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$634,900
5 Beds ⋅ 4 Baths ⋅ VAFV2044776 MLS
Your Next Chapter Starts Here! Space, style, flexibility, and a backyard made for entertaining — all tucked away on a quiet cul-de-sac in desirable Oakdale Crossing. This impressive 5-bedroom, 4-bathroom, three-level Colonial, with new roof (2026), delivers the kind of versatile space today’s buyers are looking for, with room to work from home, host friends, grow your household, or create the ultimate hangout zone. Start with the front wraparound porch, the perfect spot for morning coffee or winding down at the end of the day. Out back, the fun really begins: multiple composite decks with a pergola overlook a private, fully fenced yard backed by mature trees, creating your own outdoor retreat. The 20' x 30' saltwater above-ground pool takes summer entertaining to the next level. Inside, beautiful hardwood floors run throughout the main and upper levels. The main level offers an easy-flowing layout with a welcoming family room featuring a gas fireplace, separate dining and living rooms, plus a spacious kitchen with upgraded countertops, breakfast bar, and breakfast room. The first floor also includes a bedroom and full bathroom — ideal for guests, a home office, or flexible living arrangements. Upstairs, the spacious primary suite feels like a private escape, complete with double sinks, jetted tub, walk-in shower, and walk-in closet. Three additional bedrooms, a full bathroom, and conveniently located laundry complete the upper level. And then there’s the lower level — a huge bonus space ready for whatever your lifestyle demands. The large family room with wet bar is made for movie nights, game days, parties, or a dedicated entertainment space. An additional room plus a full bathroom offers incredible flexibility for a home gym, office, guest suite, teen hangout, or potential in-law setup. Outside your front door, you're conveniently located near Winchester Country Club, shopping, restaurants, and schools, giving you the best of both convenience and neighborhood living. This isn't just a house — it's the space to live the way you want now, with room for whatever comes next.

314 Huntersridge Rd, Winchester
$35,000
VAFV2044820 MLS
Lot 112, 113, & 114 .40 acre per Lot. Certification letters for each. Lot 112 - 3 Bdrm Perc / Lot 113 - 4 Bdrm Perc / Lot 114 - 3 Bdrm Perc. These lots Have the Views !! Come Build your part or full time Dream Home. Located in Shawneeland with No HOA, enjoy the amenities, Large Recreational Park Area with fishing ponds connected by running streams, Playground, Picnic Pavillion(s), Basketball hoops, Tuscarora Trails, Cherokee Lake w/beach & fishing area, Swan Lake for fishing, Another Park Area w/ playground on Maple Trail. Hard top roads. Common grounds & Road maintenance & plowed in Winter. Shawneeland is a Sanitary District Fee is included in Real Estate Tax Bill. Live Rural with a short distance to Shopping, Hospital and Town. Seller is Motivated, will consider selling lots separate.

Lot 112-113-114 Tomahawk Trl, Winchester
$4,000
VAFV2044816 MLS
Lot 60 .42 acre Certification letter for 3 Bdrm Perc. Talk about view! Come Build your part or full time Dream Home. Located in Shawneeland with No HOA, enjoy the amenities, Large Recreational Park Area with fishing ponds connected by running streams, Playground, Picnic Pavillion(s), Basketball hoops, Tuscarora Trails, Cherokee Lake w/beach & fishing area, Swan Lake for fishing, Another Park Area w/ playground on Maple Trail. Hard top roads. Common grounds & Road maintenance & plowed in Winter. Shawneeland is a Sanitary District Fee is included in Real Estate Tax Bill. Live Rural with a short distance to Shopping, Hospital and Town. Seller is Motivated.

Lot 60 Tomahawk, Winchester
$471,000
3 Beds ⋅ 3 Baths ⋅ VAWI2011610 MLS
A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you can easily walkout to huge concrete patio for a great family cookout and enjoy the huge backyard. The back yard is infenced with 6ft tall white vinyl privacy fence that makes it look very elegant and secure...In the upper level of the house, you will find the masterbedroom with a masterbath, and a second bath for the 2 other bedroom. This property is minutes away from the Winchester Historic downtown and a short drive to Shenandoah University. This is a well kept property and is waiting for you to make it yours! Schedule your showing online and allow time since the seller has two little dogs to take care off when you go show it. There are video cameras at the property.

421 Longview Ave, Winchester
$525,000
4 Beds ⋅ 4 Baths ⋅ VAFV2044810 MLS
Offering three luxuriously finished levels, extensive upgrades, and a backyard designed for entertaining, this 4 bed/3.5 bath colonial is a MUST-SEE! Step inside to a grand foyer with soaring 12-foot ceilings and walls of windows flooding the home with natural light throughout. The main level features a dedicated study room accented by striking arched windows, spacious living and dining areas, an open kitchen with a window overlooking the serene backyard, and a showstopping family room wrapped in eight oversized windows with transoms that frame views of the outdoors and create a bright, airy gathering space centered around a cozy fireplace. Step outside to your own backyard retreat—an entertainer’s dream with an expansive, fully fenced lawn, large low-maintenance composite deck, spacious brick patio, and custom-built outdoor brick fireplace. Imagine summer cookouts on the deck, evenings around the fire, or simply enjoying the abundance of your own private open space. Upstairs, the expansive primary suite feels like a retreat of its own, featuring a separate sitting area perfect for a reading nook or quiet place to unwind, and two walk-in closets, including one conveniently located within the ensuite bath. The spacious primary bath features dual vanities, an oversized walk-in shower, private water closet, and dedicated space ready to add the relaxing soaking tub of your dreams. The upper level is completed by three additional spacious bedrooms with ample closet space, including one with its own walk-in closet, plus an LG washer and dryer conveniently tucked behind closed doors in the hallway for out-of-sight laundry. Head downstairs to the fully finished basement, offering even more versatile living space with a spacious recreation room and full bathroom next to a bonus room with generous closet space—giving you the flexibility to create the guest space, media room, playroom, home gym, or hobby space that fits your lifestyle. The home’s biggest-ticket improvements have already been taken care of, saving you thousands in future costly upgrades! Updates include a newer roof and siding, HVAC systems, water heater, upgraded insulation, sump pump, irrigation system, water softener, radon mitigation system, and whole-house generator, providing the ultimate peace of mind and backup power when the neighborhood experiences an outage. This home presents a RARE OPPORTUNITY, priced significantly below the tax assessed value. Seller welcomes ALL offers—bring yours and make this home your own!

114 Nassau Dr, Winchester
$299,500
3 Beds ⋅ 2 Baths ⋅ VAWI2011582 MLS
Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas. The updated kitchen features new cabinetry and stainless steel appliances, creating a clean, contemporary space perfect for everyday living and entertaining. Both bathrooms have also been thoughtfully updated, adding to the home’s fresh and modern appeal. Enjoy your morning coffee or unwind at the end of the day on the covered front porch. The partially fenced yard provides space to enjoy the outdoors, while the storage shed offers convenient additional space for tools, lawn equipment, and seasonal items. Convenient rear-entry parking provides easy access to the home, with additional street parking available in front. The unfinished basement provides valuable additional storage and utility space. With its attractive updates, functional floor plan, outdoor space, storage shed, and convenient parking, 621 Watson Avenue is a standout opportunity in Winchester! Whether you're searching for a comfortable place to call home or a great investment property, this beautifully refreshed duplex is ready for its next owner. Schedule your tour on ShowingTime today and see why 621 Watson Avenue stands out! ***Seller finishing final touches, ready for tours starting 9/15/26.

621 Watson Ave, Winchester
$349,999
4 Beds ⋅ 2 Baths ⋅ VAFV2044756 MLS
Welcome to 120 Comanche Trail in Shawneeland! Offering over 1,800 finished sq. ft., this 4-bedroom, 2-bath home combines thoughtful updates with plenty of space inside and out. Recent improvements include a NEW roof, newer HVAC, new flooring, fresh paint, updated lighting, and updated bathrooms. The primary bedroom features a walk-in closet and private en-suite bath, creating a comfortable retreat. The fully finished walkout basement expands the living space with a huge additional bedroom, bonus room and plenty of storage. Ideal for guests, a home office, recreation space, or multi-generational living. Outside, enjoy a large private lot surrounded by mature trees with established garden beds and a fire pit. A 1-car garage and spacious driveway provide plenty of parking for guests. Located on the lower end of Shawneeland, approximately 15 minutes from Winchester Medical Center, Downtown Winchester, shopping, dining, and major commuter routes. Community amenities include a lake, private beach, playgrounds, sports fields, and more. NO HOA - Shawneeland is a sanitary district maintained by Frederick County. The septic system was completely redone in November of 2024 for additional buyer peace of mind. Updated, spacious, private, and conveniently located—this home is ready for its next owner!

120 Comanche Trl, Winchester
$479,900
5 Beds ⋅ 3 Baths ⋅ VAFV2044802 MLS
This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the updates today's buyers are looking for. Homes in this sought-after neighborhood rarely come to market, making this a special opportunity in one of the area's most convenient commuter locations. Inside, you'll find a comfortable blend of hardwood, tile, and carpet flooring, built-in shelving, fresh paint in many areas, and charming details including chair rail and crown molding in select rooms. The living area features an antique stained-glass mantle that has been beautifully refinished and incorporated above the gas fireplace, creating a distinctive focal point. Upstairs, four large bedrooms provide plenty of comfortable living space, including a spacious primary bedroom with its own private bathroom. A finished and conditioned third-floor loft adds a huge, flexible bonus space ready to meet your needs; perfect for a 5th bedroom, playroom, office, game room, or additional living area. Storage abounds throughout this versatile space, offering possibilities to suit a variety of lifestyles. The kitchen is designed for both everyday living and entertaining, with an oversized island offering abundant storage, a butcher block top, and an eat-up bar area. Granite countertops are complemented by a white subway tile backsplash and a dramatic floor-to-ceiling accent wall. Recent improvements include a new water softener, a 2018 water heater, and a new washer and dryer installed in 2026. The HVAC systems are approximately two and three years old and have been recently serviced. The roof is less than five years old, while newer HardieBoard siding and windows provide additional peace of mind. Step outside to the large covered rear porch, finished with beadboard and a ceiling fan, overlooking the spacious fenced backyard. Mature trees and established landscaping create a private setting that is ideal for relaxing, entertaining, or enjoying outdoor time. The paved driveway adds convenience, while the no-HOA neighborhood provides added flexibility. Perfectly positioned close to town, schools, and everyday amenities while offering quick access to Route 7 for commuters, this home combines a well-established neighborhood setting with an exceptionally convenient location. A home with genuine character, meaningful improvements, and a level of care that is evident throughout.

109 Julee Dr, Winchester
$459,900
3 Beds ⋅ 2 Baths ⋅ VAFV2044768 MLS
Enjoy easy one-level living in this well-maintained ranch home conveniently located in Winchester, close to commuter routes, shopping, restaurants, and everyday amenities. The inviting front porch is the perfect spot to relax and enjoy warm evenings. Inside, hardwood floors flow through the living room, kitchen, and dining area, while the bedrooms feature comfortable carpeting. A dedicated laundry room adds convenience, and the unfinished basement provides plenty of storage and future possibilities. Step outside to the backyard, where a deck offers the perfect setting for entertaining, relaxing, or enjoying outdoor gatherings. A shed provides additional storage, while the two-car garage offers plenty of parking and workspace. A great combination of comfort, convenience, and outdoor living!

991 Front Royal Pike, Winchester
$325,000
4 Beds ⋅ 2 Baths ⋅ VAWI2011592 MLS
Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own!

805 S Kent St, Winchester
$3,500,000
VAFV2044790 MLS
Be sure to see the video and 3D tour to fully explore this property! <br><br> Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term Rental + Development Lots! <br>br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals.<br><br> For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership.<br><br> The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals.<br><br> The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional.<br><br> Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

Winchester
$552,000
4 Beds ⋅ 3 Baths ⋅ VAFV2044754 MLS
Beautifully remodeled Colonial in Pioneer Heights. Designed with primary suite; ideal home office configuration. All large bedrooms, large hardwood living room with stone wood fireplace, new natural gas upstairs furnace and a/c, upgraded insulation in attic, oversized garage and large deck. New paint, LVPk flooring in baths and kitchen. Must see.

100 Winns Cir, Winchester
$395,600
4 Beds ⋅ 2 Baths ⋅ VAFV2044446 MLS
You are going to love this spacious, one-level ranch located on a half-acre lot in a great location! Here are some of the key features and recent updates: - Huge 20x26 family room with Red Oak hardwood floors, a brick fireplace, and newly replaced French doors that open onto a large L-shaped front deck. - Bedrooms & Baths: New paint and new flooring throughout bedrooms and bathrooms master bath features a new vanity and new ceramic tile flooring, which is also featured in the hallway bath. master bedroom has full bath -Laundry: 8x8 laundry room complete with washer, dryer, cabinets, and counter space. -Kitchen and living room has Bruce flooring All new painting through out house - Upgrades: New ceiling fans in all rooms. The water pump, septic tank, and attic air handler for the AC unit have all been replaced. Both decks have been recently remodeled and resealed. - Garaging & Parking: you are going to love the Oversized 20x28 garage with front and back entry doors, plus a second attached 12×20 garage with entry door from the main garage! Large driveway with a 10+ car capacity and turnaround area. - Outdoor Space: Fenced backyard with a 10x12 back deck and beautiful pastoral views in both the front and back. Large L-shaped deck on front of house This home offers peaceful country living while remaining convenient to local grocery stores, restaurants, gas stations, schools, and major commuter routes this ranch offers the space & amenities you been dreaming of....... LOOK NO FURTHER!

178 Payne Rd, Winchester
$549,900
5 Beds ⋅ 4 Baths ⋅ VAFV2044748 MLS
“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
$359,000
3 Beds ⋅ 2 Baths ⋅ VAWI2011584 MLS
Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick home features 3 bedrooms, 1.5 bathrooms, a 2-car driveway, and three beautifully finished levels of move-in-ready living space. From the tree-lined sidewalks and charming street lighting, you are welcomed onto a main level boasting gorgeous original hardwood floors, a convenient main-level half bath, a spacious formal dining room, and a warm living room anchored by a cozy wood-burning fireplace. The efficient kitchen offers a brand-new stove, plenty of storage and prep space, and a dedicated pantry for ultimate organization. The entire home has been freshly painted inside, with brand-new carpet installed across the stairs and bedrooms—including the large primary bedroom upstairs. Head downstairs to find a full, finished basement that provides additional living space, an abundance of extra storage, and a dedicated laundry area. Major mechanical updates offer complete peace of mind, including an all-brick exterior, a newer roof, newer HVAC, and newer windows throughout. Step outside to your private oasis—an extensive patio framed by beautiful mature trees that backs directly to the scenic Park Place Park, offering an extended backyard feel and peaceful views with no rear neighbors. Complete with a large storage shed to easily house all of your tools, lawn equipment, or outdoor gear. Conveniently located near shopping, dining, walking trails, and major commuter routes. Come see this home and schedule your private tour today!

812 Appleseed Ct, Winchester
$355,000
2 Beds ⋅ 2 Baths ⋅ VAWI2011574 MLS
Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer HVAC, a 4 year old roof, LVP flooring, updated bath, 2 bedrooms + 2 full bath. The 1 car garage is heated and cooled for year round comfort. There is space for a car and small workshop. You'll feel welcomed in this neighborly community where people walk, socialize and have planned activities at the well appointed Community Center. It is right around the corner from this home. Also, this home is located near the Abrams Creek Wetlands Preserve, perfect for walking + biking. Hospital + Down Town Winchester are 10 minutes away. Priced well and ready for you, come take a look today.

1847 Melvor Ln, Winchester
$375,000
3 Beds ⋅ 2 Baths ⋅ VAFV2044758 MLS
265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, and an adjoining area for dining. The main living room provides space for seating, with an additional finished room on the lower level. The primary bedroom includes a walk-in closet with shelving for organization and an adjoining bathroom with a shower and vanity. A rear deck connects to the home through sliding doors, extending the usable space outdoors. A dedicated laundry area includes cabinetry and a folding counter. The layout combines everyday living with practical storage.

265 Mcdonald Rd, Winchester
$409,000
4 Beds ⋅ 1 Baths ⋅ VAWI2011520 MLS
Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

322 E Piccadilly, Winchester
$435,000
3 Beds ⋅ 2 Baths ⋅ VAFV2044502 MLS
No HOA in the heart of Winchester! This charming brick rancher features three bedrooms, two baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the main level. The layout includes a versatile sunroom with a private entrance and a kitchen equipped with stainless steel appliances. The basement expands your living space with a wet bar, separate entrance, and another fireplace! This home provides timeless construction and incredible potential. Walk outside to the spacious, fully fenced backyard with a storage shed. Enjoy ample parking with an oversized attached garage. Don’t miss the opportunity to own this home in an excellent location, just steps from Winchester Country Club and minutes to shopping, dining, and commuter routes. *Seller is also offering a one-year Home Warranty with the sale of the property!

131 Country Club Cir, Winchester
$317,265
3 Beds ⋅ 2 Baths ⋅ VAFV2044700 MLS
Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of character and potential, this home boasts a classic floor plan just waiting for your cosmetic updates and personal design vision. The main level features a bright living area filled with natural light, a dedicated dining space, and original hardwood flooring. Three comfortably sized bedrooms complete the upper level, including a primary bedroom with its own private en-suite bath. The full basement offers so much room to expand with a laundry area, a finished area for a possible sleeping room, ample heavy shelving units for crafting, storage or a workshop, and a walkout with sliding doors. Beyond the front door lies a vibrant, amenity-rich community known for its warm atmosphere. Neighborhood residents enjoy access to a spring-fed/man-made lake featuring a sandy beach area, swimming, fishing, and a boat ramp (gas motors are not permitted). Cherokee Beach is open to residents without a beach pass, additional smaller ponds and scenic streams located throughout the community, two community playgrounds, wooded nature walks and trails, pavilion spaces, open sports areas, and picnic spots, and covered/lighted mailbox stations and covered school bus stops.

148 Doe Trl, Winchester
$289,900
3 Beds ⋅ 4 Baths ⋅ VAFV2044686 MLS
Spacious three-level townhome in a desirable Winchester community, conveniently located near Sunnyside and Old Town Winchester! Offering generously sized bedrooms, three and a half baths, and flexible living space across three levels, this home has room for everyone. The main level features a comfortable family room, dining area, kitchen, and convenient powder room, with access to the spacious rear deck overlooking mature trees and HOA owned property. The private wooded setting creates a peaceful outdoor oasis, perfect for relaxing, grilling, or entertaining. Upstairs, you'll find two spacious bedrooms, each with its own full bath, providing excellent privacy and comfort. The finished basement adds even more versatility with a large recreation room, additional bonus/bedroom space, and a full bathroom. Whether used for guests, a home office, hobbies, or recreation, the lower level offers valuable additional living space. Enjoy the best of both convenience and tranquility, with a private, tree-lined setting while being just minutes from Sunnyside, Old Town Winchester, shopping, dining, parks, and commuter routes. A wonderful opportunity to enjoy spacious townhome living in a great location with flexible space and a private backyard setting.

114 Tudor Dr, Winchester
$515,000
2 Beds ⋅ 3 Baths ⋅ VAFV2044428 MLS
Welcome to 100 Gooseberry Drive, located in Winchester's established Cross Creek Village community! This meticulously maintained brick rancher offers true main-level living in one of the communities most spacious and sought-after floor plans. The main level features formal living and dining rooms, a kitchen with breakfast nook, and a bright bonus sunroom. The generous primary suite is filled with natural light and features its own cozy gas fireplace, spacious en-suite bath, and walk-in closet. A guest bedroom, additional full-bath, and dedicated laundry complete the main level. The attached two-car garage provides direct access to the home as well as a private side-entrance leading upstairs to a thoughtfully designed guest suite- ideal for visitors, a home studio or additional climate controlled storage! Enjoy easy outdoor living on a quiet corner lot, with a private fenced in back-patio perfect for enjoying morning coffee or summer grilling! Set within a vibrant 55+ community, this home offers comfort, convenience and low-maintenance living just minutes from major shopping, dining & more! Schedule your private tour today!

100 Gooseberry Dr, Winchester
$900,000
VAWI2011572 MLS
This building located at 435 N. Cameron Street in Winchester, Virginia, formerly housed the Winchester Rescue Mission. Architecturally, it is a two-story, brick commercial building featuring prominent display windows across the front. The brickwork was formerly painted a crisp white, contrasted by dark framing around the windows and doors. Presently, there is a hand painted mural that covers the entire front of the building and the south side. The building with approximately 7,292 SF on two floors is sited on a lot with land area of 0.17 +/- acres with approximately 50 feet of frontage on Cameron Street. There are approximately 14 rooms. The building was constructed in 1931. The property has served as a homeless shelter since it was purchased for the nonprofit in July 1973. In recent years, the shelter has provided emergency overnight lodging for men and women, alongside hot meals, spiritual counseling, and mental health services. The facility had provided approximately 60 beds for men and women. Because the shelter consistently ran out of beds at peak capacity, the operators had to turn away individuals daily and the organization broke ground and expanded their facilities at their new facility on 2655 Valley Avenue.

435 N Cameron St, Winchester
$805,000
4 Beds ⋅ 4 Baths ⋅ VAFV2044518 MLS
CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Owners Suite floorplan the Boxwood Farm model with standard 10' Main Level Ceilings Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

Tumble Leaf Lane, Winchester
$750,000
VAFV2044708 MLS
Development Opportunity at Front Royal Pike and Airport Road Located at the signalized intersection of Front Royal Pike (U.S. 522) and Airport Road, this highly visible corner property sits within one of Winchester’s growing commercial corridors. The property is currently zoned RP (Residential Performance), with potential for a variety of future uses subject to rezoning, special-use approval, and other applicable governmental requirements. Its prominent corner position, substantial road frontage, and proximity to established and expanding commercial development make it well suited for consideration as a retail, service, office, or mixed-use site. An attractive opportunity for investors, developers, or businesses seeking a strategically positioned property with excellent visibility and long-term growth potential in the Winchester market.

721 Front Royal Pike, Winchester
$374,900
3 Beds ⋅ 3 Baths ⋅ VAWI2011570 MLS
"Come On Down To Cidermill" Beautiful 3 bedroom, 2 1/2 bath duplex style townhome at end of street! All 3 bedrooms on upper level. Spacious family room, large eat in kitchen and back deck with stairs down to the yard. Large laundry room on basement level. One car garage and spacious driveway. Conveniently located in Winchester City. Home has just been remolded with the following: All new LVP flooring throughout, freshly painted on the inside, front door painted, garage door painted, shutters painted, handrail out front painted, deck remodeled, fresh mulch, bushes trimmed, new stainless-steel appliances and a new HVAC system! Hurry this one won't last long!

1957 Cidermill Ln, Winchester
$439,000
5 Beds ⋅ 3 Baths ⋅ VAFV2043352 MLS
Welcome to this newly renovated and thoughtfully designed 5-bedroom, 3-full-bath home offering exceptional flexibility for modern living or rental income. Featuring two full kitchens, two dining areas, and potentially two separate living spaces, this home provides a unique opportunity to create two distinct living areas under one roof. Bottom level has two separate entrances in front and rear and for privacy and convenience, the layout ideal for extended family, guests, roommates, or potential rental use. Newly renovated, this home combines the comfort of modern updates with the versatility buyers are looking for. Whether you're seeking a spacious primary residence or an investment opportunity with potential rental income, this property offers the space and flexibility to make it your own. Don't miss this rare opportunity to own a beautifully renovated home with multiple living possibilities!

300 Pembridge Dr, Winchester
$699,000
7 Beds ⋅ 5 Baths ⋅ VAWI2011542 MLS
Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester
$525,000
4 Beds ⋅ 4 Baths ⋅ VAFV2044280 MLS
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
$1,450,000
VAWI2011560 MLS
5900 sf of Old Town elegance located in the middle of the walking mall at the fountain. 2 floors of finished space that currently is used for retail on the mail level and a kitchen lab on the second floor. Two entrances from the front off of the walking mall and two entrances from the rear. Property included 10 parking spaces off of Indian Alley. Call broker for showing and further details.

Winchester