Roxbury, CT Homes

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  /40

  $1,235,000

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

  22 E Woods Rd, Roxbury, CT 06783

  Completely reimagined from top to bottom, 22 E. Woods Rd. is a home where elevated design meets everyday comfort. From the moment you step inside, gleaming hardwood floors, abundant natural light, and an inviting open floor plan create a warm and welcoming atmosphere that feels equally suited to quiet mornings and lively gatherings. At the heart of the home is a stunning custom kitchen featuring

  Andy Sachs Compass Connecticut, LLC

  22 E Woods 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 $993,043

  Last Listing Agent Cathy Masi Flagpole Realty Inc

  67 Transylvania Rd, Roxbury, CT 06783
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  /40

  Est $1,042,026

  Not Listed For Sale

  336 South St, Roxbury, CT 06783

  • 4 Beds
  • 2.5 Baths
  • 2,556 Sq Ft
  • Built 1989

  336 South St, Roxbury, CT 06783

  Last Sold Summary

  Last Listing Agent Karen Gilmore Redfin Corporation
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  /40

  $1,920,000

  $555K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,874 Sq Ft

  1030 Washington Woodbury Rd, Roxbury, CT 06783

  NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong

  Judith Auchincloss Klemm Real Estate Inc

  1030 Washington Woodbury Rd, Roxbury, CT 06783
• 

  $1,650,000

  Sold Oct 23, 2025

  78 Garnet Rd, Roxbury, CT 06783

  • 3 Beds
  • 3.5 Baths
  • 3,302 Sq Ft
  • Built 1991

  Last Sold Summary

  • 1% Below List Price
  • $500/SF
  • 23 Days On Market

  Last Listing Agent Andrew Murphy E.J. Murphy Realty

  78 Garnet Rd, Roxbury, CT 06783
• 

  Est $506,554

  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

  • 160 Days On Market

  Last Listing Agent Maria Taylor 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
• 

  $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 $989,382

  Last Listing Agent Ann Gerschefski William Raveis Real Estate

  34 Bacon Rd, Roxbury, CT 06783
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  Est $1,388,732

  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

  • 238 Days On Market

  Last Listing Agent Brian Gee Brian Gee Real Estate LLC
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  /38

  $1,495,000

  $240K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 6,395 Sq Ft

  99 Carriage Ln, Roxbury, CT 06783

  Welcome to 99 Carriage Lane, a private Roxbury estate offering over 6,000 square feet of refined living space, exceptional privacy on nearly four acres, and the opportunity to create a true resort-style outdoor retreat with approved pool plans. Set at the end of a quiet cul-de-sac, this beautifully renovated residence blends timeless architectural details with modern amenities and sophisticated

  Debra Tricarico Houlihan Lawrence

  99 Carriage Ln, 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 $664,995

  Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

  55 Mallory Rd, Roxbury, CT 06783
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  Est $709,591

  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

  • 182 Days On Market

  Last Listing Agent Judith Auchincloss Klemm Real Estate Inc
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  /27

  $3,995,000

  • 5 Beds
  • 5.5 Baths
  • 7,121 Sq Ft

  47 Squire Rd, Roxbury, CT 06783

  A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms

  Maria Taylor Klemm Real Estate Inc

  47 Squire Rd, Roxbury, CT 06783
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  $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 $331,965

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  67 Botsford Hill Rd, Roxbury, CT 06783
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  Est $1,513,103

  Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 4 Baths
  • 3,337 Sq Ft
  • Built 1998

  Unlisted Address

  Last Sold Summary

  • 204 Days On Market

  Last Listing Agent Donna J. Matula William Raveis Real Estate
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  /36

  $995,000

  $200K PRICE DROP Pending

  • 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
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  $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 $609,346

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

  322 North St, Roxbury, CT 06783
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  Est $1,373,699

  Not Listed For Sale

  235 North St, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 3,379 Sq Ft
  • Built 1980

  235 North St, Roxbury, CT 06783

  Last Sold Summary

  • 295 Days On Market

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty
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  /40

  $1,495,000

  $105K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,452 Sq Ft

  380 Southbury Rd, Roxbury, CT 06783

  Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray

  ROSEANN BLANTON Berkshire Hathaway NE Prop.

