Homes in ZIP Code 06783

• 

  

  

  /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
• 

  $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 $685,062

  Last Listing Agent MaryAnne Betso Coldwell Banker Realty

  22 E Woods Rd, Roxbury, CT 06783
• 

  Est $434,698 Not Listed For Sale

  168 Baker Rd, Roxbury, CT 06783

  • 2 Beds
  • 2 Baths
  • 1,328 Sq Ft
  • Built 1788

  168 Baker Rd, Roxbury, CT 06783

  Last Sold Summary

  • 6% Above List Price
  • $309/SF
  • 160 Days On Market

  • Last Sold Price $410,000
  • Mar 18, 2025

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
• 

  

  

  /13

  $490,000

  • 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
• 

  $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 $1,445,283

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  88 Hemlock Rd, Roxbury, CT 06783
• 

  Est $1,587,030 Not Listed For Sale

  101 South St, Roxbury, CT 06783

  • 6 Beds
  • 6 Baths
  • 5,439 Sq Ft
  • Built 1980

  101 South St, Roxbury, CT 06783

  Last Sold Summary

  • 67% Above List Price
  • $175/SF
  • 238 Days On Market

  • Last Sold Price $951,000
  • Sep 01, 2023

  Last Listing Agent Brian Gee Brian Gee Real Estate LLC
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  /37

  $2,395,000

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

  77 Tophet Rd, Roxbury, CT 06783

  Roxbury Shingle-Style Gem with Sparkling Pool! This grand residence sits off one of Litchfield County's most treasured and bucolic roads amidst boldfaced names - past and present - and backing up to a 60-acre parcel of Roxbury Land Trust. Prepare to be "wowed" by the sun-flooded double height living room, gorgeous eat-in-kitchen, formal dining room, four-season sunroom, wood-paneled library/den,

  Rick Distel Compass Connecticut, LLC

  77 Tophet 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 $2,639,855

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  18 Mallory Rd, Roxbury, CT 06783
• 

  Est $694,386 Not Listed For Sale

  44 Baker Rd, Roxbury, CT 06783

  • 5 Beds
  • 2.5 Baths
  • 2,501 Sq Ft
  • Built 1962

  44 Baker Rd, Roxbury, CT 06783

  Last Sold Summary

  • 26% Above List Price
  • $220/SF
  • 182 Days On Market

  • Last Sold Price $550,000
  • Dec 09, 2024

  Last Listing Agent Judith Auchincloss Klemm Real Estate Inc
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  /12

  $2,000,000

  • Land
  • 26.48 Acres
  • $75,529 per Acre

  55 Ranney Hill Rd, Roxbury, CT 06783

  If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS!

  Sharon McGuire William Pitt Sotheby's Int'l

  55 Ranney Hill 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
• 

  Est $1,338,826 Not Listed For Sale

  36 Chalybes Rd, Roxbury, CT 06783

  • 4 Beds
  • 3 Baths
  • 4,572 Sq Ft
  • Built 1969

  36 Chalybes Rd, Roxbury, CT 06783

  Last Sold Summary

  • 5% Above List Price
  • $279/SF
  • 256 Days On Market

  • Last Sold Price $1,275,000
  • Apr 21, 2025

  Last Listing Agent Jill Sloane Brown Harris Stevens
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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
• 

  $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 $961,520

  Last Listing Agent Melissa Karaffa William Raveis Real Estate

  88 Mallory Rd, Roxbury, CT 06783
• 

  Est $751,899 Not Listed For Sale

  154 Transylvania Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,290 Sq Ft
  • Built 1987

  154 Transylvania Rd, Roxbury, CT 06783

  Last Sold Summary

  • 8% Above List Price
  • $305/SF
  • 96 Days On Market

  • Last Sold Price $699,000
  • Jun 28, 2024

  Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty
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  /31

  $950,000

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft

  50 Southbury Rd, Roxbury, CT 06783

  Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, and a separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway.

