3,789

Middlebury, CT Homes

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  • 288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

    $225,000 Sold Sep 24, 2025

    288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

    • Land
    • 3.32 Acres
    • $67,771 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 330 Days On Market

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 4, Middlebury, CT 06762
    • 5 Pommel Ln, Middlebury, CT 06762

      Est $559,198 Not Listed For Sale

      5 Pommel Ln, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,461 Sq Ft
      • Built 1996
      5 Pommel Ln, Middlebury, CT 06762

      Last Sold Summary

      • 13% Above List Price
      • $201/SF
      • 60 Days On Market

      Last Sold Price $495,000

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 152 Glenwood Ave, Middlebury, CT 06762
    152 Glenwood Ave, Middlebury, CT 06762
    152 Glenwood Ave, Middlebury, CT 06762
    /19

    $244,900

    • 2 Beds
    • 1 Bath
    • 1,085 Sq Ft

    152 Glenwood Ave, Middlebury, CT 06762

    2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar leading into living room and dining area. This is a wonderful opportunity to indulge in Middlebury's rural New England charm and suburban high-end amenities. Access to I 84, RT 8, and public transportation makes commuting to lower Fairfield County, NYC or Boston appealing. But if staying local is more your

    Don Orsini West View Properties, LLC

    152 Glenwood Ave, Middlebury, CT 06762
  • 1 Independence Cir, Middlebury, CT 06762

    $615,000 Sold Oct 30, 2025

    1 Independence Cir, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 3,224 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Below List Price
    • $191/SF
    • 120 Days On Market

    Current Estimated Value $614,005

    Last Listing Agent Carol D'Amato Regency Real Estate, LLC

    1 Independence Cir, Middlebury, CT 06762
    • 9 Caveson Ct, Middlebury, CT 06762

      Est $549,606 Not Listed For Sale

      9 Caveson Ct, Middlebury, CT 06762

      • 2 Beds
      • 2.5 Baths
      • 2,050 Sq Ft
      • Built 1996
      9 Caveson Ct, Middlebury, CT 06762

      Last Sold Summary

      • 2% Below List Price
      • $273/SF
      • 64 Days On Market

      Last Sold Price $560,000

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 75 Gleneagle Rd, Middlebury, CT 06762
    75 Gleneagle Rd, Middlebury, CT 06762
    75 Gleneagle Rd, Middlebury, CT 06762
    /24

    $229,900

    • Land
    • 4.67 Acres
    • $49,229 per Acre

    75 Gleneagle Rd, Middlebury, CT 06762

    LOCATION, LOCATION, LOCATION!!! ONLY LOT FOR SALE IN THIS PRIVATE, 11 LOT SUBDIVISION OF QUALITY-BUILT HIGH END HOMES. SUBDIVISION HAS THE UNIQUE BONUSES OF PUBLIC WATER & SEWER (ALREADY EXTENDED TO LOT) AND CLOSE PROXIMITY TO LOCAL RETAIL AND HIGHWAYS. 4.67 ACRE SITE TUCKED AWAY AT THE END OF A TURN-AROUND TO THE LEFT OF THE ELABORATE GAZEEBO AND LAND TRUST PROPERTY.

    Scott Tedesco Tedesco Real Estate

    75 Gleneagle Rd, Middlebury, CT 06762
  • 45 E Farms Rd, Middlebury, CT 06762

    $1,100,000 Sold May 19, 2025

    45 E Farms Rd, Middlebury, CT 06762

    • 4 Beds
    • 6 Baths
    • 5,054 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $218/SF
    • 48 Days On Market

    Current Estimated Value $1,129,910

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    45 E Farms Rd, Middlebury, CT 06762
    • 17 Caveson Ct, Middlebury, CT 06762

      Est $566,645 Not Listed For Sale

      17 Caveson Ct, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,290 Sq Ft
      • Built 1996
      17 Caveson Ct, Middlebury, CT 06762

      Last Sold Summary

      • 17% Above List Price
      • $211/SF
      • 105 Days On Market

      Last Sold Price $482,500

      Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  • 0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    /9

    $509,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft

    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762

    Last remaining unit! An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
  • 32 Yale Ave, Middlebury, CT 06762

