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$724,000
5 Beds ⋅ 4 Baths ⋅ VAFV2043330 MLS
Welcome to 342 Canyon Rd, a spacious and beautifully maintained home in the desirable Twin Lakes Overlook community on Winchester's east side. Situated on a beautifully landscaped corner lot of nearly 0.40 acres, this impressive home offers over 4,264 finished square feet with a thoughtfully designed floor plan perfect for both everyday living and entertaining. The inviting great room features a stunning stone fireplace, while the gourmet kitchen boasts a large center island, abundant cabinetry, and a bright breakfast area. A private main-level office provides the ideal space for working from home or a quiet study. Upstairs, you'll find four generously sized bedrooms, two full bathrooms, dual staircases, and an additional hallway for added convenience. The oversized primary suite has been custom expanded to include a spacious sitting area, creating a true owner's retreat. The partially finished walk-out basement includes a full bedroom, full bath and a wide staircase leading to the backyard, offering excellent flexibility for a recreation room, guest space, home gym, or future finishing. Enjoy outdoor living on the rear deck overlooking mature landscaping that provides exceptional privacy, with seasonal lake views and a nearby walking path to the lake. Additional highlights include a side-loading garage, one of the largest floor plans in the neighborhood, and high-speed Glo Fiber Optic internet. Conveniently located near shopping, dining, schools, and major commuter routes, this exceptional home offers the perfect combination of space, comfort, and versatility. Huge primary suite and bonus room/bedroom over garage. School bus stop is at the front door so kids can wait inside for the bus! And confirm Will is notified through text message for all showing confirmations it is vacant so it should be courtesy go and show. (Photographer is coming today)

342 Canyon Rd, Winchester
$600,000
3 Beds ⋅ 2 Baths ⋅ VAWI2011162 MLS
Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The home spans approximately 3,480 square feet (1,844 main living areas + 804 sunroom + 832 basement). The traditional floor plan offers a formal dining room, perfect for hosting gatherings, while the butler's pantry adds a touch of convenience for entertaining. The kitchen is equipped with upgraded countertops and modern appliances, including a built-in microwave, cooktop, range hood, wall oven, dishwasher, and refrigerator, making meal preparation a joy. The home boasts three well-appointed bedrooms, each with ample closet space, including a walk-in closet in the master suite. The bathrooms are designed for comfort, featuring a full bath with a tub shower and a convenient half bath for guests. The property also includes a connecting stairway to the basement, where you'll find additional storage and laundry facilities. Outside, the extensive hardscape provides a relaxing outdoor space, perfect for enjoying the fresh air or hosting outdoor gatherings. A shed offers extra storage options for gardening tools or recreational equipment. Living in this vibrant community means enjoying the benefits of nearby parks, schools, and public services. The City of Winchester is known for its friendly atmosphere and active community life, with local events and activities that foster a sense of belonging. With on-street parking and a location that offers easy access to local amenities, this home is a perfect blend of comfort, style, and community spirit. Experience the charm of this Colonial residence and make it your own, where every corner feels like home. (See documents for improvements list)

1311 Handley Ave, Winchester
$715,000
3 Beds ⋅ 4 Baths ⋅ VAFV2043346 MLS
Spacious contemporary craftsman style home built in 2007 on .5 acre lot with rare 3 car attached side load garage as well as a detached 2 car & 1 car garages behind the home. This is a car lover's dream with a total 6 garaged parking spaces as well as the driveway or perfect for home based business (with appropriate County approval) - NO HOA!!! Located next to the green space of Kernstown Battlefield. The main level of the home boasts a two story foyer, inviting living room, large dining room and cozy family room with floor to ceiling stone gas fireplace. Kitchen is a chef's dream with oversized island, granite countertops, newer stainless steel appliances and walk-in pantry, upgraded cabinets, hardwood floors and pendant lights! Breakfast room with upgraded lighting - the perfect spot for a morning coffee or tea. There's a mud room as well as two half bathrooms on the main level. On your way up to the bedroom level there is a home office space/den - perfect to work from home, craft or as a swing guest space. The upper level offers a spacious primary bedroom with a double tray ceiling, recessed lights, ceiling fan and walk-in closet. The primary bathroom has a walk-in shower with body spray shower stall, jetted soaking tub & water closet. Two additional spacious secondary bedrooms are served by a hall bathroom with double-sinks and a shower. The home is served by public water and sewer and has a well as a secondary water source to water your gardens and landscaping. Well, garage freezer & satellite dish all convey as-is. Updates included but are not limited to: Water Heater 2024, HVAC approximately 5 years old, newer French door refrigerator and brand new dishwasher, updates to lighting and more! Crawl space was re-insulated in Summer of 2026.

