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$2,600,000
Included in this sale are 2 buildings with 6 townhouse units each. The buildings exteriors have new windows, doors, siding, fencing, and paved parking. Each unit is comprised of 2 bedrooms and 1.5 baths. 11 of the units have been fully updated throughout. New additions included but not limited to hvac, washer dryer hook ups, new hot water heaters, and LVP . Currently running at full occupancy with all tenants in good standing.

525 Gray Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Weichert, REALTORS.

$2,400,000
Positioned on the north side of Winchester, this parcel sits in a prime industrial and logistics corridor. Prominent neighbors such as GEODIS, Kraft Schenker Distribution Center, Monoflo International, Green Bay Packaging, Miller Milling Company, and the BWI4 Amazon Fulfillment Center underscore its strategic location. The property is currently zoned Rural Agriculture (RA) and is already designated Industrial in the County's adopted Comprehensive Plan, which supports and assists in the rezoning process. The site offers dual road frontage on two state-maintained roads — paved frontage on Redbud Road and additional frontage on Milburn Road, which is scheduled for VDOT asphalt paving in 2026. The new VDOT road (Norman Drive) will run along the northern boundary, creating a third point of access. The property is located minutes from Interstate 81, Route 11, and the 37 Bypass. Utilities are easily accessible, with water and sewer mains within 500 feet and on-site electricity service lines. The nearly flat, cleared land enables cost-effective and straightforward development.

Redbud Road, Winchester

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

Selling Office: Sager Real Estate.

$2,200,000
LOCATION, LOCATION! 17,000 sq feet Professional office space located in prime downtown Winchester's business district! All-brick building features 3 finished floors - the 2 above grade levels feature spacious reception areas, exam rooms, private offices, break rooms, kitchenette, bathrooms, and the finished basement provides great bull-pen / gathering space with tons of storage/shelving. Space was formally a medical office. Nice details provide lots of character throughout, including some hardwood floors, crown molding and chair rail. Elevator and multiple staircases for accessibility options. Private parking lots provides 45 parking spaces! ALSO LISTED FOR LEASE - MLS #VAWI2003440

20 S Stewart St, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Keller Williams Realty.

$2,000,000
5 Beds ⋅ 6 Baths
This extraordinary 5-bedroom, 6-bathroom estate sits on 14.44 acres across two parcels—5.0 acres on the front lot and 9.44 acres with the residence—just minutes from Winchester, Virginia. Designed for both everyday living and elegant entertaining, this home combines timeless style with modern luxury. Inside, hardwood floors and soaring ceilings enhance open, light-filled spaces. The recently renovated kitchen is a chef's dream, featuring a 48-inch Wolf gas range with six burners and infrared griddle, GE Monogram appliances including a pebble ice maker, and a striking quartz waterfall island with coordinating backsplash. Throughout the home, Visual Comfort chandeliers, recessed lighting, and brass Emtek hardware add refinement, while radiant floor heating on the first level ensures year-round comfort. A private gym, spacious bedrooms, and a serene primary suite elevate everyday living. All bathrooms have been updated within the last four years and now feature quartz vanity countertops. This property is made for all seasons, with three indoor fireplaces, four outdoor stone fireplaces, and a heated pool with hot tub. Expansive stone and concrete hardscaping, a hardwired exterior sound system, and professional landscape lighting create an inviting backdrop for entertaining. Practical updates include a new HVAC system (2021), a new septic system (2022), and a custom Aegis Technologies security system with exterior cameras. An attached 3-car garage plus a detached 3-car garage provide abundant parking and storage. Located just 8 minutes from Winchester Medical Center and downtown Winchester shopping, dining, and commuter routes, this home offers the perfect balance of seclusion and convenience. Don't miss the opportunity to own one of Winchester's most distinctive properties!

821 Apple Pie Ridge Rd, Winchester

Listing courtesy of HomeZu.com of Virginia. Contact:

Selling Office: KW United.

$1,750,000
16 lots with 4 bedroom perks - zoned RA. Total Acreage including dedicated right of way -52.7566 Acres. Owner will consider a joint venture or owner financing to a qualified buyer

2189 Cedar Grove Rd, Winchester

Listing courtesy of Adams-Nelson & Associates Inc. Contact:

Selling Office: Realty ONE Group Old Towne.

