1,384

Roxbury, CT Homes

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  • 19 Good Hill Terrace, Roxbury, CT 06783
    19 Good Hill Terrace, Roxbury, CT 06783
    19 Good Hill Terrace, Roxbury, CT 06783
    /40

    $1,499,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 3,022 Sq Ft

    19 Good Hill Terrace, Roxbury, CT 06783

    Welcome to this enchanting Roxbury home that feels like a private oasis. This stunning property sits on over 7 acres and features a heated saltwater pool, a chef's kitchen with an open concept that overlooks the great room with vault ceilings, and radiant heated floors that leads to the patio, gardens, and pool. A custom built heated 2 story post and beam barn that offers a 3-car garage was built

    Tanya Uhelsky RE/MAX RISE

    19 Good Hill Terrace, Roxbury, CT 06783
  • 381 South St, Roxbury, CT 06783

    $1,725,000 Sold Apr 25, 2025

    • 4,112 Sq Ft
    • $420/SF
    • 186 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2011

    381 South St, Roxbury, CT 06783

    Meander over a small bridge and through tall pines to reach this distinctive 4 bedroom home on 6 very private acres. A gracious wood paneled central foyer directs you into the living room, dining room, or through to a thoughtfully designed great room. The kitchen features a wrap-around island with bar stools, high-end appliances walk-in pantry/laundry. It also opens to the breakfast nook and

    Stacey Matthews W. Raveis Lifestyles Realty

    381 South St, Roxbury, CT 06783
  • 88 Hemlock Rd, Roxbury, CT 06783
    88 Hemlock Rd, Roxbury, CT 06783
    88 Hemlock Rd, Roxbury, CT 06783
    /27

    $1,495,000 Under Contract

    • 2 Beds
    • 2.5 Baths
    • 3,389 Sq Ft

    88 Hemlock Rd, Roxbury, CT 06783

    Exquisite Barn House with Heated Pool. Set Along a Very Low Traveled Unpaved Town Road, This is a Very Chic & Sophisticated Retreat. Wonderful Public Rooms Include: Large Living Room with Vaulted Ceiling, Fireplace & Antique Beams; A Library which Envelopes you with an Antique Board Ceiling, Fireplace & French Doors; Formal Dining Room & A Timeless Eat-in Kitchen which Speaks to Family Room that

    Graham Klemm Klemm Real Estate Inc

    88 Hemlock Rd, Roxbury, CT 06783
  • 36 Chalybes Rd, Roxbury, CT 06783

    $1,275,000 Sold Apr 21, 2025

    • 4,572 Sq Ft
    • $279/SF
    • 256 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1969

    36 Chalybes Rd, Roxbury, CT 06783

    Welcome to Hollywood Hills meets Roxbury! This exceptional 4-bedroom, 3-bath home sits on 2.1 acres and features a vast studio perfect for artists, Pilates, yoga, or entertaining! The light-filled home boasts a gourmet eat-in kitchen with custom cabinetry, imported Spanish floor tiles, and top-of-the-line appliances, including a Subzero refrigerator, Wolf range/grill, Wolf wall oven, and Bosch

    Jill Sloane Brown Harris Stevens

    36 Chalybes Rd, Roxbury, CT 06783
  • 242 Tophet Rd, Roxbury, CT 06783
    242 Tophet Rd, Roxbury, CT 06783
    242 Tophet Rd, Roxbury, CT 06783
    /25

    $895,000 Open Thu 12PM - 2PM

    • 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
  • 130 E Flag Swamp Rd, 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
  • 200 North St, Roxbury, CT 06783
    200 North St, Roxbury, CT 06783
    200 North St, Roxbury, CT 06783
    /20

    $525,000

    • Land
    • 9 Acres
    • $60,764 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
  • 201 Painter Hill 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
  • 22 E Woods Rd, Roxbury, CT 06783
    22 E Woods Rd, Roxbury, CT 06783
    22 E Woods Rd, 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
  • 24 Roxbury Rd, Woodbury, CT 06798

    $769,000 Sold Apr 01, 2025

    • 4,012 Sq Ft
    • $192/SF
    • 313 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    24 Roxbury Rd, Woodbury, CT 06798

    Located in The Beautiful Hills of Litchfield County on the Woodbury / Roxbury Line! Lots of Privacy Awaits You in this Beautiful Colonial/Contemporary on 9.97 Acres of Serenity w/ Mature Trees, Plantings, Lush Greenery & the Peaceful Sounds of Transylvania Brook that Flows Behind the Home. Inground Heated Gunite Swimming Pool w/ Beautiful Stonework, Fenced in Yard & 3 Good Size Sheds. Very Unique

    Debbie Kranidis Preston Gray Real Estate

    24 Roxbury Rd, Woodbury, CT 06798
  • 67 Transylvania Rd, Roxbury, CT 06783
    67 Transylvania Rd, Roxbury, CT 06783
    67 Transylvania Rd, Roxbury, CT 06783
    /39

    $989,000

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

    67 Transylvania Rd, Roxbury, CT 06783

    This much-admired residence is privately located on a quiet country road, with 3-plus acres of lawn and light woods lined by old stone walls. The flat, sweeping driveway curves past the house to the 3-car attached garage and circular driveway. The welcoming open foyer steps down to a living area with cathedral ceilings, Palladian window and gas fireplace which flows into the dining area separated

