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

Light Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$250,000
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
$849,000
6 Beds ⋅ 5 Baths
UP TO $5000 SELLER CONCESSION FOR PAINT. CALL FOR DETAILS. Welcome to this stunning Colonial estate nestled in the highly sought-after Raven Pointe neighborhood of Winchester, VA. This exceptional home flawlessly pairs a grand interior layout with panoramic views, perfectly situated directly adjacent to peaceful farmland while remaining just 7 minutes away from historic Old Town Winchester. Built in 2016, this stone-accented detached single-family home boasts a massive 4,714 total finished square feet across three fully completed levels. Positioned on a beautifully manicured 0.27-acre lot, it offers an incredible footprint featuring 6 bedrooms, 4 full bathrooms, and 1 half bathroom—delivering unparalleled space and versatility for multi-generational living or working from home. The main level welcomes you with an open, light-filled architectural flow anchored by high ceilings and formal dining spaces. Cozy up next to one of the 2 fireplaces or enjoy entertaining guests in the spacious living area. A massive primary suite functions as your own private oasis, accompanied by generously sized additional bedrooms upstairs. The lower level features a fully finished walk-out basement equipped with interior access and structural step-up design, ready for a home theater, gym, or separate recreation space. Includes a spacious 2-car attached front-entry garage with an automated door opener. Situated immediately next to sprawling local farmland, offering an authentic country-style retreat without sacrificing suburban convenience. Experience the premium neighborhood presentation of Raven Pointe with a low, budget-friendly fee of just $95 annually. Don't miss the chance to own this meticulously maintained, newer-construction masterpiece that balances rural tranquility with city conveniences. Schedule your tour today!

226 Summerfield Dr, Winchester

Listing courtesy of CENTURY 21 New Millennium. Contact: 7035564222
$310,000
3 Beds ⋅ 2 Baths
Adorable rancher in Shawneeland with access to a lake, trails, beach, and fishing. Ideally you wish for spacious living quarters,3 bedrooms, 2 full baths, and a walkout basement with a finished room for gym/office/den..well we have all that and more so come take a gander and make it your own before the summer ends.

204 Cochise Trl, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$959,000
3 Beds ⋅ 3 Baths
Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning modern farmhouse nestled on twenty wooded and open acres with pleasant peaceful views. This thoughtfully designed home features spacious living areas, modern finishes, exterior that blends beautifully with its natural surroundings. Perfect for those seeking privacy, peace, and the beauty of nature, yet with convenient access to nearby amenities. Plenty of room for outdoor recreation, gardening, or simply enjoying the view from your porch. Build your dream lifestyle here – endless possibilities on unrestricted land! Escape to a serene retreat of rolling meadows, shady woodlands, and sparkling little ponds. Here, the land is alive—deer wander gracefully through the trees, wild turkeys stride across the fields, and songbirds fill the air with music. Bring your horses, cows, goats, or sheep to graze the open pastures, or simply enjoy the peace of living alongside nature. This is more than just land—it’s a private sanctuary where farm life, wildlife, and natural beauty come together in perfect harmony.” In the summer, kids might toss in a line, pulling out a perch or even a fat catfish. Families might watch dragonflies skimming the water’s edge. At night, fireflies light up the grasses around the pond, adding to the magic. Builder is also willing to build your plans. Price is projected and subject to change.

Light Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$345,000
3 Beds ⋅ 2 Baths
Why wait to build? This beautifully finished, move-in-ready home offers all the benefits of new construction without the wait. Offering modern style, quality craftsmanship, and low-maintenance living a short distance from Winchester this new home is nestled on a beautiful lot in Wilde Acres. This thoughtfully designed 3-bedroom, 2-bath home features an open floor plan with luxury vinyl plank flooring and today’s most sought-after finishes. The spacious kitchen is the heart of the home, showcasing granite countertops, a large peninsula, stainless steel appliances, white shaker cabinetry, and black fixtures. The primary suite offers a private bath with granite countertops and a walk-in shower, while two additional bedrooms provide space for family, guests, or a home office. The finished lower-level family room offers flexible living space for entertaining, recreation, or remote work, and the oversized garage provides great storage. Enjoy the peace and privacy of mountain living with convenient access to Mountain Falls Park, featuring a lake, playground, picnic area, and outdoor recreation. Move-in ready and thoughtfully finished throughout, this home offers the perfect blend of comfort, style and value. Some photos virtually staged. Owner/agent.

