201

Winchester, VA Homes for Sale under $400,000

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  • /51

    $224,900

    $34K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,173 Sq Ft

    8 Brookland Ct Unit 8, Winchester, VA 22602

    2 Bed, 2 bath condominium. New appliances, including water heater and heat pump. Gas fireplace, open concept with separate dining room. Patio/ porch with french doors and skylights in living room allow tons of natural light. Primary suite includes walk-in closet. Conveniently located off rt 7 and 81.

    Vicki Broy RE/MAX Roots

    8 Brookland Ct Unit 8, Winchester, VA 22602
  • /52

    $369,990

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 1,756 Sq Ft

    229 Monteith Dr, Winchester, VA 22601

    The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. ***OFFERING UP TO $5K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED

    Brittany Newman DRB Group Realty, LLC

    229 Monteith Dr, Winchester, VA 22601
  • /19

    $141,500

    • Land
    • 11.1 Acres
    • $12,748 per Acre

    0 Hodges Lot 14 Ln, Winchester, VA 22603

    Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

    Chad Pangle Whitetail Properties Real Estate, LLC

    0 Hodges Lot 14 Ln, Winchester, VA 22603
  • /23

    $127,750

    • Land
    • 8.11 Acres
    • $15,752 per Acre

    0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602

    Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by making for easy and

    Chad Pangle Whitetail Properties Real Estate, LLC

    0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602
  • /2

    $175,000

    $25K PRICE DROP
    • 1 Bed
    • 1 Bath

    5737 N Frederick Pike, Winchester, VA 22603

    4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable.Sold As Is With

    Tracy Link Coldwell Banker Premier

    5737 N Frederick Pike, Winchester, VA 22603
  • /39

    $290,000

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft

    126 Marple Rd, Winchester, VA 22603

    Charming Cape Cod-style home located at 126 Marple Rd in the desirable north end of Winchester! This well-maintained 3-bedroom, 1.5-bath home offers timeless character, functional living space, and a convenient commuter-friendly location. The main level features a bedroom with a 1/2 bath, a living room, a dining room, and a kitchen. Upstairs, you’ll find additional bedrooms with a shared

    RoxAnn Grimes RE/MAX Roots

    126 Marple Rd, Winchester, VA 22603
  • /33

    $348,000

    $12K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    302 Wentworth Dr, Winchester, VA 22601

    Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on

    Heloisa Amar Samson Properties

    302 Wentworth Dr, Winchester, VA 22601
  • /22

    $334,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    308 Fawn Dr, Winchester, VA 22602

    Nestled in the charming Wilde Acres community, this delightful Colonial home offers a perfect blend of comfort and style. Built in 2009, this residence features 3 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and daily living. The inviting layout encompasses 1,680 sq. ft. of thoughtfully designed living space, ideal for both entertaining and quiet evenings at home.

    Steve DuBrueler Coldwell Banker Premier

    308 Fawn Dr, Winchester, VA 22602
  • /32

    $399,900

    $29K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,419 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 Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

    Janet Flaherty Keller Williams Realty

    118 1/2 E Cork St, Winchester, VA 22601
  • /26

    $374,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    HomeSite 5 Shuoner Ct, Winchester, VA 22602

    MOVE IN READYSt. Paul Townhome TBB | 3 BR | 2.5 BA | 1-Car Garage | Finished Lower LevelBeautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living designed for today's lifestyle.Home HighlightsOpen-concept main level — perfect for entertaining family and friendsGranite countertopsStainless steel

    Jimmy Thomas New Home Star Virginia, LLC

    HomeSite 5 Shuoner Ct, Winchester, VA 22602
  • /9

    $379,990

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

    109 Heirloom Way, 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
    109 Heirloom Way, Winchester, VA 22603
  • /19

    $381,690

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft

    652 Arden Ct, Winchester, VA 22601

    652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

    D.R. Horton Builder
    652 Arden Ct, Winchester, VA 22601
  • /14

    $389,990

    New Construction
    • 3 Beds
    • 4 Baths
    • 1,905 Sq Ft

    116 Swansong Place, Winchester, VA 22603

    The three-level Skyline model masterfully combines a traditional exterior with a contemporary, open-concept floor plan. On the main level, you’ll find an expansive living room, bathed in natural light from numerous windows, flows effortlessly into the dining area and kitchen. The kitchen is designed with an L-shaped countertop and an island that borders the dining room. A cozy nook serves as a

