Roxbury, CT Homes

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  /31

  $950,000

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft

  50 Southbury Rd, Roxbury, CT 06783

  Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, and a separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway.

  Jeff Phillips William Pitt Sotheby's Int'l

  50 Southbury Rd, Roxbury, CT 06783
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  $2,547,500 Sold Jan 30, 2026

  277 Painter Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,559 Sq Ft
  • Built 1911

  Last Sold Summary

  • 1% Below List Price
  • $996/SF
  • 28 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  277 Painter Hill Rd, Roxbury, CT 06783
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  Est $1,349,586 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,445 Sq Ft

  76 Davenport Rd, Roxbury, CT 06783

  76 Davenport Rd, Roxbury, CT 06783
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  $599,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,682 Sq Ft

  55 Mallory Rd, Roxbury, CT 06783

  If privacy in the Litchfield Hills is your aspiration, this is the place for you! Gated entrance to this rustic Country Cape w/ covered porch set back off the road. Property abuts land locked acreage & Roxbury Land Trust surrounds much of the neighborhood. The current & ONLY owner constructed this quality built home with lasting craftsmanship. To say it has good bones is an understatement. 4th

  Gina Jacobs Gina Jacobs Real Estate

  55 Mallory Rd, Roxbury, CT 06783
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  $940,000 Sold May 07, 2025

  80 Transylvania Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 3,088 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $304/SF
  • 195 Days On Market

  Current Estimated Value $999,784

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

  80 Transylvania Rd, Roxbury, CT 06783
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  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,087 Sq Ft

  294 North St, Roxbury, CT 06783

  294 North St, Roxbury, CT 06783
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  $1,095,000

  • 5 Beds
  • 5 Baths
  • 2,804 Sq Ft

  286 South St, Roxbury, CT 06783

  Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen.

  Kathryn Clair William Pitt Sotheby's Int'l

  286 South St, Roxbury, CT 06783
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  $2,700,000 Sold Dec 16, 2025

  Unlisted Address

  • 5 Beds
  • 5.5 Baths
  • 5,455 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $495/SF
  • 134 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  Unlisted Address
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  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,091 Sq Ft

  277 Southbury Rd, Roxbury, CT 06783

  277 Southbury Rd, Roxbury, CT 06783
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  /20

  $499,000

  • Land
  • 8.64 Acres
  • $57,755 per Acre

  200 North St, Roxbury, CT 06783

  ENGINEERING and DRIVEWAY APPROVED! THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. THIS IS THE LAST AVAILABLE LOT FROM PHASE II, (LOT #1) AND IT MUST BE SEEN AND HEARD TO UNDERSTAND HOW YOUR FUTURE HEIRLOOM HOME WILL BE

  Jill Sloane Brown Harris Stevens

  200 North St, Roxbury, CT 06783
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  $5,250,000 Sold Apr 12, 2025

  62 Davenport Rd, Roxbury, CT 06783

  • 4 Beds
  • 6 Baths
  • 6,228 Sq Ft
  • Built 1790

  Last Sold Summary

  • 16% Below List Price
  • $843/SF
  • 210 Days On Market

  Last Listing Agent Jeff Phillips William Pitt Sotheby's Int'l

  62 Davenport Rd, Roxbury, CT 06783
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  Est $1,359,204 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,040 Sq Ft

  167 Tophet Rd, Roxbury, CT 06783

  167 Tophet Rd, Roxbury, CT 06783
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  /40

  $3,200,000

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  4 Judge Rd, Roxbury, CT 06783

  Complete Equestrian Facility with Cape Cod Style Home. An ideal property for horse enthusiasts, trainers, or those seeking a turn-key boarding operation. This thoughtfully designed equestrian facility offers 16 matted stalls, a spacious indoor riding arena, and an elevated viewing area with a kitchen-perfect for hosting clinics, lessons, or simply watching rides in comfort. The barn also includes

  Heather Crabtree RE/MAX RISE

  4 Judge Rd, Roxbury, CT 06783
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  $1,400,000 Sold Aug 22, 2025

  88 Hemlock Rd, Roxbury, CT 06783

  • 2 Beds
  • 2.5 Baths
  • 3,389 Sq Ft
  • Built 1985

  Last Sold Summary

  • 20% Below List Price
  • $413/SF
  • 60 Days On Market

  Current Estimated Value $1,443,013

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  88 Hemlock Rd, Roxbury, CT 06783
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  Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,808 Sq Ft

  19 Golden Harvest Rd, Roxbury, CT 06783

  19 Golden Harvest Rd, Roxbury, CT 06783
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  /7

  $275,000

  • Land
  • 3.02 Acres
  • $91,060 per Acre

  0 Booth Rd, Roxbury, CT 06783

  Get away to the Country! Such a peaceful location to build your dream home. Lightly traveled road. All of nature loves the location, so will you!