$1,688,000
Professional office building for sale in downtown Historic Winchester. Located at the Intersection of W. Piccadilly Street and N. Braddock Street. Located directly across the street from the Handley Public Library and Kimberly's Gifts & Boutique. Great downtown location with off-street parking. Interior features include beautiful hardwood floors, updated cherry molding and wainscotting. This historic building is 60% leased and known as the Old Post Office, which was built in 1910. This building has first and second floor area totaling 11,060 SF. The basement level is leased and finished and features total floor area of 3,333 SF. NOTE: There are two offices available. One has a floor area of 3,000 SF and the second has a floor area of 2,705 SF. $17,335.75/MO + $4.00 CAM

40 W Piccadilly St, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

Selling Office: Oakcrest Commercial Real Estate.

$1,650,000
Turn Key Auto Service Center! Over 11K SF of garage, shop, service areas, warehousing, and customer/office/reception area. Faces Pleasant Valley Road with EXCELLENT VISIBILITY! 27x13 paint booth conveys. List of additional equipment available separately. Long standing, successful auto body/repair location ready for next generation! Multiple drive in doors and work bays. Could have multiple businesses. Zone CM1. Could also be contractors office, buildings supplies, machine shop, etc. Asking $1.5M.

116 Bruce Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Unrepresented.

$1,600,000
5 Beds ⋅ 4 Baths
This unique property is the definition of an oasis in the woods. Surrounded by 180 glorious private acres, this home dazzles with grandeur while blending natural elements that mesh with the environment. The handsome hunter green standing seam metal roof with matching accents against wood siding is the ideal look for this 4,166 square foot architectural marvel. Indoors, there’s a thoughtful combination of plank walls, hardwood floors, tile, wall treatments, wrought iron, and stone to augment the theme. On the main level, the vaulted great room is a showstopper where dining and gathering spaces share a bank of windows overlooking a breathtaking view of the great outdoors. A floor to ceiling stone fireplace is a commanding feature of the family room. The gourmet kitchen, which connects to the space, features two walls of staggered height cabinets, giving you ample room for storage and prep, with panels covering the Sub-Zero refrigerator for a seamless look. Sleek granite counters go with the theme, and grace the matching island, which holds a commercial-style Viking stove and double oven plus overhead ventilation hood. Dine-in seating for four is a nice island bonus. A sunken den down the hall provides a cozier space perfect for entertaining or relaxing and benefits from another stone fireplace, wet bar, and abundant windows. Two generously sized main-floor bedrooms add to the versatility of this home and share a decadent en suite bath. You’ll appreciate the gorgeous touches, luxury vanity and bathtub, large walk-in shower, private commode, and linen closet. A laundry room and half-bath are also situated on this level, as well as access to the attached garage, and outdoor spaces. Upstairs, you’ll find a suite with adjoining living quarters. Both offer ample space for furniture and desired extras, and one side includes a lovely sitting room featuring an opulent fireplace and hearth. The rooms share a decadent full bath with a double vanity, soaking tub, doorless shower, and private commode. This floor also includes a media or entertainment room (or 5th bedroom), and a centrally located mini kitchen in the hallway alcove allows for storage of snacks and drinks. Outdoors, a viewing tower stretching three stories (accessible from the first and second levels) allows you to enjoy mountain views, glimpse abundant wildlife, and contains spots for seating and outdoor dining. There’s also a backyard patio and fire pit area. With so much nature at your fingertips, you can meander through the woods and pause at the creek traversing part of the property. The home is for sale furnished, so it’s not only meticulously designed and curated, but quite literally move-in ready. Whether you deign to live here full-time or as a weekend retreat, this extraordinary home is ready for you now.

1631 Back Mountain Rd, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Samson Properties.

$1,550,000
Welcome to a truly rare offering — a first-time release of an extraordinary 128+ acre estate parcel, perfectly suited for the discerning buyer seeking privacy, natural beauty, and limitless potential. This is one of only three exclusive lots masterfully curated from a 439-acre legacy estate, designed with elegance, intention, and long-term value in mind. Tucked behind private, impeccably constructed roadways, Lot 1 offers sweeping panoramic views, gently rolling topography, and multiple cleared, level homesites ideal for a custom luxury residence, private compound, or family estate. With the On-site electric service, approved 5-bedroom perc site combined with the hand selected homesite locations meticulously cleared your future residence is closer than you could have imagined. Miles of private walking, hiking, and four-wheeling trails allow you to enjoy both privacy and commanding views The natural beauty of the land is unparalleled—sun-drenched meadows, mature woodlands, and breathtaking vistas provide the perfect canvas for an estate that’s as grand or understated as your vision demands. The subdivision is fully approved and recorded, with final tax map IDs and GIS updates currently in process. This land represents not only a stunning homesite but also a long-term investment in a region poised for enduring value. Under 20 minutes from Winchester City limits and just a little over an hour from DC you couldn't ask for a a better full time location or weekend escape.

