1,377

Roxbury, CT Homes

Section Image
    • 168 Baker Rd, Roxbury, CT 06783

      Est $445,384 Not Listed For Sale

      168 Baker Rd, Roxbury, CT 06783

      • 2 Beds
      • 2 Baths
      • 1,328 Sq Ft
      • Built 1788
      168 Baker Rd, Roxbury, CT 06783

      Last Sold Summary

      • 9% Above List Price
      • $309/SF
      • 160 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

  • 200 North St, Roxbury, CT 06783
    200 North St, Roxbury, CT 06783
    200 North St, Roxbury, CT 06783
    /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
  • 80 Transylvania Rd, Roxbury, CT 06783

    $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 $997,556

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

    80 Transylvania Rd, Roxbury, CT 06783
    • 101 South St, Roxbury, CT 06783

      Est $1,408,946 Not Listed For Sale

      101 South St, Roxbury, CT 06783

      • 6 Beds
      • 6 Baths
      • 5,439 Sq Ft
      • Built 1980
      101 South St, Roxbury, CT 06783

      Last Sold Summary

      • 48% Above List Price
      • $175/SF
      • 238 Days On Market

      Last Sold Price $951,000

      Last Listing Agent Brian Gee Brian Gee Real Estate LLC

  • 4 Judge Rd, Roxbury, CT 06783
    4 Judge Rd, Roxbury, CT 06783
    4 Judge Rd, Roxbury, CT 06783
    /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
  • Unlisted Address

    $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

    Current Estimated Value $2,736,580

    Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

    Unlisted Address
    • 44 Baker Rd, Roxbury, CT 06783

      Est $751,031 Not Listed For Sale

      44 Baker Rd, Roxbury, CT 06783

      • 5 Beds
      • 2.5 Baths
      • 2,501 Sq Ft
      • Built 1962
      44 Baker Rd, Roxbury, CT 06783

      Last Sold Summary

      • 37% Above List Price
      • $220/SF
      • 182 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Judith Auchincloss Klemm Real Estate Inc

  • 179 South St, Roxbury, CT 06783
    179 South St, Roxbury, CT 06783
    179 South St, Roxbury, CT 06783
    /13

    $985,000

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft

    179 South St, Roxbury, CT 06783

    Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity

    Kathryn Clair William Pitt Sotheby's Int'l

    179 South St, Roxbury, CT 06783
  • 118 Chalybes Rd W, Roxbury, CT 06783

    $754,500 Sold Feb 11, 2026

    118 Chalybes Rd W, Roxbury, CT 06783

    • 6 Beds
    • 5 Baths
    • 4,260 Sq Ft
    • Built 1730

    Last Sold Summary

    • 16% Below List Price
    • $177/SF
    • 558 Days On Market

    Last Listing Agent Catherine Aaron Berkshire Hathaway NE Prop.

    118 Chalybes Rd W, Roxbury, CT 06783
    • 154 Transylvania Rd, Roxbury, CT 06783

      Est $807,759 Not Listed For Sale

      154 Transylvania Rd, Roxbury, CT 06783

      • 3 Beds
      • 2.5 Baths
      • 2,290 Sq Ft
      • Built 1987
      154 Transylvania Rd, Roxbury, CT 06783

      Last Sold Summary

      • 16% Above List Price
      • $305/SF
      • 96 Days On Market

      Last Sold Price $699,000

      Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty

  • 0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    /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
  • 62 Davenport Rd, Roxbury, CT 06783

    $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
    • 3 Southbury Rd, Roxbury, CT 06783

      Not Listed For Sale

      3 Southbury Rd, Roxbury, CT 06783

      • 4 Beds
      • 2.5 Baths
      • 3,016 Sq Ft
      • Built 1796
      3 Southbury Rd, Roxbury, CT 06783

      Last Sold Summary

      • $406/SF
      • 138 Days On Market

      Last Sold Price $1,225,000

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

  • 204 North St Unit Lot 3, Roxbury, CT 06783
    204 North St Unit Lot 3, Roxbury, CT 06783
    204 North St Unit Lot 3, Roxbury, CT 06783
    /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
  • 88 Hemlock Rd, Roxbury, CT 06783

    $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 $1,467,703

    Last Listing Agent Graham Klemm Klemm Real Estate Inc

    88 Hemlock Rd, Roxbury, CT 06783
    • 76 Davenport Rd, Roxbury, CT 06783

      Est $1,376,939 Not Listed For Sale

      76 Davenport Rd, Roxbury, CT 06783

      • 2 Beds
      • 3 Baths
      • 2,445 Sq Ft
      • Built 1989
      76 Davenport Rd, Roxbury, CT 06783

