Roxbury, CT Homes

• 

  $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 $916,663

  Last Listing Agent Melissa Karaffa William Raveis Real Estate

  88 Mallory Rd, Roxbury, CT 06783
• 

  Est $465,321

  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
• 

  

  

  /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
• 

  $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 $888,988

  Last Listing Agent Cathy Masi Flagpole Realty Inc

  67 Transylvania Rd, Roxbury, CT 06783
• 

  Est $1,443,650

  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
• 

  

  /40

  $1,995,000

  $480K 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
• 

  $1,378,000

  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 $1,313,030

  Last Listing Agent William Bolls Compass Connecticut, LLC

  22 Highmeadow Ln, Roxbury, CT 06783
• 

  Est $691,709

  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
• 

  

  /37

  $1,685,000

  $110K PRICE DROP Pending

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

  31 Hickory Ln, Roxbury, CT 06783

  This special home is located in one of Roxbury's most desirable neighborhoods on a quiet dead end road. A long, winding & very private driveway leads up to the commanding double-story porticoed entrance. The traditional colonial layout includes a central chef's kitchen which rests between the formal living, media & dining rooms. The main floor is completed by an office, 2 half baths, and a 2-room

  Philippa Malkin W. Raveis Lifestyles Realty

  31 Hickory Ln, 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 $958,985

  Last Listing Agent Ann Gerschefski William Raveis Real Estate

  34 Bacon Rd, Roxbury, CT 06783
• 

  Est $1,408,998

  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
• 

  

  /35

  $2,045,000

  $150K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 5,113 Sq Ft

  88 Rucum Rd, Roxbury, CT 06783

  Located in picturesque Roxbury, CT-nestled in southern Litchfield County and under two hours from New York City-this exquisite barn-style residence offers the perfect blend of rustic charm and modern luxury. Set on 8 sprawling acres, the property features an expansive lawn, beautifully curated specimen plantings, and a sparkling pool with integrated spa-ideal for both relaxation and entertaining.

  Pels Matthews W. Raveis Lifestyles Realty

  88 Rucum Rd, 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 $629,659

  Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

  55 Mallory Rd, Roxbury, CT 06783
• 

  Est $1,273,750

  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
• 

  

  /37

  $2,395,000

  Pending

  • 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
• 

  $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 $2,077,000

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  67 Botsford Hill Rd, Roxbury, CT 06783
• 

  Est $1,235,677

  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
• 

  

  /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
• 

  $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 $566,015

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

  322 North St, Roxbury, CT 06783
• 

  Est $2,860,009

  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
• 

  

  /38

  $1,495,000

  $240K PRICE DROP

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

  99 Carriage Ln, Roxbury, CT 06783

  Looking to escape the hectic pace of city life? Welcome to this peaceful, beautifully renovated 4-bedroom home, originally built in 2005, offering the perfect blend of comfort and tranquility. Featuring 2.5 baths and a spacious open-concept living and dining area, this home is ideal for hosting gatherings and entertaining with ease. The modern kitchen is a dream for any home chef, complete with

  Debra Tricarico Houlihan Lawrence

  99 Carriage Ln, 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 $706,659

  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
• 

  

  /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
• 

  $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 $917,903

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

  11 Hodge Rd, Roxbury, CT 06783
• 

  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
• 

  

  /36

  $995,000

  $200K PRICE DROP

  • 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
• 

  Est $1,223,861

  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
• 

  

  /40

  $1,550,000

  $50K 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
• 

  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
• 

  

  /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
• 

  Est $553,937

  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
• 

  

  /29

  $1,049,000

  $50K 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
• 

  Est $1,151,637

  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
• 

  

  /33

  $1,500,000

  $180K PRICE DROP

  • 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
• 

  Est $779,931

  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
• 

  

  /33

  $618,000

  Open Sat 1PM - 2PM

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

  188 Bacon Rd, Roxbury, CT 06783

  Chic Country Cabin in Bucolic Litchfield County. Escape to your own peaceful retreat offering the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. 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. The living areas are ideal for relaxing or entertaining, and the kitchen has

  William Bolls Compass Connecticut, LLC

  188 Bacon Rd, 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

  • 361 Days On Market
• 

  

  /23

  $796,783

  $88K PRICE DROP

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

  94 Judds Bridge Rd, Roxbury, CT 06783

  Location! Once in a blue moon, a piece of property becomes available in one of the most desirable locations. This opportunity is on a quiet dirt road, with nearly 9 acres of privacy and tranquility in the Mine Hill Preserve area of Roxbury. One level cottage and two substantial barns. Enter through a field gate with a paved driveway, to this rural compound, tucked in, with rolling land and woods.

  WENDY WESTCOTT W. Raveis Lifestyles Realty

  94 Judds Bridge Rd, Roxbury, CT 06783
• 

  Est $1,285,451

  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

  • 28 Days On Market

Showing Results 81 - 120, Page 3 of 18