1,377

Roxbury, CT Homes

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  • 78 Garnet Rd, Roxbury, CT 06783
    78 Garnet Rd, Roxbury, CT 06783
    78 Garnet Rd, Roxbury, CT 06783
    /38

    $1,695,000 Under Contract

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

    78 Garnet Rd, Roxbury, CT 06783

    A split rail fence along the meandering drive leads you to this beautiful and sophisticated farmhouse on 15.29 acres of peaceful countryside. Storybook wrap-around porch, new Gunite heated saltwater pool, separate guest apartment, enormous barn, apple trees, perennial gardens and pond are highlights. The pristine house has recessed wood paneling and floors, window seats, built-ins and crown

    Maria Taylor Klemm Real Estate Inc

    78 Garnet 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
  • 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
  • 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
  • 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
  • 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
  • 19 Spargo Rd, Roxbury, CT 06783
    19 Spargo Rd, Roxbury, CT 06783
    19 Spargo Rd, Roxbury, CT 06783
    /30

    $1,250,000

    • 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
  • 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
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /40

    $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
  • 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
  • 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
  • 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
  • 88 Mallory Rd, Roxbury, CT 06783
    88 Mallory Rd, Roxbury, CT 06783
    88 Mallory Rd, Roxbury, CT 06783
    /35

    $917,500

    • 4 Beds
    • 2.5 Baths
    • 3,004 Sq Ft

    88 Mallory Rd, Roxbury, CT 06783

    Welcome to wonderful! Enjoy privacy & seclusion on a gorgeous rural road in southern Roxbury. This custom-built, well-designed home is now offered to new stewards by the original owner, ready for year-round country living or a weekend retreat! The expansive property features the 4.5-acre home site plus excess of 8.99 acres for a variety of options...inground pool site, paddocks, animal structures

    Melissa Karaffa William Raveis Real Estate

    88 Mallory Rd, Roxbury, CT 06783
  • 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
  • 0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    /2

    $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
  • 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
  • 8 Bayberry Hill, Roxbury, CT 06783
    8 Bayberry Hill, Roxbury, CT 06783
    8 Bayberry Hill, Roxbury, CT 06783
    /35

    $4,500,000

    • 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
  • 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
  • 61 Mallory Rd, Roxbury, CT 06783
    61 Mallory Rd, Roxbury, CT 06783
    61 Mallory Rd, Roxbury, CT 06783
    /40

    $999,000

    • 4 Beds
    • 3.5 Baths
    • 3,919 Sq Ft

    61 Mallory Rd, Roxbury, CT 06783

    Welcome to 61 Mallory Road, Roxbury, CT - a timeless 4-bedroom, 3.5-bath Colonial offering nearly 4,000 sq. ft. of refined living. Thoughtfully designed and built by the current owner in 2000 and freshly painted, this home is nestled on over 4 beautiful acres along a quiet country road, providing a serene retreat with convenient access to Roxbury Center, Bridgewater, and Southbury. Upon entering,

    Riley Winfield William Raveis Real Estate

    61 Mallory Rd, Roxbury, CT 06783
  • 208 E Flag Swamp Rd, 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
  • Lot 3 Chalybes Rd, Roxbury, CT 06783
    Lot 3 Chalybes Rd, Roxbury, CT 06783
    Lot 3 Chalybes Rd, Roxbury, CT 06783
    /13

    $399,000

    • Land
    • 4.03 Acres
    • $99,032 per Acre

    Lot 3 Chalybes Rd, Roxbury, CT 06783

    Discover Your 4 acre Dream Homesite in 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

    Kathryn Clair William Pitt Sotheby's Int'l

    Lot 3 Chalybes Rd, Roxbury, CT 06783
  • 130 Tophet Rd, Roxbury, CT 06783

    $4,360,000 Sold Feb 03, 2025

    • 3,500 Sq Ft
    • $1246/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
  • Lot 4 Chalybes Rd W, Roxbury, CT 06783
    Lot 4 Chalybes Rd W, Roxbury, CT 06783
    Lot 4 Chalybes Rd W, 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
  • 52 Welton 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
  • 18 Tunnel Rd, Roxbury, CT 06783
    18 Tunnel Rd, Roxbury, CT 06783
    18 Tunnel Rd, Roxbury, CT 06783
    /29

    $1,149,000

    • 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
  • 60 Good Hill Rd, Roxbury, CT 06783

    $1,650,000 Sold Jan 16, 2025

    • 4,928 Sq Ft
    • $335/SF
    • 49 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1996

    60 Good Hill Rd, Roxbury, CT 06783

    A Meandering Private Driveway Over a Small Brook Leads to this Very Private Stucco-Clad Colonial Set on 10+ Acres. Splash Around in the Pool with Separate Cabana. 4 Bedrooms, 3.5 Baths Including Main Level Bedroom & Bath. Large Eat In Kitchen with Dining Area & Tons of Counter Space. Dramatic Great Room with Fireplace & Sweeping Staircase. Generous Primary Bedroom Suite with Full Bath, Ample

    Graham Klemm Klemm Real Estate Inc

    60 Good Hill Rd, Roxbury, CT 06783

Showing Results 41 - 80, Page 2 of 18

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