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223 Asbury Rd, Winchester
$540,000
5 Beds ⋅ 4 Baths
“Pioneer Heights Colonial” - Welcome to this beautifully maintained colonial in the desirable Pioneer Heights neighborhood, ideally situated just off Route 7 for easy commuter access. Offering five bedrooms and 3.5 baths, this spacious home has been thoughtfully updated and improved over the years, providing a comfortable blend of classic character and modern convenience. The heart of the home is the updated kitchen, featuring custom cabinetry, granite countertops, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Throughout the home, you'll find updated bathrooms, newer carpeting, and numerous additional improvements that make this home truly move-in ready. The finished basement adds valuable living space and versatility, complete with a walkout, comfortable living area, fifth bedroom, and full bathroom. Ample storage space provides plenty of room for seasonal items, hobbies, or household needs. Step outside and enjoy multiple spaces designed for relaxing and entertaining. A rear porch leads to a deck and backyard patio, creating an easy flow for outdoor gatherings, morning coffee, or quiet evenings. The meticulously manicured front yard is a standout, featuring lush green grass, thoughtfully maintained mulch beds, and beautiful flower gardens—all complemented by an underground sprinkler system for easy lawn care. With generous living space, numerous updates, attractive outdoor amenities, and a convenient location close to Route 7, this Pioneer Heights home offers the space, comfort, and accessibility you've been looking for. Schedule your appointment to see it today!

223 Asbury Rd, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

Selling Office: Samson Properties.

1202 Handley Ave, Winchester
$540,000
3 Beds ⋅ 4 Baths
Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite with an expansive walk-in closet and private en-suite bath. The bright and inviting living room flows seamlessly into the kitchen, complete with granite countertops, abundant cabinetry, and a charming pass-through to the separate dining area. Just off the kitchen, you'll find a conveniently located laundry area with additional cabinetry and countertop workspace. Step outside to a private patio, perfect for entertaining or relaxing after an evening downtown. A fenced side yard provides additional outdoor space for pets, gardening, or play. Upstairs, an open loft creates the perfect reading nook, home office, or cozy sitting area, alongside two additional bedrooms and a full bath. The expansive partially finished basement provides exceptional flexibility, featuring a bonus room, full bathroom, second laundry area, and abundant storage, with plenty of room for future customization. Combining architectural character, flexible living spaces, and an exceptional location, this home presents a unique opportunity in the heart of Winchester.

1202 Handley Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Pearson Smith Realty, LLC.

1300 Caroline St, Winchester
$540,000
4 Beds ⋅ 4 Baths
Welcome to 1300 Caroline Street—where timeless design meets everyday functionality in one of Winchester’s most convenient locations. Perfectly positioned on a spacious 0.32-acre corner lot, this beautifully maintained residence offers 4 bedrooms, 3.5 bathrooms, a finished basement, and a desirable 2-car side-load garage. The main level showcases a thoughtfully renovated kitchen featuring updated appliances, tile flooring, and a seamless flow into the formal dining room. Hardwood floors carry throughout the sun-filled formal living and family rooms, where the inviting family room is anchored by a classic brick-encased wood burning fireplace and custom built-ins—creating a warm, refined gathering space. Upstairs, you’ll find three generously sized guest bedrooms and a well-appointed hall bath. The primary suite offers a peaceful retreat with hardwoods and a private en-suite bath. The finished lower level expands your living space with a second brick-encased fireplace, a full bathroom, and a spacious laundry room complete with built-in cabinetry for exceptional storage. A large unfinished area provides ideal climate-controlled storage, and the walk-up access adds convenience and flexibility. Outdoors, enjoy a lush, green setting designed for entertaining—featuring a spacious deck that flows down to a thoughtfully designed patio, perfect for hosting family, friends, or summer barbecues. Ideally located just moments from major commuter routes i.e., I-81, Rte. 37, 50, and 522 this home offers easy access to everything you need. Enjoy close proximity to downtown Winchester, where you’ll find exceptional local shopping and dining, and just a quick 2-minute drive to The Winchester Medical Center. Set within a community that blends charm, sophistication, and everyday convenience—with the added benefit of no HOA—this is a rare opportunity to experience elevated living in the heart of Winchester Virginia!

1300 Caroline St, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

Selling Office: Century 21 Redwood Realty.

112 Zinnia Ln, Winchester
$539,990
3 Beds ⋅ 3 Baths
This stunning twin/semi‑detached home is move‑in ready and located within a desirable 55+ gated community. Designed for effortless main‑level living, the home features both a primary and secondary bedroom on the first floor—perfect for comfort and convenience. An open floor plan seamlessly connects the family room and kitchen, creating an inviting space ideal for both entertaining and quiet evenings at home. The kitchen shines with a spacious island, gourmet stainless steel appliances, and elegant quartz countertops. Thoughtful design continues throughout, with abundant natural light and modern finishes. The second level offers a private third bedroom and a full bath, ideal for guests or additional living space. At the rear of the home, relax and unwind on the serene screened‑in porch. Residents enjoy exceptional community amenities, including a sparkling outdoor pool, fitness center, and tennis courts—all within a secure, gated setting. Experience a lifestyle centered on comfort, connection, and convenience at Hiatt Pointe. Your dream home awaits. Ask about Builder incentives!

112 Zinnia Ln, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

Selling Office: Unrepresented.

