Roxbury, CT Homes

• 

  Est $1,584,307 Not Listed For Sale

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

  35 Painter Ridge Rd, Roxbury, CT 06783

  35 Painter Ridge Rd, Roxbury, CT 06783
• 

  

  

  /25

  $1,275,000

  • 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
• 

  $1,600,000 Sold Apr 11, 2025

  • 3,123 Sq Ft
  • $512/SF
  • 103 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2000

  130 E Flag Swamp Rd, Roxbury, CT 06783

  Offered on 34+/- acres subject to lot line revision. Abuts 100's of acres of conserved land. Long private driveway past pond to architect designed contemporary farmhouse with barn and workshop. Great room with privacy sliders allowing kitchen to be closed off if desired. Hidden media wall, views over lawn and stonewalls, modern wood stove in living room. Fabulous screen porch looking towards

  Pels Matthews W. Raveis Lifestyles Realty

  130 E Flag Swamp Rd, Roxbury, CT 06783
• 

  Est $1,431,499 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,575 Sq Ft

  7 Wakelee Rd, Roxbury, CT 06783

  7 Wakelee Rd, Roxbury, CT 06783
• 

  

  

  /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
• 

  $840,000 Sold Apr 03, 2025

  • 1,720 Sq Ft
  • $488/SF
  • 146 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  201 Painter Hill Rd, Roxbury, CT 06783

  Painter Hill Cottage, a delightful 3BDR, 2 Bath cottage with heated, Gunite pool. Here is an opportunity to take this home to the next level on one of the most desirable roads in Roxbury. It provides a light and bright interior with an easy-living, one-level floor plan. A new deck is under construction and will be completed on or before 12/30/24. Enjoy the morning sunrise and beautiful light

  Diana Bisselle William Pitt Sotheby's Int'l

  201 Painter Hill Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,698 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /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
• 

  $1,800,000 Sold Mar 26, 2025

  • 5,100 Sq Ft
  • $353/SF
  • 63 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1851

  108 Davenport Rd, Roxbury, CT 06783

  This is the perfect country getaway estate property, a vintage home that has been totally renovated in the 21st century. This 4BR home, 2BR guest house, heated in-ground pool with cabana and modern barn are privately sited on over 6 beautifully landscaped acres in the heart of charming Roxbury in the beautiful hills of Litchfield County. Take in the view of the property from your covered deck, or

  Richard Pomerantz William Pitt Sotheby's Int'l

  108 Davenport Rd, Roxbury, CT 06783
• 

  Est $716,994 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,940 Sq Ft

  3 Jonathan Dr, Roxbury, CT 06783

  3 Jonathan Dr, Roxbury, CT 06783
• 

  

  /22

  $399,000

  • Land
  • 4.01 Acres
  • $99,501 per Acre

  Lot 1 Chalybes Rd W, Roxbury, CT 06783

  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 of Roxbury's natural beauty and recreational amenities, with the lot located just minutes from the

  Kathryn Clair William Pitt Sotheby's Int'l

  Lot 1 Chalybes Rd W, Roxbury, CT 06783
• 

  $545,000 Sold Mar 19, 2025

  • 2,321 Sq Ft
  • $235/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1930

  34 Spargo Rd, Roxbury, CT 06783

  Roxbury Cape, beautiful property has Barn/Guest House, Pond, Inground Pool on Private with over 4.3 acres. Renovated and modernized; new heat pumps, new roof, new kitchen and baths. House has hardwood floors throughout, screened Porch and is close to town. Barn has semi finished first floor but is unusable currently having been damaged from fallen tree. Inground pool not maintained; barn and

  Karan Garewal Winwin Realty

  34 Spargo Rd, Roxbury, CT 06783
• 

  Est $1,886,278 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,801 Sq Ft

  80 Rocky Mountain Rd, Roxbury, CT 06783

  80 Rocky Mountain Rd, Roxbury, CT 06783
• 

  

  /25

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft

  242 Tophet Rd, Roxbury, CT 06783

  Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene

  Kathryn Clair William Pitt Sotheby's Int'l

  242 Tophet Rd, Roxbury, CT 06783
• 

  $410,000 Sold Mar 18, 2025

  • 1,328 Sq Ft
  • $309/SF
  • 160 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1788

  168 Baker Rd, Roxbury, CT 06783

  Built ca 1788, this petite and cozy antique boasts two original fireplaces on the main level and wide board wood floors on the second level. Loved by the current owner for the past 25 years, the home is charming and comfortable. The living room is flanked by built-in bookcases and has a Vermont Casting wood stove that warms the original section of the home. The eat-in kitchen is nicely sized with