503 Grouse, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$400,000
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
ONE-OF-A-KIND HOME WITH INCREDIBLE FLEXIBILITY! This custom all-brick Winchester home offers a layout you simply don't find every day—4 bedrooms, 4 full baths, two main-level bedrooms, flexible private living spaces, a detached 2-car garage and NO HOA! Step inside to a bright, welcoming floor plan featuring beautiful hardwood floors, abundant natural light, custom built-ins and a cozy gas fireplace. The spacious gourmet kitchen offers granite countertops, stainless steel appliances, generous pantry space and a large breakfast area that flows easily into the dining and living spaces—perfect for everyday living and entertaining. One of this home's standout features is its main-level living potential. The primary suite is conveniently located on the main floor with a private bath and walk-in closet, while a second main-level bedroom and nearby full bath provide exceptional flexibility for guests, a home office or additional living space. Main-level laundry with a utility sink adds even more convenience. Upstairs, you'll discover a private and versatile living area with its own main-level entrance, sitting/living space, two additional bedrooms and a full bath—creating an ideal setup for extended stays, guests, work-from-home needs or anyone wanting additional privacy and separation. And there's even more! The detached two-car garage includes additional finished living space above, complete with a bedroom, full bath and kitchen/living area—opening the door to an incredible variety of possibilities. Outside, enjoy multiple parking options with front and rear driveways, an attached covered carport, detached garage and additional street parking. All of this is tucked into an established Winchester neighborhood convenient to downtown Winchester, Route 7, shopping, dining, medical facilities and major commuter routes. All brick. Four full baths. Two main-level bedrooms. Flexible living spaces. Detached garage. No HOA. This isn't your typical Winchester home—come see just how many possibilities 687 Woodland Avenue has to offer.

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:

$369,990
3 Beds ⋅ 3 Baths
Main-level living at its best in Hiatt Pointe at Snowden Bridge—a gated 55+ active adult community. This low-maintenance villa features a primary bedroom and laundry on the entry level, a screened rear porch, and a one-car garage. Upstairs offers two spacious bedrooms with walk-in closets and a full bath, plus a finished storage area! Enjoy a stylish kitchen with quartz counters, stainless steel appliances, and white elegant cabinetry. Resort-style amenities include pickleball and bocce courts, clubhouse, fitness and yoga studios, outdoor kitchen, pool and hot tub—plus snow removal, trash, and recycling included. Ask about builder incentives today!

404 Granite Ridge Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$495,000
3 Beds ⋅ 2 Baths
OPEN HOUSE 08/30/2026 FROM 1:00 PM - 3:00 PM Welcome to this charming historic home in Old Town Winchester. This spacious 3-bedroom Colonial blends timeless character with modern comfort in a convenient downtown location. Thoughtfully updated with today’s buyer in mind, this inviting residence offers upgraded amenities while preserving its classic appeal. Ideally situated within walking distance from the heart of historic Old Town Winchester, you’ll enjoy the convenience of being close to local shops, restaurants, entertainment, downtown amenities, Shenandoah Valley Museum, and Valley Health Medical Facilities. Adding to the appeal, the home is tucked along a private one-way street, offering a quieter, more peaceful setting while keeping you just steps from everything downtown Winchester has to offer. Outside, the detached garage offers exceptional versatility for parking, storage, hobbies, home gym, or a workshop.