    Brookfield Residential Builder
    116 Swansong Place, Winchester, VA 22603
  • /23

    $349,990

    New Construction
    • 3 Beds
    • 1.5 Baths
    • 1,893 Sq Ft

    117 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
    117 Castaway Place, Winchester, VA 22603
  • /40

    $399,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,251 Sq Ft

    709 Ross St, Winchester, VA 22601

    NEW AND READY TO MOVE IN!!!BRAND NEW SINGLE FAMILY COLONIAL WITH 3 BEDROOM, 2.5 BATH! NO HOA!Be the first to call this beautiful new construction yours. Conveniently located just outside the City of Winchester and close to shopping, this home offers an open layout designed for entertaining. The great room leads into the spacious kitchen featuring an oversized island, granite countertops,

    Donna Anderson Samson Properties

    709 Ross St, Winchester, VA 22601
  • /22

    $371,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,000 Sq Ft

    HOMESITE 112 Shuoner Ct, Winchester, VA 22602

    110 SHUONER Ct – Model Home | We Have spec homes Summer 2026 Delivery AvailableSt. Paul TBB | 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger DeckBeautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living — customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom.Home

    Jimmy Thomas New Home Star Virginia, LLC

    HOMESITE 112 Shuoner Ct, Winchester, VA 22602
  • /81

    $339,999

    $15K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,824 Sq Ft

    120 Scirocco Ln, Winchester, VA 22602

    This beautifully maintained 3-bedroom, 1.5-bath townhome offers three finished levels of living space with even more potential in the basement to create an additional bedroom, office, or recreation room.Step inside to find numerous recent updates, including new LVP flooring, fresh paint, updated lighting, new carpet upstairs, updated interior door hardware, a new washer and dryer, and a

    Nicole Mongold Mountains Edge Realty LLC

    120 Scirocco Ln, Winchester, VA 22602
  • /37

    $359,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,219 Sq Ft

    1856 Melvor Ln, Winchester, VA 22601

    Low-maintenance, one-level living in Winchester! Located on a corner lot in an established 55+ community, 1856 Melvor Lane offers 2 bedrooms, 2 full baths, an open floor plan, and thoughtful updates throughout.Cathedral ceilings and natural light give the main living area an open, airy feel, while luxury vinyl plank flooring extends through most of the home. Fresh interior paint and

    Natasha Roberts Realty ONE Group Old Towne

    1856 Melvor Ln, Winchester, VA 22601
  • /22

    $399,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    123 Killbuck Trail, Winchester, VA 22602

    Limited time builder offering $10,000 in closing costs with acceptable offer.House Nearing completion!Premium 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 upgraded cabinetry, sleek granite countertops, a central island, and a sunny

    Jim Thomson Realty ONE Group Old Towne

    123 Killbuck Trail, Winchester, VA 22602
  • /26

    $349,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft

    156 Geronimo Trail, Winchester, VA 22602

    Welcome to your own private retreat in Shawneeland, where wooded surroundings, community amenities, and comfortable one-level living come together just minutes from Winchester. Tucked among mature trees on a beautifully landscaped lot, this 3-bedroom, 2-bath ranch offers the perfect blend of privacy, character, and move-in-ready comfort. The fully fenced front yard creates a peaceful outdoor

    Traci Shoberg Samson Properties

    156 Geronimo Trail, Winchester, VA 22602
  • /8

    $289,900

    • 2 Beds
    • 1.5 Baths
    • 1,024 Sq Ft

    2640 Limestone Ct, Winchester, VA 22601

    Nestled in the charming City of Winchester, this exquisite end-of-row townhouse has undergone a remarkable transformation, with major renovations completed in 2026 that elevate it to a new standard of luxury living. The timeless Colonial architectural style, complemented by a classic brick exterior, exudes elegance and warmth, inviting you to experience a lifestyle of comfort and sophistication.

    Meridee Powars Link Realty Services LLC

    2640 Limestone Ct, Winchester, VA 22601
  • /31

    $319,999

    $39K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    608 Dunlap St, Winchester, VA 22601

    Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort.