    $390,000 Sold Jan 14, 2026

    32 Yale Ave, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,861 Sq Ft
    • Built 1925

    Last Sold Summary

    • $210/SF
    • 54 Days On Market

    Current Estimated Value $392,403

    Last Listing Agent Martha Quaratella Coldwell Banker Realty

    32 Yale Ave, Middlebury, CT 06762
    • 130 White Ave, Middlebury, CT 06762

      Est $385,544 Not Listed For Sale

      130 White Ave, Middlebury, CT 06762

      • 3 Beds
      • 1 Bath
      • 1,244 Sq Ft
      • Built 1955
      130 White Ave, Middlebury, CT 06762

      Last Sold Summary

      • 10% Above List Price
      • $281/SF
      • 3 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Frank Durante William Raveis Real Estate

  • 6 Brookside Dr, Middlebury, CT 06762
    6 Brookside Dr, Middlebury, CT 06762
    6 Brookside Dr, Middlebury, CT 06762
    /40

    $599,995 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,745 Sq Ft

    6 Brookside Dr, Middlebury, CT 06762

    Welcome to 6 Brookside Drive, a beautifully appointed home set in a peaceful wooded setting, offering privacy while remaining conveniently close to everyday amenities. Inside, the home showcases a stunning open-concept design highlighted by a soaring 2-story family room with a gas fireplace & abundant natural light. The kitchen features granite countertops, gas cooking, high-end appliances &

    Nikki Defrancesco Coldwell Banker Realty

    6 Brookside Dr, Middlebury, CT 06762
  • 13 Caveson Ct, Middlebury, CT 06762

    $530,000 Sold Mar 24, 2026

    13 Caveson Ct, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 2,011 Sq Ft
    • Built 1996

    Last Sold Summary

    • $264/SF
    • 129 Days On Market

    Current Estimated Value $560,350

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    13 Caveson Ct, Middlebury, CT 06762
    • 7 Foster St, Middlebury, CT 06762

      Est $364,239 Not Listed For Sale

      7 Foster St, Middlebury, CT 06762

      • 2 Beds
      • 1.5 Baths
      • 724 Sq Ft
      • Built 1950
      7 Foster St, Middlebury, CT 06762

      Last Sold Summary

      • 12% Above List Price
      • $448/SF
      • 6 Days On Market

      Last Sold Price $324,000

      Last Listing Agent Arben Belica William Raveis Real Estate

  • 0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762
    0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762
    0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762
    /9

    $519,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762

    An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762
  • 348 Kelly Rd, Middlebury, CT 06762

    $360,000 Sold Jan 30, 2026

    348 Kelly Rd, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1934

    Last Sold Summary

    • 7% Above List Price
    • $469/SF
    • 24 Days On Market

    Current Estimated Value $347,948

    Last Listing Agent Stephanie Oliver Dave Jones Realty, LLC

    348 Kelly Rd, Middlebury, CT 06762
    • 700 South St, Middlebury, CT 06762

      Est $1,664,144 Not Listed For Sale

      700 South St, Middlebury, CT 06762

      • 5 Beds
      • 7 Baths
      • 5,811 Sq Ft
      • Built 1980
      700 South St, Middlebury, CT 06762

      Last Sold Summary

      • 5% Below List Price
      • $301/SF
      • 542 Days On Market

      Last Sold Price $1,750,000

      Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  • 0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    /9

    $509,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762

    An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
  • 0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

    $63,250 Sold Dec 05, 2025

    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

    • Land
    • 0.76 Acre
    • $83,224 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 80 Days On Market

    Last Listing Agent Rebecca Zandvliet Coldwell Banker Realty 2000

    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
    • 133 1/2 Steinmann Ave, Middlebury, CT 06762

      Est $502,037 Not Listed For Sale

      133 1/2 Steinmann Ave, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,083 Sq Ft
      • Built 1941
      133 1/2 Steinmann Ave, Middlebury, CT 06762

      Last Sold Summary

      • 3% Below List Price
      • $247/SF
      • 69 Days On Market

      Last Sold Price $515,000

      Last Listing Agent Karen Griffin Coldwell Banker Realty

  • 0 N Benson Rd Unit 62, Middlebury, CT 06762
    0 N Benson Rd Unit 62, Middlebury, CT 06762
    0 N Benson Rd Unit 62, Middlebury, CT 06762
    /9