      Last Sold Summary

      • 11% Above List Price
      • $507/SF
      • 392 Days On Market

      Last Sold Price $1,240,000

      Last Listing Agent GRACE FRANJOLA Berkshire Hathaway Home Services

  • 11 Ravenrock, Roxbury, CT 06783
    11 Ravenrock, Roxbury, CT 06783
    11 Ravenrock, Roxbury, CT 06783
    /35

    $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
  • 396 Southbury Rd, Roxbury, CT 06783

    $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 $714,066

    Last Listing Agent Mirella D'Antonio William Raveis Real Estate

    396 Southbury Rd, Roxbury, CT 06783
    • 294 North St, Roxbury, CT 06783

      Not Listed For Sale

      294 North St, Roxbury, CT 06783

      • 3 Beds
      • 3.5 Baths
      • 3,087 Sq Ft
      • Built 1970
      294 North St, Roxbury, CT 06783

      Last Sold Summary

      • $421/SF
      • 65 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Claire Maestroni W. Raveis Lifestyles Realty

  • 18 Mallory Rd, Roxbury, CT 06783

    $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 $2,560,345

    Last Listing Agent Graham Klemm Klemm Real Estate Inc

    18 Mallory Rd, Roxbury, CT 06783
    • 277 Southbury Rd, Roxbury, CT 06783

      Not Listed For Sale

      277 Southbury Rd, Roxbury, CT 06783

      • 3 Beds
      • 3 Baths
      • 3,091 Sq Ft
      • Built 2007
      277 Southbury Rd, Roxbury, CT 06783

      Last Sold Summary

      • $372/SF
      • 57 Days On Market

      Last Sold Price $1,150,000

      Last Listing Agent Todd Sargent Coldwell Banker Realty

  • 178 Baker Rd, Roxbury, CT 06783

    $808,000 Sold Mar 11, 2026

    178 Baker Rd, Roxbury, CT 06783

    • 1 Bed
    • 1.5 Baths
    • 1,449 Sq Ft
    • Built 1804

    Last Sold Summary

    • 8% Above List Price
    • $558/SF
    • 49 Days On Market

    Last Listing Agent Maureen Maher Berkshire Hathaway NE Prop.

    178 Baker Rd, Roxbury, CT 06783
    • 167 Tophet Rd, Roxbury, CT 06783

      Est $1,365,438 Not Listed For Sale

      167 Tophet Rd, Roxbury, CT 06783

      • 3 Beds
      • 3.5 Baths
      • 4,040 Sq Ft
      • Built 1960
      167 Tophet Rd, Roxbury, CT 06783

      Last Sold Summary

      • 26% Above List Price
      • $267/SF
      • 279 Days On Market

      Last Sold Price $1,080,000

      Last Listing Agent Rebecca Zandvliet Coldwell Banker Realty 2000

  • 88 Mallory Rd, Roxbury, CT 06783

    $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 $977,163

    Last Listing Agent Melissa Karaffa William Raveis Real Estate

    88 Mallory Rd, Roxbury, CT 06783
    • 19 Golden Harvest Rd, Roxbury, CT 06783

      Not Listed For Sale

      19 Golden Harvest Rd, Roxbury, CT 06783

      • 4 Beds
      • 6 Baths
      • 5,808 Sq Ft
      • Built 1998
      19 Golden Harvest Rd, Roxbury, CT 06783

      Last Sold Summary

      • $478/SF
      • 361 Days On Market

      Last Sold Price $2,775,000

      Last Listing Agent Rick Distel Compass Connecticut, LLC

  • 67 Transylvania Rd, Roxbury, CT 06783

    $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

    Current Estimated Value $895,243

    Last Listing Agent Cathy Masi Flagpole Realty Inc

    67 Transylvania Rd, Roxbury, CT 06783
    • 35 Painter Ridge Rd, Roxbury, CT 06783

      Est $1,373,318 Not Listed For Sale

      35 Painter Ridge Rd, Roxbury, CT 06783

      • 2 Beds
      • 3 Baths
      • 2,799 Sq Ft
      • Built 1980
      35 Painter Ridge Rd, Roxbury, CT 06783