1400 Valley Ave, Winchester
$537,000
Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. Each Unit has 3 bedrooms and 1.5 baths. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both units for a strong investment. The new roof and gutters were installed just last year and both full bathrooms have been updated to include walk-in tiled showers. The heating fuel was converted to natural gas and new boilers were installed in 2011. Each unit has separate utilities except for water and sewer. With its unique character, flexible layout, and proven rental history, this property offers endless possibilities for living, investing, or both!

1400 Valley Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Real Broker, LLC.

315 Walker St, Winchester
$535,000
3 Beds ⋅ 3 Baths
Beautiful brick split-foyer home tucked away on a quiet dead-end street in the desirable Whittier Acres community. This location is one of Winchester’s best kept secrets! 315 Walker St has nearly 2,900 finished square feet, combining space, flexibility, and a peaceful setting just minutes from Old Town Winchester, Winchester Medical Center, and everyday conveniences. The main level features a functional, flowing layout with spacious living and dining areas, an updated kitchen with stainless steel appliances, refreshed cabinetry, and a modern backsplash. A bright four-season sunroom overlooking the backyard is perfect for morning coffee, a home office, reading space, or an additional dining area. The lower level provides a large recreation area, half bath, and oversized laundry room (15' x 9') with exterior egress and excellent potential for conversion to a 4th bedroom or flex space by relocating the washer/dryer nearby. With full heating and cooling and 8-foot ceilings, the lower level offers a comfortable additional living space ideal for guests, hobbies, or everyday use. Major updates offer peace of mind, including a new roof, two heat pump HVAC systems, and water heater (all 2023), along with updated flooring, lighting, and refreshed interior finishes throughout. Outside, the property sits on a 0.36-acre lot with perennial landscaping, terraced natural stone outcroppings, and a large, established Basswood tree. An inviting front porch enhances curb appeal, while the true two-car side-entry garage and wide driveway provide excellent functionality and privacy. Enjoy the added benefit of being less than a block from Whittier Park, featuring a playground, soccer field, basketball court, and open green space. This home provides a rare opportunity to own a well-maintained, thoughtfully-updated home in one of Winchester’s most convenient neighborhoods.

315 Walker St, Winchester

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

Selling Office: Colony Realty.

3691 Green Spring Rd, Winchester
$535,000
4 Beds ⋅ 2 Baths
Welcome to 3691 Green Spring Road, a rare Winchester property offering the space, privacy, and outdoor lifestyle buyers are searching for. Set on 6.81 acres, this 4 bedroom, 2 bath home gives you room to spread out, explore, garden, entertain, or simply enjoy a quieter setting surrounded by nature. The property features a beautiful brick patio, a nice flat usable area in the front, and a trail/walking path that leads into the trees for a peaceful retreat right at home. Inside, you will find hardwood flooring throughout, a recently renovated kitchen, and updated bathrooms that brings a fresh feel to the home. The layout offers a unique and flexible flow with comfortable living spaces and plenty of potential to fit a variety of needs and lifestyles. A brand new 50 year architectural shingle roof installed in March 2026 adds long term peace of mind. Whether you are looking for acreage, privacy, outdoor living, or a home with character in the Winchester area, this one stands out. Schedule your showing and experience the setting for yourself.

3691 Green Spring Rd, Winchester

Listing courtesy of RE/MAX Gateway. Contact:

Selling Office: Century 21 Redwood Realty.

157 Oak Dr, Winchester
$534,000
4 Beds ⋅ 3 Baths
STOP THE PRESSES!! This PRICE ADJUSTMENT is not a typo! The weather is warmer and Spring is in the air.... This home is ready for YOU! <br><br> Welcome home to 157 Oak Dr. in Winchester, VA—an inviting property offering comfort, thoughtful updates, and a peaceful setting. This home has been refreshed with luxury vinyl plank flooring throughout most of the home and fresh paint, creating a clean, move-in-ready feel. Be Sure to Watch The Video to Experience Even More of This Home! <br><br> The primary suite has been remodeled, including an updated bathroom and walk-in closet, creating a comfortable retreat. A large bonus room over the 2-car garage offers endless possibilities—home office, playroom, gym, or guest space. But wait, there is more! The garage has built in work benches and tool storage. <br><br> The home features dual-zoned heating and cooling for added comfort, with the upper-level heat pump replaced in 2021, as well as a new water filtration system installed in 2022. Surrounded by trees for privacy, this property offers a serene setting while remaining just minutes from Winchester’s medical facilities, restaurants, and shopping. Convenient access to I-81 makes commuting easy. <br><br> Do Not Miss Your Opportunity to Tour This Home! Call Your Agent or The Listing Agent Today

157 Oak Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Keller Williams Realty.

289 Westview Dr, Winchester
$530,000
3 Beds ⋅ 2 Baths
Welcome to your private contemporary retreat at 289 Westview Drive in Winchester, VA! This truly exceptional property offers the ultimate escape, situated on over 13 magnificent acres with gorgeous mature trees, stunning views, and unparalleled peace and quiet. Step inside the sun-filled main level, featuring an open layout that seamlessly connects the living room, dining room, and kitchen. Highlights include vaulted ceilings, elegant hardwood floors, and a cozy wood stove perfect for those chilly evenings. The main floor features the spacious primary bedroom with an ensuite bath and private access directly to the fabulous rear deck. Also on the main level is a generously-sized bonus room offering private access to the sunroom. This space would make a perfect craft room, playroom or home office. The upper level expands the living space with two additional bedrooms and another full bathroom, providing ample room for family or guests. Outdoor living is truly superb here. The expansive rear deck is ideal for entertaining or simply enjoying the tranquil view of your beautiful yard. Additional outdoor amenities include a charming screened-in porch and a delightful gazebo, perfect for relaxing or al fresco dining. Practical amenities include a large detached garage for covered parking and storage, which also features an unfinished bonus space above. This rare, private estate offers a tranquil, removed lifestyle while maintaining easy access to daily conveniences and amenities. Come discover the unmatched beauty and secluded comfort of 289 Westview Drive today.