336 Apple Valley Rd, Winchester
$1,650,000
4 Beds ⋅ 5 Baths ⋅ VAFV2043458 MLS
Built in 1774, before America was America, this remarkable 31-acre estate has stood through the birth of a nation, and today it's ready for its next chapter. This is history you can live in, a piece of the past, built for the life you're living now. Hardwood floors run throughout, and the spacious kitchen opens effortlessly into the family room and dining space, the kind of layout that makes everyday living and entertaining equally easy, with direct access to either the back patio or covered side porch. Four bedrooms include a primary suite with its own private & covered porch overlooking the 31.74 acres and pond, a quiet spot to start or end the day. Additional flexible bonus rooms offer options for guest space, an office, or extra bedrooms as needed, alongside 3 full and 2 half baths across. A 3-car attached garage adds everyday convenience. Outside, the property opens into 31.74 sweeping, scenic acres. A picturesque pond anchors the grounds, a substantial 100' x 50' barn with its own electric service offers exceptional storage or workshop space, ready for hobby farming, equipment, or a creative studio of your own. Just 15 minutes to downtown Winchester and minutes from local attractions like the Museum of the Shenandoah Valley, with Washington, DC only 84 miles away, this is countryside living with the city still within reach. A rare chance to own a true piece of American history, lived in, loved, and ready for its next 250 years.

582 Miller Rd, Winchester
$599,000
4 Beds ⋅ 3 Baths ⋅ VAFV2043446 MLS
Nestled against a backdrop of mature trees, this nearly new 4-bedroom, 3-bath home offers beautiful finishes and modern comfort in the sought-after Raven Oaks community. Conveniently located with easy access to Routes 50 and I-81, this home is just minutes from Shenandoah University, Jim Barnett Park, shopping, restaurants, and everyday conveniences. Historic Old Town Winchester is only about three miles away, offering local dining, boutiques, entertainment, and community events. A fence and deck already in place for you. The thoughtfully designed floor plan features a main-level bedroom and full bath, perfect for guests or multi-generational living. The open-concept kitchen, dining, and living area showcases quartz countertops, stainless steel appliances, and an electric fireplace, creating a stylish and inviting gathering space. Luxury vinyl plank flooring extends throughout the main level. Upstairs, you'll find a spacious loft, a private primary suite with an attached bath, two additional bedrooms, a full hall bath, and the convenience of a bedroom-level laundry room. The unfinished basement offers plenty of storage and future expansion potential with rough-in plumbing for a full bath. Enjoy outdoor living on the deck overlooking the fenced backyard that backs to trees. Residents also have access to the community pool, making this home the perfect blend of comfort, convenience, and neighborhood amenities. Check out the 3-D Tour attached to this listing.

139 Poe Dr, Winchester
$325,000
2 Beds ⋅ 2 Baths ⋅ VAFV2043444 MLS
Pride of ownership shines throughout this exceptionally well-maintained and thoughtfully updated home! Numerous improvements completed within the past few years make this property truly move-in ready, including new interior doors and upper kitchen cabinetry in 2024, new flooring on the upper level and stairs in 2023, a new refrigerator, washer and dryer in 2023, and a new front porch in 2022. Additional updates include new exterior doors and lower-level windows in 2024, along with new ceiling fans, updated light fixtures and an abundance of recessed lighting added throughout the home in 2026. Both bathrooms were refreshed in 2026 with new vanities, toilets and flooring, and a new mini-split system was also added in 2026. The split-level design offers comfortable and versatile living spaces, with the kitchen, dining area and a cozy sitting area on the main level. The spacious lower-level family room provides plenty of room to relax or entertain and also includes the laundry area. Upstairs, you'll find three bedrooms and two full baths. Step outside to enjoy the large rear deck, perfect for outdoor dining and entertaining, overlooking a nice, level yard. With so many recent improvements already completed, this lovingly cared-for home is ready for its next owners to simply move in and enjoy! The Shawneeland community offers so much for the outdoor enthusiast and for lots of family fun!! Truly a great place to call "home" :)

109 Gannentaha Trl, Winchester
$539,000
4 Beds ⋅ 4 Baths ⋅ VAFV2043442 MLS
Step into the lifestyle you deserve at 111 Sovereign Ct in Freedom Manor! This 3-level, 4-bedroom, 3.5-bath home is crafted for modern living. The main level has an open-concept layout that makes entertaining a breeze. Whether you are hosting a large group or relaxing in the family room, the layout is designed to flow seamlessly. The upper-level primary suite is your personal sanctuary, with three additional bedrooms to meet all of your needs. The partially finished lower level with a full bath offers the possibility of a fifth bedroom. This additional flex space provides room to grow or to create that home gym or game room you’ve always wanted. Outside, the large, level yard and private deck invite you to relax and unwind. You will also realize continued savings from the solar panels, which will be paid in full at settlement! Located near I-81 and Old Town Winchester, you are perfectly positioned for work and play. The loan for the solar panels will be paid by the seller at closing. WANT TO SAVE ON YOUR MOVE? YOU CAN FINANCE THROUGH THE PENFED CREDIT UNION'S VIB PROGRAM? As a VIB (Very Important Buyer), you can save an average of $2,300 on closing costs when financing with PenFed Credit Union. Enjoy waived appraisal, origination, and credit report fees, plus a unique 3-year refinance advantage. ASK ME FOR DETAILS ON HOW TO QUALIFY!!

