1,372

Roxbury, CT Homes

Section Image
  • 0 Southbury Rd, Roxbury, CT 06783
    0 Southbury Rd, Roxbury, CT 06783
    0 Southbury Rd, Roxbury, CT 06783
    /3

    $425,000

    • Land
    • 6.71 Acres
    • $63,338 per Acre

    0 Southbury Rd, Roxbury, CT 06783

    Rare in the Litchfield Hills-a flat, lightly wooded 6.71-acre buildable lot with a stream and stone walls. Perc'd for a spacious 4 bedroom custom home, and potential for a long private driveway. Perc's are 20 years old may have to be redone based on your plan.

    Jeff Phillips William Pitt Sotheby's Int'l

    0 Southbury Rd, Roxbury, CT 06783
    • 177 Bacon Rd, Roxbury, CT 06783

      Est $938,216

      Not Listed For Sale

      177 Bacon Rd, Roxbury, CT 06783

      • 3 Beds
      • 3 Baths
      • 2,450 Sq Ft
      • Built 1985
      177 Bacon Rd, Roxbury, CT 06783

      Last Sold Summary

      • 229 Days On Market

  • 0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    /7

    $274,500

    • Land
    • 3.02 Acres
    • $90,894 per Acre

    0 Booth Rd, Roxbury, CT 06783

    Get away to the Country! Such a peaceful location to build your dream home. Lightly traveled road. All of nature loves the location, so will you!

    Sindy Butkus Klemm Real Estate Inc

    0 Booth Rd, Roxbury, CT 06783
    • 7 Wakelee Rd, Roxbury, CT 06783

      Est $1,335,180

      Not Listed For Sale

      7 Wakelee Rd, Roxbury, CT 06783

      • 4 Beds
      • 2.5 Baths
      • 2,575 Sq Ft
      • Built 1998
      7 Wakelee Rd, Roxbury, CT 06783

      Last Sold Summary

      • 20 Days On Market

  • 33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    /27

    $1,595,000

    $54K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,716 Sq Ft

    33 Sentry Hill Rd, Roxbury, CT 06783

    Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room,

    Peter Klemm Klemm Real Estate Inc

    33 Sentry Hill Rd, Roxbury, CT 06783
    • Unlisted Address

      Not Listed For Sale

      Unlisted Address

      • 3 Beds
      • 3.5 Baths
      • 3,698 Sq Ft
      • Built 1792
      Unlisted Address

      Last Sold Summary

      • 40 Days On Market

  • 204 North St Unit Lot 3, Roxbury, CT 06783
    204 North St Unit Lot 3, Roxbury, CT 06783
    204 North St Unit Lot 3, Roxbury, CT 06783
    /16

    $775,000

    • Land
    • 26.68 Acres
    • $29,048 per Acre

    204 North St Unit Lot 3, Roxbury, CT 06783

    1st Time LISTED! LOT 3 at 204 North Street has 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 25 acre lot features un-touched historic stone walls, a beautiful stream flowing, gently

    Jill Sloane Brown Harris Stevens

    204 North St Unit Lot 3, Roxbury, CT 06783
    • 68 Carriage Ln, Roxbury, CT 06783

      Est $1,094,800

      Not Listed For Sale

      68 Carriage Ln, Roxbury, CT 06783

      • 5 Beds
      • 4.5 Baths
      • 4,102 Sq Ft
      • Built 2004
      68 Carriage Ln, Roxbury, CT 06783

      Last Sold Summary

      • 129 Days On Market

  • 25 Highmeadow Ln, Roxbury, CT 06783
    25 Highmeadow Ln, Roxbury, CT 06783
    25 Highmeadow Ln, Roxbury, CT 06783
    /40

    $1,795,000

    • 4 Beds
    • 4 Baths
    • 4,310 Sq Ft

    25 Highmeadow Ln, Roxbury, CT 06783

    Sprawling 4-bedroom colonial as part of a peaceful and private 17-acre estate in desirable Roxbury, CT. Sighted well on open rolling lawns with sweeping sunrise/sunset views, this property offers country living with exceptional versatility. The sun-filled eat-in kitchen features has sliders that open to a jumbo 58' deck with awning and open views. Generous main-level spaces include a dramatic