  Jeff Phillips William Pitt Sotheby's Int'l

  50 Southbury Rd, Roxbury, CT 06783
• 

  $895,000 Sold Jan 23, 2026

  67 Transylvania Rd, Roxbury, CT 06783

  • 4 Beds
  • 4 Baths
  • 3,624 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $247/SF
  • 65 Days On Market

  Current Estimated Value $895,562

  Last Listing Agent Cathy Masi Flagpole Realty Inc

  67 Transylvania Rd, Roxbury, CT 06783
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  Not Listed For Sale

  3 Southbury Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 3,016 Sq Ft
  • Built 1796

  3 Southbury Rd, Roxbury, CT 06783

  Last Sold Summary

  • $406/SF
  • 138 Days On Market

  • Last Sold Price $1,225,000
  • Oct 21, 2024

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
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  /36

  $1,049,000

  • 5 Beds
  • 5 Baths
  • 2,804 Sq Ft

  286 South St, Roxbury, CT 06783

  Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen.

  Kathryn Clair William Pitt Sotheby's Int'l

  286 South St, Roxbury, CT 06783
• 

  $1,378,000 Sold Jul 08, 2025

  22 Highmeadow Ln, Roxbury, CT 06783

  • 4 Beds
  • 4 Baths
  • 3,481 Sq Ft
  • Built 1985

  Last Sold Summary

  • $396/SF
  • 44 Days On Market

  Current Estimated Value $1,382,370

  Last Listing Agent William Bolls Compass Connecticut, LLC

  22 Highmeadow Ln, Roxbury, CT 06783
• 

  Est $1,230,798 Not Listed For Sale

  76 Davenport Rd, Roxbury, CT 06783

  • 2 Beds
  • 3 Baths
  • 2,445 Sq Ft
  • Built 1989

  76 Davenport Rd, Roxbury, CT 06783

  Last Sold Summary

  • 1% Below List Price
  • $507/SF
  • 392 Days On Market

  • Last Sold Price $1,240,000
  • Dec 30, 2024

  Last Listing Agent GRACE FRANJOLA Berkshire Hathaway Home Services
• 

  

  /20

  $499,000

  • Land
  • 8.64 Acres
  • $57,755 per Acre

  200 North St, Roxbury, CT 06783

  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 IS THE LAST AVAILABLE LOT FROM PHASE II, (LOT #1) AND IT MUST BE SEEN AND HEARD TO UNDERSTAND HOW YOUR FUTURE HEIRLOOM HOME WILL BE

  Jill Sloane Brown Harris Stevens

  200 North St, Roxbury, CT 06783
• 

  $959,000 Sold Mar 30, 2026

  34 Bacon Rd, Roxbury, CT 06783

  • 4 Beds
  • 4 Baths
  • 3,686 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Above List Price
  • $260/SF
  • 29 Days On Market

  Current Estimated Value $1,305,188

  Last Listing Agent Ann Gerschefski William Raveis Real Estate

  34 Bacon Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  294 North St, Roxbury, CT 06783

  • 3 Beds
  • 3.5 Baths
  • 3,087 Sq Ft
  • Built 1970

  294 North St, Roxbury, CT 06783

  Last Sold Summary

  • $421/SF
  • 65 Days On Market

  • Last Sold Price $1,300,000
  • Sep 06, 2024

  Last Listing Agent Claire Maestroni W. Raveis Lifestyles Realty
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  /13

  $985,000

  • 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
• 

  $615,000 Sold Mar 17, 2026

  55 Mallory Rd, Roxbury, CT 06783

  • 4 Beds
  • 3 Baths
  • 2,682 Sq Ft
  • Built 1995

  Last Sold Summary

  • 21% Below List Price
  • $229/SF
  • 176 Days On Market

  Current Estimated Value $602,497

  Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

  55 Mallory Rd, Roxbury, CT 06783
• 

  Est $568,596 Not Listed For Sale

  34 Spargo Rd, Roxbury, CT 06783

  • 2 Beds
  • 2 Baths
  • 2,321 Sq Ft
  • Built 1930

  34 Spargo Rd, Roxbury, CT 06783

  Last Sold Summary

  • 4% Above List Price
  • $235/SF
  • 12 Days On Market

  • Last Sold Price $545,000
  • Mar 19, 2025

  Last Listing Agent Karan Garewal Winwin Realty
• 

  