108 Morgan St, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

$244,900
2 Beds ⋅ 2 Baths
Discover the charm of Parkplace Condominiums, where comfort meets convenience in a vibrant community. This inviting 2-bedroom, 2-bathroom unit features modern stainless steel appliances, including a built-in microwave, dishwasher, and electric oven, making meal prep a delight. Enjoy the ease of in-unit laundry with washer and dryer hookups, ensuring your daily routines are seamless. Nestled in a friendly neighborhood, residents benefit from well-maintained grounds with included lawn care, snow removal, and trash services. The community is close to local parks, perfect for leisurely strolls or weekend picnics. Excellent schools are just a stone's throw away, providing quality education options for all ages. With a strong sense of community and convenient access to public services, Parkplace is more than just a home; it's a place to create lasting memories. Experience the warmth and comfort of this lovely unit, where every detail is designed for your enjoyment.

136 Brookland Ct Unit #6, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$1,800,000
4.93 acres with great interstate exposure. End of cul de sac. Owners have proposed platt showing parcel subdivided into 4 parcels

Sulky, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$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
$420,000
3 Beds ⋅ 3 Baths
Welcome to the neighborhood of Apple Ridge in Eastern Frederick County. You won't find a nicer home or more quiet cul-d-sac anywhere let alone one that has been more tastefully remodeled. The owners have completed so much updating here, including a brand new tub, faucet annd surround in the primary bedroom. It has a transferable lifetime warranty. This 3 bedroom 2.5 bath home has a welcoming front porch & overlooks the woods and open field of the private common ground area. Picnics, walks,sports and quiet time will be enjoyed there. So much has been updated here. There are new LVP floors, new wall to wall carpet, new granite counter tops, fresh paint, new light fixtures, newer architectural roof, water heater, HVAC and more. You will love the large kitchen which includes an island and a good sized breakfast room with sliders to the large rear deck with steps to the garage. Step down into the 20X12 family room with a real woodburning brick fireplace to enjoy on those colder winter nights. The formal dining room is large and your dining room furniture will find a home here. There are three bedrooms including a large primary with a walk in closet and private bath. The bathrooms have new modern vanities, toilets and new vinyl plank flooring. The owner has made a large investment to install a new Primary Bath "Bath Fitters" soaking tub with all new plumbing fixtures and tub surround. The new tub has a transferable warranty. There is a one car attached garage with a pull down staircase to the floored and lighted storage attic. This home is full of sunshine that pours through the windows. The private cul-d- sac make you feel at home, safe, and somehow removed from the day to day hussle & bussle. The top of the driveway provides a perfect spot for a parking area. Being just minutes from Rt. 7E and Downtown Winchester adds to the unique and special nature of this very special place that you will want to call home. Come and have a visit. You will be glad that you did.

104 Kapok Cir, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$350,000
3 Beds ⋅ 2 Baths
Welcome to this beautiful 3-bedroom, 2-bathroom split-level home, a brand-new build nestled on a spacious 0.26-acre lot in the Mountain Falls Park community. Enjoy a warm welcome with a cozy covered porch. Inside, the home features luxury vinyl plank flooring throughout, providing a modern, durable finish. The kitchen is a chef's delight, with stainless steel appliances, premium shaker-style cabinets, and sleek granite countertops that add both style and functionality. The primary bath offers a touch of luxury, with granite countertops and a convenient stall shower. Each bedroom has thoughtfully designed built-in shelving in the closets, adding extra storage and organization. The lower level boasts a spacious family room, perfect for gatherings, as well as a convenient laundry room. For vehicle storage and projects, the oversized 20'10" x 23'2" two-car garage provides ample space. Outside, the Mountain Falls Park community offers amenities, including a common area, lake, picnic area, playground, and more—ideal for outdoor recreation and family fun. This stunning new home combines comfort, style, and a scenic location—schedule your visit today to experience it for yourself! Check out the video attached to this listing!

