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$650,000
4 Beds ⋅ 4 Baths
Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including elegant formal living and dining rooms ideal for entertaining. The heart of the home features an inviting open-concept kitchen and family room, creating the perfect space for everyday living and gathering with family and friends. A bright and airy sunroom provides the perfect spot to relax while overlooking the backyard. The finished basement offers exceptional flexibility with abundant space for a recreation room, home theater, fitness area, office, or guest suite. A spacious 2-car garage provides plenty of storage and convenience. Ideally situated in a prime location close to shopping, dining, schools, commuter routes, and all that Winchester has to offer, this impressive home combines space, convenience, and timeless appeal. If you're searching for a move-in-ready home with generous living areas and an unbeatable location, 1529 Dalton Place is one you won't want to miss. All sizes are approximate.

1529 Dalton Pl, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$1,495,000
Great Warehouse in the City of Winchester, approximately 13,000 sq. ft. will be vacant by end of October

567 N Cameron St, Winchester

Listing courtesy of Compass. Contact: (703) 310-6111
$375,000
3 Beds ⋅ 2 Baths
Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

1004 Pennsylvania Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$180,000
3 Beds ⋅ 1 Baths
Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to transform it into a distinctive home while building meaningful sweat equity. The level backyard provides plenty of usable outdoor space, and the rear alley creates the possibility of adding a gated entrance for convenient off-street parking behind the home. A rare opportunity to reimagine a well-located Winchester property and make it entirely your own.

309 Liberty Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$1,395,000
Legacy Investment Opportunity: Prime, Turn-Key Asset in Downtown Historic District! 7500 SF over four floors, located on the celebrated Walking Mall, Winchester, VA, the fastest-growing metro area in Virginia! This historic building has been fully modernized and is 100% occupied with a strong leasing history. List Price: $1,395,000. CAP Rate: 7.5%. Annual Net Rent: $106K. The property features a strategic mix of four stabilized leases, including prime ground-floor retail and Class A office suites across the second, third, and fourth floors. This is a very rare income opportunity!

185 Loudoun St N, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$719,000
7 Beds ⋅ 5 Baths
Situated on a prominent corner lot in an exclusive cul-de-sac enclave of distinguished homes, this impressive stone-front residence offers exceptional space, comfort, and timeless appeal in one of the area’s most desirable neighborhoods. Ideally located near fine dining, shopping, banks, and everyday conveniences, the home combines luxury living with unmatched accessibility. Built in 2011 and meticulously maintained, freshly painted, with new wall to wall carpet, this expansive residence features 7 bedrooms and 5 full bathrooms thoughtfully designed for both elegant entertaining and comfortable everyday living. A dramatic two-story foyer creates a grand first impression, flanked by formal living and dining rooms that add sophistication and charm. The upper level includes a luxurious owner’s suite with a spacious bedroom and spa-inspired bath, along with generously sized secondary bedrooms, including a Jack-and-Jill bath and an additional hall bath arrangement designed for convenience and privacy. The main level offers a desirable guest suite with a full bath, ideal for multigenerational living or visiting guests. At the heart of the home is a beautifully appointed gourmet kitchen featuring upgraded cabinetry, granite countertops, a center island, breakfast area, and seamless flow into the expansive family room. The finished lower level provides exceptional versatility with a large recreation/family room, an additional suite, and three flexible rooms perfectly suited for guest accommodations, home offices, fitness space, or playrooms. Step outside to the inviting deck overlooking the gently rolling backyard — an ideal setting for relaxing mornings, outdoor dining, and entertaining in a peaceful, private setting. House blueprints provided in this listing are for reference only and may not accurately reflect the current structure. Call your real estate agent and schedule a showing today!

2700 Loyalty Ct, Winchester

Listing courtesy of Elcy & Co. Realty, LLC.. Contact: 5403230675
$429,000
4 Beds ⋅ 2 Baths
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

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$500,900
4 Beds ⋅ 3 Baths
Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides a generous recreation room, an additional bedroom, and a full bath, offering flexible space for guests, a home office, or everyday living. Enjoy the fully fenced backyard with a patio, perfect for relaxing or entertaining, along with the convenience of an attached 2-car garage. Ideally located near shopping, dining, schools, parks, and major commuter routes, this home combines comfort, versatility, and a convenient Winchester location.

