Roxbury, CT Homes

• 

  Est $580,069 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,275 Sq Ft

  14 Wellers Bridge Rd, Roxbury, CT 06783

  14 Wellers Bridge Rd, Roxbury, CT 06783
• 

  

  

  /35

  $3,998,000

  • 4 Beds
  • 5.5 Baths
  • 7,063 Sq Ft

  11 Ravenrock, Roxbury, CT 06783

  A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in the beautiful Litchfield Hills with spectacular views that go on for miles. This property includes a four bedroom, five and a half bath main residence, in ground heated Gunite pool, tennis court, one-bedroom caretaker's apartment over a 3-bay garage, two bedroom guest apartment and greenhouse. This compound

  Maria Taylor Klemm Real Estate Inc

  11 Ravenrock, Roxbury, CT 06783
• 

  $769,000 Sold Apr 01, 2025

  24 Roxbury Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 4,012 Sq Ft
  • Built 1987

  Last Sold Summary

  • 38% Below List Price
  • $192/SF
  • 313 Days On Market

  Current Estimated Value $1,150,846

  Last Listing Agent Debbie Kranidis Preston Gray Real Estate

  24 Roxbury Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,926 Sq Ft

  25 Holmes Rd, Roxbury, CT 06783

  25 Holmes Rd, Roxbury, CT 06783
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  /38

  $3,050,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 4,071 Sq Ft

  103 Chalybes Rd W, Roxbury, CT 06783

  TO BE BUILT - A Home by CORBO! A rare opportunity to build your dream home on approximately 16 private acres in Roxbury, CT-one of lower Litchfield County's most sought-after towns. This award-winning Colonial reproduction pairs timeless architecture with modern craftsmanship and is ideally positioned for western exposure and unforgettable sunsets (subject to tree clearing and final siting).

  Christopher Haggerty Around Town Real Estate LLC

  103 Chalybes Rd W, Roxbury, CT 06783
• 

  $1,378,000 Sold Jul 08, 2025

  22 Highmeadow Ln, Roxbury, CT 06783

  • 4 Beds
  • 4 Baths
  • 3,481 Sq Ft
  • Built 1985

  Last Sold Summary

  • $396/SF
  • 44 Days On Market

  Current Estimated Value $1,399,785

  Last Listing Agent William Bolls Compass Connecticut, LLC

  22 Highmeadow Ln, Roxbury, CT 06783
• 

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,758 Sq Ft

  72 Welton Rd, Roxbury, CT 06783

  72 Welton Rd, Roxbury, CT 06783
• 

  $1,275,000 Sold Apr 21, 2025

  36 Chalybes Rd, Roxbury, CT 06783

  • 4 Beds
  • 3 Baths
  • 4,572 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Below List Price
  • $279/SF
  • 256 Days On Market

  Current Estimated Value $1,314,348

  Last Listing Agent Jill Sloane Brown Harris Stevens

  36 Chalybes Rd, Roxbury, CT 06783
• 

  Est $845,980 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,708 Sq Ft

  51 Judds Bridge Rd, Roxbury, CT 06783

  51 Judds Bridge Rd, Roxbury, CT 06783
• 

  $410,000 Sold Mar 18, 2025

  168 Baker Rd, Roxbury, CT 06783

  • 2 Beds
  • 2 Baths
  • 1,328 Sq Ft
  • Built 1788

  Last Sold Summary

  • 4% Below List Price
  • $309/SF
  • 160 Days On Market

  Current Estimated Value $437,908

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  168 Baker Rd, Roxbury, CT 06783
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  Not Listed For Sale

  00 Hemlock Rd, Roxbury, CT 06783

  00 Hemlock Rd, Roxbury, CT 06783
• 

  $840,000 Sold Feb 19, 2025

  208 E Flag Swamp Rd, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 3,974 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $211/SF
  • 221 Days On Market

  Current Estimated Value $707,728

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.

  208 E Flag Swamp Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  00 Cedar Ridge, Roxbury, CT 06783

  00 Cedar Ridge, Roxbury, CT 06783
• 

  $1,600,000 Sold Apr 11, 2025

  130 E Flag Swamp Rd, Roxbury, CT 06783

  • 2 Beds
  • 2.5 Baths
  • 3,123 Sq Ft
  • Built 2000

  Last Sold Summary

  • 6% Below List Price
  • $512/SF
  • 103 Days On Market

  Current Estimated Value $1,667,187

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  130 E Flag Swamp Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  00 Booth Rd, Roxbury, CT 06783

  00 Booth Rd, Roxbury, CT 06783
• 

  $2,858,000 Sold May 02, 2025

  42 Berry Rd, Roxbury, CT 06783

  • 4 Beds
  • 5.5 Baths
  • 3,043 Sq Ft
  • Built 2018

  Last Sold Summary

  • 3% Below List Price
  • $939/SF
  • 15 Days On Market

  Current Estimated Value $2,956,914

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  42 Berry Rd, Roxbury, CT 06783
• 

  Est $666,315 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  70 Southbury Rd, Roxbury, CT 06783

  70 Southbury Rd, Roxbury, CT 06783
• 

  $1,800,000 Sold Aug 28, 2025

  67 Botsford Hill Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 4,800 Sq Ft
  • Built 1988

  Last Sold Summary

  • 18% Below List Price
  • $375/SF
  • 116 Days On Market

  Current Estimated Value $1,687,511

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  67 Botsford Hill Rd, Roxbury, CT 06783
• 

