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Redbud Road, Winchester
$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.

20 S Stewart St, Winchester
$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.

821 Apple Pie Ridge Rd, Winchester
$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.

Off Mount Olive Rd, Winchester
$1,850,000
Premier builder opportunity!!! Cluster of prime building lots conveniently located less than 10 minutes west of Winchester. What was once the well known Rotz Farm and is now the brand new Ridgeview Glen community. Quiet and peaceful setting with immediate access to US-50 - Northwestern Pike of less than a quarter mile. This land is ideally positioned between scenic Flint Ridge and flowing Hogue Creek. Supreme builder opportunity consisting of the 22 ready to go building lots in Phases 1, 2, and 3 of the recently approved Ridgeview Glen Subdivision. All lots feature 4 bedroom septic certification letters which are already on record with the county health department. The lone exception is Lot 12 which has a 3 bedroom septic certification letter and the Rural Preservation which actually has two 4 bedroom septic certification letters. Access is secured via extensive state maintained road frontage on US-50, Back Mountain Road, and Mount Olive Road creating multiple points of access. Utilities are close by making for easy and affordable hookups. These lots have gently sloping topography. Stellar mountain views can be seen year round from most of the lots. These parcels are zoned Rural Areas (RA) and currently have no covenants, no restrictions, and no HOA.

Off Mount Olive Rd, Winchester

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

Selling Office: Seneca Land, LLC.

40 W Piccadilly St, Winchester
$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.

1631 Back Mountain Rd, Winchester
$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.

128.556 Acres Laurel Grove Rd, Winchester
$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.

632 Dry Creek Ln, Winchester
$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.

194 Glendobbin Ln, Winchester
$1,325,000
4 Beds ⋅ 4 Baths
Welcome to an extraordinary custom-built all-brick estate nestled on five beautifully manicured acres in the highly sought-after Apple Pie Ridge area. This exceptional property blends timeless elegance, quality craftsmanship, and modern updates to create a truly one-of-a-kind retreat. From the moment you arrive, the winding approach and picturesque setting set the stage for what's inside. Designed for both grand entertaining and everyday comfort, the home features three spacious bedrooms, three full bathrooms, and two half baths, with flexible living spaces that can easily accommodate a bedroom, guest suite, or recreation room. The heart of the home is the spectacular gourmet kitchen, where culinary enthusiasts will appreciate granite countertops, a commercial-size refrigerator, two Wolf wall ovens, a cooktop with downdraft ventilation, an expansive multi-level island with prep sink, and instant hot water. The kitchen flows effortlessly into the inviting family room with custom built-ins and a cozy gas fireplace, while the adjoining sunroom fills the home with natural light and offers panoramic views of the backyard oasis. Outside, resort-style living awaits. The inground pool is the centerpiece of the backyard, creating the perfect setting for relaxing afternoons, gatherings, and unforgettable summer entertaining. A brick patio overlooks the beautifully landscaped grounds, offering a peaceful space to unwind and enjoy the privacy of your surroundings. The primary suite is a private sanctuary complete with its own gas fireplace, cedar-lined walk-in closets with custom built-ins, and an impressive spa-inspired bath featuring a jetted soaking tub and separate shower. Additional bedrooms are generously sized, while a spacious office with custom built-ins provides the ideal work-from-home space. A large bonus room with a full bath offers endless possibilities and the fourth-floor bedroom is an incredible private retreat that any teenager or overnight guest will love. Movie nights become an event in the dedicated theater room, while the expansive unfinished basement offers tremendous potential for additional finished living space, a home gym, workshop, or recreation area. Car collectors, hobbyists, and outdoor enthusiasts will appreciate the attached and detached garages with room for up to six vehicles. The detached heated and cooled three-bay garage includes a full bath, separate septic system, and unfinished space above offering endless possibilities. This meticulously maintained home has been thoughtfully updated with two new HVAC systems, a new hot water heater, a new water softener, a new dishwasher, and a new washer and dryer. The original portion of the home also features premium Andersen windows with upgraded screens, enhancing both energy efficiency and timeless appeal. Properties of this caliber rarely become available.

