Roxbury, CT Homes

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  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  38 W Mountain Ln, Roxbury, CT 06783

  Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceilings with exposed beams and abundant skylights fill the interior with natural light, highlighting the warmth of

  Maria Taylor Klemm Real Estate Inc

  38 W Mountain Ln, Roxbury, CT 06783
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  /33

  $11,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  Unlisted Address

  Meander down the most scenic of Roxbury dirt roads to reach "Tunnel Road 4-BR" tucked between the Shepaug River, historic wood Judd's Bridge and Farm and 1000 acres of Steep Rock land trust with endless hiking trails. Pristine renovated private country home with year round 8'x 16' spa pool, wood burning fireplace and open floor plan. Dine or relax on the granite terrace or covered front porch.

  Peter Klemm Klemm Real Estate Inc

  Unlisted Address
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  $1,825,000 Sold Aug 07, 2025

  44 South St, Roxbury, CT 06783

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

  Last Sold Summary

  • 9% Below List Price
  • $529/SF
  • 319 Days On Market

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

  44 South St, Roxbury, CT 06783
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  Est $3,639,677 Not Listed For Sale

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

  44 Chalybes Rd, Roxbury, CT 06783

  44 Chalybes Rd, Roxbury, CT 06783
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  $699,900

  • 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
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  /25

  $12,900 total monthly price

  • 4 Beds
  • 4 Baths
  • 2,396 Sq Ft
  • House for Rent

  247 Painter Hill Rd, Roxbury, CT 06783

  Mint St. Barth's-style home in perfect hilltop neighborhood with heated pool. Exceptional interior design with two wood burning fireplaces and vaulted ceilings. SUMMER June - August $26,900/month, Memorial - Labor Day $69,900. OFF-SEASON: September - May $12,900/month--If over 3 months, subtract $1,000 per month. And no tax is due. ANNUAL: $159,000. Inquire for other/shorter rental terms.

  Peter Klemm Klemm Real Estate Inc

  247 Painter Hill Rd, Roxbury, CT 06783
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  $1,725,000 Sold Apr 25, 2025

  381 South St, Roxbury, CT 06783

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

  Last Sold Summary

  • 14% Below List Price
  • $420/SF
  • 186 Days On Market

  Current Estimated Value $1,778,588

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  381 South St, Roxbury, CT 06783
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  Est $1,972,745 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,693 Sq Ft

  49 Garnet Rd, Roxbury, CT 06783

  49 Garnet Rd, Roxbury, CT 06783
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  /25

  $849,000

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

  242 Tophet Rd, Roxbury, CT 06783

  Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene

  Kathryn Clair William Pitt Sotheby's Int'l

  242 Tophet Rd, Roxbury, CT 06783
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  /22

  $13,900 total monthly price

  • 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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  $1,400,000 Sold Feb 28, 2025

  21 Hemlock Rd, Roxbury, CT 06783

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

  Last Sold Summary

  • 12% Below List Price
  • $469/SF
  • 191 Days On Market

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

  21 Hemlock Rd, Roxbury, CT 06783
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  Est $889,723 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,249 Sq Ft

  112 Southbury Rd, Roxbury, CT 06783

  112 Southbury Rd, Roxbury, CT 06783
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  $3,995,000

  • 5 Beds
  • 6 Baths
  • 5,940 Sq Ft

  8 Bayberry Hill, Roxbury, CT 06783

  Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Library, Inviting Family Room, and a Spacious Eat-in Kitchen with Top-tier Appliances. The Refined Primary Suite Features a

  Graham Klemm Klemm Real Estate Inc

  8 Bayberry Hill, Roxbury, CT 06783
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  /30

  $13,900 total monthly price

  • 6 Beds
  • 3.5 Baths
  • 2,716 Sq Ft
  • House for Rent

  33 Sentry Hill Rd, Roxbury, CT 06783

  Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.