289 Westview Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

107 Ardeyth Ln, Winchester
$529,900
4 Beds ⋅ 4 Baths
Welcome to 107 Ardeyth Lane! This well-maintained 4-bedroom, 3.5-bath Colonial offers generous living space, thoughtful updates, and an inviting backyard retreat. The bright kitchen features white cabinetry, Corian solid-surface countertops, stainless steel appliances, tile backsplash, and pendant and recessed lighting. Attractive laminate wood flooring flows through the main living areas, creating a warm and updated feel. The finished basement provides valuable additional living space with plenty of room for recreation, entertaining, a home office, or hobbies. Numerous improvements add comfort and peace of mind, including a new HVAC system in 2025, newer hot water heater, water softener, updated kitchen appliances, washing machine, and laminate wood flooring. The roof was reshingled approximately 7 years ago, per seller, and the storage building also received a newer roof. Step outside to a backyard designed for relaxing and entertaining. The spacious patio features a covered gazebo and hot tub that conveys, while the fenced backyard with low-maintenance white vinyl picket fencing provides plenty of usable outdoor space. A storage building offers additional room for lawn and outdoor equipment. An attached garage and paved driveway complete the package. Located in Frederick County with a Winchester address, the home provides convenient access to shopping, dining, commuter routes, and area amenities. The property is also located within a USDA-eligible area, offering another potential financing option for qualified buyers. With its spacious floor plan, finished basement, numerous updates, and backyard retreat, 107 Ardeyth Lane is ready to welcome its next owner!

107 Ardeyth Ln, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Pearson Smith Realty, LLC.

135 Wappinger Ter, Winchester
$528,490
5 Beds ⋅ 4 Baths
The Deerfield offers a smart, stylish layout with five bedrooms and four-and-a-half baths—perfect for both everyday living and entertaining. The kitchen features a large center island, quartz countertops, stainless steel Whirlpool® appliances, and a walk-in pantry, all open to the dining area and great room. Upstairs, you’ll find four spacious bedrooms, a convenient laundry room with washer and dryer included, and a private primary suite with an en suite bath and generous walk-in closet. The finished walkout lower level adds valuable living space with a recreation room, an additional bedroom, and a full bathroom—ideal for guests or flexible living needs. Enjoy added privacy with a homesite backing to trees. Perfect timing for a summer move-in, with completion expected July/August. 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.

135 Wappinger Ter, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

110 Grindstone Dr, Winchester
$527,500
4 Beds ⋅ 4 Baths
Private pool, half-acre homesite, main-level living, and a fully finished lower-level living suite make this one of Winchester's most unique opportunities. Situated on a .53-acre lot established before the development of Red Fox Run, this property offers a level of privacy, outdoor space, and flexibility rarely found in today's subdivision homes. The main level features three bedrooms and three full baths, including a private primary suite thoughtfully separated from the secondary bedrooms. Recently refinished hardwood floors, fresh interior paint, refreshed exterior elements, and newly painted pool decking create a move-in-ready home. Natural light fills the spacious family room through an oversized picture window, while the dining area and dedicated laundry room add everyday convenience. Outside, the fully fenced concrete pool and expansive entertaining areas create the ideal setting for summer gatherings, outdoor dining, and relaxed evenings at home. The fully finished walkout basement offers exceptional versatility with a separate entrance, full kitchen, full bath, bedroom, family room, and additional flex space. Whether used for multigenerational living, an in-law suite, guest accommodations, extended family, a home office, or potential supplemental income opportunities, the layout provides flexibility rarely available in the Winchester market. Don’t miss this home with a private pool, oversized lot, finished basement with kitchen, separate living quarters, main-level living, or multigenerational design! Opportunities to own a property with this level of privacy, functionality, outdoor enjoyment, and flexible living space are increasingly difficult to find.

110 Grindstone Dr, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Spring Hill Real Estate, LLC..

302 Canyon Rd, Winchester
$525,000
4 Beds ⋅ 4 Baths
Welcome to a home designed for the way you live, with room to work, entertain, relax, and make the space your own. Located in Senseny Glen, this 4-bedroom, 3.5-bath, three-level Colonial offers an ideal blend of comfort, flexibility, and convenience. Major exterior updates include a new roof in December 2021 and new siding in 2022. The recently remodeled main level features luxury vinyl plank flooring throughout, an updated kitchen, dedicated home office, dining room, breakfast area, and an inviting family room with a gas fireplace. And don’t overlook the front porch, the perfect spot for morning coffee, an evening glass of wine, or simply enjoying the neighborhood. Upstairs, the spacious primary suite offers a private retreat with a double vanity, separate shower, and jetted tub. Three additional bedrooms, a full bath, and access to a floored attic provide plenty of room for family, guests, hobbies, and storage. The finished lower level adds even more living and entertaining space with a generous rec room, built-ins, wet bar, windows, full bath, and walk-up access to the backyard. Think movie nights, game days, a home gym, guest space, or simply a place to spread out. Outside, enjoy a fully fenced backyard with a deck and mature trees, creating a private setting for outdoor dining, gardening, pets, or relaxing with friends and family. Senseny Glen puts you close to schools, shopping, restaurants, and everyday conveniences while still giving you the space and feel of an established neighborhood. More than just extra square footage, this home gives you the flexibility to make every level work for you.