  Sindy Butkus Klemm Real Estate Inc

  0 Booth Rd, Roxbury, CT 06783
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  $545,000 Sold Mar 19, 2025

  34 Spargo Rd, Roxbury, CT 06783

  • 2 Beds
  • 2 Baths
  • 2,321 Sq Ft
  • Built 1930

  Last Sold Summary

  • 1% Below List Price
  • $235/SF
  • 12 Days On Market

  Current Estimated Value $560,706

  Last Listing Agent Karan Garewal Winwin Realty

  34 Spargo Rd, Roxbury, CT 06783
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  Est $1,501,636 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,799 Sq Ft

  35 Painter Ridge Rd, Roxbury, CT 06783

  35 Painter Ridge Rd, Roxbury, CT 06783
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  /16

  $775,000

  • Land
  • 26.68 Acres
  • $29,048 per Acre

  204 North St Unit Lot 3, Roxbury, CT 06783

  1st Time LISTED! LOT 3 at 204 North Street has ENGINEERING and DRIVEWAY APPROVED! THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. This 25 acre lot features un-touched historic stone walls, a beautiful stream flowing, gently

  Jill Sloane Brown Harris Stevens

  204 North St Unit Lot 3, Roxbury, CT 06783
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  $645,000 Sold Apr 25, 2025

  396 Southbury Rd, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 2,382 Sq Ft
  • Built 1943

  Last Sold Summary

  • $271/SF
  • 62 Days On Market

  Current Estimated Value $671,826

  Last Listing Agent Mirella D'Antonio William Raveis Real Estate

  396 Southbury Rd, Roxbury, CT 06783
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  Est $948,960 Not Listed For Sale

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

  177 Bacon Rd, Roxbury, CT 06783

  177 Bacon Rd, Roxbury, CT 06783
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  /34

  $3,595,000

  • 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
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  $299,000 Sold Feb 20, 2025

  0 Hemlock Rd, Roxbury, CT 06783

  • Land
  • 5.24 Acres
  • $57,061 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 173 Days On Market

  Last Listing Agent Jay McGorty McGorty Real Estate Services

  0 Hemlock Rd, Roxbury, CT 06783
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  Est $1,341,650 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,575 Sq Ft

  7 Wakelee Rd, Roxbury, CT 06783

  7 Wakelee Rd, Roxbury, CT 06783
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  $2,575,000 Sold Aug 29, 2025

  18 Mallory Rd, Roxbury, CT 06783

  • 3 Beds
  • 3.5 Baths
  • 3,384 Sq Ft
  • Built 1750

  Last Sold Summary

  • 14% Below List Price
  • $761/SF
  • 53 Days On Market

  Current Estimated Value $2,506,772

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  18 Mallory Rd, Roxbury, CT 06783
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  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,698 Sq Ft

  Unlisted Address

  Unlisted Address
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  $856,900 Sold Mar 04, 2025

  195 Painter Hill Rd, Roxbury, CT 06783

  • 2 Beds
  • 2.5 Baths
  • 2,322 Sq Ft
  • Built 1980

  Last Sold Summary

  • 32% Above List Price
  • $369/SF
  • 30 Days On Market

  Current Estimated Value $959,563

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

  195 Painter Hill Rd, Roxbury, CT 06783
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  Est $671,845 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,940 Sq Ft

  3 Jonathan Dr, Roxbury, CT 06783

  3 Jonathan Dr, Roxbury, CT 06783
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  $917,500 Sold Aug 21, 2025

  88 Mallory Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 3,004 Sq Ft
  • Built 1999

  Last Sold Summary

  • $305/SF
  • 82 Days On Market

  Current Estimated Value $965,880

  Last Listing Agent Melissa Karaffa William Raveis Real Estate

  88 Mallory Rd, Roxbury, CT 06783
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  Est $986,491 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,102 Sq Ft

  68 Carriage Ln, Roxbury, CT 06783

  68 Carriage Ln, Roxbury, CT 06783
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  $895,000 Sold Jan 23, 2026

  67 Transylvania Rd, Roxbury, CT 06783

  • 4 Beds
  • 4 Baths
  • 3,624 Sq Ft
  • Built 1989

  Last Sold Summary

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

  Last Listing Agent Cathy Masi Flagpole Realty Inc

  67 Transylvania Rd, Roxbury, CT 06783
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  Est $1,523,962 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,666 Sq Ft

  1 Church St, Roxbury, CT 06783

  1 Church St, Roxbury, CT 06783
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  $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
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  Est $696,240 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,806 Sq Ft

  37 Painter Hill Rd, Roxbury, CT 06783

  37 Painter Hill Rd, Roxbury, CT 06783
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  $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 $1,367,459

  Last Listing Agent William Bolls Compass Connecticut, LLC

  22 Highmeadow Ln, Roxbury, CT 06783
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  Est $1,309,605 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,591 Sq Ft

  219 Good Hill Rd, Roxbury, CT 06783

  219 Good Hill Rd, Roxbury, CT 06783
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  $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 $1,314,828

  Last Listing Agent Jill Sloane Brown Harris Stevens

  36 Chalybes Rd, Roxbury, CT 06783
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  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,433 Sq Ft

  214 Tophet Rd, Roxbury, CT 06783

  214 Tophet Rd, Roxbury, CT 06783
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  $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 $435,296

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  168 Baker Rd, Roxbury, CT 06783
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  Est $963,359 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,540 Sq Ft

  95 Transylvania Rd, Roxbury, CT 06783

  95 Transylvania Rd, Roxbury, CT 06783

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