Roxbury, CT Homes

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  /38

  $850,000

  • 3 Beds
  • 2 Baths
  • 2,489 Sq Ft

  47 South St, Roxbury, CT 06783

  Step back in time and own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic

  

  Michelle Alvord

  Berkshire Hathaway NE Prop.

  47 South St, Roxbury, CT 06783
• Explore Roxbury

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  /28

  $16,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 3,089 Sq Ft
  • House for Rent

  5 North St, Roxbury, CT 06783

  NEW PRICE Summer 2026: July and/or August at $16,500 per month. Quintessential Litchfield County Retreat with Fabulous Gunite Pool in the Heart of the Town of Roxbury on 4 +/- pastoral acres. 4 bedroom and 2 and 1/2 bath charming Colonial with Great Room/Family Room with vaulted ceilings, Eat-in Country Kitchen, Formal Living Room with wood-burning fireplace, Formal Dining Room and a Wonderful

  Melinda Dubow Klemm Real Estate Inc

  5 North St, Roxbury, CT 06783
• 

  $1,764,000

  Sold Jul 20, 2026

  176 Apple Ln, Roxbury, CT 06783

  • 4 Beds
  • 4.5 Baths
  • 3,566 Sq Ft
  • Built 1972

  Last Sold Summary

  • 12% Below List Price
  • $495/SF
  • 32 Days On Market

  Current Estimated Value $1,974,976

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

  176 Apple Ln, Roxbury, CT 06783
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  Not Listed For Sale

  44 South St, Roxbury, CT 06783

  • 3 Beds
  • 3.5 Baths
  • 3,450 Sq Ft
  • Built 1792

  44 South St, Roxbury, CT 06783

  Last Sold Summary

  • 319 Days On Market

  Last Listing Agent Lenore Mallett William Pitt Sotheby's Int'l
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  /39

  $1,799,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,326 Sq Ft

  2 Pickett Rd, Roxbury, CT 06783

  Presenting a truly rare opportunity for BRAND NEW CONSTRUCTION in Roxbury, CT, this luxury residence offers approximately 3,300+ SF of meticulously designed living space, including a spacious finished basement & attached double garage. Enjoy exquisite finishes throughout, highlighted by 6" white oak hardwood flooring, custom architectural millwork and decorative shiplap details. The gourmet

  Alan O'Doherty William Pitt Sotheby's Int'l

  2 Pickett Rd, Roxbury, CT 06783
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  /29

  $8,500 Per Month

  • 3 Beds
  • 3.5 Baths
  • 3,389 Sq Ft
  • House for Rent

  Unlisted Address

  Oct-May Rental. Newly Renovated & Exquisitely Appointed Barn House. Set Along a Very Low Traveled Unpaved Town Road, This is a Very Chic & Sophisticated 3Bedroom, 3.5 Bath Retreat Including: A Main Level Primary Bedroom with Fireplace & New Full Bath. Wonderful Public Rooms Include: Large Living Room with Vaulted Ceiling, Fireplace & Antique Beams; Formal Dining Room & A Timeless Eat-in Kitchen

  Graham Klemm Klemm Real Estate Inc

  Unlisted Address
• 

  $320,000

  Sold Nov 25, 2025

  0 Wellers Bridge Rd, Roxbury, CT 06783

  • Land
  • 25.01 Acres
  • $12,795 per Acre

  Last Sold Summary

  • 42% Below List Price
  • 747 Days On Market

  Last Listing Agent David Hughes Century 21 AllPoints Realty

  0 Wellers Bridge Rd, Roxbury, CT 06783
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  Not Listed For Sale

  00 Chalybes Rd W, Roxbury, CT 06783

  00 Chalybes Rd W, Roxbury, CT 06783

  Last Sold Summary

  • 439 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
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  /37