302 Canyon Rd, Winchester

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

Selling Office: RLAH @properties.

122 Armstrong Pl, Winchester
$525,000
4 Beds ⋅ 3 Baths
"Welcome to 122 Armstrong Place, a beautifully maintained 4-bedroom, 3-bath retreat located in the heart of Winchester. Spanning 2,706 square feet, this property blends classic charm with modern comfort. Step inside to discover gleaming wood floors, an expansive eat-in kitchen fully equipped for culinary needs, and an inviting dining space. Enjoy the flexibility of a main-level bedroom perfect for guests or an office, alongside a relaxing primary suite with its own private bath. Outside, the timeless brick facade and spacious 10,000+ square-foot lot offer plenty of room for enjoyment. Featuring central air, on-site parking, and easy access to local amenities, this home is the perfect haven for comfortable, modern living.122 Armstrong Place (Winchester, VA 22602) is a spacious 4-bedroom, 3-bathroom single-family home featuring 2,706 square feet of living space on a 10,018 square-foot lot. Highlighted by a classic brick exterior, the home boasts eat-in kitchen spaces, wood floors, and a versatile first-floor bedroom.This versatile property features a highly scannable marketing description you can use to attract buyers or renters:Property Highlights & Details:Total Living Space: 2,706 sq. ft. of well-designed, comfortable living space.Bedrooms & Bathrooms: 4 spacious bedrooms (including a convenient entry-level option) and 2.5 bathrooms, including a private primary/master bath.Gourmet Features: A bright, eat-in kitchen equipped with top-tier included appliances (microwave, range, oven, refrigerator, dishwasher, and garbage disposal).Interior Touches: Beautiful wood floors throughout, stylish ceiling fans, and an open-concept dining area.Exterior & Convenience: Classic, durable brick exterior, central cooling, Natural Gas baseboard HW heating, and on-site parking. Interior photography coming soon.

122 Armstrong Pl, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Colony Realty.

1239 Cedar Grove Rd, Winchester
$525,000
3 Beds ⋅ 2 Baths
HUGE price improvement on this property! Sellers have found home of choice and are ready to move. Experience the perfect blend of historic artistry and modern convenience in this stunning 3-bedroom, 2-bath Craftsman-style retreat. Set on 3.27 sprawling, unrestricted acres, this property offers the rare freedom to create your own homestead, workshop, or private escape. The iconic front porch, complete with a classic swing, welcomes you into a home defined by "honest" craftsmanship. Inside, you’ll find beautiful original hardwood floors and those signature built-in nooks that provide both character and clever storage. The heart of the home is an updated kitchen featuring a dedicated pantry, and built-ins seamlessly bridging the gap between vintage soul and modern functionality. Designed for longevity and ease, the layout includes a coveted main-level BONUS ROOM currently used as the primary bedroom by the owners. Outside, the living space doubles with a huge patio perfect for entertaining, and a back deck easily accessed from the bonus room to enjoy morning coffee or an evening nightcap. The property is further enhanced by a 2-car detached garage and multiple outbuildings, offering endless possibilities for hobbies, storage, or animals. One of the outbuildings could potentially be converted easily to an accessory dwelling unit! Whether you’re enjoying the sunset from the back porch, a rainy day on the front porch swing or exploring your wooded surroundings, this property is a true sanctuary with no strings attached. This home is just 2 miles from 522 making it convenient for work, shopping, or dining out! The garden is already planted with tomatoes, peppers, cucumber and squash! Reap the harvest in your new home! Schedule your tour today.

