This isn't just a house — it's the space to live the way you want now, with room for whatever comes next.

314 Huntersridge Rd, Winchester

Winchester Real Estate

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