111 Sovereign Ct, Winchester
$489,900
3 Beds ⋅ 2 Baths ⋅ VAFV2043454 MLS
Welcome to this beautifully refreshed 3-bedroom, 2-bath rancher in Chapel Hill. After hearing buyer feedback that the home felt dated, the sellers invested thousands of dollars and brought in a builder and design team to thoughtfully update the property for its next owner. The kitchen received a complete refresh with quartz countertops, a redesigned single-level peninsula, stainless steel appliances, a porcelain sink, tile backsplash, updated hardware, modern fixtures, and fresh lighting. The result is a bright, current space that feels both functional and inviting. Additional improvements include a new hall bathroom vanity with a quartz top, new switch plates and outlets throughout, a serviced and inspected HVAC system, a fully functioning gas fireplace, and a new vapor barrier in the crawl space. The sellers also addressed the items identified in a prior home inspection. Outside, the home has been power-washed, the landscaping has been trimmed, and the storage shed was updated with new plywood, shingles, and a ridge vent. The home's roof is approximately 8 to 10 years old, and the covered front porch adds classic curb appeal. With substantial improvements already completed, this home offers a refreshed interior, important maintenance updates, and the opportunity to move in and enjoy from day one. Conveniently located off Route 522 South, approximately two miles beyond Costco, the home provides easy access to shopping, dining, and everyday conveniences.

231 Bentley Ave, Winchester
$489,900
4 Beds ⋅ 3 Baths ⋅ VAFV2043450 MLS
Welcome to this beautiful new construction home offering over 2300 square feet of living space, This spacious home features 4 bedrooms, 2 1/2 bathrooms, and an attached garage with automatic garage door openers. The main level showcases hardwood flooring throughout, elegant crown molding, and an open inviting layout ideal for everyday living and entertaining. The kitchen is highlighted by granite countertop, generous cabinet space, and bar. With modern finishes, ample living space, and the convenience of a brand new home, this property will be ready to move in very soon!

181 Manor Dr, Winchester
$849,000
6 Beds ⋅ 5 Baths ⋅ VAFV2043430 MLS
UP TO $5000 SELLER CONCESSION FOR PAINT. CALL FOR DETAILS. Welcome to this stunning Colonial estate nestled in the highly sought-after Raven Pointe neighborhood of Winchester, VA. This exceptional home flawlessly pairs a grand interior layout with panoramic views, perfectly situated directly adjacent to peaceful farmland while remaining just 7 minutes away from historic Old Town Winchester. Built in 2016, this stone-accented detached single-family home boasts a massive 4,714 total finished square feet across three fully completed levels. Positioned on a beautifully manicured 0.27-acre lot, it offers an incredible footprint featuring 6 bedrooms, 4 full bathrooms, and 1 half bathroom—delivering unparalleled space and versatility for multi-generational living or working from home. The main level welcomes you with an open, light-filled architectural flow anchored by high ceilings and formal dining spaces. Cozy up next to one of the 2 fireplaces or enjoy entertaining guests in the spacious living area. A massive primary suite functions as your own private oasis, accompanied by generously sized additional bedrooms upstairs. The lower level features a fully finished walk-out basement equipped with interior access and structural step-up design, ready for a home theater, gym, or separate recreation space. Includes a spacious 2-car attached front-entry garage with an automated door opener. Situated immediately next to sprawling local farmland, offering an authentic country-style retreat without sacrificing suburban convenience. Experience the premium neighborhood presentation of Raven Pointe with a low, budget-friendly fee of just $95 annually. Don't miss the chance to own this meticulously maintained, newer-construction masterpiece that balances rural tranquility with city conveniences. Schedule your tour today!

226 Summerfield Dr, Winchester
$439,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043378 MLS
Welcome to 180 Quaker Lane, where timeless charm meets thoughtful updates! Nestled on a peaceful one-acre lot in the desirable Glenside subdivision, this beautifully maintained Cape-Cod home offers 3 bedrooms, 2.5 bathrooms, a 2 car attached garage, and over 1,900 finished square-feet of comfortable living space. The main level features an updated kitchen, a formal living room anchored by a cozy gas fireplace, a dedicated dining room, and convenient laundry and half-bath. An additional family/flex room provides the perfect space for entertaining, a home office, playroom, or second living area. Upstairs, you'll find three generously sized bedrooms, including the spacious primary suite complete with a walk-in closet and private en-suite bath. Two additional guest bedrooms feature hardwood flooring, abundant natural light, and share a well-appointed full bath in the hall. The outdoor living is equally impressive. Relax year-round in the fully screened porch, or step onto the recently added rear deck - an ideal extension off the dining area for effortless indoor-outdoor entertaining. The deck overlooks the spacious backyard framed by mature trees and lush landscaping, offering both privacy and room to enjoy the outdoors. Two storage sheds convey with the property, providing ample space for lawn equipment , tools, or hobbies. Located just off Apple Pie Ridge Road with no HOA , this move-in ready home combines peaceful living with everyday convenience. This one will not last long, schedule your private tour today! Recent updates include the new roof in 2021, replaced HWH in 2025, and addition of the rear-deck in 2026.