1239 Cedar Grove Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Colony Realty.

102 Blackpowder Ct, Winchester
$521,500
4 Beds ⋅ 3 Baths
Welcome to 102 Blackpowder Court, a beautiful stone-front colonial nestled in a quiet, tree-backed cul-de-sac just 2 miles from downtown Winchester. This light-filled home features 4 bedrooms and 2.5 baths, offering ample space for living and NO HOA. A light-filled 2-story foyer greets you and gives a seamless feel of access to the home's other areas. A large living room leads to the dining room via a large doorway, lending a feeling of oneness to these two spaces. The foyer is a center point of access to the heart of the home; the open concept kitchen and family room. The kitchen features stainless appliances, 5-burner gas stove and center island perfect for food prep, serving and gathering. There is a desk, work area and pantry. Adjacent to the kitchen area is a bright dining area with French doors that lead to a large rear deck for outdoor dining and relaxation. Kitchen and dining areas flow seamlessly together into the large family room with fireplace and hard wood floors. The entire space is light-filled and provides beautiful views of the tree-lined backyard. The main level living space is completed by a half bathroom and large laundry room with garage access. Upstairs, you'll find a spacious primary suite with vaulted ceilings and adjoining walk-in closet that is spacious and filled with natural light. The ensuite bathroom is accessed via double doors and features tile floors, dual vanity, corner soaking tub, and walk-in shower. Three additional bedrooms provide space for family and guests. 3 of the 4 bedrooms are newly carpeted. The second full bath is comprised of 2 rooms, the first w/dual vanity and the second w/shower-tub combination and toilet. Exit from each bedroom opens to the bright 2-story foyer below. The walkout basement is a blank canvas of space with plumbing roughed-in for future bathroom. Extra storage is at your fingertips as is potential for additional bedroom, office, home gym, home theatre or family room. The possibilities are endless for your personal customization. The two-car garage is easily accessed from the main level through the laundry room. Cabinets offer storage and workspace at the rear of the garage, making this the perfect area for parking, projects, storage, and hobbies. Step outside to the yard or the expansive rear deck to enjoy the tranquility of the fenced back yard, complete with the privacy of evergreen trees. Look closely as there's a stone fence that marks the property line. New roof was installed in 2018. High speed internet is available. A Guardian Security System is in place but not currently in use. For history buffs, the nearby Civil War landmark, Star Fort, is owned and preserved by the Shenandoah Valley Battlefields Foundation and maintained by Frederick County for $60 a year. Wanting convenience for commuting and access to amenities? You have both! Just 3 miles to Historic Downtown Winchester, and central to a 45-block National Register Historic District, there's a pedestrian mall with over 40 restaurants, cafes, and pubs offering outdoor dining, shopping, historic attractions and family-oriented activities throughout the year. Museum of the Shenandoah Valley (Summer Concert Series & Gardens at Night) , Shenandoah Valley Discovery Museum, Shenandoah University (Summer Music Theatre), and the Valley Health Campus are all just minutes away. For commuters, distances to major routes and airports are as follows: I37-1mi, I81-4mi, Route 7-6mi, Washington Dulles International Airport 56mi, and Ronald Reagan Washington National Airport 81mi. With fresh paint, newly carpeted bedrooms, newer roof, and great layout, this home is move-in ready and a fantastic fit for anyone looking for quality, space, and location at just the right price.

102 Blackpowder Ct, Winchester

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

Selling Office: Colony Realty.

105 Lenore Ln, Winchester
$520,000
3 Beds ⋅ 2 Baths
Welcome to this better-than-new former model home, built in 2024 and thoughtfully upgraded throughout—Offering the ideal blend of style, space, and value, this move-in ready home features an open-concept layout, 10' ceilings, a beautifully upgraded kitchen with modern finishes, and spacious living areas designed for both everyday comfort and entertaining. Generously sized bedrooms and well-appointed bathrooms provide room to grow, while the overall design reflects today’s most sought-after features. Skip the wait and added expense of new construction—this home already includes the upgrades you want in a location poised for continued growth and convenience. Home warranty offered to give you additional piece of mind. Come check this home out today and see all that this area has to offer.

105 Lenore Ln, Winchester

Listing courtesy of New Dimensions Realty Group LLC. Contact:

Selling Office: Samson Properties.

Brush Creek Road, Winchester
$515,000
This land is located north of Winchester in the Cross Junction area of the county. Part of what was once a much larger family farm and on the market for the first time since the 1950’s. Access is secured via road frontage of nearly 2000 ft on paved and state maintained Brush Creek Road. Terrific location for your next country home estate or recreational retreat. An electricity service line is already running on the property making for an affordable connection. Frontage on lovely Brush Creek of more than 2000 ft adds to the character and beauty of this parcel. The land is a mix of open pasture and wooded acreage. Zoned Rural Areas (RA). Live the way you want with no restrictions, no covenants, and no HOA! Many types of wildlife call this tract home including deer, turkey, and small game. Enjoy hiking, camping, and recreation of all types on this land. The many amenities of Winchester are just a short drive away. All the fun and adventure of the Cacapon Resort State Park are only a few minutes away also.

Brush Creek Road, Winchester

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

Selling Office: Pearson Smith Realty, LLC.

100 Alliance Ct, Winchester
$515,000
6 Beds ⋅ 4 Baths
Come enjoy this beautiful 3-year young home. A spacious open floor plan is perfect for large families or entertaining friends and family. LVP flooring runs throughout the whole house except for a small area in the basement. The stunning kitchen features wrap around cabinets, a large center island and a separate pantry for all of your storage needs. There is also a flex space in the main level, perfect for an office, den, play room, etc. Upstairs are 3 secondary bedrooms that share a hall bathroom. The spacious primary suite features a spa-like bathroom, with dual sinks, walk-in shower and relaxing soaker tub. The finished basement offers an abundance of additional living space, with a large den, 2 additional bedrooms and one full bathroom. Enjoy the outdoors in the beautiful patio and also all of the nearby outdoor activities.

100 Alliance Ct, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Serhant.

105 Travis Ct, Winchester
$514,900
4 Beds ⋅ 3 Baths
Welcome to 105 Travis Court, a spacious and beautifully maintained colonial situated on a desirable corner lot just outside Winchester city limits. This inviting 4-bedroom, 2.5-bath home offers over 2,300 finished square feet, plus a large unfinished walkout basement with excellent potential for future living space, a recreation room, home gym, workshop, or additional storage. The main level features beautiful hardwood flooring, a formal living room, formal dining room, and a comfortable family room with a cozy gas fireplace. The kitchen opens to the family room and breakfast area, creating a warm and functional space for everyday living and entertaining. Newer appliances, attractive cabinetry, generous counter space, and easy access to the covered porch make this area the heart of the home. Upstairs, the spacious primary suite includes a private bath, while three additional bedrooms and a full hall bath provide plenty of room for family, guests, or a home office. The unfinished walkout basement features large windows and French doors leading to the rear patio, offering natural light and endless possibilities for expansion. Additional highlights include a new roof installed in 2022, a two-car attached garage, a welcoming full front porch, a covered rear porch with ceiling fan, and a patio overlooking the yard. Conveniently located near shopping, dining, schools, and major commuter routes. Appointments only: One hour notice. Agents please leave Business Card