128.556 Acres Laurel Grove Rd, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Keller Williams Realty.

$1,550,000
14 UNIT APARTMENT BUILDING, OLD TOWN WINCHESTER! PRIVATE PARKING FOR 15 VEHICLES! Very rarely does this come around, actual multifamily density within ONE BLOCK of the Walking Mall! All units in good condition. All SEPARATELY METERED ELECTRIC, Tenants reimburse Landlord on gas, water/sewer. History of stable, long term tenants. NOI $130K+. Asking $1.7M. Pictures are all current, P&L and rent roll will be provided before showings are scheduled. Qualified buyers only.

406 N Loudoun St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Realty ONE Group Old Towne.

$1,525,000
4 Beds ⋅ 4 Baths
Set on 65 picturesque acres just outside of Winchester, 632 Dry Creek Lane offers a rare blend of refined living and exceptional land, an ideal private retreat within easy reach of Washington, DC. Designed for comfortable single-level living, the 4-bedroom, 4-bath home offers approximately 3,367 finished square feet filled with natural light and sweeping countryside views. A dramatic vaulted great room with stone hearth and gas fireplace anchors the home, while the spacious kitchen features quality cabinetry, an oversized island, and a layout that opens to the main living areas. The main-level primary suite provides a private retreat with screened porch, dual walk-in closets, and a redesigned bath. Additional highlights include two main-level bedrooms, a newly enclosed loft bedroom with balcony, and a full walkout basement with full bath for future expansion. A peaceful creek winds through the property, complemented by established riding and walking trails. Equestrian amenities include two barns, a 100’x200’ lighted arena, 10 fenced pastures, and run-in sheds. A custom recreation barn offers additional finished space with indoor and outdoor entertaining areas, completing this peaceful, turnkey escape with exceptional versatility.

632 Dry Creek Ln, Winchester

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Porch & Stable Realty, LLC.

$1,500,000
4 Beds ⋅ 4 Baths
APPLE PIE RIDGE...A Legacy Unbroken: Lost Stream Farm, a 7-Generation Family Heirloom Welcome to Lost Stream Farm, a place where history isn't just a date in a book—it's alive in the brick and stone of every wall. Dating back to the late 1700s, this Quaker-built dwelling has been a cherished family home for an astonishing seven generations. For the very first time in 235 years, it's now ready for new owners to become its next stewards. Nestled on just over 11 acres at the top of Apple Pie Ridge—the heart of Winchester's famous apple country—this property is a testament to a family's deep connection to the land. This is a home built from the earth it stands on; the original brick and stone were meticulously sourced from the property itself, a physical manifestation of a family's enduring legacy. This family was among the earliest orchardists in Frederick County, a legacy that helped earn Winchester its "Apple Capital of the World" title. You can feel this profound history in the gentle landscape, from the apple orchards that once flourished to the very ground that was cared for over centuries. The original bell, once rung to call in the workers from the apple orchards, still stands on the property as a tribute to this rich past. Stepping inside this 4-story brick manor house is like stepping into a living story. The home was thoughtfully expanded in the early 1900s, doubling its size while seamlessly preserving its historical integrity. For over 50 years, John and Katie Anderson lovingly cared for this home, becoming its stewards and meticulously undertaking major renovations that honored its past while providing modern comfort. A new standing seam metal roof (2017) was installed, and the home features six fireplaces. Major updates include Central Heat and Air Conditioning (2022), a new bathroom with a walk-in, glass-walled shower, and a gorgeous kitchen with a built-in stovetop in the old fireplace and beautiful handmade cabinets. Outside, the property is a true sanctuary, located just 5 minutes from Winchester Medical Center and 10 minutes from downtown Winchester. A beautifully renovated 2-car garage (2025) was seamlessly integrated with the property’s original spring house, a historic structure that once supplied water to the home. The active spring overflow feeds a stream that runs along the property and is a wildlife sanctuary for deer, turkey, birds, and other animals. There is a separate, small spring-fed pond on the property which has fish and turtles. The back patio provides a peaceful escape, where a serene koi pond flourishes with lush vegetation and koi fish, surrounded by vibrant flowers that bloom throughout the seasons. A separate garden shed, an equipment shed, and a charming 2-story bank barn offer endless possibilities. The land itself is a rare find, composed of two parcels, offering a unique opportunity to build or protect the surrounding land. This is more than a home; it’s an invitation to own a serene, private slice of history—a place for long walks, gardens, or horses, and sipping a glass of tea on the expansive front porch swing. A property that has never been sold and has waited nearly 235 years to find its next guardian. NOTE: This listing includes 2 parcels of land totaling 11.36 acres. Public records and other sources only show the valuation for the property as the manor home on 6.3 acres. An additional 5.06 acre parcel is included (with permit approved for 3-bedroom septic). Schedule your private tour today. PLEASE, NO DRIVE-BYS as the driveway has no turnaround without going directly to the residence.