      Last Sold Summary

      • 12% Below List Price
      • $557/SF
      • 28 Days On Market

      Last Sold Price $1,560,000

      Last Listing Agent Peter Klemm Klemm Real Estate Inc

  • 24 Roxbury Rd, Woodbury, CT 06798

    $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 $1,158,276

    Last Listing Agent Debbie Kranidis Preston Gray Real Estate

    24 Roxbury Rd, Woodbury, CT 06798
    • 177 Bacon Rd, Roxbury, CT 06783

      Est $995,166 Not Listed For Sale

      177 Bacon Rd, Roxbury, CT 06783

      • 3 Beds
      • 3 Baths
      • 2,450 Sq Ft
      • Built 1985
      177 Bacon Rd, Roxbury, CT 06783

      Last Sold Summary

      • 11% Above List Price
      • $367/SF
      • 229 Days On Market

      Last Sold Price $900,000

      Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  • 22 Highmeadow Ln, 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 $1,404,594

    Last Listing Agent William Bolls Compass Connecticut, LLC

    22 Highmeadow Ln, Roxbury, CT 06783
    • 7 Wakelee Rd, Roxbury, CT 06783

      Est $1,401,025 Not Listed For Sale

      7 Wakelee Rd, Roxbury, CT 06783

      • 4 Beds
      • 2.5 Baths
      • 2,575 Sq Ft
      • Built 1998
      7 Wakelee Rd, Roxbury, CT 06783

      Last Sold Summary

      • 4% Above List Price
      • $524/SF
      • 20 Days On Market

      Last Sold Price $1,350,000

      Last Listing Agent Kathryn Clair William Pitt

  • 36 Chalybes 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 $1,342,577

    Last Listing Agent Jill Sloane Brown Harris Stevens

    36 Chalybes Rd, Roxbury, CT 06783
    • Unlisted Address

      Not Listed For Sale

      Unlisted Address

      • 3 Beds
      • 3.5 Baths
      • 3,698 Sq Ft
      • Built 1792
      Unlisted Address

      Last Sold Summary

      • $879/SF
      • 40 Days On Market

      Last Sold Price $3,250,000

      Last Listing Agent Graham Klemm Klemm Real Estate Inc

  • 55 Mallory Rd, Roxbury, CT 06783

    $615,000 Sold Mar 17, 2026

    55 Mallory Rd, Roxbury, CT 06783

    • 4 Beds
    • 3 Baths
    • 2,682 Sq Ft
    • Built 1995

    Last Sold Summary

    • 21% Below List Price
    • $229/SF
    • 176 Days On Market

    Current Estimated Value $633,404

    Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

    55 Mallory Rd, Roxbury, CT 06783
    • 3 Jonathan Dr, Roxbury, CT 06783

      Est $698,246 Not Listed For Sale

      3 Jonathan Dr, Roxbury, CT 06783

      • 3 Beds
      • 2 Baths
      • 1,940 Sq Ft
      • Built 1982
      3 Jonathan Dr, Roxbury, CT 06783

      Last Sold Summary

      • 62% Above List Price
      • $222/SF
      • 77 Days On Market

      Last Sold Price $430,000

      Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  • 130 E Flag Swamp Rd, 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 $1,742,200

    Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

    130 E Flag Swamp Rd, Roxbury, CT 06783
    • 68 Carriage Ln, Roxbury, CT 06783

      Est $1,142,908 Not Listed For Sale

      68 Carriage Ln, Roxbury, CT 06783

      • 5 Beds
      • 4.5 Baths
      • 4,102 Sq Ft
      • Built 2004
      68 Carriage Ln, Roxbury, CT 06783

      Last Sold Summary

      • 32% Above List Price
      • $211/SF
      • 129 Days On Market

      Last Sold Price $865,000

      Last Listing Agent Kathryn Clair William Pitt

  • 42 Berry 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 $2,990,537

    Last Listing Agent Graham Klemm Klemm Real Estate Inc

    42 Berry Rd, Roxbury, CT 06783
    • 1 Church St, Roxbury, CT 06783

      Est $1,494,591 Not Listed For Sale

      1 Church St, Roxbury, CT 06783

      • 4 Beds
      • 2.5 Baths
      • 3,666 Sq Ft
      • Built 1784
      1 Church St, Roxbury, CT 06783

      Last Sold Summary

      • 15% Above List Price
      • $355/SF
      • 114 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

  • 67 Botsford Hill 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 $334,000

    Last Listing Agent Maria Taylor Klemm Real Estate Inc

    67 Botsford Hill Rd, Roxbury, CT 06783

Showing Results 81 - 120, Page 3 of 18

Connecticut Litchfield County Roxbury

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group