Roxbury, CT Homes

• 

  $1,500,000 Sold Nov 18, 2025

  253 Tophet Rd, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 2,437 Sq Ft
  • Built 1890

  Last Sold Summary

  • 12% Below List Price
  • $616/SF
  • 225 Days On Market

  Last Listing Agent Peter Klemm Klemm Real Estate Inc

  253 Tophet Rd, Roxbury, CT 06783
• 

  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
• 

  

  

  /40

  $2,200,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,677 Sq Ft

  81 Chalybes Rd W, Roxbury, CT 06783

  TO BE BUILT - A New Classic by Connecticut Residential. Here's your chance to create something truly special in the heart of lower Litchfield County. Tucked away on over 4 private acres in picturesque Roxbury, this proposed home by Connecticut Residential blends timeless Colonial charm with modern-day comfort-thoughtfully designed for today's lifestyle while honoring traditional New England

  Christopher Haggerty Around Town Real Estate LLC

  81 Chalybes Rd W, Roxbury, CT 06783
• 

  $615,000 Sold Jun 30, 2025

  79 Wellers Bridge Rd, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 2,769 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Above List Price
  • $222/SF
  • 12 Days On Market

  Current Estimated Value $613,869

  Last Listing Agent Amy Jeanfaivre Family Realty Group, LLC

  79 Wellers Bridge Rd, Roxbury, CT 06783
• 

  Est $1,450,865 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
• 

  

  /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
• 

  $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 $1,018,419

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

  80 Transylvania Rd, Roxbury, CT 06783
• 

  Est $1,404,094 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
• 

  

  /22

  $1,949,000

  • 4 Beds
  • 3.5 Baths
  • 4,517 Sq Ft

  45 Moosehorn Rd, Roxbury, CT 06783

  Pristine 4+ bedroom large (4,517 sq. ft.) private home on a scenic dirt road - perfect for walking, jogging and biking surrounded by Moosehorn Land Preserve and country estates. Magnificent design incorporating picturesque country views, over-sized living room, dining room for 12+, chef's kitchen, vaulted ceilings, hardwood floors and two gas fireplaces. Heated pool surrounded by endless summer

  Peter Klemm Klemm Real Estate Inc

  45 Moosehorn Rd, Roxbury, CT 06783
• 

  $1,240,000 Sold Dec 30, 2024

  76 Davenport Rd, Roxbury, CT 06783

  • 2 Beds
  • 3 Baths
  • 2,445 Sq Ft
  • Built 1989

  Last Sold Summary

  • 25% Below List Price
  • $507/SF
  • 392 Days On Market

  Current Estimated Value $1,333,488

  Last Listing Agent GRACE FRANJOLA Berkshire Hathaway NE Prop.

  76 Davenport Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

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

  Unlisted Address

  Unlisted Address
• 

  

  /34

  $689,000

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

  55 Mallory Rd, Roxbury, CT 06783

  NEW PRICE! If privacy in the Litchfield Hills is your aspiration, this is the place for you! Pass through the gated entrance to this rustic Country Cape w/ covered front porch set back 500 ft 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

  Gina Jacobs Gina Jacobs Real Estate

  55 Mallory Rd, Roxbury, CT 06783
• 

  $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
• 

  Est $760,891 Not Listed For Sale

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

  3 Jonathan Dr, Roxbury, CT 06783

  3 Jonathan Dr, Roxbury, CT 06783
• 

  

  /21

  $1,575,000

  • 3 Beds
  • 4 Baths
  • 2,396 Sq Ft

  247 Painter Hill Rd, Roxbury, CT 06783

  Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by Roxbury's best historic estate neighborhood, farms and homes of artists, actors and writers. Magnificent open floor plan with 2-3 bedrooms on main floor, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch and another bedroom in finished lower level. Dine or relax on the flagstone

  Peter Klemm Klemm Real Estate Inc

  247 Painter Hill 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
• 

  Est $1,470,731 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
• 

  