180 Quaker Ln, Winchester
$310,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043422 MLS
Adorable rancher in Shawneeland with access to a lake, trails, beach, and fishing. Ideally you wish for spacious living quarters,3 bedrooms, 2 full baths, and a walkout basement with a finished room for gym/office/den..well we have all that and more so come take a gander and make it your own before the summer ends. Septic is 1 bedroom (2 person occupancy)

204 Cochise Trl, Winchester
$329,000
4 Beds ⋅ 2 Baths ⋅ VAFV2043386 MLS
Welcome home to 111 Geronimo Trail, a beautifully updated raised ranch home nestled in the peaceful, wooded neighborhood of Shawneeland. Tucked away on rolling, hilly roads and surrounded by mature trees, this property offers a true nature-retreat feel with the effortless flow of a classic ranch design. The exterior features a long driveway for plentiful parking, a handy storage shed, and an awesome tree house guaranteed to bring hours of fun. Before stepping inside, you'll love the expansive front deck, which serves as the perfect spot to sit back, relax, and take in the quiet, scenic surroundings. Inside, the main level feels bright and modern, featuring a large living room with gleaming floors that seamlessly flows into the kitchen. The heart of the home stands out with its fun, vibrant mint green cabinetry and convenient bar seating, perfect for morning coffee or casual meals. The intelligent floor plan offers excellent privacy, featuring two spacious bedrooms with hardwood floors and a full bathroom on one side of the home, matched by another two bedrooms and a second full bathroom on the opposite side. The lower level extends your living space significantly with a finished walkout basement. Here, a massive family room offers endless possibilities for a game room or media space, anchored by a cozy pellet stove with a stunning stone accent wall and tile surround—ideal for chilly winter evenings. Complete with laundry facilities, direct walkout access to the yard, and a separate den with fantastic potential to serve as a fifth bedroom or home office, this mountain-like escape truly has it all!

111 Geronimo Trl, Winchester
$959,000
3 Beds ⋅ 3 Baths ⋅ VAFV2043380 MLS
Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning modern farmhouse nestled on twenty wooded and open acres with pleasant peaceful views. This thoughtfully designed home features spacious living areas, modern finishes, exterior that blends beautifully with its natural surroundings. Perfect for those seeking privacy, peace, and the beauty of nature, yet with convenient access to nearby amenities. Plenty of room for outdoor recreation, gardening, or simply enjoying the view from your porch. Build your dream lifestyle here – endless possibilities on unrestricted land! Escape to a serene retreat of rolling meadows, shady woodlands, and sparkling little ponds. Here, the land is alive—deer wander gracefully through the trees, wild turkeys stride across the fields, and songbirds fill the air with music. Bring your horses, cows, goats, or sheep to graze the open pastures, or simply enjoy the peace of living alongside nature. This is more than just land—it’s a private sanctuary where farm life, wildlife, and natural beauty come together in perfect harmony.” In the summer, kids might toss in a line, pulling out a perch or even a fat catfish. Families might watch dragonflies skimming the water’s edge. At night, fireflies light up the grasses around the pond, adding to the magic. Builder is also willing to build your plans. Price is projected and subject to change.

Light Rd, Winchester
$999,000
4 Beds ⋅ 3 Baths ⋅ VAWI2011144 MLS

517 Merrimans Ln, Winchester
$350,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043342 MLS
Why wait to build? This beautifully finished, move-in-ready home offers all the benefits of new construction without the wait. Offering modern style, quality craftsmanship, and low-maintenance living a short distance from Winchester this new home is nestled on a beautiful lot in Wilde Acres. This thoughtfully designed 3-bedroom, 2-bath home features an open floor plan with luxury vinyl plank flooring and today’s most sought-after finishes. The spacious kitchen is the heart of the home, showcasing granite countertops, a large peninsula, stainless steel appliances, white shaker cabinetry, and black fixtures. The primary suite offers a private bath with granite countertops and a walk-in shower, while two additional bedrooms provide space for family, guests, or a home office. The finished lower-level family room offers flexible living space for entertaining, recreation, or remote work, and the oversized garage provides great storage. Enjoy the peace and privacy of mountain living with convenient access to Mountain Falls Park, featuring a lake, playground, picnic area, and outdoor recreation. Move-in ready and thoughtfully finished throughout, this home offers the perfect blend of comfort, style and value. Some photos virtually staged. Owner/agent.

503 Grouse, Winchester
$435,000
4 Beds ⋅ 2 Baths ⋅ VAWI2011154 MLS
Seller offering closing cost assistance on select offers—contact the listing agent for details. Welcome to this beautifully renovated historic home in the heart of Old Town Winchester, where timeless charm meets modern living. This move-in-ready 4-bedroom, 2-bath home has been thoughtfully updated throughout, featuring a stunning kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and designer finishes. Enjoy new flooring, fresh paint, updated lighting, and renovated bathrooms. Outside, relax on the inviting covered front porch or entertain on the rear patio overlooking the spacious fenced backyard. Just minutes away from the Winchester Walking Mall, restaurants, shopping, breweries, parks, and local events, this turnkey home offers the perfect blend of historic character, modern updates, and an unbeatable location. Schedule your private tour today!

