Winchester County, VA Homes

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  $265,000

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  106 W Southwerk St, Winchester, VA 22601

  This charming 3-bedroom, 1.5-bath Colonial is perfectly located just minutes from Old Town Winchester and steps from Handley High School, giving you easy access to local restaurants, shops, and community events. Enjoy slow mornings on the covered front porch with your coffee, or gather with friends and family on the spacious back deck. Inside, you’ll find warm, comfortable living spaces filled

  Laura White ERA Oakcrest Realty, Inc.

  106 W Southwerk St, Winchester, VA 22601
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  /7

  $1,200 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  811 S Braddock St Unit 6, Winchester, VA 22601

  2 bedroom 1 bath 2nd floor apartment now available. Less than 1 block away from Handley High School. Hardwood floors throughout. Water/sewer included, tenant pays electric. Coin op laundry located in finished basement area. Application requried, Apply on listers website or NVAR or VAR rental application with $50 application fee paid by cash or money order, no personal checks. No animals. No

  Mandie Gladwell OliveTree Property Group, LLC

  811 S Braddock St Unit 6, Winchester, VA 22601
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  /64

  $615,900 Sold Jan 05, 2026

  400 Handley Ave, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,575 Sq Ft
  • Built 1928

  Last Sold Summary

  • $239/SF
  • 12 Days On Market

  Current Estimated Value $597,618

  Last Listing Agent Jeff Boppe Long & Foster Real Estate, Inc.

  400 Handley Ave, Winchester, VA 22601
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  /39

  Est $433,420 Not Listed For Sale

  421 Longview Ave, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft
  • Built 2001

  421 Longview Ave, Winchester, VA 22601

  Last Sold Summary

  • 2% Above List Price
  • $272/SF
  • 91 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Brandon Buchholz-White Long & Foster
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  /36

  $335,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,684 Sq Ft

  601 Hollingsworth Dr, Winchester, VA 22601

  Work where you live. Relax where you work. Welcome to 601 Hollingsworth Drive — a uniquely versatile Winchester home that blends comfortable living with exciting entrepreneurial potential, and ready for its next chapter.Inside, hardwood floors and a classic fireplace set a warm, inviting tone throughout the main level. Currently configured as 2 bedrooms and 1.5 baths, the home was originally

  Craig Alexander Coldwell Banker Premier

  601 Hollingsworth Dr, Winchester, VA 22601
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  /77

  $1,725 per month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601

  COMPLETELY FURNISHED RENTALPerfect for traveling professionals or students.Furnished one bedroom located behind the beautiful Handley library. This quaint one bedroom apartment is on the 3rd floor of a historic home facing Fairmont Ave. It has terrific views and a spectacular view of fireworks on Apple Blossom, July 4th and New Years Eve. Beautiful details and wainscotting, built in

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601
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  /45

  $515,000 Sold Jul 29, 2025

  331 Ridge Ave, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 1,881 Sq Ft
  • Built 1965

  Last Sold Summary

  • $274/SF
  • 15 Days On Market

  Current Estimated Value $514,172

  Last Listing Agent Lori Bales Keller Williams Realty

  331 Ridge Ave, Winchester, VA 22601
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  /33

  Est $423,439 Not Listed For Sale

  417 Circle Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft
  • Built 2023

  417 Circle Dr, Winchester, VA 22601

  Last Sold Summary

  • 1% Above List Price
  • $307/SF
  • 120 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Vihang Nair EXP Realty, LLC
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  /10

  $449,000

  • Land
  • 0.09 Acre
  • $4,988,889 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
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  /31

  $2,100 per month

  • 2 Beds
  • 1 Bath
  • 813 Sq Ft
  • House for Rent

  516 Hollingsworth Dr, Winchester, VA 22601

  Now available for rent, this beautifully maintained rancher at 516 Hollingsworth Drive offers exceptional flexibility with lease options tailored to fit your needs. For added convenience and peace of mind, all utilities are included in the monthly rent, providing you with a streamlined, all-inclusive living experience. This inviting residence provides effortless one-level living and shines with