  380 Southbury Rd, Roxbury, CT 06783
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  $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
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  Est $1,303,537

  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

  • 256 Days On Market

  Last Listing Agent Jill Sloane Brown Harris Stevens
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  /20

  $1,269,000

  $31K PRICE DROP

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

  85 Good Hill Rd, Roxbury, CT 06783

  Completely remodeled 3 bedroom, 2.5 bath open concept home, with two fireplaces (one with wood burning insert), kitchen with stainless appliances, granite counters and large island. Property is private - boarders 18 acre land trust and farm land. Gunite pool (propane heater) with pavilion and fire pit for entertaining. Hot tub off main bedroom patio. Property features stone walls, steps and

  Jason Saphire www.HomeZu.com

  85 Good Hill Rd, Roxbury, CT 06783
• 

  $912,500

  Sold Nov 19, 2025

  11 Hodge Rd, Roxbury, CT 06783

  • 4 Beds
  • 3 Baths
  • 2,982 Sq Ft
  • Built 1851

  Last Sold Summary

  • 30% Below List Price
  • $306/SF
  • 141 Days On Market

  Current Estimated Value $990,889

  Last Listing Agent Karen Casey William Pitt Sotheby's Int'l

  11 Hodge Rd, Roxbury, CT 06783
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  Est $2,832,408

  Not Listed For Sale

  42 Berry Rd, Roxbury, CT 06783

  • 4 Beds
  • 5.5 Baths
  • 3,043 Sq Ft
  • Built 2018

  42 Berry Rd, Roxbury, CT 06783

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Graham Klemm Klemm Real Estate Inc
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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
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  Est $802,316

  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

  • 96 Days On Market

  Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty
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  /29

  $995,000

  $104K PRICE DROP

  • 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 Spa 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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  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

  • 138 Days On Market

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
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  /29

  $589,990

  Open House 8/23 Coming Soon

  • 3 Beds
  • 3 Baths
  • 1,248 Sq Ft

  21 Carriage Ln, Roxbury, CT 06783

  Coming Soon! A former artist retreat is waiting for you! This Ranch/Rambler style home boasts an open concept with vaulted ceilings. Enjoy all the privacy that Roxbury and the Litchfield Hills offers, yet have convenient access to major highways. The home offers 3 bedrooms and 3 full baths. There is opportunity to convert the lower level into a in-law space should you desire. The outdoor space is

  Frank Durante William Raveis Real Estate

  21 Carriage Ln, Roxbury, CT 06783
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  Est $1,334,446

  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

  • 392 Days On Market

  Last Listing Agent GRACE FRANJOLA Berkshire Hathaway NE Prop.
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  /33

  $618,000

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft

  188 Bacon Rd, Roxbury, CT 06783

  Best Litchfield County Opportunity! Escape to your own peaceful country retreat with the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. Less than 2 hours from NYC, this home has lots of character and a flexible layout with 2 bedrooms, 2 full bathrooms plus an upper level guest room/office/rec room. Main floor layout with separate spaces set up well for

  William Bolls Compass Connecticut, LLC

  188 Bacon Rd, Roxbury, CT 06783
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  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

  • 65 Days On Market

  Last Listing Agent Claire Maestroni W. Raveis Lifestyles Realty
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  /25

  $649,719

  $235K PRICE DROP Pending

  • 2 Beds
  • 1.5 Baths
  • 1,990 Sq Ft

  94 Judds Bridge Rd, Roxbury, CT 06783

  Compelling opportunity nestled in the heart of Roxbury's coveted Battleswamp and Mine Hill Preserve area. This remarkable 8.9 acre property features approximately four acres of open meadows, dramatic stone outcroppings, sweeping lawns, woodland privacy and natural beauty. Extensive road frontage- over 800ft along the most peaceful pristine roads- enjoy walking paths, bike rides. This setting

  WENDY WESTCOTT W. Raveis Lifestyles Realty

  94 Judds Bridge Rd, Roxbury, CT 06783
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  Est $587,756

  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

  • 12 Days On Market

  Last Listing Agent Karan Garewal Winwin Realty
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  /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
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  Est $1,271,072

  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

  • 57 Days On Market

  Last Listing Agent Todd Sargent Coldwell Banker Realty
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  /7

  $269,500

  $6K PRICE DROP

  • Land
  • 3.02 Acres
  • $89,238 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
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  Est $883,114

  Not Listed For Sale

  8 Old Ln, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft
  • Built 2006

  8 Old Ln, Roxbury, CT 06783

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Brandy Granata Coldwell Banker Realty
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  /27

  $1,499,000

  $150K 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
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  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

  • 361 Days On Market

  Last Listing Agent Rick Distel Compass Connecticut, LLC

Showing Results 81 - 120, Page 3 of 18