  $3,200,000

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

  4 Judge Rd, Roxbury, CT 06783

  Exceptional equestrian estate featuring a fully equipped horse facility and charming Cape-style home. Ideal for equestrians, trainers, or boarding professionals, the property offers 16 rubber-matted stalls, a large well-lit indoor arena, and a second-floor viewing lounge with kitchen amenities-perfect for lessons, clinics, and entertaining. The barn includes a wash stall, feed room, hay storage,

  Pat Lahoud Lahoud William Pitt Sotheby's Int'l

  4 Judge Rd, Roxbury, CT 06783
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  /21

  $3,450 Per Month

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • House for Rent

  10 (UPPER) Sentry Hill Rd, Roxbury, CT 06783

  Upper 3-bedroom, 2-bath now available from 8/1/26 @ $4,500 for August, 9/'26 Academic/Annual @ $3,500. Featured in CTC & G January 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 3-bedroom, 2 bath home rests on five acres with a gentle stream running through it.

  Melinda Dubow Klemm Real Estate Inc

  10 (UPPER) Sentry Hill Rd, Roxbury, CT 06783
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  $1,925,000

  Sold Feb 17, 2026

  143 Tophet Rd, Roxbury, CT 06783

  • 4 Beds
  • 5.5 Baths
  • 5,848 Sq Ft
  • Built 2005

  Last Sold Summary

  • 26% Below List Price
  • $329/SF
  • 259 Days On Market

  Current Estimated Value $2,044,568

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  143 Tophet Rd, Roxbury, CT 06783
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  Not Listed For Sale

  0 Hemlock Rd, Roxbury, CT 06783

  0 Hemlock Rd, Roxbury, CT 06783

  Last Sold Summary

  • 173 Days On Market

  Last Listing Agent Jay McGorty McGorty Real Estate Services
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  /30

  $475,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,614 Sq Ft

  137 Davenport Rd, Roxbury, CT 06783

  INCREDIBLE OPPORTUNITY TO OWN IN THE PAINTER HILL RD AREA OF ROXBURY! This 1,600 sq ft, 3-bedroom, 2-bathroom Ranch home with a 2-car garage sits on a sun-filled, gently sloping lot with tremendous potential for the new Homeowner. The home features a new roof, furnace, water heater and bilco doors giving you a solid foundation to make it your own. The septic was last pumped September 2025, and

  Lisa Provino The Provino Group LLC

  137 Davenport Rd, Roxbury, CT 06783
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  /38

  $15,000 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,862 Sq Ft
  • House for Rent

  24 Old Roxbury Rd, Roxbury, CT 06783

  Available Oct 1, 2026 @ $15,000/mo. Perched high on a scenic Roxbury hillside, this new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing meditation on color and space. The open floor plan

  Stacey Matthews W. Raveis Lifestyles Realty

  24 Old Roxbury Rd, Roxbury, CT 06783
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  $1,966,500

  Sold Dec 22, 2025

  32 Grassy Hill Rd, Roxbury, CT 06783

  • 4 Beds
  • 5 Baths
  • 4,728 Sq Ft
  • Built 2002

  Last Sold Summary

  • 21% Below List Price
  • $416/SF
  • 256 Days On Market

  Current Estimated Value $2,062,033

  Last Listing Agent Rick Distel Compass Connecticut, LLC

  32 Grassy Hill Rd, Roxbury, CT 06783
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  Est $1,797,930

  Not Listed For Sale

  60 Good Hill Rd, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 4,928 Sq Ft
  • Built 1996

  60 Good Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Graham Klemm Klemm Real Estate Inc
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  /18

  $3,995,000

  Under Contract

  • Land
  • 57.19 Acres
  • $69,855 per Acre

  20 Painter Hill Rd, Roxbury, CT 06783

  A masterclass in privacy and scale. A newly constructed stone-lined & gated driveway ascends through 57+ acres of pristine Litchfield County landscape to a magnificent hilltop sanctuary. This estate-quality offering, spanning two separate parcels, is defined by its dramatic sweeping views and an extraordinary sense of quietude. Enveloped by the protected forests of the Roxbury Land Trust, the