194 Glendobbin Ln, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Colony Realty.

100 Country Club Cir, Winchester
$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..

2216 Laurel Grove Rd, Winchester
$1,200,000
4 Beds ⋅ 3 Baths
Welcome to 2216 Laurel Grove Rd, an exceptional custom-built modern farmhouse offering privacy, beautiful views, and relaxed country living on 30 unrestricted acres, all while keeping hospitals, shopping, dining, wineries, and entertainment conveniently close. Approximately 10 acres are cleared and fenced, creating incredible flexibility for horses, recreation, animals, hobbies, or simply enjoying your own private piece of the countryside. Inside, the home features 4 bedrooms and 2.5 baths conveniently located on the main level, complemented by an open and inviting floor plan, beautifully refinished birch hardwood floors, fresh interior paint, and thoughtfully updated finishes throughout. The expansive primary suite is a true retreat with a beautifully updated bath featuring a luxurious soaking tub and a large walk-in closet. Generously sized secondary bedrooms provide ample space for family or guests, while the versatile loft offers additional flexible living space. The basement is already plumbed for a future bathroom, providing even more possibilities. At the heart of the home is the upgraded chef's kitchen, designed for both entertaining and everyday living, featuring a striking granite island, gas/propane cooktop, wine cooler, generous cabinetry and prep space, and new island lighting. Step outside to an incredible private backyard retreat highlighted by a Vanguard hot tub, Trex decking and railing, stamped-concrete patios, new porch posts and stairs, updated exterior lighting, brick-finished columns, and a spacious fenced area ideal for dogs. For the equestrian enthusiast, approximately 4 acres feature new no-climb horse fencing with hot-top wire, paddock fencing, and an automatic Bar-Bar-A waterer. Additional horse amenities include a 10' x 24' run-in shed, 60' x 40' dry lot, and solar lighting. A versatile 44' x 24' metal barn/building with four doors provides outstanding space for horses, equipment, vehicles, storage, hobbies, or a workshop. With 30 acres to enjoy, the property offers endless opportunities for hiking, ATV riding, horseback riding, outdoor recreation, relaxing with your dogs, or simply taking in the peaceful surroundings and countryside views. Extensive recent improvements include a new 50-year roof, rear gutters with Gutter Helmet guards, new 5-ton and 3.5-ton heat pumps and basement air handlers, complete attic insulation replacement upgraded to R-49, rebuilt front porch masonry, refinished hardwood floors, new loft flooring, fresh interior paint, new front door and security storm door, new water softener system and tank, reverse osmosis system and RO tank, new smoke and CO detectors, new ceiling fans and lighting, new hot tub pump and heater, and GloFiber fiber-optic internet. A rare opportunity to enjoy acreage, privacy, equestrian amenities, recreation, and a beautifully updated home—all in one remarkable property.

2216 Laurel Grove Rd, Winchester

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Burch Real Estate Group, LLC.

Wardensville Grade, Winchester
$1,200,000
If you’ve been searching for space to breathe, this is it. Spanning 140.54 acres of wide-open and wooded land, this incredible property on Wardensville Grade offers the kind of peace, privacy, and freedom that’s getting harder to find. The moment you step onto the land, you’ll feel it, room to breathe, space to roam, and endless possibilities in every direction. There’s a beautiful homesite just waiting for you, perfectly positioned to overlook a peaceful pond. Imagine your future front porch here-morning coffee with mountain air, evenings filled with quiet sunsets, and nothing but the sounds of nature around you. Whether you’re looking to build your dream home, create a family compound, or design the ultimate weekend retreat, this land gives you the flexibility to do it your way. With NO HOA and NO restrictions, you have the freedom to build, farm, hunt, ride UTVs and four-wheelers, or even create your own private shooting range. No one telling you what to do, just land that works for your vision. Spend your days exploring your own trails, watching wildlife, or simply unplugging from the noise of everyday life. With a mix of open fields and wooded acreage, you get both stunning views and natural privacy, ideal for a homestead, hunting property, or long-term investment. And while it feels like a true getaway, you’re still conveniently located within reach of Winchester and major routes like 522, I-81, and I-66, making commuting or weekend trips easy. This is more than just land, it’s a chance to build something lasting. A place to gather, grow, and create a legacy for generations to come. Big land. Big sky. Endless potential.

Wardensville Grade, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Realty ONE Group Old Towne.

819 Armistead St, Winchester
$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..

1617 Merrimans Ln, Winchester
$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.

456 Marple Rd, Winchester
$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.

270 Sotheby Ct, Winchester
$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.

2321 Cedar Grove Rd, Winchester
$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.

130 Babbs Mountain Rd, Winchester
$1,091,981
3 Beds ⋅ 3 Baths
Modern Elegance on 1.6 Acres – To Be Built! Experience contemporary living at its finest with this stunning 3-bedroom, 2.5-bathroom home, expertly designed by Fauver and Browning Homes. Nestled on 1.6 scenic acres just outside Winchester, this home offers breathtaking views of the rolling meadows leading to Apple Pie Ridge. Spanning 2,102 sq. ft., this home blends modern design with thoughtful functionality. Expansive windows, soaring ceilings, and an open-concept layout create a bright and inviting atmosphere. The gourmet kitchen is a chef’s dream, featuring a huge island with barstool seating, perfect for entertaining while preparing meals. The main-level primary suite is a private retreat, boasting vaulted ceilings, large glass doors to the patio, a spa-like ensuite with a free-standing tub, oversized shower, and walk-in closets. The living room seamlessly connects to the deck and patio, allowing for effortless indoor-outdoor living. Upstairs, you’ll find a second bedroom, a full bath, and a versatile loft space—ideal for a third bedroom, home office, gym, or bonus room. The two-car garage completes this exceptional home, offering convenience and style in a serene yet accessible location. Looking for more space or personalized touches? Work directly with the builder to add square footage, finish a lower level, or choose from a variety of upgrade options to suit your style and needs. Pricing will vary based on selected customizations and finishes. Now’s your chance to create a home that’s uniquely yours—from layout to luxury details! Don’t miss the opportunity to own a contemporary masterpiece in Frederick County—tailored to your lifestyle! Contact listing agent today to learn more!

130 Babbs Mountain Rd, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Re/Max Roots.

107 Lacosta Ct, Winchester
$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.

207 Westview Dr, Winchester
$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.

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