105 Travis Ct, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Long & Foster Real Estate, Inc..

121 Fortress Dr, Winchester
$510,000
4 Beds ⋅ 4 Baths
Welcome home to this spacious 4-bedroom, 3.5-bath Colonial in the conveniently located Star Fort subdivision. Offering three finished levels of comfortable living space, this home combines functionality, charm, and an ideal location. The main level features beautiful hardwood floors, a formal dining room, and a large family room with a cozy gas fireplace that flows into the spacious kitchen, complete with a breakfast bar, abundant cabinetry, and generous counter space, making it perfect for everyday living and entertaining. Upstairs, the spacious primary suite offers a private retreat with a beautifully updated bath featuring a tiled walk-in shower. The upper level also includes the convenience of a laundry area, two additional generously sized bedrooms, and a full hall bath. The finished walkout lower level provides exceptional flexibility with a large recreation room featuring a pellet stove, a fourth bedroom, and a full bath, making it ideal for guests, a home office, or multi-generational living. Step outside to enjoy the screened porch overlooking the large, fully fenced backyard with mature trees, a patio, and a storage shed, perfect for relaxing, entertaining, or play. You'll also love spending evenings on the charming covered front porch with its classic porch swing, the perfect spot to enjoy summer sunsets. Additional highlights include a newer roof, providing added peace of mind. Conveniently located near shopping, restaurants, schools, and commuter routes, this move-in-ready home offers the perfect combination of space, comfort, and convenience.

121 Fortress Dr, Winchester

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

Selling Office: ERA Oakcrest Realty, Inc..

102 Wagtail Ln Unit HOMESITE 1024, Winchester
$510,000
3 Beds ⋅ 3 Baths
LAST OPPORTUNITY for a 34-wide END VILLA at Hiatt Pointe (55+) by Van Metre Homes in Winchester, VA. Find Homesite 1024, the designer-curated MODEL HOME is the last remaining Vale 34-F2 floorplan and has never been lived in before. This MOVE-IN READY end villa offers 2,279 finished square feet across two levels with three bedrooms, two full baths, one half bath, designer finished and upgrades, 9-foot ceilings, a welcoming front porch, and a finished front-load two-car garage. Luxury Vinyl Plank flooring extends throughout the main living areas and primary bedroom. The gourmet kitchen features a large island, white soft-close cabinetry, white quartz countertops, white backsplash, Samsung stainless steel gas appliances, a walk-in pantry, and flows seamlessly into the dining area and great room. In the great room, enjoy an electric fireplac and an 18' x 10' walkout outdoor patio. The main-level primary suite features a coffered ceiling, walk-in closet, and spa-inspired bathroom with dual vanities, white quartz countertops, and a roll-in frameless shower with floor-to-ceiling tile. Upstairs, a spacious retreat, two bedrooms each with walk-in closets, and a full bathroom provide flexible living space. Additional highlights include an IQ Panel 4 home automation package, smart thermostat, structured wiring, whole-home security and automation, a tankless gas water heater, and solar panel readiness. Being a new build, your home is constructed to the highest energy efficiency standards and comes with a post-settlement warranty. Take advantage of closing cost assistance by choosing Intercoastal Mortgage and Walker Title. This home is available for self-guided touring through NterNow, no agent or appointment required. Buyers may visit independently during daylight hours. Scan the QR code at the door for instant access and follow a few quick prompts to let yourself in. For more information, visit our website or call Van Metre Homes.-------Discover Hiatt Pointe at Snowden Bridge, a gated active adult community designed for 55+ living, where every day brings new opportunities to connect, unwind, and thrive. Start your morning with a yoga session or workout in the fitness center before joining friends for a game of pickleball or billiards. In the afternoon, lounge by the outdoor pool and hot tub, then gather around the gas fire table as the sun sets. The clubhouse serves as the heart of the community, offering inviting spaces for social events, group activities, and quiet relaxation. Outdoor kitchens and scenic patio areas set the stage for effortless entertaining, while a low-maintenance lifestyle ensures more time for what matters most. With easy access to Route 7, I-81, and I-66, Hiatt Pointe offers the perfect blend of resort-style amenities and a welcoming, connected community.-------*Other homes sites and delivery dates may be available. Pricing, offers, and availability are subject to change without notice. Images, renderings, and site plans are for illustrative purposes only and may not reflect actual homes or features. Some images and renderings may depict interior designs created in collaboration with AI or may represent a similar home. Additional terms and conditions may apply. Please see a Van Metre Sales Advisor for details.

102 Wagtail Ln Unit HOMESITE 1024, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: Unrepresented.

121 Van Gogh Ter, Winchester
$510,000
4 Beds ⋅ 3 Baths
121 Van Gogh Terrace offers something hard to find in Sovereign Village — the convenience of neighborhood living with an oversized, private backyard that truly feels like your own retreat. Tucked away on a quiet cul-de-sac, this home welcomes you with a front porch overlooking the neighborhood and a flat yard framed by beautiful mature trees in both the front and back, creating an inviting and private setting. Inside, the main level offers flexible living spaces designed to fit your lifestyle, including a living room, dining area, kitchen with newer appliances, and an additional flex room perfect for a home office, playroom, sitting room, or whatever best suits your needs. Upstairs you’ll find the spacious owner’s suite with an en suite bathroom featuring a walk-in shower and soaking tub, along with three additional bedrooms. You’ll love the oversized fourth bedroom with its own walk-in closet. The unfinished walkout basement provides excellent storage or future expansion potential with direct access to the backyard. Additional updates include a brand new roof with 30-year shingles and a transferable warranty for added peace of mind. Enjoy living in a neighborhood where you can walk to the community pool and local elementary school while being conveniently located on Winchester’s desirable east side, just minutes from shopping, restaurants, Route 7, and I-81. Quick closing possible.