604 Gatling Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$649,900
3 Beds ⋅ 2 Baths
**HUGE PRICE REDUCTION** Nearly new and designed for easy main-level living, this beautifully maintained Winchester ranch offers 2,242 finished square feet on the main level plus a full 2,242-square-foot walkout lower level—more than 4,400 total square feet of space and opportunity. Built in 2024, the warm, open floor plan features 9-foot ceilings, abundant natural light, durable LVP flooring and a spacious family room that flows seamlessly into the kitchen. The kitchen is finished with quartz countertops, stainless steel appliances, a large center island with seating and a separate sun-filled breakfast area. Just off the kitchen, glass doors open to the covered rear porch overlooking the fenced backyard and protected wooded setting beyond. The spacious primary suite offers a peaceful retreat with a spa-inspired bath featuring dual vanities, soaking tub and separate glass shower. Additional main-level spaces provide flexibility for bedrooms, guests or a dedicated home office. A mudroom with built-ins and desk space, along with an oversized walk-in pantry featuring custom real-wood shelving, adds exceptional everyday functionality. The full walkout lower level nearly doubles the home's total footprint and provides approximately 2,242 additional square feet ready to customize for a recreation room, guest suite, home gym, theater, office or additional living space. Enjoy the benefits of a nearly new home without the construction process, including an established fenced yard, covered outdoor living space, low HOA and a private setting backing to protected land. Conveniently located in Abrams Pointe with easy access to Winchester amenities, shopping, dining and commuter routes.

132 Triangle Ct, Winchester

Listing courtesy of RE/MAX Gateway, LLC. Contact: (703) 652-5777
$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:

$549,000
5 Beds ⋅ 3 Baths
Welcome home to this stunning 5-bedroom, 3-bath, 3-story Colonial located in the highly desirable Sovereign Village community on the east side of Winchester. Offering space, comfort, and thoughtful updates throughout, this home is designed to fit every stage of life. Step inside to find beautiful hardwood floors and a warm, inviting living room featuring a gas fireplace just off the kitchen—perfect for gathering and everyday living, office and dining room also complement the main floor. The main level offers a convenient bedroom and full bathroom, ideal for guests, multi-generational living, or a home office. Upstairs, you’ll find a spacious primary bedroom complete with an en suite bath and walk-in closet, three additional bedrooms, a full hall bathroom, and an upper-level laundry room for added convenience.Recent updates provide peace of mind, including HVAC (2023) with whole house humidifier, natural gas tankless hot water heater (2024), built-in microwave and dishwasher (2024), and refrigerator (2025). Outside the garage there is 30-amp RV electricity and is already wired for a future 50-amp upgrade. Enjoy your own private backyard retreat backing to open field views, where roaming deer are an occasional bonus. Outdoor living shines with a large deck, impressive stone patio, and oversized storage shed. Need more space? The spacious unfinished walk-up basement offers endless possibilities for future expansion, recreation, or customization. Conveniently located near schools, shopping, and commuter routes—this exceptional home truly has it all.

440 Canyon Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$290,000
3 Beds ⋅ 2 Baths
Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning insert, and laminate flooring throughout. Enjoy sun and shade from the comfortable deck and spacious yard with plenty of room for outdoor gatherings, gardening, or creating your own private oasis. The community features acres of greenspace, a large lake, several ponds, and playgrounds. Don't miss the opportunity to make this cozy retreat your own!

132 Geronimo Trl, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (304) 263-7800
$49,900
"Build Your Home On Henry" This beautiful 3-Acre lot is located in Mountain Falls Park. With mature trees you can enjoy your privacy. Enjoy the community lake, common area, playground and picnic area! Has a 3-bedroom perc. Bring your vision to life!

0 Henry Dr., Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$409,900
4 Beds ⋅ 3 Baths
Well-maintained split foyer in a spectacular commuter location, just minutes from I-81 and a short drive to Old Town Winchester. This inviting home features hardwood floors throughout the main living areas, an open-concept floor plan, a cozy fireplace in the living room, and a spacious kitchen with a center island. The main level offers new carpet in the bedrooms, including a generous primary suite with a walk-in closet and an attached private bath. The finished lower level provides exceptional additional living space with a large den, a full bathroom, a bedroom with a walk-in closet, a laundry room complete with a utility sink, and a separate storage room. Step outside to enjoy the Trexx deck overlooking the fully fenced backyard—perfect for entertaining, relaxing, or letting pets play. Combining comfort, functionality, and an unbeatable location, this home is ready for you to move in and enjoy.

