Roxbury, CT Homes

• 

  $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

  Current Estimated Value $968,761

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

  11 Hodge Rd, Roxbury, CT 06783
• 

  Est $884,805 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

  • 2% Below List Price
  • $367/SF
  • 229 Days On Market

  • Last Sold Price $900,000
  • Jan 15, 2025

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty
• 

  

  

  /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
• 

  Est $1,250,471 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

  • 7% Below List Price
  • $524/SF
  • 20 Days On Market

  • Last Sold Price $1,350,000
  • Apr 12, 2024

  Last Listing Agent Kathryn Clair William Pitt
• 

  

  

  /40

  $1,795,000

  • 4 Beds
  • 4 Baths
  • 4,310 Sq Ft

  25 Highmeadow Ln, Roxbury, CT 06783

  Fantastic opportunity to own an estate in bucolic southern Litchfield County, complete with saltwater gunite pool, open rolling lawns, sunrise/sunset views, and equestrian facilities. Spanning over 17 private acres, this property is anchored by a handsome 4-bedroom colonial home loaded with charm and lots of room to entertain. The eat-in kitchen is the heart of the home with a DCS stove, Sub-Zero

  William Bolls Compass Connecticut, LLC

  25 Highmeadow Ln, Roxbury, CT 06783
• 

  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
  • Apr 15, 2024

  Last Listing Agent Graham Klemm Klemm Real Estate Inc
• 

  

  /4

  $2,000,000 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 3,198 Sq Ft

  18 Ranney Hill Rd, Roxbury, CT 06783

  Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble

  Sharon McGuire William Pitt Sotheby's Int'l

  18 Ranney Hill Rd, Roxbury, CT 06783
• 

  Est $618,358 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

  • 44% Above List Price
  • $222/SF
  • 77 Days On Market

  • Last Sold Price $430,000
  • May 09, 2023

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
• 

  

  /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
• 

  Est $1,057,511 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

  • 22% Above List Price
  • $211/SF
  • 129 Days On Market

  • Last Sold Price $865,000
  • Dec 23, 2024

  Last Listing Agent Kathryn Clair William Pitt
• 

  

  /33

  $689,000

  • 4 Beds
  • 2 Baths
  • 2,008 Sq Ft

  216 Baker Rd, Roxbury, CT 06783

  Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached room currently used as an office. The main level with a den, living room with fireplace, dining room, and a