  Peter Klemm Klemm Real Estate Inc

  33 Sentry Hill Rd, Roxbury, CT 06783
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  $795,000 Sold May 16, 2025

  13 Evergreen Dr, Roxbury, CT 06783

  • 3 Beds
  • 3 Baths
  • 2,931 Sq Ft
  • Built 1998

  Last Sold Summary

  • 31% Below List Price
  • $271/SF
  • 322 Days On Market

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  13 Evergreen Dr, Roxbury, CT 06783
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  Est $1,117,090 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft

  27 Mine Hill Rd, Roxbury, CT 06783

  27 Mine Hill Rd, Roxbury, CT 06783
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  /13

  $549,000

  • Land
  • 24.84 Acres
  • $22,101 per Acre

  69 Moosehorn Rd, Roxbury, CT 06783

  Build your dream on this designated "Scenic Road" abutting spectacular land trust trails. The lot consists of 24.8+/- acres, with a 9+/- acre building envelop. The building site is to be accessed from a future driveway running at the South border, along the Land Trust access point. The lightly wooded property rises to an 820-foot elevation and is resplendent with mature trees, ferns, moss and

  Stacey Matthews W. Raveis Lifestyles Realty

  69 Moosehorn Rd, Roxbury, CT 06783
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  $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 $1,409,484

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  30 Hickory Ln, Roxbury, CT 06783
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  Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,341 Sq Ft

  24 Baker Rd, Roxbury, CT 06783

  24 Baker Rd, Roxbury, CT 06783
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  /13

  $1,155,000

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

  24 Hickory Ln, Roxbury, CT 06783

  This beautifully updated Post & Beam residence offers exceptional craftsmanship and modern amenities throughout. Set on a serene, wooded 3-acre lot with mature landscaping, the property offers privacy and convenience - just 15 minutes from shopping and I-84.

  Sidney Nazario Coldwell Banker Realty

  24 Hickory Ln, Roxbury, CT 06783
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  $1,837,500 Sold Sep 16, 2025

  27 Wakelee Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 2,640 Sq Ft
  • Built 1815

  Last Sold Summary

  • 25% Below List Price
  • $696/SF
  • 357 Days On Market

  Current Estimated Value $1,837,914

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  27 Wakelee Rd, Roxbury, CT 06783
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  Est $2,091,763 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,559 Sq Ft

  98 Bacon Rd, Roxbury, CT 06783

  98 Bacon Rd, Roxbury, CT 06783
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  /40

  $775,000 Pending

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

  118 Chalybes Rd W, Roxbury, CT 06783

  Step into a world of charm and timeless elegance in Roxbury, CT. This bucolic estate spans 5.18 acres and offers a blend of historic charm and rustic sophistication. Explore the six-bedroom main house, complete with five bathrooms and five fireplaces, wood beams and stunning wide plank flooring bring warmth and style. This tranquil home embodies classic Connecticut living with its antique patina

  Catherine Aaron Berkshire Hathaway NE Prop.

  118 Chalybes Rd W, Roxbury, CT 06783
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  $1,465,000 Sold Aug 22, 2025

  19 Good Hill Terrace, Roxbury, CT 06783

  • 3 Beds
  • 3 Baths
  • 3,022 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $485/SF
  • 41 Days On Market

  Current Estimated Value $1,479,497

  Last Listing Agent Tanya Uhelsky RE/MAX RISE

  19 Good Hill Terrace, Roxbury, CT 06783
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  Est $959,509 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,301 Sq Ft

  28 Garnet Rd, Roxbury, CT 06783

  28 Garnet Rd, Roxbury, CT 06783
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  $685,000

  • 4 Beds
  • 2.5 Baths
  • 3,476 Sq Ft

  22 E Woods Rd, Roxbury, CT 06783

  Sunsets beyond compare await you at the end of the curved driveway, up to your secluded 6.89-acre lot. This home needs updates, however is a tremendous opportunity to live in Roxbury CT, with 3,476 Sq feet, 11 rooms, 4 bedrooms on upper level, boasting hardwood flooring & large closets. Primary suite has large walk-in shower stall & two walk-in closets. Many possibilities with the two large