  Chris Roszko Colony Realty

  516 Hollingsworth Dr, Winchester, VA 22601
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  /30

  $285,000 Sold Jan 30, 2026

  1116 Opequon Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • Built 1972

  Last Sold Summary

  • $242/SF
  • 19 Days On Market

  Current Estimated Value $283,100

  Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

  1116 Opequon Ave, Winchester, VA 22601
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  /35

  Est $386,484 Not Listed For Sale

  416 Superior Ave, Winchester, VA 22601

  • 4 Beds
  • 1.5 Baths
  • 2,508 Sq Ft
  • Built 1965

  416 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 10% Above List Price
  • $140/SF
  • 6 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Jeanne Mezzatesta Colony Realty
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  /14

  $1,499,000

  • Land
  • 2 Acres
  • $749,500 per Acre

  1625 Amherst St, Winchester, VA 22601

  Introducing a fantastic development opportunity! This parcel features 2 flat acres of commercial land in a prime location. Located on a major thoroughfare into downtown Winchester and a half mile from Winchester Medical Center, this lot is ideal for your commercial venture. The lot offers excellent road frontage and good topography. Ideal for medical/dental office, office space, restaurant, or

  Dan Whitacre Colony Realty

  1625 Amherst St, Winchester, VA 22601
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  /22

  $1,575 per month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  210 N Kent St Unit A, Winchester, VA 22601

  2 bedroom, 1 bathroom, 1st floor condo. Great location just short walk to heart of historic downtown Winchester. Gas furnace. City water/sewer. Washer/dryer provided. 1 Off-street parking spot. Pets on case-by-case basis.

  210 N Kent St Unit A, Winchester, VA 22601
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  /43

  $340,000 Sold Apr 14, 2025

  2924 Grace St, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,285 Sq Ft
  • Built 1975

  Last Sold Summary

  • $265/SF
  • 5 Days On Market

  Current Estimated Value $346,136

  Last Listing Agent Kristen Kerns Roberts Realty Group, LLC

  2924 Grace St, Winchester, VA 22601
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  /20

  Est $424,655 Not Listed For Sale

  2812 Baldwin St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,262 Sq Ft
  • Built 1956

  2812 Baldwin St, Winchester, VA 22601

  Last Sold Summary

  • 1% Above List Price
  • $186/SF
  • 93 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Jennifer Sacco RE/MAX
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  /51

  $310,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,118 Sq Ft

  423 Shenandoah Place, Winchester, VA 22601

  Welcome to 423 Shenandoah Place! This charming one-level home offers 3 bedrooms and 1 full bath, combining comfort, convenience, and location all in one. Located on a quiet cul-de-sac in a peaceful neighborhood, you’ll love the sense of privacy while still being close to everything. Step inside to find warm wood floors and a bright, inviting layout that makes everyday living easy. The kitchen

  Phil Asper Keller Williams Realty/Lee Beaver & Assoc.

  423 Shenandoah Place, Winchester, VA 22601
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  /77

  $2,450 per month

  • 4 Beds
  • 3.5 Baths
  • 1,923 Sq Ft
  • Townhouse for Rent

  1818 Blythe Way, Winchester, VA 22601

  Welcome to the Stunning, BRAND NEW 4 Bed 3.5 Bath stately GREY brick townhome in Abrams Crossing at Meadow Branch. Perfectly located in the heart of Winchester! This home offers the bonus of bumpouts, adding extra square footage for a comfy chair or cozy reading nook in the living room and 2nd bedroom. From the moment you park in the driveway, your eyes will follow the distinct patterns of the

  Latasha Hall LHall Realty LLC

  1818 Blythe Way, Winchester, VA 22601
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  /28

  $304,900 Sold Oct 02, 2025

  2923 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 858 Sq Ft
  • Built 1961

  Last Sold Summary

  • $355/SF
  • 3 Days On Market

  Current Estimated Value $305,582

  Last Listing Agent Anna Fox NextHome Realty Select

  2923 S Pleasant Valley Rd, Winchester, VA 22601
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  /52

  Est $404,867 Not Listed For Sale

  209 W Cedarmeade Ave, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,702 Sq Ft
  • Built 1998

  209 W Cedarmeade Ave, Winchester, VA 22601

  Last Sold Summary

  • 8% Above List Price
  • $220/SF
  • 124 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Gina Chatham Century 21 Redwood Realty
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  /10