21 E Germain St, Winchester
$420,000
2 Beds ⋅ 2 Baths ⋅ VAWI2011142 MLS
Welcome to 1826 Kershaw Lane in Willow Lawn Cottages, one of Winchester, Virginia's most sought-after 55+ active adult communities, offering low-maintenance, single-level living just minutes from Historic Old Town Winchester. This beautifully maintained 2-bedroom, 2-bath ranch home showcases exceptional pride of ownership with beautiful hardwood flooring, soaring vaulted ceilings, and an open floor plan filled with natural light. The kitchen features a decorative ceramic tile backsplash, an updated Moen faucet, a new refrigerator, and a new microwave, combining style and functionality for the home chef. The spacious primary suite offers a relaxing retreat with a private en-suite bath and generous closet space. A second bedroom and full bathroom provide comfortable accommodations for family and guests. The inviting sunroom is bathed in natural light, creating the perfect space for morning coffee, reading, hobbies, or a home office. Additional updates include new gas fireplace logs, adding warmth and charm to the living area. Outside, you'll enjoy a beautifully landscaped garden that creates a peaceful setting for relaxing or entertaining. French drains have also been installed to enhance drainage and provide added peace of mind. Residents of Willow Lawn Cottages enjoy a friendly community atmosphere with convenient access to Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, Jim Barnett Park, the Museum of the Shenandoah Valley, and the Winchester Green Circle Trail. Shopping, dining, healthcare, and year-round events are just minutes away.

1826 Kershaw Ln, Winchester
$750,000
4 Beds ⋅ 3 Baths ⋅ VAFV2043290 MLS
RARE FIND! Discover the freedom and possibilities that come with 12.17 wooded acres—no HOA, no restrictions, just endless opportunity. Whether you're dreaming of creating a self-sufficient homestead, establishing a hobby farm, enjoying outdoor recreation, or simply escaping to your own private retreat, this exceptional property is ready to make it happen. The outdoor amenities are truly unmatched. A paved driveway leads to the home with both asphalt and gravel parking areas. Three powered outbuildings provide incredible flexibility, including a 20' x 40' insulated building complete with a chimney and lean-to, plus two additional sheds, one with its own lean-to. The established goat pen and chicken pen are equipped with both water and electric, making it easy to begin or expand your homesteading lifestyle. Outdoor enthusiasts will appreciate the private shooting range with berm, existing ATV trails winding through the woods, a 50-amp RV hookup, covered carport, and a relaxing hot tub to unwind after a day spent enjoying your land. The well-maintained brick rancher offers over 3,096 square feet of thoughtfully designed living space with 4 bedrooms and 3 full bathrooms. The beautifully updated kitchen is both stylish and functional, featuring luxury vinyl plank flooring, recessed lighting, rich earth-toned cabinetry and countertops, and an LG stainless steel appliance package less than one year old. Crown molding enhances the main-level living areas, while the formal dining room provides the perfect setting for holiday gatherings, complete with a cozy fireplace for added ambiance. Large windows fill the spacious living room with natural light, and a second fireplace creates a warm and inviting atmosphere during cooler months. The main level also includes three generously sized bedrooms and two full bathrooms. The fully finished lower level expands your living space with a spacious recreation room featuring tile flooring and an impressive stone fireplace with a wood stove that has a stainless steel liner. This level also offers a private bedroom suite with a full bathroom, bonus room, and separate laundry room—ideal for guests, multi-generational living, or additional workspace. Laundry hookups are conveniently located on both levels, and there is a water treatment system and sump pump in the basement. This property is highly accessible, located just minutes from major highways and everyday conveniences, with an airport and top-tier medical care within a 15-minute drive. Properties offering this combination of unrestricted acreage, move-in-ready living, functional outbuildings, and exceptional outdoor amenities are becoming increasingly difficult to find. Whether you're looking to homestead, raise animals, enjoy outdoor recreation, or simply embrace country living without restrictions, this property offers the lifestyle you've been searching for. Don't miss this rare opportunity to own a truly one-of-a-kind property with room to live, work, play, and grow!