    William Bolls Compass Connecticut, LLC

    25 Highmeadow Ln, Roxbury, CT 06783
    • 1 Church St, Roxbury, CT 06783

      Est $1,336,743

      Not Listed For Sale

      1 Church St, Roxbury, CT 06783

      • 4 Beds
      • 2.5 Baths
      • 3,666 Sq Ft
      • Built 1784
      1 Church St, Roxbury, CT 06783

      Last Sold Summary

      • 114 Days On Market

  • 18 Ranney Hill Rd, Roxbury, CT 06783
    18 Ranney Hill Rd, Roxbury, CT 06783
    18 Ranney Hill Rd, Roxbury, CT 06783
    /34

    $2,000,000

    Open Sat 12PM - 2PM
    • 4 Beds
    • 3.5 Baths
    • 3,198 Sq Ft

    18 Ranney Hill Rd, Roxbury, CT 06783

    Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble

    Sharon McGuire William Pitt Sotheby's Int'l

    18 Ranney Hill Rd, Roxbury, CT 06783
  • 11 Ravenrock, Roxbury, CT 06783
    11 Ravenrock, Roxbury, CT 06783
    11 Ravenrock, Roxbury, CT 06783
    /34

    $3,395,000

    $1M PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 7,063 Sq Ft

    11 Ravenrock, Roxbury, CT 06783

    A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in the beautiful Litchfield Hills with spectacular views that go on for miles. This property includes a four bedroom, five and a half bath main residence, in ground heated Gunite pool, tennis court, one-bedroom caretaker's apartment over a 3-bay garage, two bedroom guest apartment and greenhouse. This compound

    Maria Taylor Klemm Real Estate Inc

    11 Ravenrock, Roxbury, CT 06783
  • 20 Wellers Bridge Rd, Roxbury, CT 06783
    20 Wellers Bridge Rd, Roxbury, CT 06783
    20 Wellers Bridge Rd, Roxbury, CT 06783
    /20

    $725,000

    • 3 Beds
    • 2.5 Baths
    • 2,059 Sq Ft

    20 Wellers Bridge Rd, Roxbury, CT 06783

    This handsome 1820's Colonial, set behind large shade trees on 1.33 acres just off the Green, is an easy walk to the Library, Booth School, Apple Lane Park, Churches, Tennis courts, and a morning cuppa at the Roxbury Market. Major renovation in 2018 included New HVAC, New wiring, Rebuilt Porch and more. New Well installed dedicated to this property replaced shared source. Interior makeover

    WAYNE PISKURA Klemm Real Estate Inc

    20 Wellers Bridge Rd, Roxbury, CT 06783
  • 216 Baker Rd, Roxbury, CT 06783
    216 Baker Rd, Roxbury, CT 06783
    216 Baker Rd, Roxbury, CT 06783
    /33

    $679,000

    $10K PRICE DROP
    • 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
    • 15 Farm Rd, Roxbury, CT 06783

      Est $2,200,718

      Not Listed For Sale

      15 Farm Rd, Roxbury, CT 06783

      • 4 Beds
      • 5 Baths
      • 4,337 Sq Ft
      • Built 1995
      15 Farm Rd, Roxbury, CT 06783

      Last Sold Summary

      • 83 Days On Market

    • 24 Roxbury Rd, Woodbury, CT 06798

      Est $1,143,319

      Not Listed For Sale

      24 Roxbury Rd, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 4,012 Sq Ft
      • Built 1987
      24 Roxbury Rd, Woodbury, CT 06798

      Last Sold Summary

      • 313 Days On Market

    • 52 Welton Rd, Roxbury, CT 06783

      Est $1,456,897

      Not Listed For Sale

      52 Welton Rd, Roxbury, CT 06783

      • 4 Beds
      • 3.5 Baths
      • 3,233 Sq Ft
      • Built 2021
      52 Welton Rd, Roxbury, CT 06783

      Last Sold Summary

      • 323 Days On Market

    • 92 Hemlock Rd, Roxbury, CT 06783

      Est $1,465,126

      Not Listed For Sale

      92 Hemlock Rd, Roxbury, CT 06783

      • 4 Beds
      • 5 Baths
      • 3,600 Sq Ft
      • Built 2023
      92 Hemlock Rd, Roxbury, CT 06783

      Last Sold Summary

      • 175 Days On Market

Showing Results 121 - 160, Page 4 of 18

Connecticut Litchfield County Roxbury

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group