    $545,400 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft

    0 N Benson Rd Unit 62, Middlebury, CT 06762

    An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 62, Middlebury, CT 06762
  • 0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762

    $593,360 Sold Oct 10, 2025

    0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Built 2025

    Last Sold Summary

    • 17% Above List Price
    • $304/SF
    • 0 Days On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762
    • 2056 Straits Turnpike, Middlebury, CT 06762

      Est $275,705 Not Listed For Sale

      2056 Straits Turnpike, Middlebury, CT 06762

      • 2 Beds
      • 1.5 Baths
      • 2,528 Sq Ft
      • Built 1953
      2056 Straits Turnpike, Middlebury, CT 06762

      Last Sold Summary

      • 38% Above List Price
      • $79/SF
      • 10 Days On Market

      Last Sold Price $200,000

      Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  • 0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
    /9

    $523,920 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762

    An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
  • 116 Yale Ave, Middlebury, CT 06762

    $495,000 Sold Dec 04, 2025

    116 Yale Ave, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,311 Sq Ft
    • Built 1998

    Last Sold Summary

    • 1% Above List Price
    • $214/SF
    • 51 Days On Market

    Current Estimated Value $492,122

    Last Listing Agent Dave Jones Dave Jones Realty, LLC

    116 Yale Ave, Middlebury, CT 06762
    • 346 South St, Middlebury, CT 06762

      Est $1,012,511 Not Listed For Sale

      346 South St, Middlebury, CT 06762

      • 6 Beds
      • 7 Baths
      • 5,938 Sq Ft
      • Built 1958
      346 South St, Middlebury, CT 06762

      Last Sold Summary

      • 27% Above List Price
      • $135/SF
      • 38 Days On Market

      Last Sold Price $800,000

      Last Listing Agent Margaret Muir William Pitt

  • 6 Deer Run Rd, Middlebury, CT 06762
    6 Deer Run Rd, Middlebury, CT 06762
    /2

    $810,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    6 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    6 Deer Run Rd, Middlebury, CT 06762
  • 16 Winding Trail, Middlebury, CT 06762

    $625,000 Sold Apr 10, 2026

    16 Winding Trail, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,646 Sq Ft
    • Built 2014

    Last Sold Summary

    • $236/SF
    • 29 Days On Market

    Last Listing Agent Georgieanna Fisher Home Selling Team

    16 Winding Trail, Middlebury, CT 06762
    • 53 White Deer Rock Rd, Middlebury, CT 06762

      Est $1,341,449 Not Listed For Sale

      53 White Deer Rock Rd, Middlebury, CT 06762

      • 6 Beds
      • 7 Baths
      • 6,318 Sq Ft
      • Built 2006
      53 White Deer Rock Rd, Middlebury, CT 06762

      Last Sold Summary

      • 38% Above List Price
      • $154/SF
      • 154 Days On Market

      Last Sold Price $970,000

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • 15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge Rd, Middlebury, CT 06762
    /38

    $794,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    15 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    15 Hunting Ridge Rd, Middlebury, CT 06762
  • 29 Winding Trail Unit 29, Middlebury, CT 06762

    $520,000 Sold Aug 08, 2025

    29 Winding Trail Unit 29, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft
    • Built 2015

    Last Sold Summary

    • 8% Below List Price
    • $244/SF
    • 117 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    29 Winding Trail Unit 29, Middlebury, CT 06762
    • 11 Strathmore Rd, Middlebury, CT 06762

      Est $650,406 Not Listed For Sale

      11 Strathmore Rd, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,722 Sq Ft
      • Built 1984
      11 Strathmore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 1% Below List Price
      • $241/SF
      • 15 Days On Market

      Last Sold Price $655,000

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • 408 Breakneck Hill Rd, Middlebury, CT 06762
    408 Breakneck Hill Rd, Middlebury, CT 06762
    408 Breakneck Hill Rd, Middlebury, CT 06762
    /30

    $625,000 Under Contract

    • 2 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    408 Breakneck Hill Rd, Middlebury, CT 06762

    Charm abounds in this remodeled classic cape with 2 car garage, central air, and massive 1st floor master suite! Remodeled eat-in-kitchen with granite countertops, stainless steel appliances, tile backsplash and breakfast bar. Living room with fireplace and hardwood floors. Dining room with hardwood floors. Luxurious master suite with built-ins, walk-in california closet, and large remodeled

    John Donato Jr Showcase Realty, Inc.