  /33

  $1,630,000

  • 3 Beds
  • 2.5 Baths
  • 2,440 Sq Ft

  85 Good Hill Rd, Roxbury, CT 06783

  At the end of a long, winding private driveway, this exceptional Roxbury estate offers total seclusion & tranquility-surrounded entirely by protected land trust. Just 2 miles from Roxbury Center and a scenic 2-hr drive from NYC, this rare property is the perfect country escape or full-time residence. The main home is in impeccable, move-in condition, featuring dramatic vaulted ceilings in both

  Pat Lahoud Lahoud William Pitt Sotheby's Int'l

  85 Good Hill Rd, Roxbury, CT 06783
• 

  $1,800,000 Sold Aug 28, 2025

  67 Botsford Hill Rd, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 4,800 Sq Ft
  • Built 1988

  Last Sold Summary

  • 18% Below List Price
  • $375/SF
  • 116 Days On Market

  Current Estimated Value $358,000

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  67 Botsford Hill Rd, Roxbury, CT 06783
• 

  Est $1,188,293 Not Listed For Sale

  277 Southbury Rd, Roxbury, CT 06783

  • 3 Beds
  • 3 Baths
  • 3,091 Sq Ft
  • Built 2007

  277 Southbury Rd, Roxbury, CT 06783

  Last Sold Summary

  • 3% Above List Price
  • $372/SF
  • 57 Days On Market

  • Last Sold Price $1,150,000
  • May 17, 2024

  Last Listing Agent Todd Sargent Coldwell Banker Realty
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  /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
• 

  $500,000 Sold Sep 05, 2025

  322 North St, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Above List Price
  • $358/SF
  • 84 Days On Market

  Current Estimated Value $599,167

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.

  322 North St, Roxbury, CT 06783
• 

  Not Listed For Sale

  19 Golden Harvest Rd, Roxbury, CT 06783

  • 4 Beds
  • 6 Baths
  • 5,808 Sq Ft
  • Built 1998

  19 Golden Harvest Rd, Roxbury, CT 06783

  Last Sold Summary

  • $478/SF
  • 361 Days On Market

  • Last Sold Price $2,775,000
  • May 03, 2024

  Last Listing Agent Rick Distel Compass Connecticut, LLC
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  /27

  $1,649,000

  • 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
• 

  $2,501,000 Sold Nov 21, 2025

  Unlisted Address

  • 5 Beds
  • 6 Baths
  • 8,091 Sq Ft
  • Built 2005

  Last Sold Summary

  • $309/SF
  • 88 Days On Market

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

  Unlisted Address
• 

  Est $1,349,220 Not Listed For Sale

  35 Painter Ridge Rd, Roxbury, CT 06783

  • 2 Beds
  • 3 Baths
  • 2,799 Sq Ft
  • Built 1980

  35 Painter Ridge Rd, Roxbury, CT 06783

  Last Sold Summary

  • 14% Below List Price
  • $557/SF
  • 28 Days On Market

  • Last Sold Price $1,560,000
  • Oct 18, 2024

  Last Listing Agent Peter Klemm Klemm Real Estate Inc
• 

  

  /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
• 

  $1,875,000 Sold Jun 04, 2025

  257 Southbury Rd, Roxbury, CT 06783

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

  Last Sold Summary

  • 6% Below List Price
  • $608/SF
  • 75 Days On Market

  Current Estimated Value $1,848,286

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  257 Southbury Rd, Roxbury, CT 06783
• 

  Est $884,805 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

  • 2% Below List Price
  • $367/SF
  • 229 Days On Market

  • Last Sold Price $900,000
  • Jan 15, 2025

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty
• 

  

  /40

  $1,795,000 Open Sat 12PM - 2PM

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

  25 Highmeadow Ln, Roxbury, CT 06783

  Fantastic opportunity to own an estate in bucolic southern Litchfield County, complete with saltwater gunite pool, open rolling lawns, sunrise/sunset views, and equestrian facilities. Spanning over 17 private acres, this property is anchored by a handsome 4-bedroom colonial home loaded with charm and lots of room to entertain. The eat-in kitchen is the heart of the home with a DCS stove, Sub-Zero

  William Bolls Compass Connecticut, LLC

  25 Highmeadow Ln, Roxbury, CT 06783

Showing Results 81 - 120, Page 3 of 18