121 Van Gogh Ter, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Jim Barb Realty, Inc..

112 Westwood Cir, Winchester
$510,000
4 Beds ⋅ 3 Baths
NO HOA! ALL brick rambler nestled on a corner 1/2 an acre of mature trees lot in Winchester right off Route 522 and 2 miles to I-81! This spacious home (over 2,600 square feet of finished living space on ONE LEVEL) features 4 generously sized bedrooms and 3 full bathrooms, offering comfort and flexibility for any lifestyle. The heart of the home is an oversized kitchen with updates—stainless steel appliances, with granite countertops and storage with so many cabinets and perfect for cooking on the huge island and entertaining. Hardwood floors flow throughout the main living areas, including a separate formal dining room and an inviting huge living room with pocket doors for added privacy. All the bedrooms have hardwood floors. Enjoy year-round relaxation in the bright and airy sunroom with ceiling fans and skylights, overlooking the lush backyard. A detached oversized 2-car garage provides ample space for vehicles, tools, and storage. And about 2600 of unfinished basement, ready for new owner to finish. Property is private and peaceful, yet conveniently located to I-81, shopping, restaurants, and so much more. NO HOA!

112 Westwood Cir, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

Selling Office: Crum Realty, Inc..

120 Trellis View Ln, Winchester
$509,990
4 Beds ⋅ 3 Baths
Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa, blending style and functionality in a single-level open layout and finished loft, complete with a 2-car garage. This stunning 1,492 sq. ft. residence features three bedrooms and two baths on the main level, with the finished loft offering an additional 676 sq ft of living space with an additional bedroom, full bath, and storage closet. The kitchen comes equipped with a walk-in corner pantry, stainless steel appliances, soft close white shaker-style cabinets, and a modern island with quartz counter-tops and a farmhouse style sink. The primary suite is nestled at the back of the home, featuring a spacious walk-in closet and an en-suite bathroom. Two additional bedrooms in the front of the home provide versatility and privacy. And with the laundry room conveniently located off the main foyer, you'll have everything you need right at your fingertips. Embrace low-maintenance living and make The Freeport your perfect new home this summer! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

120 Trellis View Ln, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

Selling Office: Non Subscribing Office.

4494 Cedar Creek Grade, Winchester
$509,000
4 Beds ⋅ 3 Baths
Escape to Your Private Almost 3-Acre Oasis: The Ultimate Modern Homestead! Rarely does a property offer the perfect synergy of a high-end interior renovation and a fully functional hobby farm. Nestled on a lush, 2.87-acre lot, this stunning 4-bedroom, 3-full bath home has been reimagined from top to bottom. As you enter the circular driveway lined with budding spring trees, you’ll feel the peace of the countryside combined with the confidence of a home upgraded. THE RESIDENCE: Step inside to a sun-drenched floor plan featuring a renovated kitchen complete with custom soft-close cabinetry, sleek tile backsplash, and brand-new stainless steel appliances. The primary suite is a true retreat, boasting a luxury tiled bathroom and a massive walk-in closet with custom-built organization systems. Functional beauty continues throughout with modern trim, updated vanities, and custom cabinetry in every closet. UPPER LEVEL: The upper level offers a seamless blend of open space and privacy. An airy, gallery-style loft with new flooring and an open-rail balcony provides a stunning transition into a generous 4th bedroom. This versatile 'bonus' area is an ideal nook for sewing, crafting, or a quiet reading lounge overlooking the great room. THE EXTERIOR & HOBBY FARM: A homesteader’s dream come true! Start your morning gathering fresh eggs from the chicken coop or harvesting produce from the established raised garden beds. The equestrian or livestock enthusiast will love the 2-stall barn and the lush, fully fenced paddock. A thoughtful, removable walkway connects the home to the barn, ensuring "mud-free" chores during the snowy Virginia months and spring showers. THE SHOP: For the mechanic or hobbyist, the 900 sq. ft. (30x30) detached garage is a showstopper. Featuring extra-high ceilings, dedicated electric service, and heat, it’s the ultimate workspace for year-round projects. PEACE OF MIND: Forget the "to-do" list—the big-ticket items are done! Systems: New Roof, New Windows, New Hot Water Heater. Renovated kitchen, with custom cabinets and SS appliances. Septic: Pumped with new grinder and float (2026). ALL receipts in binder on counter. Basement Potential: The lower has a partially finished room with a walk-out glass door ready for your final flooring choice to add instant additional living space. Would make a great office, TV room, home schooling area and more.There is roughed-in plumbing for an additional bathroom, and a designated laundry area—. Additional heating can be found with the woodstove in the lower level with blower. From the pollinator gardens to the brand-new interior, this isn't just a house; it’s a lifestyle. Schedule your tour today and see spring come alive at 4494 Cedar Creek Grade!

