1,355

Roxbury, CT Homes

Section Image
    • 49 Garnet Rd, Roxbury, CT 06783

      Est $1,771,278

      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

      Last Listing Agent Maureen Burmann William Raveis Real Estate

  • 268 South St, Roxbury, CT 06783
    268 South St, Roxbury, CT 06783
    268 South St, Roxbury, CT 06783
    /39

    $3,600,000

    • 5 Beds
    • 4.5 Baths
    • 6,190 Sq Ft

    268 South St, Roxbury, CT 06783

    Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite

    Peter Klemm Klemm Real Estate Inc

    268 South St, Roxbury, CT 06783
  • 27 Wakelee Rd, 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 $1,769,397

    Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

    27 Wakelee Rd, Roxbury, CT 06783
    • 195 Painter Hill Rd, Roxbury, CT 06783

      Est $998,792

      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

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

  • 297 Painter Hill Rd, Roxbury, CT 06783
    297 Painter Hill Rd, Roxbury, CT 06783
    297 Painter Hill Rd, Roxbury, CT 06783
    /38

    $4,495,000

    • 4 Beds
    • 7 Baths
    • 6,139 Sq Ft

    297 Painter Hill Rd, Roxbury, CT 06783

    Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room.

    Peter Klemm Klemm Real Estate Inc

    297 Painter Hill Rd, Roxbury, CT 06783
  • 19 Good Hill Terrace, 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 $1,498,486

    Last Listing Agent Tanya Uhelsky Century 21 AllPoints Realty

    19 Good Hill Terrace, Roxbury, CT 06783
    • 201 Painter Hill Rd, Roxbury, CT 06783

      Est $881,472

      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

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

  • 38 W Mountain Ln, Roxbury, CT 06783
    38 W Mountain Ln, Roxbury, CT 06783
    38 W Mountain Ln, Roxbury, CT 06783
    /26

    $760,000

    $35K PRICE DROP Under Contract
    • 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
  • 0 Good Hill Rd, 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
    • 112 Southbury Rd, Roxbury, CT 06783

      Est $848,433

      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

      Last Listing Agent Judith Auchincloss Klemm Real Estate Inc

  • Lot 1 Chalybes Rd W, Roxbury, CT 06783
    Lot 1 Chalybes Rd W, Roxbury, CT 06783
    Lot 1 Chalybes Rd W, Roxbury, CT 06783
    /10

    $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
  • 315 North St, 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 $1,378,784

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

    315 North St, Roxbury, CT 06783
    • 27 Mine Hill Rd, Roxbury, CT 06783

      Est $1,085,544

      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

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

  • 56 Gold Mine Rd, Roxbury, CT 06783
    56 Gold Mine Rd, Roxbury, CT 06783
    56 Gold Mine Rd, Roxbury, CT 06783
    /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
  • 253 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
    • 257 Southbury Rd, Roxbury, CT 06783

      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

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

  • 50 Southbury Rd, Roxbury, CT 06783
    50 Southbury Rd, Roxbury, CT 06783
    50 Southbury Rd, Roxbury, CT 06783
    /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
  • 277 Painter Hill Rd, 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 $2,613,557

    Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

    277 Painter Hill Rd, Roxbury, CT 06783
    • 130 Tophet Rd, Roxbury, CT 06783

      Est $2,447,368

      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

      Last Listing Agent Judith Auchincloss Klemm Real Estate Inc

  • 307 North St, Roxbury, CT 06783
    307 North St, Roxbury, CT 06783
    307 North St, Roxbury, CT 06783
    /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
  • Unlisted Address

    $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 $2,821,767

    Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

    Unlisted Address
    • 24 Baker Rd, 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

      Last Listing Agent Luis Sanchez eXp Realty

  • 11 Evergreen Dr, Roxbury, CT 06783
    11 Evergreen Dr, Roxbury, CT 06783
    /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
  • 118 Chalybes Rd W, 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
    • 22 Highmeadow Ln, Roxbury, CT 06783

      Est $1,351,103

      Not Listed For Sale

      22 Highmeadow Ln, Roxbury, CT 06783

      • 4 Beds
      • 4 Baths
      • 3,481 Sq Ft
      • Built 1985
      22 Highmeadow Ln, Roxbury, CT 06783