117 Old Dominion Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$739,900
5 Beds ⋅ 5 Baths
Nestled towards the end of a quiet dead-end street in the sought-after Raven Pointe community, this stunning 5-bedroom, 4.5-bath home offers the perfect blend of elegance, functionality, and convenience. Ideally located for commuters with easy access to major routes, you’ll enjoy peaceful neighborhood living without sacrificing accessibility. Designed with flexibility in mind, the highly desirable main-level owner’s suite features a spacious walk-in closet and spa-like bath with a soaking tub and separate shower, making one-level living a breeze. With generous living space throughout, this home is also perfectly suited for multigenerational living, offering room for parents, in-laws, grandparents, or extended family. Inside, you’ll find rich hardwood floors and spacious living areas filled with natural light. The gourmet kitchen features stainless steel appliances, a six-burner commercial-style range, built-in microwave, upgraded countertops, abundant cabinetry, and a cozy breakfast area. The adjoining family room creates the perfect gathering space, while the formal dining room is ideal for holidays and entertaining. The fully finished basement provides additional living space for a recreation room, home theater and gym. The oversized attached garage includes built-in storage, space for a workshop and an additional refrigerator/freezer, while the expansive driveway offers plenty of parking. Additional upgrades include a tankless water heater, whole-house generator, battery backup sump pump, and an upgraded water treatment system for added comfort and peace of mind. This exceptional home combines timeless style, flexible living, and an unbeatable commuter-friendly location on one of Raven Pointe’s most desirable streets.

136 Cahille Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$629,000
4 Beds ⋅ 3 Baths
Seller is offering a $2,500 credit toward the purchaser's closing costs, mortgage rate buy-down, prepaid expenses, moving costs, or other allowable buyer expenses. Situated on approximately 2.57 acres in Frederick County, this beautifully maintained 4-bedroom, 2.5-bath Traditional home offers nearly 3,000 square feet of thoughtfully designed living space. Built in 2020, the home features a sought-after main-level primary suite, solid oak flooring throughout most of the main level, and a bright, open floor plan designed for everyday living and entertaining. The kitchen is the heart of the home, featuring a brand new refrigerator, double oven (2024), dishwasher, microwave, generous workspace, and seamless flow into the adjoining living and dining areas. Upstairs, you'll find three additional bedrooms, a full bath, a versatile bonus room, and an additional sitting area, offering flexible space for guests, a home office, hobbies, or playroom. Outside, enjoy the large covered front porch, covered rear deck, patio, fenced area, recently paved driveway (2025), and over 2.5 acres of space to relax, garden, or simply enjoy the peaceful surroundings. This home has been exceptionally well maintained and includes new storm doors (2026), a recently serviced HVAC system with a new condensate pump, freshly painted upstairs bathroom, water softener, water filtration system, annual UV water treatment, and a recently inspected alternative septic system. Conveniently located just outside Winchester, you'll enjoy the perfect balance of country living with easy access to shopping, dining, commuter routes, and outdoor recreation.

115 Marion Dr, Winchester

Listing courtesy of Preslee Real Estate. Contact: 5402274416
$239,000
2 Beds ⋅ 2 Baths
Fantastic location! This spacious second-floor condo offers more square footage than most units in the community and features an open, light-filled layout, and durable flooring throughout with NO carpet. The thoughtfully designed floor plan includes a large living room, separate dining area, two generously sized bedrooms, and two full bathrooms. The primary suite offers a private bath, a large closet, and plenty of room for a king-sized bed. The kitchen was remodeled in recent years with quality cabinets, quartz countertops, undercabinet lighting, and new appliances. A separate laundry room with a full-size washer and dryer adds everyday convenience. Step outside to the private deck overlooking the common area and mature trees, creating a peaceful outdoor retreat. An additional private storage unit, conveniently located right next to the condo, provides valuable extra space for seasonal items, bicycles, or other belongings. Condo fee covers common area maintenance, trash, water, sewer and snow removal. One assigned parking space per unit. Seller to provide a credit towards painting of $3,000.