609 Quartzite Cir, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$379,000
3 Beds ⋅ 4 Baths
Welcome home to this beautifully maintained 3-bedroom, 2-full-bath/2 half bath, end-of-row townhouse! Perfectly situated in a highly desirable, family-friendly neighborhood, step inside to find gleaming hardwood floors and large, sunlit rooms that offer plenty of space to live and entertain. The heart of the home features a spacious kitchen that flows seamlessly onto a private rear deck—perfect for morning coffee or weekend barbecues. Outside features a private backyard with lovely patio and shed. Cozy up by one of the two beautiful fireplaces, located on both the main level and in the fully finished basement. The lower level provides excellent flexible space for a family room, home office, or gym. This move-in-ready property comes complete with all appliances and boasts a newer roof for ultimate peace of mind. Enjoy the convenience of dedicated off-street parking and a location that can't be beat. You are just minutes away from beautiful downtown shopping, vibrant restaurants, and houses of worship. Don't miss your chance to own this turnkey gem in an ideal community. See list of improvements in Documents.

2055 Cidermill Ln, Winchester

Listing courtesy of Colony Realty. Contact:

$360,000
3 Beds ⋅ 3 Baths
Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water heater, 2025 - new sewer line under driveway & from driveway to street, new LVP in kitchen, 2026 - replaced / leveled living room floor & subfloor, new LVP. Schedule your tour today!

117 E Pall Mall St, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$334,900
3 Beds ⋅ 3 Baths
New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter thoroughfares. No HOA.

913 Orchard Hill Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$449,000
4 Beds ⋅ 2 Baths
Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a true gem—a finished attic with an exposed brick wall, providing a unique, flexible space ideal for a home office, a creative studio, or a quiet retreat. Step outside and discover the large covered front porch. Adorned with a stylish wooden ceiling, it's the perfect spot to relax and enjoy the neighborhood. The rear deck and fully-fenced backyard offer a private oasis for outdoor gatherings. Situated on a desirable corner lot, the home's prime location puts you just moments away from Winchester's best shopping, dining, and schools. Parking is a breeze with a detached garage and a private driveway, providing abundant off-street parking—a valuable convenience in this downtown neighborhood. Offering recently updated HVAC on 3 levels.

420 W Cork St, Winchester

Listing courtesy of Colony Realty. Contact:

$295,000
3 Beds ⋅ 1 Baths
1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room for sleeping or work-from-home use. Outdoors, a covered front porch offers a shaded sitting area, a rear deck extends the usable outdoor space, and a fully fenced backyard defines the grounds for outdoor activities. Clean interior finishes complete this well-maintained residence with practical amenities throughout every room.. Included 100-Day Home Warranty with buyer activation

1314 S Braddock St, Winchester

Listing courtesy of Open Door Brokerage, LLC. Contact: 4804625392
$435,000
3 Beds ⋅ 2 Baths
Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice rack & a tile backsplash. The primary suite includes a remodeled primary bath (2023). There is a cozy sun porch on the rear of the home. Enjoy your morning coffee on the inviting front porch or out on the rear deck. The partially finished basement offers a large recreation room with wood stove for all your favorite hobbies. There is also a spacious storage room for your holiday decor, etc. The fenced backyard has a fire pit perfect for cooler fall evenings. There is also a shed for storing your gardening tools.

338 Lanny Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$675,000
Position your business in the heart of Winchester's premier retail corridor. This highly visible commercial outparcel offers an outstanding opportunity for retail, restaurant, medical, financial, or service-oriented development in one of the region's strongest shopping destinations. Located just off South Pleasant Valley Road with immediate access to Interstate 81, the property is surrounded by major national retailers including Lowe's, Walmart, Kohl's, Home Depot, Apple Blossom Mall, and numerous restaurants, hotels, and service businesses, creating exceptional consumer traffic throughout the day. The property sits within Winchester's primary retail trade area, drawing customers from the Shenandoah Valley, Northern Virginia, West Virginia, and Maryland. Current operating drive-thru. Property Highlights Prime 0.57-acre commercial outparcel Zoned CM-1 allowing a wide variety of commercial uses. Utilities available with water and sewer connections. Excellent access from Patsy Cline Boulevard and South Pleasant Valley Road. Minutes from I-81 interchange. Surrounded by established national retailers and restaurants. Strong daytime employment and regional consumer base. Ideal for: Quick-service or fast-casual restaurant Coffee shop Medical or dental office Financial institution Retail showroom Professional office Convenience retail Specialty retail Whether you're developing a flagship retail location, constructing a freestanding commercial building, or creating a custom build-to-suit opportunity, this site offers the visibility, accessibility, and surrounding retail synergy needed for long-term success.