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent William Bolls Compass Connecticut, LLC

  • 28 Garnet Rd, Roxbury, CT 06783
    28 Garnet Rd, Roxbury, CT 06783
    28 Garnet Rd, Roxbury, CT 06783
    /35

    $950,000

    $100K 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
  • 31 Hickory Ln, Roxbury, CT 06783

    $1,600,000

    Sold Jul 20, 2026

    31 Hickory Ln, Roxbury, CT 06783

    • 4 Beds
    • 5 Baths
    • 6,169 Sq Ft
    • Built 1977

    Last Sold Summary

    • 11% Below List Price
    • $259/SF
    • 244 Days On Market

    Current Estimated Value $1,549,438

    Last Listing Agent Philippa Malkin W. Raveis Lifestyles Realty

    31 Hickory Ln, Roxbury, CT 06783
    • 13 Evergreen Dr, Roxbury, CT 06783

      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

      Last Listing Agent Graham Klemm Klemm Real Estate Inc

  • 8 Bayberry Hill, Roxbury, CT 06783
    8 Bayberry Hill, Roxbury, CT 06783
    8 Bayberry Hill, Roxbury, CT 06783
    /35

    $3,650,000

    $850K PRICE DROP Pending
    • 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
  • 18 Mallory 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 $2,604,166

    Last Listing Agent Graham Klemm Klemm Real Estate Inc

    18 Mallory Rd, Roxbury, CT 06783
    • 98 Bacon Rd, Roxbury, CT 06783

      Est $2,154,145

      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

      Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  • 77 Judds Bridge Rd, Roxbury, CT 06783
    77 Judds Bridge Rd, Roxbury, CT 06783
    77 Judds Bridge Rd, Roxbury, CT 06783
    /39

    $1,295,000

    • 4 Beds
    • 2.5 Baths
    • 2,901 Sq Ft

    77 Judds Bridge Rd, Roxbury, CT 06783

    A custom-designed Judds Bridge Colonial in a coveted location, privately set amid mature trees and established plantings. A dramatic double-height marble foyer introduces the home's beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned interiors include formal living and dining rooms, office or bonus room, an open and eat-in kitchen with solid cherry

    Joseph Lorino Klemm Real Estate Inc

    77 Judds Bridge Rd, Roxbury, CT 06783
  • 77 Tophet Rd, Roxbury, CT 06783

    $2,300,000

    Sold Jul 07, 2026

    77 Tophet Rd, Roxbury, CT 06783

    • 4 Beds
    • 4.5 Baths
    • 6,670 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $345/SF
    • 47 Days On Market

    Current Estimated Value $2,401,094

    Last Listing Agent Rick Distel Compass Connecticut, LLC

    77 Tophet Rd, Roxbury, CT 06783
    • 108 Davenport 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

      Last Listing Agent Richard Pomerantz William Pitt Sotheby's Int'l

  • 23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    /25

    $999,000

    $96K PRICE DROP
    • 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
  • 178 Baker Rd, 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
    • 12 Old Roxbury Rd, Roxbury, CT 06783

      Est $1,326,889

      Not Listed For Sale

      12 Old Roxbury Rd, Roxbury, CT 06783

      • 3 Beds
      • 2.5 Baths
      • 3,440 Sq Ft
      • Built 1987
      12 Old Roxbury Rd, Roxbury, CT 06783

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Karen Gilmore Redfin Corporation

  • 69 Moosehorn Rd, Roxbury, CT 06783
    69 Moosehorn Rd, Roxbury, CT 06783
    69 Moosehorn Rd, Roxbury, CT 06783
    /13

    $490,000

    $59K PRICE DROP
    • Land
    • 24.84 Acres
    • $19,726 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
  • 88 Mallory Rd, 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 $963,195

    Last Listing Agent Melissa Karaffa William Raveis Real Estate

    88 Mallory Rd, Roxbury, CT 06783
    • 80 Transylvania Rd, Roxbury, CT 06783

      Est $976,747

      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

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

Showing Results 41 - 80, Page 2 of 18

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