    Richard Butcher Coldwell Banker Premier

    608 Dunlap St, Winchester, VA 22601
  • /38

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,368 Sq Ft

    2159 Harvest Dr, Winchester, VA 22601

    Spotless, refreshed, and completely move-in ready! This 3-bedroom, 1.5 bath home has been updated top to bottom with a fresh neutral color palette (the entire home has been repainted), hardwood floors in the living and dining room, and brand-new plush carpet on the bedroom level. Additional Interior Highlights include a chef's dream kitchen with a new stainless refrigerator with ice maker, new

    Erika De Azagra ERA Oakcrest Realty, Inc.

    2159 Harvest Dr, Winchester, VA 22601
  • /42

    $379,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,198 Sq Ft

    820 Cedar Grove Rd, Winchester, VA 22603

    REDUCED, This charming brick ranch-style home, built in 1971, offers a perfect blend of comfort and functionality. With 2,198 sq. ft. of thoughtfully designed space, this residence features three inviting bedrooms plus a bonus room and two full bathrooms, ideal for relaxation and privacy. The traditional floor plan is enhanced by beautiful hardwood and ceramic tile flooring, creating a warm and

    Wendy Conner Coldwell Banker Premier

    820 Cedar Grove Rd, Winchester, VA 22603
  • /21

    $262,000

    $7K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    321 N Kent St, Winchester, VA 22601

    Attention investors...24 month lease in place and new HVAC! 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

    Amy Capitano MarketPlace REALTY

    321 N Kent St, Winchester, VA 22601
  • /45

    $399,900

    $40K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    211 Marple Rd, Winchester, VA 22603

    Set on nearly two acres just minutes from historic downtown Winchester, this beautifully maintained one-level home delivers the rare combination of open country space and everyday convenience. A classic covered front porch welcomes you in, opening to a bright, open-concept kitchen and living with 10' ceilings. This central living area is designed for easy flow — cooking, gathering, and relaxing

    Scott Wachtel Century 21 Redwood Realty

    211 Marple Rd, Winchester, VA 22603
  • /41

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    147 Doe Trail, Winchester, VA 22602

    Nestled in the Shawneeland community, this delightful Colonial home, built in 2021, offers a perfect blend of modern comfort and timeless appeal. With three spacious bedrooms and two and a half bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover warm hardwood floors that flow throughout the main living areas, creating an inviting atmosphere. The

    Wendy Conner Coldwell Banker Premier

    147 Doe Trail, Winchester, VA 22602
  • /57

    $115,000

    • 528 Sq Ft

    403 Stag Trail, Winchester, VA 22602

    Ever dreamed of owning your own private A-frame cabin in the woods? Whether you're searching for the perfect weekend retreat, a unique short-term rental opportunity, or a peaceful getaway to enjoy with family, friends, or clients, this charming mountain cabin is full of potential. Tucked away in a quiet, wooded setting with easy year-round access, this hidden gem offers the perfect balance of

    Chris Roszko Colony Realty

    403 Stag Trail, Winchester, VA 22602
  • /40

    $289,000

    $11K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,173 Sq Ft

    110 Brookland Ct Unit 10, Winchester, VA 22602

    Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transformed right down to the studs! Offering luxury finishes rarely found at this price point, this stunning residence is unlike anything else available in Frederick County under $300,000.Every detail has been thoughtfully updated, including a new gas furnace, new HVAC system, new flooring throughout,

    Traci Shoberg Samson Properties

    110 Brookland Ct Unit 10, Winchester, VA 22602
  • /40

    $359,990

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 1,756 Sq Ft

    237 Monteith Dr, Winchester, VA 22601

    The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room***OFFERING UP TO $5K IN CLOSING