731 Apple Pie Ridge Rd, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: RE/MAX Roots.

$1,465,656
4 Beds ⋅ 4 Baths
Welcome to Stonymeade ! -2 acre Home Site in Winchester Virginia Base price shown is for the Huntwick Farm floorplan and we have many other plans including those with first floor primary suites, farmhouse kitchens, and multi-generational options. All homes include exceptional standard features including 10' main level ceilings, Hardwood floors, upgraded cabinetry and countertops, extensive trim package, and HardiePlank exterior. Plans are ready to be customized!

Lot 62 Gravenstein, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: Slones Real Estate.

$1,400,000
Five acres of B2 land near Costco, Army Corp of Engineers, Frederick Country Public Safety Building, and the new One Logistics Park commercial center. An adjacent parcel of ten acres is available for sale for a combined parcel of 15 acres. Perfect for a large-scale commercial development.

260 Costello, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Realty FC.

$1,337,500
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:

Selling Office: Link Realty Services LLC.

$1,300,000
Excellent 1031 opportunity in Winchester, Virginia. This interstate commercial property is strategically located immediately off I-81, Exit 315, and is leased with over seven years remaining on the current term. Key highlights include NOI: Currently $83,000 per year.Tenant: A good credit tenant is in place, responsible for real estate taxes and insurance. Property Condition: The building is in excellent condition and is located next to a Five Guys restaurant. Previous Use: The property was previously a restaurant and still has an intact kitchen. This is a prime investment in Virginia's fastest-growing community, offering an unbeatable location and market. Asking price for this occupied property with a good-standing tenant is $1.5 million.

1359 Berryville Ave, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Unrepresented Buyer Office.

$1,250,000
5 Beds ⋅ 5 Baths
This regal 1950s Colonial, named Eagle Gate, sits atop a knoll overlooking 6.34 pastoral acres on the east side of Winchester. This elegant home dazzles with nearly 4,000 finished square feet, three levels, five bedrooms, 4.5 baths, an expansive garage, a swimming pool, and renovations and updates that elevate the living experience to decadent. Majestic pillars are the hallmark of the handsome façade, but the entire home and grounds are thoughtful, inviting, and pleasing. The standout architectural features begin on the exterior, and when you walk into the grand foyer, you’ll glimpse the elegant paint and wall covering choices, rich hardwood floors, and trim details you’ll find throughout the home. The living room allows for ample furniture configurations and is centered by a wood-burning fireplace. The formal dining room is spacious enough for a large table and chairs, complementary buffets or display cabinets and the dentil molding, chair rail, and trio of colors adds style. The kitchen is a dream with bright white cabinetry, subway tile backsplash, granite counters, and top-of-the-line appliances, which are integrated seamlessly. The Wolf stove features a gas range and is flanked by a microwave and a Bosch warming drawer. A butcher block-topped island with seating provides additional workspace and storage, matching an additional display cabinet. The den departs visually with its warm, wood-paneled walls, built-ins, and exposed ceiling beams, is flooded with natural light, plus finds added ambiance from a gas fireplace. The sunroom captivates with its light and airy space, plus French doors that open to the fenced outdoor patio. There’s room for lounging and dining and with its gas fireplace and wet bar, you’ll enjoy this leisurely space year-round. A chic half-bath rounds out this level. Upstairs, the owner’s suite affords space for bedroom and sitting or dressing room furniture amidst soothing colors and comes with dual closets. The luxurious ensuite, lined with tile and marble elements, contains a water closet, soaking tub, walk-in shower, vanity, and plentiful storage, and leads to a private outdoor deck. There are two more lavish bedrooms, which contain custom closets and built-ins, with a full bath. The top level also holds two more large bedrooms, a full bath, and a bonus room to utilize however you wish. The partially finished basement provides dedicated storage, wine storage, an extra refrigerator, laundry facilities, and a full bath, along with space for exercise equipment or entertainment. Step into your backyard oasis, where you’ll enjoy a refreshing pool that’s surrounded by a hardscaped terrace ready for lounges and outdoor dining. The hot tub is nearby, conveniently placed on the patio. The adjacent three-bay garage not only gives you room for your vehicles and other storage, but a covered porch along one side of the pool. A smaller outbuilding is perfect for pool or garden storage. A lower-placed barn is perfect for a workshop, studio, or additional storage. The acreage is an unusual amenity for a property on the east side of town. Since it borders Abrams Creek, you’re awarded access to this beautiful creek, and the lush lawn and mature hardwoods offer resplendent views and areas to roam, play, and entertain. Located across from the Winchester Country Club and down the street from Jim Barnett Park places you close to downtown and every amenity the city offers, and it includes public water and sewer with natural gas. Beautifully renovated and maintained, this remarkable, uncommon real estate opportunity isn’t likely to be on the market long.