535 Patsy Cline Blvd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com
$300,000
3 Beds ⋅ 1 Baths
In the heart of Winchester with 3 bedrooms and 1 full bath. Hardwood floors, fresh paint, kitchen with granite countertops, appliances, including full-sized washer and dryer. Lots of storage and private fenced backyard. Close to amenities. You don't want to miss this one!

361 E Piccadilly St, Winchester

Listing courtesy of Keller Williams Realty/Lee Beaver & Assoc.. Contact: 7033302222
$379,000
3 Beds ⋅ 4 Baths
Situated in the charming Orchard Hill subdivision, this delightful twin home offers a perfect blend of comfort and functionality. Built in 1987, this Colonial-style residence boasts a classic brick exterior that exudes warmth and character. With over 2,000 square feet of thoughtfully designed living space, this home is ideal for those seeking a cozy retreat. As you approach the property, you'll appreciate the inviting sidewalks that lead you to the entrance, enhancing the neighborhood's friendly atmosphere. The well-maintained lot, spanning 0.1 acres, provides a manageable outdoor space, perfect for gardening or enjoying a quiet afternoon in the sun. An outbuilding adds extra storage or workspace, catering to your organizational needs. Step inside to discover a fully finished walkout basement, offering versatile space that can be transformed into a recreation room, home office, or guest suite. The interior features a harmonious blend of carpet, luxury vinyl plank, and vinyl flooring, ensuring both style and comfort throughout the home. The heart of the home is the spacious kitchen, equipped with modern appliances including a dishwasher, smooth top range, refrigerator, microwave, and range hood. The adjoining dining area flows seamlessly into the living space, where a fireplace creates a cozy ambiance for those chilly evenings. With three generous bedrooms and three full bathrooms plus an additional half bath, this home provides ample space for relaxation and privacy. The convenience of upper-floor laundry adds to the home's appeal, making daily chores a breeze. Parking is easy with a driveway accommodating two vehicles, ensuring you and your guests have easy access. This property is not just a house; it's a place where memories are made. Whether you're hosting friends for a barbecue in the backyard or enjoying a quiet evening on the incredible screened in porch this home offers the perfect backdrop for your lifestyle. Experience the charm and comfort of Orchard Hill living-your new home awaits!

2104 Stoneleigh Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$600,000
3 Beds ⋅ 2 Baths
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

Listing courtesy of MarketPlace REALTY. Contact:

$259,000
1 Beds ⋅ 1 Baths
Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban Lofts Condominium, where history and modern living come together. Located in a home built in 1825, this unique property is just a short stroll to Winchester's favorite restaurants, boutique shopping, coffee shops, museums, and downtown events. Renovated in 2021, the condo offers stylish updates while preserving its historic character. The kitchen features quartz countertops, stainless steel appliances, a new refrigerator, and a new island with an integrated sink that creates the perfect gathering space. Fresh paint, modern lighting, a beautifully updated bathroom, and a built-in bookcase add to the home's appeal. The exposed brick fireplace serves as a striking architectural feature, adding warmth and character to the living room. (Fireplace is decorative only.) Whether you're looking for your own place in the heart of downtown or an investment opportunity, this low-maintenance condo offers the best of both worlds; historic charm, modern finishes, and an unbeatable location where you can leave the car behind and enjoy everything Winchester has to offer.

135 S Kent St Unit #202, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$795,000
Well established, reputable, and long-standing auto service center in a prime location at the intersection of Millwood Avenue and Pleasant Valley Road directly across from Shenandoah University. Presently doing business as Jim’s Auto Service Center. Excellent location, visibility, exposure, and sign location opportunities. Two bay garage doors equipped with two pneumatic lifts, providing new tire sales, tire repairs, batteries, oil changes, lube and filter replacement, fluids, flushing, belts and hoses, brake services, air conditioning services, wheel balancing, frontend alignment and more. The sales price includes the business, long-standing list of loyal customers and specified equipment and tools. Tours by appointment only with the exclusive listing agent. Call agent now for more details.