    Brittany Newman DRB Group Realty, LLC

    237 Monteith Dr, Winchester, VA 22601
  • /20

    $154,650

    • Land
    • 12.9 Acres
    • $11,988 per Acre

    0 Hodges Lot 11 Ln, Winchester, VA 22603

    Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

    Chad Pangle Whitetail Properties Real Estate, LLC

    0 Hodges Lot 11 Ln, Winchester, VA 22603
  • /65

    $389,999

    • 3 Beds
    • 3.5 Baths
    • 2,232 Sq Ft

    114 Comanche Trail, Winchester, VA 22602

    Mountain living meets modern convenience! This immaculate Shawneeland home offers the ultimate retreat while keeping you perfectly close to both the community entrance and the beach. Meticulously maintained and completely move-in ready, this property truly has it all. Step inside to find freshly painted walls throughout, highlighted by gleaming hardwood floors on the main level and cozy, plush

    Hailey Mooney Real Broker, LLC

    114 Comanche Trail, Winchester, VA 22602
  • /46

    $372,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft

    ADAMS Plan at Retreat at Winding Creek - Townhomes, Winchester, VA 22602

    The 1,889 sq. ft. Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite counter tops, stainless steel appliances, and recessed lighting in the kitchen. Create the rec room, home office or 4th bedroom of your dreams in the lower level bonus space! The Adams comes with a 12'x10' deck off the rear of the home, perfect for outdoor

    D.R. Horton Builder
    137 Seminole Dr Unit 36203787, Winchester, VA 22602
  • /13

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    519 Virginia Ave, Winchester, VA 22601

    This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water

    Katherine Solenberger Colony Realty

    519 Virginia Ave, Winchester, VA 22601
  • /15

    $289,000

    $41K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    211 Fair Ln, Winchester, VA 22603

    Beautifully newly remodeled ranch-style home set on a spacious 0.62-acre flat lot. This move-in ready residence features a fully updated interior with a modern kitchen complete with granite countertops, brand-new stainless steel appliances, and all-new cabinetry. The home showcases rich hardwood flooring throughout and has been thoughtfully upgraded with new windows and a newer metal roof for

    Kenny Ritenour Samson Properties

    211 Fair Ln, Winchester, VA 22603
  • /30

    $379,900

    • 2 Beds
    • 1.5 Baths
    • 1,186 Sq Ft

    711 E Cork St, Winchester, VA 22601

    This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

    Marco Novillo Spring Hill Real Estate, LLC.

    711 E Cork St, Winchester, VA 22601
  • /38

    $349,900

    $19K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,256 Sq Ft

    201 Marple Rd, Winchester, VA 22603

    2.44 Acres with 1-Car Attached + 3-Bay Detached Workshop Garage — Close to WinchesterSolid 1953 stucco home on 2.44 acres with a small wet weather pond and livestock fencing—ready for animals, a hobby farm, or just keeping the property secure. 1,256 square feet, 3 bedrooms, 1 full bath, and an unfinished basement. 2 Bedrooms are on the main level.Check out the shop space! The

    Scott Wachtel Century 21 Redwood Realty

    201 Marple Rd, Winchester, VA 22603
  • /33

    $330,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,218 Sq Ft

    544 Bluebird Trail, Winchester, VA 22602

    Opportunity is knocking! The Sellers are Motivated and open to reasonable offers. If your considering making a move, now is the time to take a closer look!Escape to the peaceful mountain community of Wilde Acres and discover this charming 3-bedroom, 2-bath home situated on a spacious ½-acre lot. This well-maintained property offers privacy, tranquility, and numerous recent upgrades

    Dona Shiley ERA Oakcrest Realty, Inc.

    544 Bluebird Trail, Winchester, VA 22602
  • /38

    $350,000

    New Construction $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,072 Sq Ft

    604 Gatling Dr, Winchester, VA 22602

    Welcome to this beautiful 3-bedroom, 2-bathroom split-level home, a brand-new build nestled on a spacious 0.26-acre lot in the Mountain Falls Park community. Enjoy a warm welcome with a cozy covered porch. Inside, the home features luxury vinyl plank flooring throughout, providing a modern, durable finish. The kitchen is a chef's delight, with stainless steel appliances, premium shaker-style

    Sheila Pack RE/MAX Roots

    604 Gatling Dr, Winchester, VA 22602
  • /2

    $299,000

    $66K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,678 Sq Ft

    719 National Ave, Winchester, VA 22601

    Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many

    Windy Harris Hunt Country Sotheby's International Realty

    719 National Ave, Winchester, VA 22601

Showing Results 81 - 120, Page 3 of 6

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