3764 Northwestern Pike, Winchester
$569,000
4 Beds ⋅ 4 Baths ⋅ VAWI2011132 MLS
Exceptional opportunity to own this beautifully crafted custom all-brick home on Winchester's desirable east side, nestled in an established neighborhood just minutes from Route 7, downtown Winchester, schools, shopping, dining, hospitals, and major commuter routes. Designed for both everyday living and entertaining, this impressive residence features an open-concept floor plan with gleaming hardwood floors, abundant natural light, custom built-ins, and a cozy gas fireplace. The contemporary gourmet kitchen showcases granite countertops, stainless steel appliances, a spacious pantry, and a generous breakfast area, flowing seamlessly into the Large dining and living spaces. The thoughtfully designed layout offers four spacious bedrooms, each with access to a full bathroom. On the main level, you'll find a welcoming guest bedroom with a nearby full bath, along with the luxurious primary suite featuring a private ensuite bath with a tub/shower combination and walk-in closet. A convenient laundry room with utility sink is located just off the kitchen and provides access to a covered carport and outdoor sitting area. A private upper-level suite includes its own entrance on main level with a connected living room, two upper level bedrooms, and full bath, and sitting area making it ideal for an in-law suite, au pair quarters, or private guest accommodations. Adding even more versatility, the detached two-car garage is topped by a fully equipped apartment complete with a bedroom, full bath, and kitchen/living area—perfect for rental income, multigenerational living, a home office, or long-term guests. Parking is abundant with front and rear driveways, the detached two-car garage, and additional street parking. Combining timeless craftsmanship, flexible living spaces, income-producing potential, and an unbeatable location, this one-of-a-kind property truly offers something for everyone. Don't miss the opportunity to make this exceptional home yours!

687 Woodland Ave, Winchester
$424,900
4 Beds ⋅ 2 Baths ⋅ VAFV2043284 MLS
✨ Rare Opportunity on Winchester's East Side with a LOWER-LEVEL IN-LAW SUITE! 🏡 Welcome home to this spacious 4-bedroom, 2-bath beauty offering a warm, inviting layout and thoughtful updates throughout! ❤️ The main level features a generous living room, dining room, and a bright kitchen with stainless steel appliances, plus three bedrooms and a full bath—all highlighted by beautiful hardwood floors. ✨ The finished lower level is a standout feature with a private in-law suite 🏠 featuring a huge rec room, kitchenette, bedroom, full bath, abundant natural light ☀️, and convenient walk-out access. Step outside to enjoy your morning coffee on the covered front porch or unwind on the back deck. The large corner lot offers plenty of yard space for gardening, pets, or play! 📍 Perfectly located near Jim Barnett Park, Shenandoah University, schools, commuter routes, and just 1 mile from Old Town Winchester for shopping, dining, and entertainment! ✨ Recent Updates Include: 🏠 New roof (2026) with transferable warranty 🔥 Brand-new boiler (2025) 🎨 Fresh paint throughout for a bright, clean feel 🛏️ Beautifully updated lower-level bedroom 🚿 New bath & kitchen hardware for a fresh finishing touch 👕 New dryer for added convenience ⏳ Don't miss this incredible opportunity! Homes with this much space, flexibility, and location don't come along often—schedule your showing today before it's gone! 🔑🏡💕

145 Wilkins Dr, Winchester
$3,175,000
6 Beds ⋅ 7 Baths ⋅ VAWI2011110 MLS
A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

730 Merrimans Ln, Winchester
$535,000
5 Beds ⋅ 4 Baths ⋅ VAFV2043280 MLS
Welcome to 151 Travis Court, a beautifully maintained 5-bedroom, 3.5-bath Colonial tucked away at the end of a quiet cul-de-sac in the highly desirable Red Fox Run community. Situated on a spacious 0.31-acre lot backing to mature woods, this home offers the perfect combination of privacy, functional living space, and an unbeatable commuter-friendly location on Winchester's east side. From the moment you arrive, you'll appreciate the level front yard, level concrete driveway, and welcoming curb appeal. Inside, an attractive two-story foyer, hardwood flooring, and an open, light-filled floor plan create an inviting atmosphere that's equally suited for everyday living and entertaining. The spacious kitchen features granite countertops, stainless steel appliances, and abundant cabinetry while opening seamlessly to the comfortable family room with a cozy fireplace. Formal living and dining rooms provide additional gathering spaces, and the convenient main-level laundry room adds everyday practicality. Recent updates include new carpeting in the family room, updated kitchen appliances (2022), and a new refrigerator (2026). Upstairs, the generous primary suite offers a tray ceiling, oversized walk-in closet, and a private bath complete with dual vanities, a soaking tub, and separate shower. Three additional bedrooms and a full bath complete the upper level. The upstairs HVAC system was professionally serviced in June 2026, while the main-level HVAC was replaced just two years ago, providing added peace of mind. The walkout basement was professionally finished by KEE Construction in 2023, creating exceptional additional living space with a fifth bedroom, full bath, and versatile recreation area—perfect for guests, multi-generational living, a home office, or media room. Outdoor living is equally impressive with an oversized rear deck overlooking a private fenced backyard and mature wooded backdrop. While the fenced area offers plenty of room for pets and play, the property extends beyond the fence, providing an expansive 0.31-acre lot with even more privacy to enjoy. Additional highlights include architectural shingles, Glo Fiber high-speed internet, and a location just minutes from schools, shopping, dining, and Routes 7, 50, and I-81, making commuting throughout Northern Virginia and the surrounding region exceptionally convenient. If you've been searching for a move-in-ready home with five bedrooms, three finished levels, modern updates, and one of the most private settings in Red Fox Run, 151 Travis Court is ready to welcome you home.