100 Country Club Cir, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

$1,200,000
4 Beds ⋅ 5 Baths
This captivating property on Lake Serene offers a truly grand living experience— a private oasis meticulously crafted for your enjoyment. Four artfully created levels. Almost 5,000 square feet. Gorgeous waterfront views flanked by lush woods. And the backyard of your dreams. The handsome stone façade with brick features hints at the architectural details that continue inside with an arched brick entryway, wood ceilings, hardwood floors, a stone fireplace, and beautiful trim. The large living room dazzles with a vaulted wood ceiling, long window seat, floor-to-ceiling stone fireplace, and bank of windows toward the water. The gourmet kitchen welcomes you with bright hues, a coffered ceiling, and an abundance of gorgeous cherry cabinetry—including a glass-front corner cabinet perfect for display pieces. You’re going to love the oversized, double farmhouse sink and high-end countertops. An island in the center gives you even more workspace and the warming drawer is a nice bonus. The turret room is the perfect spot for dining, with ample windows and another artful wood ceiling. The main level primary suite gets its own window seat overlooking the water view, two walk-in closets, and a bright bathroom with a bubble tub, separate shower, double vanity, and marble floor. Laundry facilities and a half-bath round out the main level. Head upstairs to enjoy a generous open loft space ready to use as you desire. Head downstairs, where three sizeable bedrooms and two bathrooms are situated, along with another space perfect for an office, or crafts, hobbies, etc. The walk-out lowest level is ideal for entertaining with lounge space, another fireplace, a kitchenette/bar, a final full bathroom, and it connects to the backyard. The outdoor features of this home are resplendent and take advantage of those water views with two large decks, two separate patios, and terraces tucked in all the right places. You’ll marvel at the retaining walls, stonework, and landscaping that leads gracefully to the lake and your private dock. Enjoy swimming, canoeing, kayaking, fishing, and more on this private lake. The attention to detail in this custom-built mansion, combined with 1.3 natural acres and the privacy and tranquility it affords, makes this a truly unique and desirable property. Modern conveniences include an oversized two-car garage, central vacuum system, a security system, recessed lighting, and durable appliances. A golf cart and lake toys are also included. Tucked away in Winchester, this lovely home is only ten minutes from downtown.

291 Lake Serene Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Samson Properties.

$1,200,000
203 +/- acres of pristine rural land at 1389 Back Mountain Road in Frederick County with pastoral mountain views. Features include rolling topography and scenic Hogue Creek. Please see attached exhibits for aerial views, location map, topography, water features and building sites. Priced to sell at only $7,143. per acre.

1389 Back Mtn, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

Selling Office: Oakcrest Commercial Real Estate.

$1,149,000
5 Beds ⋅ 4 Baths
Welcome to 819 Armistead Street. Located in the prestigious Meadow Branch neighborhood, this Colonial Revival style home has a nice Georgian flair to it. Marble floors welcome you into a large foyer. To your left is a living room with arched windows and wood floors. To your right, you'll find the dining room with arched windows, wood floors, and the original chandelier and toile wall paper chosen by the original owner. Step into the beautiful, updated kitchen, with designer light fittings, hardware and cabinets, quartz countertops, wood floors, a beautiful island and a gas fireplace for those cold winter days. Off your kitchen is a large laundry room with built in cabinets, marble counters and sink. Also on the main floor is a powder room for your guests, a great room with cathedral ceilings and a large, stone wood burning fireplace. Custom drapes flank the windows overlooking either the private deck or the pool and pool house. Off the great room is a fabulous den or guest bedroom, full bath and walk in closet. Beneath the great room is a storage room perfect for the mower and work shop. Upstairs, you'll find a primary suite with a beautiful bathroom with separate tub and shower, quartz countertops, and two separate closets. You'll also find the hall bath, and 3 additional bedrooms, one with a large bonus room attached. Note the cute dormers over the garage! Downstairs, you'll find the carpeted basement, an exercise room with a concrete floor and a utility room. Extensive hardscaping and landscaping provide multiple options for relaxation. New roof in 2016. 2nd floor HVAC system new in 2023. Exterior is a beautiful stone complimented by James Hardie siding in Arctic White. 3 car garage. Professional photos coming soon. Owner is a licensed RE agent.