  Maria Taylor Klemm Real Estate Inc

  20 Painter Hill Rd, Roxbury, CT 06783
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  /22

  $30,900 Per Month

  • 3 Beds
  • 3.5 Baths
  • 4,251 Sq Ft
  • House for Rent

  45 Moosehorn Rd, Roxbury, CT 06783

  Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes. Many world class restaurants, inns

  Peter Klemm Klemm Real Estate Inc

  45 Moosehorn Rd, Roxbury, CT 06783
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  $499,000

  Sold Nov 05, 2025

  Lot 2 Chalybes Rd W, Roxbury, CT 06783

  • Land
  • 6.81 Acres
  • $73,275 per Acre

  Last Sold Summary

  • 33 Days On Market

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

  Lot 2 Chalybes Rd W, Roxbury, CT 06783
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  Est $1,686,056

  Not Listed For Sale

  130 E Flag Swamp Rd, Roxbury, CT 06783

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

  130 E Flag Swamp Rd, Roxbury, CT 06783

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty
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  /40

  $2,750,000

  $145K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,570 Sq Ft

  220 Painter Hill Rd, Roxbury, CT 06783

  Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece,

  Stacey Matthews W. Raveis Lifestyles Realty

  220 Painter Hill Rd, Roxbury, CT 06783
• 

  $1,200,000

  Sold Oct 17, 2025

  53 Transylvania Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 3,920 Sq Ft
  • Built 2000

  Last Sold Summary

  • 20% Below List Price
  • $306/SF
  • 150 Days On Market

  Current Estimated Value $1,201,673

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  53 Transylvania Rd, Roxbury, CT 06783
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  Est $977,222

  Not Listed For Sale

  208 E Flag Swamp Rd, Roxbury, CT 06783

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

  208 E Flag Swamp Rd, Roxbury, CT 06783

  Last Sold Summary

  • 221 Days On Market

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.
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  /38

  $1,099,000

  $56K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,340 Sq Ft

  24 Hickory Ln, Roxbury, CT 06783

  Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and

  Pat Lahoud Lahoud William Pitt Sotheby's Int'l

  24 Hickory Ln, Roxbury, CT 06783
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  $1,050,000

  Sold Oct 15, 2025

  19 Spargo Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 1,571 Sq Ft
  • Built 1966

  Last Sold Summary

  • 16% Below List Price
  • $668/SF
  • 147 Days On Market

  Current Estimated Value $1,060,387

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  19 Spargo Rd, Roxbury, CT 06783
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  Est $1,099,510

  Not Listed For Sale

  82 Squire Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 1,522 Sq Ft
  • Built 1880

  82 Squire Rd, Roxbury, CT 06783

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
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  /24

  $1,525,000

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  21 Hemlock Rd, Roxbury, CT 06783

  This 4 bedroom main house with 2 bedroom guest house provides a peaceful retreat just minutes from town and 1.5 hours from NYC. The cape style main house is privately sited to capture breathtaking western views and sunsets. It features a light-filled open floor plan designed for effortless everyday living and entertaining. French doors open to an expansive deck where sweeping western vistas

  Stacey Matthews W. Raveis Lifestyles Realty

  21 Hemlock Rd, Roxbury, CT 06783
• 

  $1,195,000

  Sold Nov 07, 2025

  158 Painter Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,793 Sq Ft
  • Built 2005

  Last Sold Summary

  • $428/SF
  • 40 Days On Market

  Current Estimated Value $1,271,698

  Last Listing Agent Bonnie Garguilo William Pitt Sotheby's Int'l

  158 Painter Hill Rd, Roxbury, CT 06783
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  Est $1,380,735

  Not Listed For Sale

  310 North St, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft
  • Built 1998

  310 North St, Roxbury, CT 06783

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
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  /12