151 Travis Ct, Winchester
$530,000
3 Beds ⋅ 2 Baths ⋅ VAWI2011122 MLS
Welcome to this charming historic home in Old Town. A spacious 3-bedroom Colonial, where timeless character meets modern comfort in the heart of Winchester. Thoughtfully updated with today's buyer in mind, this charming residence offers upgraded amenities while preserving its classic appeal. Inside, you'll find generous living spaces filled with natural light, along with a walk-up attic offering abundant storage or future expansion potential. The full basement is ready to be finished, providing the perfect opportunity to create additional living space, a home gym, recreation room, or workshop. Outside, the detached garage offers exceptional versatility for parking, storage, hobbies, or a workshop. Ideally situated just minutes from the heart of historic Old Town Winchester, you'll enjoy the convenience of walking to local restaurants, boutique shopping, entertainment, the Shenandoah Valley Museum, and Valley Health Winchester Medical Center. Whether you're looking for a primary residence or an investment in one of Winchester's most desirable locations, this move-in-ready home offers the perfect combination of historic charm, modern updates, and unbeatable convenience.

108 Morgan St, Winchester
$355,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043278 MLS
**Move-in ready!** Welcome to 100 Oakmont Circle, a beautifully updated 3-bedroom, 1.5-bath home filled with natural light and an open, inviting floor plan. Enjoy an updated kitchen featuring stainless steel appliances, new countertops, and a new oven/range, along with new hardwood floors in the living and dining rooms, also has a dual HVAC system. Step outside to a spacious, fully fenced backyard with mature trees offering privacy and shade. Conveniently located just off Senseny Road with quick access to Route 7 and I-81, this home is perfect for commuters while being just minutes from historic downtown Winchester walking mall, Jim Barnett Park, local shops, restaurants, and entertainment. Don't miss this wonderful opportunity to own a beautifully updated home in a prime location!

100 Oakmont Cir, Winchester
$1,239,000
4 Beds ⋅ 8 Baths ⋅ VAWI2011006 MLS
This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy. Inside, you will find a stunning kitchen with top-of-the-line appliances and pull-out drawers throughout the cabinets. The great room is a 2 story ceiling and fireplace leading to the deck and wet bar with ice machine and wine racks. The main level office has a full bath attached if you would like to use it as a main level bedroom. The living and dining rooms are open to each other leading to a sunroom off the deck. The primary bedroom as a gas fireplace, a balcony , 2 walk in closets and an updated spa like bathroom. The second bedroom has it's own bath and the 3rd and 4th bedrooms share a full bath with updated tile and floors. The basement also has a fireplace, a full bath, exercise room and plenty of storage. The pool room (in the basement leading to the pool) has a refrigerator, storage for towels and a 1/2 bath. The 3 car garage has a ton of storage, as the original kitchen cabinets are on the wall...This home is truly a showcase!

1022 Heth Pl, Winchester
$695,000
6 Beds ⋅ 5 Baths ⋅ VAFV2043064 MLS
NEW PRICE! Offering an exceptional blend of elegance, comfort, and modern updates, this meticulously maintained home is designed to impress. An impressive two-story foyer welcomes you into a thoughtfully designed floor plan featuring gleaming hardwood flooring throughout much of the main level. The formal living and dining rooms provide elegant spaces for entertaining, while the expansive family room is highlighted by a beautiful gas fireplace with a classic mantel, creating a warm and inviting gathering space for family and friends. The well-appointed kitchen combines style and functionality with granite countertops, a center island with a downdraft cooktop, two wall ovens, a pantry, and a refrigerator with an ice maker that was purchased new by the current owners. Just off the kitchen, the bright sunroom with a ceiling fan opens to a Trex deck, installed in 2024, overlooking the beautifully landscaped, fully fenced backyard. Also on the main level is a spacious private office with double doors, a convenient half bath, and a laundry room complete with a utility sink for added convenience. The outdoor living spaces are equally impressive. The Trex deck overlooks the private backyard, while the walkout lower level leads to a custom slate patio surrounded by mature landscaping and beautiful cherry trees, creating the perfect setting for relaxing, entertaining, or enjoying the peaceful surroundings. The attached garage offers built-in shelving for additional storage. The garage doors were replaced approximately two years ago, and the garage door openers with remotes were replaced in 2025. Upstairs, the spacious owner's suite serves as a luxurious retreat featuring a sitting area, cathedral ceiling, and double-door entry into the spa-inspired bath. The owner's bath includes dual vanities, a dedicated makeup area, a corner soaking tub, a separate tiled shower, and a private water closet. Bedroom two features its own en-suite bath, making it ideal for guests or extended family. Bedrooms three and four are generously sized and share a beautifully updated hall bath with a large tiled shower and a double vanity with soft-close cabinetry. The finished walkout lower level provides even more living space with new carpet installed in 2019, a spacious second family room, two additional bedrooms, and a full bath, making it perfect for guests, multi-generational living, or recreation. Step outside to the custom slate patio and enjoy the privacy of the beautifully landscaped backyard. This home has been exceptionally maintained with numerous major updates, including a new roof installed approximately two years ago, HVAC systems replaced in 2020 and 2021 that have been professionally serviced twice each year, and an 80-gallon commercial-grade water heater installed in 2019/2020. Combining timeless design, quality craftsmanship, and thoughtful improvements throughout, this move-in-ready home offers everything today's buyers are looking for.