  David Landau RE/MAX Right Choice

  216 Baker Rd, Roxbury, CT 06783
• 

  Est $1,381,572 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

  • 6% Above List Price
  • $355/SF
  • 114 Days On Market

  • Last Sold Price $1,300,000
  • Oct 25, 2024

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
• 

  Est $665,817 Not Listed For Sale

  37 Painter Hill Rd, Roxbury, CT 06783

  • 2 Beds
  • 2.5 Baths
  • 1,806 Sq Ft
  • Built 1987

  37 Painter Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • 44% Above List Price
  • $256/SF
  • 193 Days On Market

  • Last Sold Price $463,000
  • Aug 20, 2024

  Last Listing Agent John Sniffen William Pitt
• 

  Est $1,204,151 Not Listed For Sale

  219 Good Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,591 Sq Ft
  • Built 1981

  219 Good Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • $463/SF
  • 38 Days On Market

  • Last Sold Price $1,200,000
  • Aug 22, 2024

  Last Listing Agent Florence DeDampierre W. Raveis Lifestyles Realty
• 

  Not Listed For Sale

  66 Bacon Rd, Roxbury, CT 06783

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

  66 Bacon Rd, Roxbury, CT 06783

  Last Sold Summary

  • $313/SF
  • 91 Days On Market

  • Last Sold Price $735,000
  • Mar 14, 2025

  Last Listing Agent William Whitehead Berkshire Hathaway Home Services
• 

  Not Listed For Sale

  214 Tophet Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 3,433 Sq Ft
  • Built 1977

  214 Tophet Rd, Roxbury, CT 06783

  Last Sold Summary

  • $364/SF
  • 27 Days On Market

  • Last Sold Price $1,250,000
  • Apr 03, 2024

  Last Listing Agent Peter Klemm Klemm Real Estate Inc
• 

  Est $943,445 Not Listed For Sale

  95 Transylvania Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 3,540 Sq Ft
  • Built 1998

  95 Transylvania Rd, Roxbury, CT 06783

  Last Sold Summary

  • 28% Above List Price
  • $208/SF
  • 185 Days On Market

  • Last Sold Price $735,000
  • Jun 12, 2024

  Last Listing Agent Ryan Bollard William Pitt
• 

  Est $2,221,493 Not Listed For Sale

  15 Farm Rd, Roxbury, CT 06783

  • 4 Beds
  • 5 Baths
  • 4,337 Sq Ft
  • Built 1995

  15 Farm Rd, Roxbury, CT 06783

  Last Sold Summary

  • 22% Above List Price
  • $420/SF
  • 83 Days On Market

  • Last Sold Price $1,820,000
  • Jul 13, 2023

  Last Listing Agent Peter Klemm Klemm Real Estate Inc
• 

  Est $656,116 Not Listed For Sale

  150 E Flag Swamp Rd, Roxbury, CT 06783

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1994

  150 E Flag Swamp Rd, Roxbury, CT 06783

  Last Sold Summary

  • 17% Above List Price
  • $449/SF
  • 108 Days On Market

  • Last Sold Price $560,000
  • Sep 27, 2023

  Last Listing Agent Jon Magnotta Outlook Realty
• 

  Est $558,078 Not Listed For Sale

  14 Wellers Bridge Rd, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 1,275 Sq Ft
  • Built 1930

  14 Wellers Bridge Rd, Roxbury, CT 06783

  Last Sold Summary

  • 28% Above List Price
  • $343/SF
  • 34 Days On Market

  • Last Sold Price $437,626
  • May 08, 2023

  Last Listing Agent KIM-MAI MAHON W. Raveis Lifestyles Realty
• 

  Not Listed For Sale

  25 Holmes Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,926 Sq Ft
  • Built 1978

  25 Holmes Rd, Roxbury, CT 06783

  Last Sold Summary

  • $393/SF
  • 97 Days On Market

  • Last Sold Price $1,150,000
  • Feb 15, 2024

  Last Listing Agent Jacki Hornish W. Raveis Lifestyles Realty
• 

  Not Listed For Sale

  15 E Woods Rd, Roxbury, CT 06783

  • 7 Beds
  • 4.5 Baths
  • 5,477 Sq Ft
  • Built 1976

  15 E Woods Rd, Roxbury, CT 06783

  Last Sold Summary

  • $292/SF
  • 189 Days On Market

  • Last Sold Price $1,600,000
  • Dec 23, 2024

  Last Listing Agent Peter Klemm Klemm Real Estate Inc
• 

  Est $1,453,735 Not Listed For Sale

  72 Welton Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 2,758 Sq Ft
  • Built 1790

  72 Welton Rd, Roxbury, CT 06783

  Last Sold Summary

  • 6% Below List Price
  • $562/SF
  • 1 Day On Market

  • Last Sold Price $1,550,000
  • Jun 09, 2023

  Last Listing Agent April Crumrine William Pitt
• 

  Est $715,302 Not Listed For Sale

  51 Judds Bridge Rd, Roxbury, CT 06783

  • 4 Beds
  • 3 Baths
  • 3,708 Sq Ft
  • Built 1965

  51 Judds Bridge Rd, Roxbury, CT 06783

  Last Sold Summary

  • 23% Above List Price
  • $156/SF
  • 173 Days On Market

  • Last Sold Price $580,000
  • Feb 15, 2024

  Last Listing Agent Patricia Guarantano William Pitt
• 

  Not Listed For Sale

  00 Hemlock Rd, Roxbury, CT 06783

  00 Hemlock Rd, Roxbury, CT 06783