819 Armistead St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

$1,100,000
4 Beds ⋅ 6 Baths
Set on 7 picturesque acres, this exceptional property in Merrifield Estates offers space, comfort, and versatility both inside and out. The home, designed by Hilton Head architect Eric Moser and later built by Ritter Construction features 4 generously sized bedrooms and 4 full and 2 half bathrooms, with a well-designed layout that includes a main level primary suite, formal living room with fireplace, library, elegant dining room, and a warm, inviting family room anchored by a striking stone fireplace. The eat-in kitchen provides ample space for everyday living and entertaining, while a dedicated office offers flexibility for work or study. Don't miss the secret spiral staircase in the library! Outdoors, the property is equally impressive with a serene koi pond, established horse paddock with stable, and plenty of open land to enjoy. An attached two-car garage and detached 2 car garage provides abundant storage and workspace. All of this is conveniently located just minutes from town, offering the perfect balance of privacy and accessibility.

1617 Merrimans Ln, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Century 21 Redwood Realty.

$1,100,000
4 Beds ⋅ 3 Baths
Welcome to Elysian Fields Farm, a magnificent 56+ acre equestrian estate situated at 456 Marple Road in Winchester, VA. Spanning three distinct parcels and located just 10 minutes from the conveniences of town, this private retreat is defined by its timeless brick construction and a masterfully designed layout that harmonizes luxury living with top-tier agricultural infrastructure. The arrival experience is nothing short of grand, featuring a long, winding paved driveway framed by stately brick pillars and secure gates that lead over a private bridge above a serene, meandering stream. The rolling pastures and picturesque pond are secured by wood four-board fencing, all protected by a dense perimeter of mature hardwoods for ultimate seclusion. The main residence stands as a testament to enduring quality, showcasing superior solid-brick craftsmanship and meticulous attention to detail throughout its sprawling footprint. The main level features gleaming hardwood floors throughout the formal living and dining rooms, both of which are bathed in natural light from floor-to-ceiling picture windows. While the home offers a sophisticated and polished atmosphere, the true heart of the home is the breathtaking, two-story family room, which boasts soaring wooden vaulted ceilings with exposed beams and a dramatic two-story brick fireplace with a cozy gas insert. The kitchen offers a warm, refined aesthetic with rich, cherry-toned cabinetry, stainless Whirlpool appliances, and a central island with seating. For additional entertaining space, a massive bonus room/den offers durable tile flooring, built-in shelving, a second impressive brick fireplace, and direct access to an expansive rear brick patio overlooking the flat, park-like yard and pastures. This level is completed by a bright bedroom, a full bath with double sinks, and a convenient laundry room. The upper level, which also features hardwood flooring throughout, houses the primary suite with a private ensuite bath, alongside two additional bedrooms and another full bath. The estate’s exterior is a triumph of functional luxury, defined by its expansive, well-managed acreage and professional-grade outbuildings. The equestrian centerpiece of the property is a large brick barn meticulously framed by white fencing; this multi-purpose facility features heavy-duty horse stalls with durable block construction and rubber mats, a dedicated workshop, and equipment storage space. Additionally, the barn includes a full bath and a flexible extra room—ideal for a private office, studio, or tack room. The surrounding landscape consists of lush, verdant pastures designed for optimal grazing and ease of rotation, further enhanced by a practical run-in shed positioned in the distance for field-kept livestock. Whether you are an avid equestrian or seeking a multi-generational family compound, this well-manicured estate offers the rare combination of architectural cohesion, functional farm utility, and serene country privacy.

456 Marple Rd, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Redfin Corporation.

$1,100,000
4 Beds ⋅ 4 Baths
This all-brick custom home sits on 8 acres on the east side of Winchester, offering a prime commuter location with a gated entrance for added privacy. The main level includes a high-end kitchen with a gas cooktop, double wall ovens, and a large pantry, alongside a family room with a fireplace and wet bar. An additional room on this level serves as an optional living room or office, while covered porches on both the main and second floors provide ample outdoor living space. The second level features a primary suite with a gas fireplace, private covered porch, walk-in closet with custom built-ins, and an en-suite bathroom with a soaking tub and walk-in shower. The second bedroom includes its own private bathroom, while the third and fourth bedrooms are connected by a Jack and Jill bathroom. For automotive storage, the property offers a four-car garage with a large unfinished loft ready for future conversion. Built for efficiency, the home features a three-zone HVAC system and Superior brand basement foundation walls. The basement includes a wood stove and French door outside access, providing a clean slate for additional finished living space.