231 Rebecca Dr, Winchester
$429,900
3 Beds ⋅ 3 Baths ⋅ VAFV2041936 MLS
*NEW TUB/SHOWER TO BE ISTALLED IN PRIMARY BATHROOM* Welcome to the neighborhood of Apple Ridge in Eastern Frederick County. You won't find a nicer home or more quiet cul-d-sac anywhere let alone one that has been more tastefully remodeled. This 3 bedroom 2.5 bath home has a welcoming front porch & overlooks the woods and open field of the private common ground area. Picnics, walks,sports and quiet time will be enjoyed there. So much has been updated here. There is new LVP floors, new wall to wall carpet, new granite counter tops, fresh paint, new light fixtures, newer architectural roof, water heater, HVAC and more. You will love the large kitchen which includes an island and a good sized breakfast room with sliders to the large rear deck. Step down into the 20X12 family room with a real woodburning brick fireplace to enjoy on those colder winter nights. The formal dining room is large and your dining room furniture will find a home here. There are three bedrooms including a large primary with a walk in closet and private bath. The bath has a new modern vanity and new vinyl plank flooring. This home is full of sunshine that pours through the windows. The private cul-d- sac make you feel at home, safe, and somehow removed from the day to day hussle & bussle. Being just minutes from Rt. 7E and Downtown Winchester adds to the unique and special nature of this very special place that you will want to call home. Come and have a visit. You will be glad that you did.

104 Kapok Cir, Winchester
$359,500
3 Beds ⋅ 2 Baths ⋅ VAFV2043202 MLS
Welcome to this beautiful 3-bedroom, 2-bathroom split-level home, a brand-new build nestled on a spacious 0.26-acre lot in the Mountain Falls Park community. Enjoy a warm welcome with a cozy covered porch. Inside, the home features luxury vinyl plank flooring throughout, providing a modern, durable finish. The kitchen is a chef's delight, with stainless steel appliances, premium shaker-style cabinets, and sleek granite countertops that add both style and functionality. The primary bath offers a touch of luxury, with granite countertops and a convenient stall shower. Each bedroom has thoughtfully designed built-in shelving in the closets, adding extra storage and organization. The lower level boasts a spacious family room, perfect for gatherings, as well as a convenient laundry room. For vehicle storage and projects, the oversized 20'10" x 23'2" two-car garage provides ample space. Outside, the Mountain Falls Park community offers amenities, including a common area, lake, picnic area, playground, and more—ideal for outdoor recreation and family fun. This stunning new home combines comfort, style, and a scenic location—schedule your visit today to experience it for yourself! Check out the video attached to this listing!

604 Gatling Dr, Winchester
$675,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043118 MLS
Why wait to build when you can have nearly new construction today? Built just 2 years ago, this beautifully upgraded ranch-style home offers the perfect blend of modern design, quality finishes, and move-in-ready convenience; all without the wait or premium pricing of new construction. With over 2,200 square feet of main-level living, this thoughtfully designed home features 3 spacious bedrooms, 2 full bathrooms, soaring 9-foot ceilings, durable luxury vinyl plank (LVP) flooring, and an open-concept floor plan filled with natural light from oversized windows throughout. The heart of the home is the stunning chef's kitchen, complete with quartz countertops, stainless steel appliances, a large center island with seating, and an oversized walk-in pantry featuring custom real wood shelving. The adjacent breakfast area is surrounded by windows, creating the perfect space to enjoy your morning coffee while overlooking the backyard. The spacious family room flows effortlessly to the covered rear porch, creating ideal indoor-outdoor living and a peaceful place to relax while enjoying views of the protected green space beyond. The private primary suite offers a true retreat with a spa-inspired bathroom featuring dual vanities, a soaking tub, glass walk-in shower with bench and Jolie filtered showerhead, plus a generous walk-in closet. Two additional bedrooms, a full guest bathroom, an oversized laundry room, and a functional mudroom with custom built-ins and desk area complete the main level. Need more space? The full walk-out basement offers incredible potential to finish exactly how you envision; with room for a recreation room, home theater, gym, guest suite, or additional living space. Sliding glass doors lead directly to the covered patio and fully fenced backyard. One of this home's most exceptional features is its setting. Backing to protected land along Abrams Creek, you'll enjoy peaceful wooded views, added privacy, and a tranquil backdrop that's difficult to find in newer communities. With the added benefit of a low HOA, you'll enjoy the advantages of a well-maintained community while keeping monthly expenses affordable. If you've been searching for main-level living, a nearly new ranch home, modern finishes, LVP flooring, a walk-out basement, low HOA, and a premium homesite with protected views, this is one you won't want to miss. Welcome home to Triangle Court.

132 Triangle Ct, Winchester