  Last Sold Summary

  • 223 Days On Market

  • Last Sold Price $230,000
  • May 30, 2023

  Last Listing Agent Tim Tierney Klemm Real Estate Inc
• 

  Not Listed For Sale

  00 Cedar Ridge, Roxbury, CT 06783

  00 Cedar Ridge, Roxbury, CT 06783

  Last Sold Summary

  • 201 Days On Market

  • Last Sold Price $315,000
  • May 03, 2023

  Last Listing Agent Tim Tierney Klemm Real Estate Inc
• 

  Not Listed For Sale

  00 Booth Rd, Roxbury, CT 06783

  00 Booth Rd, Roxbury, CT 06783

  Last Sold Summary

  • 733 Days On Market

  • Last Sold Price $175,000
  • Nov 02, 2023

  Last Listing Agent Kathryn Clair William Pitt
• 

  Est $2,643,885 Not Listed For Sale

  20 Painter Hill Rd, Roxbury, CT 06783

  20 Painter Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • 24% Below List Price
  • 54 Days On Market

  • Last Sold Price $3,495,000
  • Jan 16, 2025

  Last Listing Agent Graham Klemm Klemm Real Estate Inc
• 

  Est $623,489 Not Listed For Sale

  70 Southbury Rd, Roxbury, CT 06783

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 2020

  70 Southbury Rd, Roxbury, CT 06783

  Last Sold Summary

  • 18% Above List Price
  • $526/SF
  • 39 Days On Market

  • Last Sold Price $530,000
  • Oct 16, 2024

  Last Listing Agent Justin Bette Century 21 Bette Real Estate
• 

  Not Listed For Sale

  21 Hemlock Rd, Roxbury, CT 06783

  • 4 Beds
  • 3 Baths
  • 2,984 Sq Ft
  • Built 2020

  21 Hemlock Rd, Roxbury, CT 06783

  Last Sold Summary

  • $469/SF
  • 191 Days On Market

  • Last Sold Price $1,400,000
  • Feb 28, 2025

  Last Listing Agent Kathryn Clair William Pitt
• 

  Est $1,156,883 Not Listed For Sale

  24 Roxbury Rd, Woodbury, CT 06798

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

  24 Roxbury Rd, Woodbury, CT 06798

  Last Sold Summary

  • 50% Above List Price
  • $192/SF
  • 313 Days On Market

  • Last Sold Price $769,000
  • Apr 01, 2025

  Last Listing Agent Debbie Kranidis Preston Gray Real Estate
• 

  Est $616,702 Not Listed For Sale

  5 Carriage Ln, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft
  • Built 1750

  5 Carriage Ln, Roxbury, CT 06783

  Last Sold Summary

  • 21% Above List Price
  • $320/SF
  • 96 Days On Market

  • Last Sold Price $510,000
  • Jul 11, 2024

  Last Listing Agent Stephanie Blake BHGRE Gaetano Marra Homes
• 

  Est $1,579,385 Not Listed For Sale

  52 Welton Rd, Roxbury, CT 06783

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

  52 Welton Rd, Roxbury, CT 06783

  Last Sold Summary

  • 5% Above List Price
  • $464/SF
  • 323 Days On Market

  • Last Sold Price $1,500,000
  • Jan 28, 2025

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
• 

  Not Listed For Sale

  00 Pickett Rd, Roxbury, CT 06783

  00 Pickett Rd, Roxbury, CT 06783

  Last Sold Summary

  • 33 Days On Market

  • Last Sold Price $79,900
  • Apr 03, 2024

  Last Listing Agent Mark Forte Finish Line Realty
• 

  Not Listed For Sale

  222 North St, Roxbury, CT 06783

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1895

  222 North St, Roxbury, CT 06783

  Last Sold Summary

  • $467/SF
  • 84 Days On Market

  • Last Sold Price $420,000
  • Nov 01, 2023

  Last Listing Agent Jill Sloane Brown Harris Stevens
• 

  Not Listed For Sale

  43 Baker Rd, Roxbury, CT 06783

  43 Baker Rd, Roxbury, CT 06783

  Last Sold Summary

  • 90 Days On Market

  • Last Sold Price $450,000
  • Jul 31, 2024

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
• 

  Not Listed For Sale

  00 Old Ln, Roxbury, CT 06783

  00 Old Ln, Roxbury, CT 06783

  Last Sold Summary

  • 364 Days On Market

  • Last Sold Price $150,000
  • Nov 06, 2023

  Last Listing Agent Sharon McGuire William Pitt
• 

  Not Listed For Sale

  Lot 6 Willow Brook Dr, Roxbury, CT 06783

  Lot 6 Willow Brook Dr, Roxbury, CT 06783

  Last Sold Summary

  • 286 Days On Market

  • Last Sold Price $450,000
  • Aug 15, 2023

  Last Listing Agent Ryan Bollard William Pitt
• 

  Not Listed For Sale

  Lot 3 Willow Brook Dr, Roxbury, CT 06783

  Lot 3 Willow Brook Dr, Roxbury, CT 06783

  Last Sold Summary

  • 286 Days On Market

  • Last Sold Price $450,000
  • Aug 15, 2023

  Last Listing Agent Ryan Bollard William Pitt
• 

  Not Listed For Sale

  Lot 1 Willow Brook Dr, Roxbury, CT 06783

  Lot 1 Willow Brook Dr, Roxbury, CT 06783

  Last Sold Summary

  • 101 Days On Market

  • Last Sold Price $480,000
  • Nov 26, 2024

  Last Listing Agent Ryan Bollard William Pitt

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