270 Sotheby Ct, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: EXP Realty, LLC.

$1,100,000
4 Beds ⋅ 4 Baths
Escape to your own private retreat! This custom log home on 21 wooded acres offers space, comfort, and endless outdoor enjoyment—without the restrictions of an HOA. Featuring over 3,200 sq. ft. on the main level plus 1,600+ finished sq. ft. in the walkout basement, this home provides room for everyone. Inside, you’ll find 4 bedrooms, 3 1/2 baths, and 2 fireplaces, along with an outdoor wood furnace for efficient heating. The lower level is an entertainer’s dream with a wall of windows, bar area, huge recreation room (pool & ping pong tables convey), a full bedroom and bath—ideal as an in-law suite or guest space. Step outside to enjoy the beauty of the land with two ponds (one stocked with bass), wooded trails, and plenty of space to explore. Car enthusiasts and hobbyists will love the abundance of garage space: two attached garages plus a detached 3+ car garage with oversized door—perfect for RVs, boats, or equipment. A rare opportunity to own a property that truly has it all—privacy, recreation, and a stunning log home to match. **PLEASE NO DRIVEBYS** Property is in forest perserve - it was renewed in 2023 - renews every 10 years, so taxes are low.

2321 Cedar Grove Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,075,000
4 Beds ⋅ 4 Baths
107 Lacosta – Private Retreat in Sought-After Ross Common Nestled on over 2 acres. This stunning colonial offers the perfect blend of privacy, comfort, and convenience—just minutes from Winchester Medical Center and downtown Winchester. Enjoy outdoor living on the expansive composite deck and patio, complete with an adjustable awning and built-in speakers—ideal for entertaining or relaxing. The fenced backyard is secure enough for dogs and includes a storage shed with electric and a three-car garage for ample parking and workspace. Inside, the main level features newer wood flooring, including in the primary bedroom. The gourmet kitchen boasts wall ovens, a Bosch high-end induction cooktop, and a spacious pantry. The kitchen is also set up for a gas cooktop if someone wants to switch to gas cooking. The family room impresses with 10-foot ceilings, abundant natural light, and a cozy fireplace. Upstairs, the generous primary suite offers a luxurious ensuite bath. A second bedroom features a private bath, while two additional bedrooms share a convenient Jack and Jill bath. A tankless water heater with a recirculator ensures comfort and efficiency. The unfinished walkout basement offers endless possibilities, with a rough-in for a future bath and a whole-home water treatment system. Septic recently inspected and in proper working order. Surrounded by a 36-hole golf course, this property combines location, privacy, and elegance—making 107 Lacosta a true retreat.

107 Lacosta Ct, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Keller Williams Realty.

$1,060,000
7 Beds ⋅ 5 Baths
Welcome to 207 Westview Drive, a secluded sanctuary nestled on just over six wooded acres in the heart of the Shenandoah Valley—mere minutes from the charm of Historic Old Town Winchester. With over 6,300 square feet of beautifully finished living space, this one-of-a-kind property offers the perfect blend of luxury, comfort, and natural beauty. Tucked deep into the trees, yet close to shops, dining, and commuter routes, this is a home that feels worlds away—yet close to everything. The main level welcomes you with sun-filled spaces, refinished hardwood floors (2024), and a layout designed for both everyday living and elegant entertaining. At the heart of the home, the kitchen is a true chef’s dream—anchored by a commercial-grade GE Monogram range beneath a striking arched stone hearth. A quartz island installed in 2024, Sub-Zero fridge/freezer, stainless steel backsplash, and KraftMaid cabinetry complete the space. A formal dining room sits just off the kitchen, while the expansive family room opens through double French doors to the rear deck and wooded views beyond. The main-level primary suite is a private retreat with a double-sided fireplace, walk-in closet with its own gas washer and dryer, and a spa-inspired bath with dual vanities, a jetted soaking tub, and separate tiled shower. A stylishly remodeled powder room rounds out this level. Upstairs, four bedrooms and two full baths provide flexibility and space. The upper-level primary suite mirrors the main-level retreat with another double-sided fireplace and en suite bath. A connecting bedroom makes an ideal nursery or sitting room. Down the hall, two additional bedrooms share a beautifully updated full bath featuring a charming clawfoot tub and separate shower. A second laundry area with gas washer and dryer offers added everyday convenience. The lower level is built for entertainment and extended living, featuring two well-sized bedrooms and a full bath with a beautifully tiled rain shower. A large movie theater room, game room, and stylish bar create the perfect setup for gatherings and relaxation, while upgraded systems throughout the home—including copper plumbing, three-zone HVAC, and LED lighting—enhance comfort and efficiency. Outside, a sparkling in-ground pool invites summer fun with full-width steps, LED lighting, an auto-cover, and plumbing in place for future heating. The expansive deck, stone patio, and firepit offer inviting outdoor spaces to relax beneath the trees. A buried 1,000-gallon propane tank (owned and conveys) fuels both the pool and the whole-house generator with automatic transfer switch, while a commercial 80-gallon water heater fed by a Rinnai tankless system ensures reliable hot water. A detached four-car garage is ready for hobbies or serious work—with 220V outlets wired in each bay, bright LED lighting, and plenty of space for tools and storage. The roof was replaced in 2019, rounding out the home’s thoughtful upgrades. Private, peaceful, and just minutes from I-81, Route 7, Route 50, and an easy drive to Dulles International Airport—207 Westview Drive is more than a home. It’s your own piece of the Valley to retreat, recharge, and truly live.