  Maria Taylor Klemm Real Estate Inc

  168 Baker Rd, Roxbury, CT 06783
• 

  Est $1,410,366 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,666 Sq Ft

  1 Church St, Roxbury, CT 06783

  1 Church St, Roxbury, CT 06783
• 

  

  /20

  $479,000

  • Land
  • 8.64 Acres
  • $55,440 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
• 

  $735,000 Sold Mar 14, 2025

  • 2,345 Sq Ft
  • $313/SF
  • 91 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1800

  66 Bacon Rd, Roxbury, CT 06783

  Welcome to 66 and 68 Bacon Rd, where a new owner's vision and the opportunity to make a property their own intersect; self-sufficient, income producing, family compound, horse farm with access Roxbury's bountiful trail-riding, organic farm, weekender's retreat, workshops for equipment, motorcycles, mountain bikes, an authentic, exciting moment to create your own country home. Originally, the

  William Whitehead Berkshire Hathaway NE Prop.

  66 Bacon Rd, Roxbury, CT 06783
• 

  Est $1,629,779 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,900 Sq Ft

  87 South St, Roxbury, CT 06783

  87 South St, Roxbury, CT 06783
• 

  

  /39

  $735,000

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

  22 E Woods Rd, Roxbury, CT 06783

  Meander up the curved driveway to your secluded 6.89-acre lot with sunsets beyond compare. This home needs updates, however is a tremendous opportunity to live in Roxbury CT, with 3,476 Sq feet, 11 rooms, 4 bedrooms on upper level, boasting hardwood flooring & large closets. Primary suite has large walk-in shower stall & two walk-in closets. Many possibilities with the two large finished rooms

  MaryAnne Betso Coldwell Banker Realty

  22 E Woods Rd, Roxbury, CT 06783
• 

  $856,900 Sold Mar 04, 2025

  • 2,322 Sq Ft
  • $369/SF
  • 30 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1980

  195 Painter Hill Rd, Roxbury, CT 06783

  Highest and best by this Thursday, January 23, 2025 by 3pm.Discover the essence of Zen in this 'in vogue', renovated 2 bedroom, 2.5 bath home. The Zen house is located off of a quiet and scenic country road in Roxbury, CT. This extraordinary one-level house is a masterpiece of tranquility. Designed by the world-renowned architect, Yann Weymouth, the house possesses light-filled rooms illuminated

  Diana Bisselle William Pitt Sotheby's Int'l

  195 Painter Hill Rd, Roxbury, CT 06783
• 

  Est $675,129 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,806 Sq Ft

  37 Painter Hill Rd, Roxbury, CT 06783

  37 Painter Hill Rd, Roxbury, CT 06783
• 

  

  /39

  $919,000

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

  67 Transylvania Rd, Roxbury, CT 06783

  This place is a real gem! It needs some updates, but the structure is solid, and the property is beyond compare. It's set on over three gorgeous acres with beautiful stone walls and a private usable yard that's perfect for a pool. Extensive stonework is present on side steps, patios, and rear gardens, complemented by a stone breezeway connecting the 3-car garage to a side entry hall. The driveway

  Cathy Masi Flagpole Realty Inc

  67 Transylvania Rd, Roxbury, CT 06783
• 

  $135,000 Sold Feb 28, 2025

  • Land
  • 7.25 Acres
  • $18,621 per Acre

  • 40 Days On Market

  Lot Davenport Rd, Roxbury, CT 06783

  7.25 acre parcel set on a quiet backroad in Roxbury, just minutes to both Roxbury Center and Washington Depot and up the road form Region 12 school. This lovely pastoral lot has an open field, stone walls, light woods and rolling land. There are wetlands at the back of the lot.

  Kathryn Clair William Pitt Sotheby's Int'l

  Lot Davenport Rd, Roxbury, CT 06783
• 

  Est $1,308,108 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,591 Sq Ft

  219 Good Hill Rd, Roxbury, CT 06783

  219 Good Hill Rd, Roxbury, CT 06783
• 

  

  /36

  $1,195,000

  • 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
• 

  $1,400,000 Sold Feb 28, 2025

  • 2,984 Sq Ft
  • $469/SF
  • 191 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2020

  21 Hemlock Rd, Roxbury, CT 06783

  Privately sited with western views and sunset! Now with 4 bedrooms in the main house and a 1500 ft Guest house with two bedrooms and 2 baths. A long driveway winds you into this idyllic retreat with western views and sunsets, nestled minutes from town. This stunning Cape Cod Farmhouse thoughtfully constructed has been expanded to include two additional bedrooms in the Main House. An additional