  MaryAnne Betso Coldwell Banker Realty

  22 E Woods Rd, Roxbury, CT 06783
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  $749,900 Sold May 19, 2025

  8 Old Ln, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft
  • Built 2006

  Last Sold Summary

  • $331/SF
  • 74 Days On Market

  Current Estimated Value $804,076

  Last Listing Agent Brandy Granata Coldwell Banker Realty

  8 Old Ln, Roxbury, CT 06783
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  Est $985,157 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,556 Sq Ft

  336 South St, Roxbury, CT 06783

  336 South St, Roxbury, CT 06783
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  $5,499,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 6,729 Sq Ft

  L7&L8 Willow Brook Dr, Roxbury, CT 06783

  New Construction Opportunity - Custom Estate on 20+ Acres in Roxbury, CT - Designed and to be built by Havens Fine Homes and ARK Design Studio. Introducing a rare and extraordinary opportunity to own a fully custom, to-be-built estate on Lots 7 & 8 Willow Brook Drive in the heart of highly sought-after Roxbury, Connecticut. Perfectly sited at the edge of the wood line, this exquisite new

  Ryan Bollard William Pitt Sotheby's Int'l

  L7&L8 Willow Brook Dr, Roxbury, CT 06783
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  $135,000 Sold Feb 28, 2025

  Lot Davenport Rd, Roxbury, CT 06783

  • Land
  • 7.25 Acres
  • $18,621 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 40 Days On Market

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

  Lot Davenport Rd, Roxbury, CT 06783
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  Est $1,566,553 Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 5,439 Sq Ft

  101 South St, Roxbury, CT 06783

  101 South St, Roxbury, CT 06783
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  /12

  $999,000

  • Land
  • 20.13 Acres
  • $49,627 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
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  $817,000 Sold Dec 19, 2025

  0 Good Hill Rd, Roxbury, CT 06783

  • Land
  • 65.79 Acres
  • $12,418 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 133 Days On Market

  Last Listing Agent Sindy Butkus Klemm Real Estate Inc

  0 Good Hill Rd, Roxbury, CT 06783
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  Est $599,127 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,501 Sq Ft

  44 Baker Rd, Roxbury, CT 06783

  44 Baker Rd, Roxbury, CT 06783
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  $750,000 Under Contract

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

  178 Baker Rd, Roxbury, CT 06783

  Welcome to the Truman Judson Historical Property. 2 homes on 11.36 private hillside acres overlooking the Shepaug River. House 1 is a beautifully restored 1,449 sq ft converted barn offering 1 bedroom, 1.5 baths, living room plus a large den. Rich in character, it features stone accent walls, exposed beams, custom built-ins, a brick wood-burning fireplace and an eat-in kitchen with island, new

  Maureen Maher Berkshire Hathaway NE Prop.

  178 Baker Rd, Roxbury, CT 06783
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  $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
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  Est $817,171 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  154 Transylvania Rd, Roxbury, CT 06783

  154 Transylvania Rd, Roxbury, CT 06783
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  /10

  $450,000

  • Land
  • 8.21 Acres
  • $54,811 per Acre

  31 Holmes Rd, Roxbury, CT 06783

  Peaceful 8.2-acre parcel located on a scenic, quiet road in Roxbury. Enveloped by mature hardwood forest with pockets of dappled sunlight and native fern understory, this magical setting offers both beauty and privacy. Set near the tri-town border of Roxbury, Washington, and Woodbury, the location offers easy access to all the amenities and charm of each town, including farmers markets, hiking

  Kathryn Bassett William Pitt Sotheby's Int'l

  31 Holmes Rd, Roxbury, CT 06783
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  $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 $622,608

  Last Listing Agent Amy Jeanfaivre Family Realty Group, LLC

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

  • 4 Beds
  • 2.5 Baths
  • 3,016 Sq Ft

  3 Southbury Rd, Roxbury, CT 06783

  3 Southbury Rd, Roxbury, CT 06783

Showing Results 41 - 80, Page 2 of 18