434 Millwood Ave, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$435,000
4 Beds ⋅ 2 Baths
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

Listing courtesy of Samson Properties. Contact: 7033788810
$420,000
2 Beds ⋅ 2 Baths
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

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$569,000
4 Beds ⋅ 4 Baths
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

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$3,175,000
6 Beds ⋅ 7 Baths
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

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$530,000
3 Beds ⋅ 2 Baths
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

Listing courtesy of Real Broker LLC- Winchester. Contact:

$255,000
Discover the potential of this 4-bedroom, 2-bath multi-family property offering 1,730 sq ft of living space on a 2,684 sq ft lot. Built in 1930, this property is a great opportunity for investors or buyers looking to renovate and add value. Don't miss your chance to make this income-producing property your next project!

384 National Ave, Winchester

Listing courtesy of The Greene Realty Group. Contact: 8882785840
$1,239,000
4 Beds ⋅ 8 Baths
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

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$1,724,000
Beautifully restored and fully modernized mixed-use building in the heart of historic Winchester. This exceptional offering includes a fully leased commercial building with three strong-credit tenants, a valuable adjacent parking lot approved for future mixed-use development, and a third floor ready for residential conversion. Located just one block from the historic Old Town Winchester Walking Mall, this legacy investment property offers more than 9,300 square feet of space with the first and second floors completely renovated and occupied. The third floor presents an outstanding value-add opportunity for apartment development, with potential eligibility for Historic Tax Credits. The property is also located within an Enterprise Zone, providing access to additional grant and incentive programs. The sale includes the adjacent parking lot (Tax ID 173-01-E-1), which is approved for multifamily development or can continue to serve as a highly desirable dedicated parking facility for tenants and customers. Current net operating income exceeds $80,000 annually, providing immediate cash flow with significant upside potential. Recent capital improvements include a metal roof, new HVAC systems, and modern tenant build-outs throughout the building. This unique asset offers a diversified income stream with retail and office tenants in place, while creating future opportunities for residential development on both the third floor and the adjacent parking lot. Ideal for a 1031 exchange buyer or investor seeking stable income, long-term appreciation, and redevelopment potential in one of the Shenandoah Valley's most desirable downtown locations. Conveniently located one block from the Braddock Street Parking Garage. Rarely does an opportunity of this caliber become available in Downtown Winchester. Contact the listing agent to schedule a private showing.

48 W Boscawen, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$524,900
3 Beds ⋅ 4 Baths
Welcome to this beautifully maintained townhome in the desirable Meadowbranch Mews community, where comfort, style, and convenience come together. Featuring three bedrooms and three-and-a-half bathrooms, this brick-front home offers timeless curb appeal and thoughtfully designed living spaces throughout. Step inside to a welcoming foyer with tile flooring that leads to an open and inviting main level. Rich hardwood floors, abundant natural light, and a neutral color palette create a warm atmosphere in the spacious living and dining areas. The kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, and a large center island with seating. Elevated ceilings enhance the home's airy feel, while a conveniently located powder room completes the main level. Upstairs, the spacious primary suite provides a relaxing retreat with a walk-in closet and private en-suite bath. Two additional bedrooms and a full hall bathroom offer plenty of space for family, guests, or a home office. The finished lower level adds exceptional flexibility with a large recreation room that can easily accommodate a media room, fitness area, playroom, or hobby space. This level also includes a guest room, full bathroom, laundry area, and generous storage. Recent updates include a new roof and gutters for added peace of mind. A private garage provides secure parking and extra storage, while the home's prime location places you just minutes from Winchester Medical Center, shopping, dining, and the charm of historic downtown Winchester. Residents of Meadowbranch Mews enjoy a low-maintenance lifestyle with community amenities that include a swimming pool, pickleball courts, picnic areas, snow removal, road maintenance, and trash service.

1352 Ramseur Ln, Winchester

Listing courtesy of Redfin Corporation. Contact:

$374,990
3 Beds ⋅ 4 Baths
END UNIT Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available! ***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* Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height, range hood, and wall oven. The first level includes a private finished recreation room and possible 4th bedroom with its own full bath and walk in shower, perfect for guests or a home office. Laundry hookups are conveniently located on the third level near the bedrooms. Step outside to a 10X14 maintenance free deck, ideal for relaxing or entertaining. Upgrades throughout make this home truly shine. Come see it for yourself. *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 8 Monteith Dr, Winchester

Listing courtesy of DRB Group Realty, LLC. Contact: 2404579391