Roxbury, CT Homes

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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
• 

  $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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  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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  /39

  $2,572,500 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,559 Sq Ft

  277 Painter Hill Rd, Roxbury, CT 06783

  This beautifully renovated 1911 colonial blends timeless charm with modern comfort in one of Roxbury's most desirable locations. The main residence offers luxury living with 2-3 bedrooms, a media room, gourmet kitchen, formal dining room, and a screened porch. The newly built guest house includes 2 bedrooms and a spacious game room/cabana with fireplace. Enjoy Summer entertaining on the covered

  Stacey Matthews W. Raveis Lifestyles Realty

  277 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 $1,830,317

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  381 South St, Roxbury, CT 06783
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  Est $2,333,287 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

  $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. Over the past five years, the home has received numerous enhancements, including a new roof, remodeled kitchen with tile flooring, all-new Pella windows and doors, asphalt driveway, 5-zone LP boiler, central A/C unit, and more. The inviting interior centers around a dramatic two-story

  Sidney Nazario Coldwell Banker Realty

  24 Hickory Ln, Roxbury, CT 06783
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  $4,360,000 Sold Feb 03, 2025

  130 Tophet Rd, Roxbury, CT 06783

  • 5 Beds
  • 5.5 Baths
  • 3,500 Sq Ft
  • Built 2020

  Last Sold Summary

  • 25% Below List Price
  • $1,246/SF
  • 214 Days On Market

  Current Estimated Value $2,829,565

  Last Listing Agent Judith Auchincloss Klemm Real Estate Inc

  130 Tophet Rd, Roxbury, CT 06783
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  Est $1,274,106 Not Listed For Sale

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

  12 Old Roxbury Rd, Roxbury, CT 06783

  12 Old Roxbury Rd, Roxbury, CT 06783
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  /40

  $775,000 Under Contract

  • 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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  $1,400,000 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 $1,003,665 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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  /37

  $1,795,000

  • 4 Beds
  • 5 Baths
  • 6,169 Sq Ft

  31 Hickory Ln, Roxbury, CT 06783

  Beautiful property in highly desirable Roxbury neighborhood. Traditional colonial with double story portico set back from quiet lane in park like setting with mature trees and gardens, huge pool, fruit trees, plenty of space for animals, stable, paddock. Detached garage in addition to under house garage with plenty of possibilities for guest house, studio, office. Large woodshed and enclosed

  Philippa Malkin W. Raveis Lifestyles Realty

  31 Hickory Ln, 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 $992,195 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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  /35

  $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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  $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

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  30 Hickory Ln, Roxbury, CT 06783
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  Est $1,624,664 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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  /29

  $999,000

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  18 Tunnel Rd, Roxbury, CT 06783

  MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round pool -- all on the best rural Roxbury scenic dirt road with walking area along the Shepaug River and nearby historic farmhouses and land preserve. All minutes to The Mayflower. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open

  Peter Klemm Klemm Real Estate Inc

  18 Tunnel Rd, Roxbury, CT 06783
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  $1,600,000 Sold Dec 23, 2024

  15 E Woods Rd, Roxbury, CT 06783

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

  Last Sold Summary

  • 20% Below List Price
  • $292/SF
  • 189 Days On Market

  Last Listing Agent Peter Klemm Klemm Real Estate Inc

  15 E Woods Rd, Roxbury, CT 06783
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  Est $605,219 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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  /35

  $2,195,000

  • 5 Beds
  • 6 Baths
  • 5,113 Sq Ft

  88 Rucum Rd, Roxbury, CT 06783

  Located in picturesque Roxbury, CT-nestled in southern Litchfield County and under two hours from New York City-this exquisite barn-style residence offers the perfect blend of rustic charm and modern luxury. Set on 8 sprawling acres, the property features an expansive lawn, beautifully curated specimen plantings, and a sparkling pool with integrated spa-ideal for both relaxation and entertaining.

  Pels Matthews W. Raveis Lifestyles Realty

  88 Rucum Rd, 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 $1,903,850

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  27 Wakelee Rd, Roxbury, CT 06783
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  Est $806,343 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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  /39

  $735,000

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

  22 E Woods Rd, Roxbury, CT 06783

  Meander up the curved driveway to your secluded 6.89-acre lot with sunsets beyond compare. 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 finished rooms

  MaryAnne Betso Coldwell Banker Realty

  22 E Woods Rd, 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 $1,470,572

  Last Listing Agent Tanya Uhelsky RE/MAX RISE

  19 Good Hill Terrace, 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
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  /6

  $234,900

  • Land
  • 3 Acres
  • $78,300 per Acre

  307 North St, Roxbury, CT 06783

  Approved Building lot with DOT approval for the driveway. Peaceful wooded lot to build your weekend or forever home! Driveway has been roughed in and leads to the building site set back well from the road. Beautiful outcroppings, mature hardwoods, antique stone walls all set in a private rolling terrain. Survey, perc test and soil survey are available. Close to Washington and Roxbury centers

  Sindy Butkus Klemm Real Estate Inc

  307 North St, 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 $804,031

  Last Listing Agent Brandy Granata Coldwell Banker Realty

  8 Old Ln, Roxbury, CT 06783
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  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,087 Sq Ft

  294 North St, Roxbury, CT 06783

  294 North 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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  $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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  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,091 Sq Ft

  277 Southbury Rd, Roxbury, CT 06783

  277 Southbury Rd, Roxbury, CT 06783
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  /40

  $919,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,624 Sq Ft

  67 Transylvania Rd, Roxbury, CT 06783

  This place is a real gem! It needs some updates, but the structure is solid, and the property is beyond compare. It's set on over three gorgeous acres with beautiful stone walls and a private usable yard that's perfect for a pool. Extensive stonework is present on side steps, patios, and rear gardens, complemented by a stone breezeway connecting the 3-car garage to a side entry hall. The driveway

  Cathy Masi Flagpole Realty Inc

  67 Transylvania Rd, 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 $1,372,512 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,040 Sq Ft

  167 Tophet Rd, Roxbury, CT 06783

  167 Tophet Rd, Roxbury, CT 06783
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  /25

  $1,275,000

  • 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
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  $1,650,000 Sold Jan 16, 2025

  60 Good Hill Rd, Roxbury, CT 06783

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

  Last Sold Summary

  • $335/SF
  • 49 Days On Market

  Current Estimated Value $1,767,313

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  60 Good Hill Rd, Roxbury, CT 06783
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  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
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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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