207 Westview Dr, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$1,049,000
3 Beds ⋅ 3 Baths
5-9-26 BEAUTY DONE/READY! Pictures are of subject property. Seize a truly unique opportunity to own a brand-new, luxury estate set on over 7 acres of private, wooded land. While this stunning property sits at the entrance to the prestigious, upper-scale 15-lot Keplinger Estates community, it does not have HOA, offering unparalleled freedom and privacy. Tucked gracefully off the main road, this secluded retreat provides a peaceful, close-to-town setting without compromising on tranquility and space. Experience the pinnacle of single-level living in this immaculate residence, meticulously designed with a flowing 3,100 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the entire main level, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Expansive Indoor/Outdoor Living: The home is designed for seamless entertaining and relaxation, featuring an extensive covered and screened deck that connects to open deck that wraps around the entire right side of the house. Full patio under covered and open decks. Walk-Out Access & Patio: The basement boasts convenient double-door walk-out access, opening onto a full-length concrete patio that extends from the breakfast room and continues beneath the expansive side deck.

2225 Cedar Grove Rd, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Non Subscribing Office.

$1,025,000
5 Beds ⋅ 7 Baths
Situated on a 2.5 acre lot in highly desirable area, this stunning Colonial home offers an open floor plan perfect for entertaining. Thoughtfully designed with a main-level ensuite and a second primary suite on the upper level; this home provides flexible living options for modern convenience. Spacious and filled with natural light, the home features a welcoming foyer, a beautiful kitchen, and multiple living and entertaining spaces. Lower level offers room for expansion and a huge storage area. Enjoy peaceful outdoor living with mature landscaping, the large front and rear porches is an extension of living space with with gorgeous views of the mountain and ridge, and plenty of room to roam. No HOA, 10 minutes to Winchester Medical Center and Walmart. 10 minutes to the new Public that is coming in August 2026, the location is convenient.

700 Miller Rd, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Colony Realty.

$1,025,000
Seize the chance to establish your business with this prime commercial office space at 650 Millwood Avenue in Winchester, VA. The first time this iconic property has been for sale in 40 years! This is an unparalleled opportunity to secure over 2,600 square feet of professional, highly versatile space featuring multiple private offices and dedicated meeting areas. The location is truly exceptional: situated directly next to Shenandoah University, the property offers incredible visibility on a major artery that sees a traffic count of around 30,000 cars per day. This prominent position is ideal for medical/professional services, financial firms, or any enterprise seeking maximum brand recognition. Crucially, the site includes convenient on-site parking for approximately 15 vehicles, guaranteeing easy access for every client and employee.

650 Millwood Ave, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: MarketPlace REALTY.

$1,014,300
6 Beds ⋅ 5 Baths
Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and floor to ceiling windows cascading natural light throughout. The wrap around stairs will wrap around your heart with charm and the thrill to make this glorious mansion your own. Ideal as a single family residence but also zoned B1 for a bed and breakfast or upscale professional offices. Private parking in the rear is another downtown rarity. Includes carriage house. Outstanding residential, commercial, or mixed use investment opportunity, located in the heart of Winchester's Old Town!

217 W Boscawen St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Samson Properties.