  $245,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2967 Sorrell Ct, Winchester, VA 22601

  This diamond in the rough has solid bones and plenty of potential for the right buyer. The HVAC system is only two years old, the water heater is brand new, and both full bathrooms have already been updated. The home could use some fresh paint, and the dishwasher is currently not working, but the major systems are in great shape—making this an excellent opportunity for a starter home or

  Jamie Cook Treck Realty LLC

  2967 Sorrell Ct, Winchester, VA 22601
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  /25

  $1,250 per month

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Condo for Rent

  24 Jackson Ave Unit 2, Winchester, VA 22601

  AFFORDABLE AND CHARMING. Freshly painted and move-in ready. Short drive to downtown, Winchester Medical Center, I-81 and Rt. 37. Convenient to shopping and services. Spacious 2-bedroom upstairs apartment with off-street parking in the rear, front porch and a private 16x12 rear deck. Eat-in kitchen with refrigerator and oven/range. No smoking. No pets. Prefer credit scores of 650 or higher,

  24 Jackson Ave Unit 2, Winchester, VA 22601
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  /19

  $226,000 Sold Jul 03, 2025

  521 1/2 N Loudoun St, Winchester, VA 22601

  • 4 Beds
  • 1.5 Baths
  • 1,277 Sq Ft
  • Built 1936

  Last Sold Summary

  • $177/SF
  • 6 Days On Market

  Current Estimated Value $255,236

  Last Listing Agent Barton Chasler Realty ONE Group Old Towne

  521 1/2 N Loudoun St, Winchester, VA 22601
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  /53

  Est $463,074 Not Listed For Sale

  102 Russelcroft Rd, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,518 Sq Ft
  • Built 1971

  102 Russelcroft Rd, Winchester, VA 22601

  Last Sold Summary

  • 29% Above List Price
  • $102/SF
  • 7 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Tanner Pack RE/MAX
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  /42

  $429,990 Pending

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

  1822 Blythe Way, Winchester, VA 22601

  1822 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA for March move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful Quartz countertops, white cabinets, and stainless-steel

  Brooks Sears D R Horton Realty of Virginia LLC

  1822 Blythe Way, Winchester, VA 22601
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  /20

  $1,650 per month

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  26 A Jackson Ave, Winchester, VA 22601

  Newly remodeled 2 bed 1.5 bath duplex unit in Winchester City! Fully fenced private backyard (fence currently being updated) and ample parking (4 spots per unit). LVP flooring, quartz countertops, stainless steel appliances and in-unit laundry! Conveniently located near old towne Winchester, shopping, Rutherford Crossing, I81 and highway 7. Tour this charming, updated rental unit today!

  Holly Graham Realty ONE Group Old Towne

  26 A Jackson Ave, Winchester, VA 22601
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  /35

  $334,900 Sold Nov 25, 2025

  2225 Harrison St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1955

  Last Sold Summary

  • $258/SF
  • 42 Days On Market

  Current Estimated Value $330,976

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  2225 Harrison St, Winchester, VA 22601
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  /27

  Est $331,152 Not Listed For Sale

  2939 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft
  • Built 1986

  2939 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 7% Above List Price
  • $259/SF
  • 2 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Anna Fox NextHome Realty Select
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  /34

  $337,000 Under Contract

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

  19 W Germain St, Winchester, VA 22601

  Life in Historic Winchester just got easier with this modern construction. Built in 2004, this Charming 3 Bedroom, 1.5 Bath home is the best of all worlds. This home has been completely & professionally remodeled in 2025 and the quality of construction shows. Fresh and bright you will find that practically everything is new. Enter to find newly finished gleaming hardwood floors (2025), crisp new

  Angela Duncan MarketPlace REALTY

  19 W Germain St, Winchester, VA 22601
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  /28

  $1,499 per month

  • 1,142 Sq Ft
  • Townhouse for Rent

  1016 Franklin St Unit 3, Winchester, VA 22601

  Beautiful Renovated 2 level Townhome, 2 master suites, 1& 1/2 bathroom with main level kitchen, dining and living room with large front and backyard with easy from parking, very good Rental price for two level , Completely Renovated, close to beautiful downtown and VRE rail station less than a mile, Winchester, off the I-81,exit 315. close to Blossom mall, City hospital, college, amazon