  /36

  $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
• 

  $3,500,000 Sold Jan 09, 2025

  44 Chalybes Rd, Roxbury, CT 06783

  • 4 Beds
  • 6.5 Baths
  • 4,950 Sq Ft
  • Built 1964

  Last Sold Summary

  • 7% Below List Price
  • $707/SF
  • 67 Days On Market

  Current Estimated Value $3,691,687

  Last Listing Agent Carolyn Klemm Klemm Real Estate Inc

  44 Chalybes Rd, Roxbury, CT 06783
• 

  Est $683,739 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
• 

  

  /20

  $479,000

  • Land
  • 8.64 Acres
  • $55,440 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
• 

  $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 $1,504,574

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  88 Hemlock Rd, Roxbury, CT 06783
• 

  Est $1,274,333 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
• 

  

  /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
• 

  $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 $565,123

  Last Listing Agent Karan Garewal Winwin Realty

  34 Spargo Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

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

  178 Baker Rd, Roxbury, CT 06783

  178 Baker Rd, Roxbury, CT 06783
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  /33

  $1,630,000

  • 3 Beds
  • 2.5 Baths
  • 2,440 Sq Ft

  85 Good Hill Rd, Roxbury, CT 06783

  At the end of a long, winding private driveway, this exceptional Roxbury estate offers total seclusion & tranquility-surrounded entirely by protected land trust. Just 2 miles from Roxbury Center and a scenic 2-hr drive from NYC, this rare property is the perfect country escape or full-time residence. The main home is in impeccable, move-in condition, featuring dramatic vaulted ceilings in both

  Pat Lahoud William Pitt Sotheby's Int'l

  85 Good Hill 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 $667,504

  Last Listing Agent Mirella D'Antonio William Raveis Real Estate

  396 Southbury Rd, Roxbury, CT 06783
• 

  Est $874,777 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,282 Sq Ft

  45 Chalybes Rd, Roxbury, CT 06783

  45 Chalybes Rd, Roxbury, CT 06783
• 

  

  /26

  $999,000

  • 4 Beds
  • 3 Baths
  • 1,782 Sq Ft

  23 Painter Hill Rd, Roxbury, CT 06783

  Mint / Move-in Condition! Pristine hilltop home with views on 3 +/- acres. Gorgeous, chic, mint renovation. Open floor plan kitchen/family room with wood-burning fireplace and French doors to a private flagstone patio. Bright and airy living room and dining room. Primary bedroom with vaulted ceilings, balcony and large ensuite renovated bath. Three more bedrooms, 1 full and 1 half bath. Only a

  Peter Klemm Klemm Real Estate Inc

  23 Painter Hill Rd, Roxbury, CT 06783
• 

  $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
• 

  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
• 

  

  /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
• 

  $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 $2,683,630

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  18 Mallory Rd, Roxbury, CT 06783
• 

  Est $919,768 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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  /27

  $1,475,000

  • 4 Beds
  • 3.5 Baths
  • 2,716 Sq Ft

  33 Sentry Hill Rd, Roxbury, CT 06783

  Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room,

  Peter Klemm Klemm Real Estate Inc

  33 Sentry Hill Rd, Roxbury, CT 06783
• 

  $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 $953,222

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

  195 Painter Hill Rd, Roxbury, CT 06783
• 

  Est $2,258,573 Not Listed For Sale

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

  15 Farm Rd, Roxbury, CT 06783

  15 Farm Rd, Roxbury, CT 06783
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  /37

  $2,850,000 New Construction

  • 5 Beds
  • 7 Baths
  • 4,777 Sq Ft

  103 Chalybes Rd W, Roxbury, CT 06783

  TO BE BUILT - A Home by CORBO! Tranquil luxury on 16 private acres in Roxbury, CT-an exceptional opportunity to bring your dream home to life in the heart of lower Litchfield County. Set well back from the road and oriented for western exposure, this stunning property offers sweeping views (subject to tree clearing and final siting) and the ultimate in privacy. Choose this thoughtfully designed

  Christopher Haggerty Around Town Real Estate LLC

  103 Chalybes Rd W, 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 $943,238

  Last Listing Agent Melissa Karaffa William Raveis Real Estate

  88 Mallory Rd, Roxbury, CT 06783

Showing Results 81 - 120, Page 3 of 18