Roxbury, CT Homes

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  /26

  $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
• 

  $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 $1,567,115

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  27 Wakelee Rd, Roxbury, CT 06783
• 

  Est $3,391,560

  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
• 

  

  

  /33

  $995,000

  $200K PRICE DROP

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

  45 Chalybes Rd, Roxbury, CT 06783

  Light-filled, modern living on a private nearly 3-acre corner lot - with room to grow. Set on a beautifully positioned corner parcel, this fully renovated home is defined by natural light and flexibility. Expansive windows and vaulted ceilings create a bright, open feel throughout the main living spaces, bringing in sunlight from multiple exposures and connecting the home to its surrounding

  Kathryn Bassett William Pitt Sotheby's Int'l

  45 Chalybes Rd, Roxbury, CT 06783
• 

  $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 $1,420,348

  Last Listing Agent Tanya Uhelsky RE/MAX RISE

  19 Good Hill Terrace, Roxbury, CT 06783
• 

  Est $1,672,841

  Not Listed For Sale

  49 Garnet Rd, Roxbury, CT 06783

  • 4 Beds
  • 4.5 Baths
  • 4,693 Sq Ft
  • Built 2016

  49 Garnet Rd, Roxbury, CT 06783

  Last Sold Summary

  • 409 Days On Market
• 

  

  /33

  $950,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,028 Sq Ft

  16 Jonathan Dr, Roxbury, CT 06783

  This is a wonderful well cared for country home in the beautiful small town of Roxbury. Situated on this dead end road you are minutes to local amenities. Take advantage of nearby hiking trails, parks and open space with Southbury, Bridgewater, Washington and Woodbury town centers just a short drive away. Only 90 minutes from NYC. The first floor has two fireplaces and is open and spacious with

  Joyce Drakeley Drakeley Real Estate, Inc.

  16 Jonathan Dr, Roxbury, CT 06783
• 

  $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
• 

  Est $933,624

  Not Listed For Sale

  195 Painter Hill Rd, Roxbury, CT 06783

  • 2 Beds
  • 2.5 Baths
  • 2,322 Sq Ft
  • Built 1980

  195 Painter Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • 30 Days On Market
• 

  

  /5

  $399,000

  • Land
  • 4.01 Acres
  • $99,501 per Acre

  Lot 1 Chalybes Rd W, Roxbury, CT 06783

  Private, Rural setting within a short walk to Roxbury Tennis courts, library and the Roxbury Market.This 4.01 acre approved building lot offers the perfect blend of tranquility and convenience, making it an exceptional opportunity to create your custom dream home. Tucked away on a quiet road, this property features beautiful, light woods that provide a serene and private setting. Enjoy the best

  Kathryn Clair William Pitt Sotheby's Int'l

  Lot 1 Chalybes Rd W, Roxbury, CT 06783
• 

  $1,400,000

  Sold Jun 09, 2026

  315 North St, Roxbury, CT 06783

  • 4 Beds
  • 4 Baths
  • 2,420 Sq Ft
  • Built 1966

  Last Sold Summary

  • 8% Above List Price
  • $579/SF
  • 28 Days On Market

  Current Estimated Value $1,138,375

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

  315 North St, Roxbury, CT 06783
• 

  Est $835,334

  Not Listed For Sale

  201 Painter Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • Built 1966

  201 Painter Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • 146 Days On Market
• 

  

  /25

  $799,000

  $50K PRICE DROP Pending

  • 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
• 

  $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
• 

  Est $809,742

  Not Listed For Sale

  112 Southbury Rd, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 2,249 Sq Ft
  • Built 1983

  112 Southbury Rd, Roxbury, CT 06783

  Last Sold Summary

  • 60 Days On Market
• 

  

  /35

  $1,795,000

  • 5 Beds
  • 6 Baths
  • 5,447 Sq Ft

  233 Southbury Rd, Roxbury, CT 06783

  Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand

  Kathryn Clair William Pitt Sotheby's Int'l

  233 Southbury Rd, 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 $615,806

  Last Listing Agent Amy Jeanfaivre Family Realty Group, LLC

  79 Wellers Bridge Rd, Roxbury, CT 06783
• 

  Est $1,006,849

  Not Listed For Sale

  27 Mine Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft
  • Built 1974

  27 Mine Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • 86 Days On Market
• 

  

  /22

  $1,095,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,031 Sq Ft

  246 North St, Roxbury, CT 06783

  Juniper Hill offers masterfully updated one level living in Roxbury, Connecticut. Dubbed a "Little Gem on the Hill" in Country Home, this unassuming ranch has been elevated with chic, yet family friendly styling. Modern comforts combine with country character in a home situated on compelling terrain. Kelly + Co Design awarded Best Interior Designer Small Home/Cottage, 2020, CT Cottage and Gardens

  Fred Bond William Pitt Sotheby's Int'l

  246 North St, Roxbury, CT 06783
• 

  $2,547,500

  Sold Jan 30, 2026

  277 Painter Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,559 Sq Ft
  • Built 1911

  Last Sold Summary

  • 1% Below List Price
  • $996/SF
  • 28 Days On Market

  Current Estimated Value $2,508,328

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  277 Painter Hill Rd, Roxbury, CT 06783
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  Not Listed For Sale

  257 Southbury Rd, Roxbury, CT 06783

  • 3 Beds
  • 3 Baths
  • 3,086 Sq Ft
  • Built 1989

  257 Southbury Rd, Roxbury, CT 06783

  Last Sold Summary

  • 75 Days On Market
• 

  