  Ram Beladia First American Real Estate

  1016 Franklin St Unit 3, Winchester, VA 22601
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  /28

  $287,000 Sold Aug 05, 2025

  946 Franklin St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1955

  Last Sold Summary

  • $199/SF
  • 34 Days On Market

  Current Estimated Value $282,006

  Last Listing Agent Stan Dull The Wiley Companies, Inc.

  946 Franklin St, Winchester, VA 22601
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  /22

  Est $332,363 Not Listed For Sale

  2935 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft
  • Built 1986

  2935 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 2% Above List Price
  • $271/SF
  • 66 Days On Market

  Last Sold Price $324,900

  Last Listing Agent Anna Fox NextHome Realty Select
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  /58

  $549,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,234 Sq Ft

  1917 Harvest Dr, Winchester, VA 22601

  Beautiful Colonial set in a quiet neighborhood with convenient access to town and I-81. The main level features gleaming hardwood floors and classic oak plantation shutters, creating a warm and inviting feel throughout. Enjoy a formal living room with built-in shelving and a formal dining room accented by a chair rail, perfect for gatherings and entertaining. The kitchen offers granite

  Brock Harris Samson Properties

  1917 Harvest Dr, Winchester, VA 22601
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  /15

  $1,750 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • House for Rent

  508 Dunlap St, Winchester, VA 22601

  Perfect 3-bedroom rental, ready for immediate occupancy! Very clean, granite countertops, with hardwood floors, full kitchen, laundry area and great backyard perfect for picnicking! Applicants MUST have good credit with score above 650. 1st Month +Security Deposit+ Last month rent required. SMALL pets permitted on a case by case basis with nonrefundable deposit and additional monthly rent. No

  Richard Butcher Coldwell Banker Premier

  508 Dunlap St, Winchester, VA 22601
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  /29

  $300,000 Sold Apr 23, 2025

  236 Opequon Ave, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft
  • Built 1945

  Last Sold Summary

  • $207/SF
  • 9 Days On Market

  Current Estimated Value $298,643

  Last Listing Agent Luis Cruz Spring Hill Real Estate, LLC.

  236 Opequon Ave, Winchester, VA 22601
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  /19

  Est $330,861 Not Listed For Sale

  2927 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft
  • Built 1983

  2927 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 7% Above List Price
  • $258/SF
  • 21 Days On Market

  Last Sold Price $309,900

  Last Listing Agent Anna Fox NextHome Realty Select
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  /2

  $199,900

  • Land
  • 0.16 Acre
  • $1,249,375 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  Steve DuBrueler Coldwell Banker Premier

  1415 Ramseur Ln, Winchester, VA 22601
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  /21

  $2,300 per month

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft
  • Townhouse for Rent

  623 Hemsworth Ln, Winchester, VA 22601

  Available for May 01 move in date! — 620 + Credit preferred but not required —Pets on a case by case basis This brand new luxury townhome comes with a huge garage, a beautiful view, and natural light throughout.The main level contains an open room perfect for any setup you want. On the second level you'll find the beautiful kitchen with a huge Island and large doors allowing for natural light

  Tanner Pack RE/MAX Roots

  623 Hemsworth Ln, Winchester, VA 22601
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  /66

  $685,000 Sold Oct 29, 2025

  2530 Goldenfield Ln, Winchester, VA 22601

  • 4 Beds
  • 5 Baths
  • 5,903 Sq Ft
  • Built 2005

  Last Sold Summary

  • $116/SF
  • 21 Days On Market

  Current Estimated Value $704,838

  Last Listing Agent Dave Spence RE/MAX Roots

  2530 Goldenfield Ln, Winchester, VA 22601
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  /21

  Est $329,179 Not Listed For Sale

  2922 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,060 Sq Ft
  • Built 1986

  2922 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 1% Above List Price
  • $307/SF
  • 12 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Anna Fox NextHome Realty Select

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