    408 Breakneck Hill Rd, Middlebury, CT 06762
  • 64 Joy Rd, Middlebury, CT 06762

    $422,000 Sold Jun 18, 2025

    64 Joy Rd, Middlebury, CT 06762

    • 3 Beds
    • 1 Bath
    • 1,688 Sq Ft
    • Built 1959

    Last Sold Summary

    • 6% Above List Price
    • $250/SF
    • 58 Days On Market

    Current Estimated Value $416,195

    Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

    64 Joy Rd, Middlebury, CT 06762
    • 36 Richardson Dr, Middlebury, CT 06762

      Est $339,719 Not Listed For Sale

      36 Richardson Dr, Middlebury, CT 06762

      • 3 Beds
      • 1.5 Baths
      • 1,398 Sq Ft
      • Built 1920
      36 Richardson Dr, Middlebury, CT 06762

      Last Sold Summary

      • 11% Above List Price
      • $218/SF
      • 62 Days On Market

      Last Sold Price $305,000

      Last Listing Agent Susan Woodfield Showcase Realty, Inc.

  • 61 Sandy Hill Rd, Middlebury, CT 06762
    61 Sandy Hill Rd, Middlebury, CT 06762
    61 Sandy Hill Rd, Middlebury, CT 06762
    /14

    $529,900

    • 3 Beds
    • 1.5 Baths
    • 1,811 Sq Ft

    61 Sandy Hill Rd, Middlebury, CT 06762

    Charming Cape in Middlebury with over 5 acres of land! This enchanting Cape features original character with hardwood floors flowing throughout its 3 comfortable bedrooms and 1.5 baths. For the outdoor enthusiast, the grounds are a rare find: a horse stable complete with a tack room awaits your equine companions, while a inground pool offers a private oasis for summer entertaining. With the added

    Arben Belica William Raveis Real Estate

    61 Sandy Hill Rd, Middlebury, CT 06762
  • 93 Fenn Rd, Middlebury, CT 06762

    $420,000 Sold Oct 09, 2025

    93 Fenn Rd, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 1,636 Sq Ft
    • Built 1951

    Last Sold Summary

    • 1% Below List Price
    • $257/SF
    • 62 Days On Market

    Current Estimated Value $415,619

    Last Listing Agent Rob Marucci Better Living Realty, LLC

    93 Fenn Rd, Middlebury, CT 06762
    • 70 Steinmann Ave, Middlebury, CT 06762

      Est $387,071 Not Listed For Sale

      70 Steinmann Ave, Middlebury, CT 06762

      • 4 Beds
      • 2 Baths
      • 1,486 Sq Ft
      • Built 1971
      70 Steinmann Ave, Middlebury, CT 06762

      Last Sold Summary

      • 17% Above List Price
      • $222/SF
      • 112 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Heather Crabtree RE/MAX RISE

  • 245 Upper Whittemore Rd, Middlebury, CT 06762
    245 Upper Whittemore Rd, Middlebury, CT 06762
    245 Upper Whittemore Rd, Middlebury, CT 06762
    /29

    $815,000

    • 3 Beds
    • 2.5 Baths
    • 2,990 Sq Ft

    245 Upper Whittemore Rd, Middlebury, CT 06762

    Enjoy magnificent sunsets from this exceptional home, privately set on just over three acres in one of the area's most desirable locations. The beautifully landscaped grounds offer both open space and a wooded backdrop for added privacy, along with views of a neighboring stone wall. An in-ground heated saltwater pool is surrounded by an expansive patio and charming pergola-perfect for outdoor

    Donna Bannon BHGRE Gaetano Marra Homes

    245 Upper Whittemore Rd, Middlebury, CT 06762
  • 28 Maple Dr, Middlebury, CT 06762

    $435,000 Sold Oct 14, 2025

    28 Maple Dr, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft
    • Built 1950

    Last Sold Summary

    • 17% Below List Price
    • $273/SF
    • 233 Days On Market

    Current Estimated Value $439,440

    Last Listing Agent Dean Giatas Fiorelli Realty, LLC

    28 Maple Dr, Middlebury, CT 06762

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