  $949,000

  Under Contract

  • Land
  • 20.13 Acres
  • $47,144 per Acre

  Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783

  Welcome to Willow Brook Drive! If your dream has been to build your new home in what feels like a Monet painting, this property will make your dream a reality. Here is your chance to have two prime lots of land, together making 20+ acres of endless possibility! With year-round beautiful meadows and enchanting woods, you can have the best of both worlds. Originally cattle pasture, the vast fields

  Ryan Bollard William Pitt Sotheby's Int'l

  Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783
• 

  $407,500

  Sold Oct 29, 2025

  238 North St, Roxbury, CT 06783

  • Land
  • 6.79 Acres
  • $60,015 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 227 Days On Market

  Last Listing Agent Jill Sloane Brown Harris Stevens

  238 North St, Roxbury, CT 06783
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  Est $1,792,752

  Not Listed For Sale

  381 South St, Roxbury, CT 06783

  • 4 Beds
  • 4.5 Baths
  • 4,112 Sq Ft
  • Built 2011

  381 South St, Roxbury, CT 06783

  Last Sold Summary

  • 186 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
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  /5

  $950,000

  • 3 Beds
  • 2 Baths
  • 1,614 Sq Ft

  137 Davenport Rd, Roxbury, CT 06783

  INCREDIBLE OPPORTUNITY TO OWN IN THE PAINTER HILL RD AREA OF ROXBURY! This 1,600 sq ft, 3-bedroom, 2-bathroom Ranch home with a 2-car garage sits on a sun-filled, gently sloping lot with tremendous potential for the new Homeowner. The home will be a Complete REMODEL with Separate Driveway. . The septic was last pumped September 2025, and annual taxes are just $3,851. Renovation by Design Builders

  Lisa Provino The Provino Group LLC

  137 Davenport Rd, Roxbury, CT 06783
• 

  $850,000

  Sold Aug 05, 2026

  45 Chalybes Rd, Roxbury, CT 06783

  • 3 Beds
  • 3.5 Baths
  • 2,725 Sq Ft
  • Built 1973

  Last Sold Summary

  • 29% Below List Price
  • $312/SF
  • 123 Days On Market

  Current Estimated Value $976,466

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

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

  6 Painter Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,816 Sq Ft
  • Built 1882

  6 Painter Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • 180 Days On Market

  Last Listing Agent Peter Klemm Klemm Real Estate Inc
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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
• 

  $1,400,000

  Sold Nov 06, 2025

  30 Hickory Ln, Roxbury, CT 06783

  • 4 Beds
  • 5.5 Baths
  • 4,721 Sq Ft
  • Built 1976

  Last Sold Summary

  • 17% Below List Price
  • $297/SF
  • 64 Days On Market

  Current Estimated Value $1,439,183

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  30 Hickory Ln, Roxbury, CT 06783
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  Est $3,498,802

  Not Listed For Sale

  44 Chalybes Rd, Roxbury, CT 06783

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

  44 Chalybes Rd, Roxbury, CT 06783

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Carolyn Klemm Klemm Real Estate Inc
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  /29

  $575,000

  Open Mon 11AM - 1:15PM

  • 3 Beds
  • 2.5 Baths
  • 2,282 Sq Ft

  90 Mallory Rd, Roxbury, CT 06783

  Diamond in the rough! This solid and expansive home is waiting for its new life, with you as the steward. It has 3 good sized bedrooms, a bonus room off the primary (which is ensuite), a large partially finished lower level, perfect for a game room, gym, man or woman cave, an open floor plan from the kitchen to the family room, a multi-level deck, an oversized 2 car garage and a large, beautiful

  Richard Pomerantz William Pitt Sotheby's Int'l

  90 Mallory Rd, Roxbury, CT 06783
• 

  $725,000

  Sold Jul 28, 2026

  242 Tophet Rd, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft
  • Built 1976

  Last Sold Summary

  • 15% Below List Price
  • $389/SF
  • 150 Days On Market

  Current Estimated Value $807,343

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

  242 Tophet Rd, Roxbury, CT 06783

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