  Est $630,339 Not Listed For Sale

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

  5 Carriage Ln, Roxbury, CT 06783

  5 Carriage Ln, Roxbury, CT 06783
• 

  $1,500,000 Sold Jan 28, 2025

  52 Welton Rd, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 3,233 Sq Ft
  • Built 2021

  Last Sold Summary

  • 16% Below List Price
  • $464/SF
  • 323 Days On Market

  Current Estimated Value $1,634,508

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  52 Welton Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  00 Pickett Rd, Roxbury, CT 06783

  00 Pickett Rd, Roxbury, CT 06783
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  $500,000 Sold Sep 05, 2025

  322 North St, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Above List Price
  • $358/SF
  • 84 Days On Market

  Current Estimated Value $526,218

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.

  322 North St, Roxbury, CT 06783
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  222 North St, Roxbury, CT 06783

  222 North St, Roxbury, CT 06783
• 

  $2,501,000 Sold Nov 21, 2025

  Unlisted Address

  • 5 Beds
  • 6 Baths
  • 8,091 Sq Ft
  • Built 2005

  Last Sold Summary

  • $309/SF
  • 88 Days On Market

  Last Listing Agent Kathryn Clair William Pitt Sotheby's Int'l

  Unlisted Address
• 

  Not Listed For Sale

  43 Baker Rd, Roxbury, CT 06783

  43 Baker Rd, Roxbury, CT 06783
• 

  $735,000 Sold Mar 14, 2025

  66 Bacon Rd, Roxbury, CT 06783

  • 3 Beds
  • 1.5 Baths
  • 2,345 Sq Ft
  • Built 1800

  Last Sold Summary

  • 5% Below List Price
  • $313/SF
  • 91 Days On Market

  Last Listing Agent William Whitehead Berkshire Hathaway NE Prop.

  66 Bacon Rd, Roxbury, CT 06783
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  Not Listed For Sale

  00 Old Ln, Roxbury, CT 06783

  00 Old Ln, Roxbury, CT 06783
• 

  $900,000 Sold Jan 15, 2025

  177 Bacon Rd, Roxbury, CT 06783

  • 3 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • Built 1985

  Last Sold Summary

  • 16% Below List Price
  • $367/SF
  • 229 Days On Market

  Current Estimated Value $1,052,289

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  177 Bacon Rd, Roxbury, CT 06783
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  Not Listed For Sale

  Lot 6 Willow Brook Dr, Roxbury, CT 06783

  Lot 6 Willow Brook Dr, Roxbury, CT 06783
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  $840,000 Sold Apr 03, 2025

  201 Painter Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • Built 1966

  Last Sold Summary

  • 6% Below List Price
  • $488/SF
  • 146 Days On Market

  Current Estimated Value $870,854

  Last Listing Agent Diana Bisselle William Pitt Sotheby's Int'l

  201 Painter Hill Rd, Roxbury, CT 06783
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  Not Listed For Sale

  Lot 3 Willow Brook Dr, Roxbury, CT 06783

  Lot 3 Willow Brook Dr, Roxbury, CT 06783
• 

  $1,875,000 Sold Jun 04, 2025

  257 Southbury Rd, Roxbury, CT 06783

  • 3 Beds
  • 3 Baths
  • 3,086 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $608/SF
  • 75 Days On Market

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  257 Southbury Rd, Roxbury, CT 06783
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  Not Listed For Sale

  Lot 1 Willow Brook Dr, Roxbury, CT 06783

  Lot 1 Willow Brook Dr, Roxbury, CT 06783
• 

  $3,495,000 Sold Jan 16, 2025

  20 Painter Hill Rd, Roxbury, CT 06783

  • Land
  • 57.19 Acres
  • $61,112 per Acre

  Last Sold Summary

  • 54 Days On Market

  Current Estimated Value $2,884,982

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  20 Painter Hill Rd, Roxbury, CT 06783
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  Not Listed For Sale

  157 South St, Roxbury, CT 06783

  157 South St, Roxbury, CT 06783
• 

  $1,325,000 Sold Jun 18, 2025

  235 North St, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 3,379 Sq Ft
  • Built 1980

  Last Sold Summary

  • 29% Below List Price
  • $392/SF
  • 295 Days On Market

  Current Estimated Value $1,335,633

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  235 North St, Roxbury, CT 06783
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  Not Listed For Sale

  0 Baker Rd, Roxbury, CT 06783

  0 Baker Rd, Roxbury, CT 06783
• 

  $912,500 Sold Nov 19, 2025

  11 Hodge Rd, Roxbury, CT 06783

  • 4 Beds
  • 3 Baths
  • 2,982 Sq Ft
  • Built 1851

  Last Sold Summary

  • 30% Below List Price
  • $306/SF
  • 141 Days On Market

  Last Listing Agent Karen Casey William Pitt Sotheby's Int'l

  11 Hodge Rd, Roxbury, CT 06783
• 

  Est $1,578,886 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,600 Sq Ft

  92 Hemlock Rd, Roxbury, CT 06783

  92 Hemlock Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  8 Evergreen Dr, Roxbury, CT 06783

  8 Evergreen Dr, Roxbury, CT 06783

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