4494 Cedar Creek Grade, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

312 W Cecil St, Winchester
$506,000
3 Beds ⋅ 2 Baths
Don’t miss your chance to live on sought-after W. Cecil in this charming, beautifully maintained historic home, just a few blocks from the walking mall. Light-filled and inviting, this home welcomes you with a classic covered front porch and warm hardwood floors that set the tone for the character throughout. The cozy living room features a recently converted gas fireplace, lovely built-ins, and crown molding. This space opens to the den featuring new pergo flooring and situated just off the kitchen, perfect for relaxing or entertaining The updated kitchen offers granite countertops, a large island, ample cabinet space, and stainless steel appliances (refrigerator and dishwasher new in 2023). The versatile bonus room addition can serve as a dining room, office, or library, and opens directly to the fenced backyard with convenient access to the garage via the rear alley. Upstairs, you’ll find three bedrooms and a refreshed full bath. Hardwood floors on the stairs and second level were recently refinished, and there’s easy access to the attic for storage. Major Recent Upgrades Include: New roof (2023) New A/C condenser and coil (2024) Refinished hardwood floors on stairs and in bedrooms New Pergo flooring in the den Fireplace converted from wood-burning to gas (2023) New concrete garage floor and stamped concrete walkway (2023) Both bathrooms refreshed with new toilets, vanities, faucets, lighting, and updated paint/wallpaper Call to see this one, it won't last long!

312 W Cecil St, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

113 Sunflower Way, Winchester
$505,000
3 Beds ⋅ 3 Baths
Brand new main level living Hemingway is Ready for you to call home! At the heart of the home, the gourmet kitchen shines with stainless steel appliances, quartz countertops, and upgraded cabinetry. The kitchen flows seamlessly into the dining and family rooms, where additional windows create a bright, inviting atmosphere—perfect for entertaining. Just beyond, a rear screened porch offers the ideal spot to relax and take in the peaceful surroundings. The spacious main-level primary suite features a walk-in closet and a spa-inspired bathroom with upgraded cabinetry, brushed nickel hardware, quartz countertops, and a seated shower with a frameless glass door. A second bedroom and full bath, also enhanced with upgraded finishes, provide comfort for family or guests. For added convenience, the laundry room is thoughtfully located just off the two-car garage. Upstairs is perfect for guests or extended family with a living space, 3rd bedroom and full bath. Nestled in Hiatt Pointe at Snowden Bridge, a vibrant 55+ active adult community, this home offers more than just beautiful design—it provides a lifestyle. Residents enjoy access to exclusive amenities, thoughtfully planned spaces, and a welcoming neighborhood atmosphere tailored for active, modern living. Ask about special fixed rate financing and closing costs!

113 Sunflower Way, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

Selling Office: Touchstone Realty, LLC.

116 Trellis View Ln, Winchester
$504,990
4 Beds ⋅ 3 Baths
Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa, blending style and functionality in a single-level open layout and finished loft, complete with a 2-car garage. This stunning 1,492 sq. ft. residence features three bedrooms and two baths on the main level, with the finished loft offering an additional 676 sq ft of living space with an additional bedroom, full bath, and storage closet. The kitchen comes equipped with a walk-in corner pantry, stainless steel appliances, soft close white shaker-style cabinets, and a modern island with quartz counter-tops and a farmhouse style sink. The primary suite is nestled at the back of the home, featuring a spacious walk-in closet and an en-suite bathroom. Two additional bedrooms in the front of the home provide versatility and privacy. And with the laundry room conveniently located off the main foyer, you'll have everything you need right at your fingertips. Embrace low-maintenance living and make The Freeport your perfect new home this July! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

116 Trellis View Ln, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

Selling Office: Keller Williams Realty.

203 Alpine Meadow Rd, Winchester
$503,000
4 Beds ⋅ 4 Baths
Located on a quiet cul-de-sac within the established and highly sought-after Apple Ridge neighborhood on the desirable east side of Winchester, this 4-bedroom, 3.5-bathroom colonial offers a spacious and open floor plan with significant recent improvements! The prime location provides quick access to Route 7 and I-81, making it an ideal choice for commuters! The exterior features a covered front porch, a relaxing screened-in back porch, and an expansive Trex deck featuring a built-in hot tub and stairs down to the spacious backyard! You can rest easy knowing all the big-ticket items have already been taken care of, including a newer architectural shingle roof, a newly repaved driveway, a new HVAC system installed in 2026, and a newer water heater, all set on a prime lot with professional landscaping and beautiful mature trees! The main level features a two-story cathedral foyer with a side entry staircase, a spacious formal living room, an elegant formal dining room, and a half bath with a bowl sink. The expansive "Horseshoe" kitchen boasts extensive counter space, ample storage, and a large peninsula with a breakfast bar, featuring high end Silestone countertops and stainless steel appliances with double ovens! Upstairs, the home provides four total bedrooms, including a primary suite with his and her closets, including a large walk-in closet! The beautifully renovated primary bathroom features an enormous walk-in shower with a frameless door, granite counters, and maple built-ins! The laundry room is conveniently located on the upper level! The fully finished walkout basement features new LVP flooring, a large recreation room, a dedicated exercise room, and a full bathroom! This property offers the perfect balance of a quiet residential setting and proximity to Winchester's best shopping, dining, and Old Town, while remaining a highly accessible commuter location close to Route 7 and I-81!

203 Alpine Meadow Rd, Winchester

Listing courtesy of Nova Home Hunters Realty. Contact:

Selling Office: Samson Properties.

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