157 Brookland Ter Unit #6, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$384,000
3 Beds ⋅ 2 Baths
This is the one you’ve been waiting for — a beautifully maintained ranch‑style home with thoughtful updates and a bright, comfortable layout throughout. A newer roof, updated HVAC, and fresh carpet provide peace of mind and move‑in readiness from day one. The primary ensuite serves as a true retreat, featuring a spa‑like bath and a walk‑in closet. Two additional bedrooms offer flexible living options with well‑planned closet storage. The large family room flows into the dining area, creating an open, welcoming space filled with natural light. Step outside to a level yard perfect for everyday enjoyment, complete with a storage shed for added convenience. The location is ideal for commuters, with quick access to Route 7, Route 50, and other major routes. Historic downtown Winchester, nearby schools, and shopping are all just minutes away. Don’t miss the chance to make this home yours

103 Elaine Drive, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$1,350,000
Prime Medical Condo suite for Sale; located adjacent to the Winchester Medical Center. 6,200 Square Feet total with 4,580 square feet immediately available. 1,620 square feet is being leased, with another year on the lease. Building is in excellent condition, fully updated and easy to maintain. Prominent and highly visible location and ample parking. Few landlord responsibilities. Huge growth market! Priced at $1,350,000. Also available for lease.

142 Linden Dr Unit #106, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$825,000
A rare commercial development opportunity awaits at 135 & 171 Bufflick Road, featuring nearly 8 acres of prime, strategic real estate in Winchester. Perfectly positioned near the airport and situated just off a highly traveled corridor, this unique property provides unbeatable visibility, high traffic exposure, and immense future potential. The dual zoning of RA and B1/B2 opens the door to a wide array of development possibilities, making it a dream canvas for investors, developers, or business owners looking to establish a footprint in a rapidly growing area. Beyond its long-term development upside, the property is a turnkey income generator from day one. It features two existing rental homes that provide immediate cash flow while you finalize your development plans. Additionally, the large, multi-bay commercial garage offers substantial extra income potential—perfect for equipment storage, automotive work, or a workshop space. Complete with a large gravel staging lot ideal for fleet parking or heavy equipment, this property is a rare find that perfectly balances immediate rental revenue with massive commercial scale.

135 & 171 Bufflick Rd, Winchester

Listing courtesy of Colony Realty. Contact:

$495,990
4 Beds ⋅ 4 Baths
The Glendale is a 2,216 square foot corner homesite, open concept two-story home with a finished basement that offers four bedrooms, three and a half bathrooms with a two-car garage. You will immediately feel at home as you enter the foyer and make your way into the spacious family room. This living space flows nicely into the eat-in kitchen with plenty of cabinets and island overlooking the family room, so you’ll never miss a beat! The large sliding glass door in the kitchen allows an abundance of natural light to brighten this home and gives easy access to the backyard. The convenient powder room along with access to the garage is tucked away off the kitchen. Upstairs, the spacious owner's suite boasts a private bathroom with dual vanity and a walk-in closet. The three sizeable secondary bedrooms provide space for everyone and the hall bathroom is conveniently located nearby along with a hall linen closet. The second-floor laundry room simplifies an everyday chore! The basement is finished with a full bathroom for additional space for movie nights, play zones, or a cozy guest suite. Ready for delivery! Up to $10,000 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

101 Seminole Dr, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139
$487,900
Circa 1920 office building in downtown Winchester. Currently used as a lawyer's office, but could easily be an office-and-residential space or a single-family home. Off-street parking.

124 S Braddock St, Winchester

Listing courtesy of Colony Realty. Contact: