171

Winchester, VA 2-Story Homes for Sale

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  • /4

    $615,434

    New Construction Coming Soon
    • 3 Beds
    • 3 Baths
    • 3,200 Sq Ft

    116 Magpie Ln, Winchester, VA 22603

    READY FOR IMMEDIATE DELIVERY! The Sierra 39-F2 at Hiatt Pointe (55+) delivers single-family living at its finest — 3 bedrooms, 3 full baths, 2-car front-load garage, and an open-concept floorplan designed for the way you actually live. Enter through the front porch into a light-filled main level featuring 9' ceilings, oak stairs, and luxury vinyl plank flooring throughout. The chef's kitchen

    Dimitri Sotiropoulos Keller Williams Realty

    116 Magpie Ln, Winchester, VA 22603
  • /26

    $544,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,264 Sq Ft

    104 Zinnia Ln, Winchester, VA 22603

    Discover relaxed, low‐maintenance living in this beautifully crafted twin/semi‐detached home, coming this summer to a sought‐after gated active‐adult community. Designed with today’s vibrant 55+ lifestyle in mind, the home offers effortless main‐level living with both a primary and secondary bedroom conveniently located on the first floor, along with a versatile den—ideal for a home office,

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    104 Zinnia Ln, Winchester, VA 22603
  • /12

    $598,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 3,056 Sq Ft

    TO BE BUILT-HOMESITE Williamson Rd, Winchester, VA 22602

    TO BE BUILT – This home has not been constructed yet. Photos are of a similar model and may show optional features. Appointment at model home – 154 Williamson Rd. Price reflects base price plus options. Estimated delivery timeline is approximately 6–7 months. The Drexel offers generous living space in a beautifully designed ranch home featuring 3 bedrooms and 3 bathrooms, with approximately 3,213

    Greta Fernandez New Home Star Virginia, LLC

    TO BE BUILT-HOMESITE Williamson Rd, Winchester, VA 22602
  • /18

    $449,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,657 Sq Ft

    366 Munsee Cir, Winchester, VA 22602

    Step into 1,657 square feet of well-designed living space in the Cabral, featuring 3 spacious bedrooms, 2.5 bathrooms, and a flexible loft upstairs—perfect for a home office, playroom, or additional lounge area. This home showcases a charming white siding exterior with stone accents, while the interior boasts sleek white kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

    Victoria Clark D R Horton Realty of Virginia LLC

    366 Munsee Cir, Winchester, VA 22602
  • /78

    $375,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    506 Grouse Dr, Winchester, VA 22602

    Seller offering a 1% rate reduction for the first year when using builder's approved lender available until 6/15/2026. This property is nestled in a charming community, this stunning new construction home offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to

    Steve DuBrueler Coldwell Banker Premier

    506 Grouse Dr, Winchester, VA 22602
  • /67

    $780,000

    New Construction $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,476 Sq Ft

    230 Tranquil Wood Ln, Winchester, VA 22602

    Tucked away on over 3 private acres in the scenic countryside of Frederick County, this newly completed modern farmhouse offers peaceful country living with the convenience of nearby Winchester ammenities and major commuter routes. Custom built by Water Creek Homes, the home showcases quality craftsmanship, elevated finishes, and carefully curated details throughout. Designed to stand apart from

    Brittney Hunt Pearson Smith Realty LLC

    230 Tranquil Wood Ln, Winchester, VA 22602
  • /18

    $374,990

    New Construction
    • 3 Beds
    • 1.5 Baths
    • 1,752 Sq Ft

    115 Castaway Place, Winchester, VA 22603

    This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

    Brookfield Residential Builder
    115 Castaway Place, Winchester, VA 22603
  • /63

    $330,000

    • 4 Beds
    • 2 Baths
    • 1,592 Sq Ft

    805 S Kent St, Winchester, VA 22601

    Very well-maintained 2-level home offering 4 bedrooms and 2 full baths in the heart of Winchester. This home features a functional layout with a blend of classic charm and thoughtful updates throughout. Pride of ownership shows inside and out, with comfortable living spaces, a fully fenced yard, and a private driveway for off-street parking. Conveniently located near downtown, shopping, and

    Carolina Mosquera Weichert, REALTORS

    805 S Kent St, Winchester, VA 22601
  • /28

    $485,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,953 Sq Ft

    PINE Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

    The Pine is a 1,953 square foot open concept home, offering four bedrooms, two and a half bathrooms and a two-car garage. A foyer with a powder room and coat closet greets you as you enter this home. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for

    D.R. Horton Builder
    137 Seminole Dr Unit 36203779, Winchester, VA 22602
  • /27

    $399,900

    New Construction $10K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    211 Inca Trail, Winchester, VA 22602

    Nearing completion! Current Shawneeland Inventory107 Pinto Trail (split foyer)208 Beaver Trail (split foyer_210 Beaver Trail (split foyer)212 Falcon Trail (coloinial)211 Inca Trail (coloinial)103 Tonto Trail (split foyer)123 Killbuck Trail (coloinial)Premium Finishes: Enjoy a builder-upgraded interior featuring gleaming hardwood floors throughout the entire home

    Jim Thomson Realty ONE Group Old Towne

    211 Inca Trail, Winchester, VA 22602
  • /33

    $289,000

    $21K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,472 Sq Ft

    323 Fairview Ave, Winchester, VA 22601

    Welcome home to this beautifully updated 2-bedroom, 1-bath single-family residence offering charm, comfort, and modern upgrades throughout. From the inviting front porch to the spacious fenced backyard, this move-in ready home combines classic character with thoughtful renovations. Inside, you’ll find brand new LVP flooring on both levels and a completely renovated kitchen featuring ceramic tile

    Jeremy Browne EXP Realty, LLC

    323 Fairview Ave, Winchester, VA 22601
  • /16

    $2,124,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,801 Sq Ft

    152.44 Acres Lot 2 Laurel Grove Rd, Winchester, VA 22602

    This is a rare opportunity to build a fully custom home tailored to your vision, crafted by Winchester’s award-winning builder, Hepler Homes. The home shown is a representative example of what can be built on this exceptional property. List price reflects the included options outlined in the documents section and is subject to change based on custom selections.The featured model offers a

    Nadeem Helfer Samson Properties

    152.44 Acres Lot 2 Laurel Grove Rd, Winchester, VA 22602
  • /35

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    112 W Germain St, Winchester, VA 22601

    100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025!This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic

    Amanda Magana RE/MAX Roots

    112 W Germain St, Winchester, VA 22601
  • /32

    $429,000

    • 2 Beds
    • 2 Baths
    • 1,031 Sq Ft

    118 1/2 E Cork St, Winchester, VA 22601

    Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Winchester’s historic downtown walking mall, offering easy access to restaurants, bars, boutiques, and entertainment. Originally built in the 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural charm, and

    Janet Flaherty Keller Williams Realty

    118 1/2 E Cork St, Winchester, VA 22601
  • /34

    $1,585,000

    New Construction
    • 4 Beds
    • 5.5 Baths
    • 4,684 Sq Ft

    Lot 4 - Honeycrisp, Winchester, VA 22603

    Remarkable and new to the market Anderson subdivision lots. Located 5 minutes from downtown Winchester and Valley Health Medical Center (2 minutes from James Wood High School) off Apple Pie Ridge. Entrance Road Under Construction, currently. These lots feature panoramic views of the entire Shenandoah Valley from Harper's Ferry to Strasburg to the Western Mountains, providing stunning views from

    JP Carr Merrifield Realty, LLC

    Lot 4 - Honeycrisp, Winchester, VA 22603
  • /37

    $420,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,806 Sq Ft

    133 Woodrow Rd, Winchester, VA 22602

    Set on the east side of Winchester in Carlisle Heights, this inviting 3 bedroom, 3 full bath split foyer offers style, function, and a commuter-friendly location just minutes from Route 7. Inside, you’ll find a bright, open feel with easy-care flooring flowing through the main living spaces and bedrooms. The kitchen has been tastefully refreshed with crisp white cabinets, stainless steel

    Kevin Pringle Samson Properties

    133 Woodrow Rd, Winchester, VA 22602
  • /94

    $795,000

    • 5 Beds
    • 4 Baths
    • 4,075 Sq Ft

    274 Woodside Ln, Winchester, VA 22603

    Welcome to 274 Woodside - a secluded house on 5.06 acres with tons of storage! This 4,310 SF rambler style home has 2 masters (one up and one down), 4 bathrooms (2 on the main floor have heated floors), a huge kitchen with tons of cabinets, a large island with a 5 burner propane cooktop, and a pantry cabinet with pull-out shelves for storage, two fireplaces - one propane and one wood-burning

    Cindy Butler Virginia Property Group, Inc.

    274 Woodside Ln, Winchester, VA 22603
  • /13

    $598,990

    New Construction $76K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,875 Sq Ft

    TO BE BUILT-HOMESITE Duke Ct, Winchester, VA 22602

    TO BE BUILT – This home has not been constructed yet. Photos are of a similar model and may show optional features. Appointment at model home – 154 Williamson Rd. Price reflects base price plus options. Estimated delivery timeline is approximately 6–7 months. The Drexel offers generous living space in a beautifully designed ranch home featuring 3 bedrooms and 3 bathrooms, with approximately 3,213

    Greta Fernandez New Home Star Virginia, LLC

    TO BE BUILT-HOMESITE Duke Ct, Winchester, VA 22602
  • /70

    $749,500

    • 6 Beds
    • 4 Baths
    • 4,672 Sq Ft

    817 Chelsea Dr, Winchester, VA 22601

    Spacious 5-6-bedroom, 4-bath brick-front rancher with a fully finished basement, offering flexible living space for today’s needs. The main level features a welcoming living room with a tray ceiling & a gas fireplace, a formal dining room with crown molding & chair rail, and a well-appointed kitchen with Corian countertops and a walk-in pantry. The primary suite is conveniently located on the

    Sheila Pack RE/MAX Roots

    817 Chelsea Dr, Winchester, VA 22601
  • /8

    $760,000

    New Construction $15K PRICE INCREASE
    • 3 Beds
    • 3.5 Baths
    • 2,550 Sq Ft

    0 Tumble Leaf Ln, Winchester, VA 22602

    CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Dogwood model ( One Story Living ) with standard 10' main level ceilings and 13' ceilings in the Family Room. Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

    Daniel Boris Pearson Smith Realty, LLC

    0 Tumble Leaf Ln, Winchester, VA 22602
  • /3

    $755,320

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    120 Malbec Ct, Winchester, VA 22602

    The Somerset home design by Maronda Homes is designed with today’s lifestyle in mind—blending open-concept living, functional spaces, and refined details into one beautifully crafted home. With 4 bedrooms, 2 to 4 bathrooms, and 3,194 square feet of living space, the Somerset offers flexibility for families at every stage of life.The heart of the home is the expansive great room, which opens to a

    Maronda Homes Builder
    120 Malbec Ct, Winchester, VA 22602
  • /27

    $399,900

    New Construction
    • 3 Beds
    • 3 Baths
    • 1,914 Sq Ft

    208 Beaver Trail, Winchester, VA 22602

    Hardwoods down. Painted. Cabinets going in. To be completed soon.Current Shawneeland Inventory107 Pinto Trail (split foyer)208 Beaver Trail (split foyer)210 Beaver Trail (split foyer)212 Falcon Tarail (colonial)211 Inca Trail (colonial)103 Tonto Trail (split foyer)123 Killbuck Trail (colonail)Stunning 3BR/3BA home on 0.33+ acre lot with public water & available

    Jim Thomson Realty ONE Group Old Towne

    208 Beaver Trail, Winchester, VA 22602
  • /20

    $299,999

    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    553 Highland Ave, Winchester, VA 22601

    Awesome Colonial Revival just four blocks from Winchester's beloved walking mall! This 1921 charmer has been completely transformed with a total make-over you'll love. Brand new stainless steel appliances make cooking a joy, while fresh vinyl laminate flooring flows throughout for easy living. New LED fixtures brighten every room, and classy bathroom updates add that spa-like touch. Tucked away

    Teri Domanski Your Home Sold Guaranteed Realty - East LLC

    553 Highland Ave, Winchester, VA 22601
  • /42

    $625,000

    • 4 Beds
    • 3 Baths
    • 2,996 Sq Ft

    1564 Perry Rd, Winchester, VA 22602

    Discover the perfect blend of comfort and contemporary living in this stunning detached home, nestled on a generous 1.35-acre lot. Built in 2009, this residence boasts a modern architectural style that harmonizes with its serene surroundings, offering a peaceful retreat from the hustle and bustle of everyday life. Step inside to find a spacious layout that invites you to create lasting memories.

    Nate Vogel Century 21 Redwood Realty

    1564 Perry Rd, Winchester, VA 22602
  • /51

    $399,999

    • 3 Beds
    • 2 Baths
    • 2,131 Sq Ft

    204 Ridge Rd, Winchester, VA 22602

    Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) on a full basement on the east side of Winchester featuring over 2100 sqft of finished living space that offers true hardwood flooring on the main level with 3 bedrooms and 1 full bath. Spacious living room that features a gas log fireplace that has a woodstove insert included. Basement is 90% finished with a

    James Amick RE/MAX Roots

    204 Ridge Rd, Winchester, VA 22602
  • /78

    $674,900

    $24K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 3,024 Sq Ft

    777 Glengary Rd, Winchester, VA 22603

    If you’ve been dreaming of wide open space, mountain views, and a home with character, this special property may be exactly what you’ve been waiting for.Nestled on 37 unrestricted acres, this beautiful property offers the best of Shenandoah Valley living. With a perfect blend of open pasture and wooded privacy, the land provides room to breathe, explore, and imagine what’s possible. A

    Sharon Farinholt Realty ONE Group Old Towne

    777 Glengary Rd, Winchester, VA 22603
  • /39

    $421,000

    • 3 Beds
    • 2.5 Baths
    • 2,277 Sq Ft

    422 S Loudoun St, Winchester, VA 22601

    Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level

    Dana Cloud Realty ONE Group Old Towne

    422 S Loudoun St, Winchester, VA 22601
  • /38

    $319,000

    $26K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,382 Sq Ft

    31 E Germain St, Winchester, VA 22601

    IMPROVED PRICING! Nestled in the heart of Winchester City’s Historic District and walkable to shops and restaurants, this charming 2-bedroom, 2-bathroom gem is a rare find! The large front porch has great curb appeal and is the perfect place for outdoor lounging. The home is filled with natural light that illuminates the clean white walls and warm hardwood flooring. The living room flows into the

    Sue-Anne DeBergh Compass

    31 E Germain St, Winchester, VA 22601
  • /79

    $1,130,000

    New Construction $70K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,211 Sq Ft

    0 Light Rd, Winchester, VA 22603

    Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning new construction nestled on twenty wooded and open acres with pleasant peaceful views. This thoughtfully designed home features spacious living areas, modern finishes, and a classic exterior that blends beautifully with its natural

    Melissa Johnston ERA Oakcrest Realty, Inc.

    0 Light Rd, Winchester, VA 22603
  • /30

    $349,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    616 Cardinal Dr, Winchester, VA 22602

    Nestled in the serene Wilde Acres community, this exquisite split foyer home, built in 2024, offers a harmonious blend of modern luxury and inviting comfort. With three spacious bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining, making it the perfect sanctuary for those who appreciate the finer things in life. Step inside to discover a thoughtfully

    Brett Shankle Samson Properties

    616 Cardinal Dr, Winchester, VA 22602
  • /19

    $649,990

    New Construction $9K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,712 Sq Ft

    249 Hydrangea Way, Winchester, VA 22602

    he Dover by D.R. Horton offers 1,958 square feet of thoughtfully designed, single-level living with 3 bedrooms, 2 full baths, and a 2-car garage. A private flex room with LVP flooring sits just off the foyer – ideal for a home office or craft room.9-foot ceilings lead into the open-concept kitchen, dining, and family room. The kitchen features quartz countertops, soft-close cabinet doors, a

    Victoria Clark D R Horton Realty of Virginia LLC

    249 Hydrangea Way, Winchester, VA 22602
  • /21

    $269,000

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    321 N Kent St, Winchester, VA 22601

    Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or den. Upstairs you will find three bedrooms, full bathroom and

    Amy Capitano MarketPlace REALTY

    321 N Kent St, Winchester, VA 22601
  • /40

    $399,500

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,838 Sq Ft

    106 Plantation Dr, Winchester, VA 22602

    Charming 4-bedroom, 2-bath rancher situated on a .34-acre lot with mature trees providing shade in both the front and back yards. Enjoy outdoor living with a fenced backyard, rear deck, and storage shed. Inside, the vaulted-ceiling living room with a wood-burning fireplace creates a bright and inviting gathering space. The walkout lower level offers excellent flexibility with a spacious family

    Sheila Pack RE/MAX Roots

    106 Plantation Dr, Winchester, VA 22602
  • /24

    $509,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,953 Sq Ft

    124 Wappinger Terrace, Winchester, VA 22602

    The Pine offers 1,964 square feet of modern living space - perfect for growing families or those who love to entertain. This well-designed single family home includes four spacious bedrooms, two and a half bathrooms, and a two-car garage on slab foundation. The open-concept design showcases a contemporary kitchen with stainless steel appliances, quartz countertops, and white cabinetry - combining

    D.R. Horton Builder
    124 Wappinger Terrace, Winchester, VA 22602
  • /86

    $1,900,000

    • 5 Beds
    • 4 Baths
    • 4,166 Sq Ft

    1631 Back Mountain Rd, Winchester, VA 22602

    This unique property is the definition of an oasis in the woods. Surrounded by 180 glorious private acres, this home dazzles with grandeur while blending natural elements that mesh with the environment. The handsome hunter green standing seam metal roof with matching accents against wood siding is the ideal look for this 4,166 square foot architectural marvel. Indoors, there’s a thoughtful

    Dan Whitacre Colony Realty

    1631 Back Mountain Rd, Winchester, VA 22602
  • /35

    $300,000

    • 2 Beds
    • 3 Baths
    • 1,028 Sq Ft

    902 Enfield Dr, Winchester, VA 22602

    Will Walraven Realty One Group Key Properties

    902 Enfield Dr, Winchester, VA 22602
  • /16

    $364,990

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 1,966 Sq Ft

    117 Bonnings Dr, Winchester, VA 22603

    MOVE-IN READY townhome in Rossum Crossing! Enjoy low-maintenance living in a convenient location close to shopping, dining, parks, schools, and major commuter routes. 3 bedrooms, 2.5 bathrooms, a finished lower level, and a private 1-car garage with additional driveway parking. The open-concept main level features a spacious family room flowing into a modern kitchen with a large island, pantry

    Maronda Homes Builder
    117 Bonnings Dr, Winchester, VA 22603
  • /33

    $349,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    16 S Pleasant Valley Rd, Winchester, VA 22601

    Welcome to 16 S Pleasant Valley Rd — a beautiful home just minutes from the heart of Winchester! Enjoy the perfect blend of convenience and comfort, with an easy walk to the Walking Mall, historic downtown, restaurants, shops, and the Museum of the Shenandoah Valley—plus quick access to major commuter routes. Inside, you’ll find a bright, inviting layout with natural light flowing from front to

    Vanessa Couture Samson Properties

    16 S Pleasant Valley Rd, Winchester, VA 22601
  • /17

    $409,900

    New Construction $10K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    123 Killbuck Trail, Winchester, VA 22602

    Current Shawneeland Inventory107 Pinto Trail (split foyer)208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail103 Tonto Trail123 Killbuck TrailPremium Finishes: Enjoy a builder-upgraded interior featuring gleaming hardwood floors throughout the entire home (including all bedrooms) and elegant tile in all bathrooms.Gourmet Kitchen: Equipped with

    Jim Thomson Realty ONE Group Old Towne

    123 Killbuck Trail, Winchester, VA 22602
  • /27

    $649,900

    New Construction
    • 4 Beds
    • 3 Baths
    • 3,000 Sq Ft

    601 Granite Ridge Dr, Winchester, VA 22603

    Brand New Main Level home is under construction and with special financing and closing cost assistance available, there is no reason to wait to make this the next place you call home! Located within Hiatt Pointe at Snowden Bridge, an active adult community for those 55 or better!This Rembrandt, located on a corner lot, a stunning home offering a harmonious blend of private sanctuaries and

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    601 Granite Ridge Dr, Winchester, VA 22603

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