  Kathryn Clair William Pitt Sotheby's Int'l

  21 Hemlock Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,449 Sq Ft

  178 Baker Rd, Roxbury, CT 06783

  178 Baker Rd, Roxbury, CT 06783
• 

  

  /7

  $275,000

  • Land
  • 3.02 Acres
  • $91,060 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
• 

  $299,000 Sold Feb 20, 2025

  • Land
  • 5.24 Acres
  • $57,061 per Acre

  • 173 Days On Market

  0 Hemlock Rd, Roxbury, CT 06783

  Roxbury is one of the most sought-after towns in western CT to live in, with its historic charm and beautifully preserved land areas that boast miles and miles of walking trails. Roxbury is situated in lower Litchfield County, only 90 minutes from NYC. With its very low taxes, you can build your dream home on this 5.23 acres of land situated within walking distance to the center of town, while

  Jay McGorty McGorty Real Estate Services

  0 Hemlock Rd, Roxbury, CT 06783
• 

  Est $803,694 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,282 Sq Ft

  45 Chalybes Rd, Roxbury, CT 06783

  45 Chalybes Rd, Roxbury, CT 06783
• 

  

  /35

  $3,995,000

  • 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
• 

  $840,000 Sold Feb 19, 2025

  • 3,974 Sq Ft
  • $211/SF
  • 221 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1986

  208 E Flag Swamp Rd, Roxbury, CT 06783

  Seclusion in Rural Roxbury. Tucked back on dirt road, 10 acres surrounded by nature, trees, birds, and wildlife..... Custom home has a mix of palladium windows, skylights, vaulted ceilings, interior balconies, three fireplaces, eclectic chandeliers and open spaces all add a Contemporary Flair to this colonial home. Primary suite with sitting area and fireplace. First floor ensuite bedroom,

  Mary Ann Bennett Drakeley Real Estate, Inc.

  208 E Flag Swamp Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,433 Sq Ft

  214 Tophet Rd, Roxbury, CT 06783

  214 Tophet Rd, Roxbury, CT 06783
• 

  

  /13

  $599,000

  • Land
  • 16 Acres
  • $37,438 per Acre

  Lot 4 Chalybes Rd W, Roxbury, CT 06783

  Prime Roxbury Location. Nestled off a picturesque classic country lane, flanked by distinguished residences and just minutes from the vibrant heart of Roxbury Center, awaits an exceptional opportunity. This approved building parcel is primed for complete development, offering a level to gently sloping terrain within a private and serene setting. Imagine crafting your ideal retreat amidst the

  Kathryn Clair William Pitt Sotheby's Int'l

  Lot 4 Chalybes Rd W, Roxbury, CT 06783
• 

  $4,360,000 Sold Feb 03, 2025

  • 3,500 Sq Ft
  • $1,246/SF
  • 214 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2020

  130 Tophet Rd, Roxbury, CT 06783

  Set on 14 private and fully fenced acres, this truly spectacular property, once owned by Walter Matthau and his wife Carol Grace, is surrounded by the Matthau Land Trust. The newly built main house was conceived by Geoff Fairbairn, a well-known Litchfield builder, with the current owners adding more features and square footage to the compound, with an eye for detail and enchanting style. The two

  Judith Auchincloss Klemm Real Estate Inc

  130 Tophet Rd, Roxbury, CT 06783
• 

  Est $918,793 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,540 Sq Ft

  95 Transylvania Rd, Roxbury, CT 06783

  95 Transylvania Rd, Roxbury, CT 06783
• 

  

  /29

  $1,025,000

  • 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 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
• 

  $1,500,000 Sold Jan 28, 2025

  • 3,233 Sq Ft
  • $464/SF
  • 323 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2021

  52 Welton Rd, Roxbury, CT 06783

  Taking to heart the famous quote “Simplicity is the ultimate sophistication” by Leonardo de Vinci, the current owners designed this brick saltbox to perfection. Much thought went into the high quality new and reclaimed materials used. The exterior is historically correct handmade Waterstruck brick with Lifespan Solid Select pressure treated trim from New Zealand, a 5/8” pressure treated cedar

  Maria Taylor Klemm Real Estate Inc

  52 Welton Rd, Roxbury, CT 06783
• 

  Est $2,187,161 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,337 Sq Ft

  15 Farm Rd, Roxbury, CT 06783

  15 Farm Rd, Roxbury, CT 06783

Showing Results 81 - 120, Page 3 of 18