  /40

  $1,375,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,620 Sq Ft

  56 Gold Mine Rd, Roxbury, CT 06783

  This cross gabled farmhouse was built in 2006 by its artisan craftsman owner, expanding upon the original foundation of a dwelling previously occupied by the caretaker of Arthur Miller's residence. The home was designed to leverage distant views east that stretch across thousands of acres of forested land to ridgelines in the towns of Woodbury and Bethlehem. The owner harvested and milled trees

  Fred Bond William Pitt Sotheby's Int'l

  56 Gold Mine 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

  Current Estimated Value $2,738,127

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  Unlisted Address
• 

  Est $2,243,582

  Not Listed For Sale

  130 Tophet Rd, Roxbury, CT 06783

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

  130 Tophet Rd, Roxbury, CT 06783

  Last Sold Summary

  • 214 Days On Market
• 

  

  /31

  $725,000

  • 5 Beds
  • 3 Baths
  • 1,365 Sq Ft

  50 Southbury Rd, Roxbury, CT 06783

  Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. At its

  Jeff Phillips William Pitt Sotheby's Int'l

  50 Southbury Rd, Roxbury, CT 06783
• 

  $754,500

  Sold Feb 11, 2026

  118 Chalybes Rd W, Roxbury, CT 06783

  • 6 Beds
  • 5 Baths
  • 4,260 Sq Ft
  • Built 1730

  Last Sold Summary

  • 16% Below List Price
  • $177/SF
  • 558 Days On Market

  Last Listing Agent Catherine Aaron Berkshire Hathaway NE Prop.

  118 Chalybes Rd W, Roxbury, CT 06783
• 

  Not Listed For Sale

  24 Baker Rd, Roxbury, CT 06783

  • 5 Beds
  • 2.5 Baths
  • 2,341 Sq Ft
  • Built 1900

  24 Baker Rd, Roxbury, CT 06783

  Last Sold Summary

  • 40 Days On Market
• 

  

  /8

  $250,000

  • Land
  • 3 Acres
  • $83,333 per Acre

  307 North St, Roxbury, CT 06783

  Approved Building lot with DOT approval for the driveway. 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. Peaceful wooded lot to build your weekend or forever home! Close to Washington and Roxbury centers

  Sindy Butkus Klemm Real Estate Inc

  307 North St, Roxbury, CT 06783
• 

  $610,000

  Sold Apr 17, 2026

  22 E Woods Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 3,476 Sq Ft
  • Built 1972

  Last Sold Summary

  • 11% Below List Price
  • $175/SF
  • 35 Days On Market

  Current Estimated Value $639,943

  Last Listing Agent MaryAnne Betso Coldwell Banker Realty

  22 E Woods Rd, Roxbury, CT 06783
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  Not Listed For Sale

  13 Evergreen Dr, Roxbury, CT 06783

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

  13 Evergreen Dr, Roxbury, CT 06783

  Last Sold Summary

  • 322 Days On Market
• 

  /2

  $1,200,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  11 Evergreen Dr, Roxbury, CT 06783

  This is 'the best deal in Roxbury"! New construction on 3.39 acre lot. The style is a classic farmhouse design Cape with a covered front porch with metal roof. There will be 9' ceiling height on the main level and 8' on the upper level. Both levels will have wood floors. The primary suite is on the main level with a large bath including a shower a free standing tub and a walk in closet. The

  Sharon McGuire William Pitt Sotheby's Int'l

  11 Evergreen Dr, 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 $1,389,721

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  88 Hemlock Rd, Roxbury, CT 06783
• 

  Est $2,091,651

  Not Listed For Sale

  98 Bacon Rd, Roxbury, CT 06783

  • 4 Beds
  • 5 Baths
  • 4,559 Sq Ft
  • Built 1996

  98 Bacon Rd, Roxbury, CT 06783

  Last Sold Summary

  • 77 Days On Market
• 

  

  /35

  $1,000,000

  $50K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,696 Sq Ft

  28 Garnet Rd, Roxbury, CT 06783

  Discover modern serenity in this private contemporary retreat nestled on 3.44 private acres. The ascending driveway assures a sense of quiet and seclusion, leading you to a home bathed in natural light from a soaring two-story wall of south-facing windows, this home perfectly blends architectural drama with a peaceful woodland backdrop. The exterior features an expansive, brand new composite deck

  Lisa Rollins Team Compass Connecticut, LLC

  28 Garnet 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 $2,493,790

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  18 Mallory Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  108 Davenport Rd, Roxbury, CT 06783

  • 4 Beds
  • 5.5 Baths
  • 5,100 Sq Ft
  • Built 1851

  108 Davenport Rd, Roxbury, CT 06783

  Last Sold Summary

  • 63 Days On Market
• 

  

  /35

  $3,650,000

  $850K PRICE DROP Under Contract

  • 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
• 

  $808,000

  Sold Mar 11, 2026

  178 Baker Rd, Roxbury, CT 06783

  • 1 Bed
  • 1.5 Baths
  • 1,449 Sq Ft
  • Built 1804

  Last Sold Summary

  • 8% Above List Price
  • $558/SF
  • 49 Days On Market

  Last Listing Agent Maureen Maher Berkshire Hathaway NE Prop.

  178 Baker Rd, Roxbury, CT 06783
• 

  Est $962,988

  Not Listed For Sale

  80 Transylvania Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 3,088 Sq Ft
  • Built 1999

  80 Transylvania Rd, Roxbury, CT 06783

  Last Sold Summary

  • 195 Days On Market
• 

  

  /25

  $1,095,000

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

  23 Painter Hill Rd, Roxbury, CT 06783

  Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must See!

  Peter Klemm Klemm Real Estate Inc

  23 Painter Hill Rd, Roxbury, CT 06783

Showing Results 41 - 80, Page 2 of 18