    Cathy Masi Flagpole Realty Inc

    67 Transylvania Rd, Roxbury, CT 06783
  • 108 Davenport 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
  • 8 Southbury Rd, Roxbury, CT 06783
    8 Southbury Rd, Roxbury, CT 06783
    8 Southbury Rd, Roxbury, CT 06783
    /17

    $759,900

    • 7 Beds
    • 4 Baths
    • 2,940 Sq Ft

    8 Southbury Rd, Roxbury, CT 06783

    Wonderful opportunity to live in the heart of prestigious Roxbury in Litchfield County. Well preserved antique colonial filled with charm. Updates include kitchen, baths and open living area leading to primary bedroom. Brand new septic, 4 car garage with storage above and period outbuildings including a barn. Washer and dryer are located on the main level, upstairs bedrooms offer privacy for

    Lisa Titcomb William Pitt Sotheby's Int'l

    8 Southbury Rd, Roxbury, CT 06783
  • 34 Spargo Rd, 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
  • 286 South St, Roxbury, CT 06783
    286 South St, Roxbury, CT 06783
    286 South St, 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
  • 168 Baker 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
  • 19 Spargo Rd, Roxbury, CT 06783
    19 Spargo Rd, Roxbury, CT 06783
    19 Spargo Rd, Roxbury, CT 06783
    /30

    $1,150,000

    • 3 Beds
    • 2.5 Baths
    • 1,571 Sq Ft

    19 Spargo Rd, Roxbury, CT 06783

    Step into timeless style and serene privacy with this beautifully maintained 1966 mid-century modern home. Set on almost 5 acres of lush, private land, this 3-bedroom, 2.5-bath residence blends classic design with modern upgrades. The just-renovated bathrooms feature high-end, spa-like finishes, while the expansive deck provides the perfect setting for outdoor entertaining or peaceful relaxation.

    Pels Matthews W. Raveis Lifestyles Realty

    19 Spargo Rd, Roxbury, CT 06783
  • 66 Bacon Rd, 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
  • 53 Transylvania Rd, Roxbury, CT 06783
    53 Transylvania Rd, Roxbury, CT 06783
    53 Transylvania Rd, Roxbury, CT 06783
    /35

    $1,395,000

    • 3 Beds
    • 2.5 Baths
    • 3,920 Sq Ft

    53 Transylvania Rd, Roxbury, CT 06783

    Fantastic Colonial in Roxbury down long private drive featuring low maintenance salt water spa pooL. The house is surrounded by nature, with multiple entertaining spaces and gardens. Amazing bird life is a natural symphony while relaxing outdoors. The home has a lovely gracious layout all with detailed millwork and a vaulted great room with almost floor to ceiling windows on three sides creating

    Pels Matthews W. Raveis Lifestyles Realty

    53 Transylvania Rd, Roxbury, CT 06783
  • 195 Painter Hill 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
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /37

    $3,250,000

    • 5 Beds
    • 5.5 Baths
    • 5,455 Sq Ft

    Unlisted Address

    Tranquility awaits down this long paved driveway in Northern Roxbury. Complete privacy with spectacular gardens, pond and orchard surrounded by dramatic rocky outcroppings. This stone and stucco home features large eat-in kitchen, formal dining and living rooms, and a spacious media room. The main floor primary suite includes a fireplace, office space, and large walk in closet. There is an addl

    Stacey Matthews W. Raveis Lifestyles Realty

    Unlisted Address
  • Lot Davenport Rd, Roxbury, CT 06783

    $135,000 Sold Feb 28, 2025

    • Land
    • 7 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
  • Lot 00 Chalybes Rd W, Roxbury, CT 06783
    Lot 00 Chalybes Rd W, Roxbury, CT 06783
    Lot 00 Chalybes Rd W, Roxbury, CT 06783
    /10

    $1,895,000

    • Land
    • 32 Acres
    • $60,044 per Acre

    Lot 00 Chalybes Rd W, Roxbury, CT 06783

    Presenting a remarkable 31.56-acre estate land in the coveted Roxbury, Connecticut. This private and serene property, with potential for stunning views, is primed and ready for building and offers a rare opportunity to create a bespoke retreat. The land features thousands of feet of historic stone walls, remnants of an old farm road, with multiple access points, highlighting its rich heritage. It

    Kathryn Clair William Pitt Sotheby's Int'l

    Lot 00 Chalybes Rd W, Roxbury, CT 06783
  • 21 Hemlock Rd, 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
  • 0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    /3

    $275,000

    • Land
    • 3.02 Acres
    • $91,060 per Acre

    0 Booth Rd, Roxbury, CT 06783

    Country roads take me to my new home! Such a peaceful location to build your dream home. All of nature loves the location, so will you!

    Sindy Butkus Klemm Real Estate Inc

    0 Booth Rd, Roxbury, CT 06783
  • 0 Hemlock Rd, Roxbury, CT 06783

    $299,000 Sold Feb 20, 2025

    • Land
    • 5 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

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