1,384

Roxbury, CT Homes

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

    $950,000

    • 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
  • 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 3 Chalybes Rd, Roxbury, CT 06783
    Lot 3 Chalybes Rd, Roxbury, CT 06783
    Lot 3 Chalybes Rd, Roxbury, CT 06783
    /13

    $499,000

    • Land
    • 4.03 Acres
    • $123,852 per Acre

    Lot 3 Chalybes Rd, Roxbury, CT 06783

    The site has just been cleared and the ability to see nearby foothill is now there for your view. 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

    Kathryn Clair William Pitt Sotheby's Int'l

    Lot 3 Chalybes Rd, 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
  • 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
  • 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
  • 18 Tunnel Rd, Roxbury, CT 06783
    18 Tunnel Rd, Roxbury, CT 06783
    18 Tunnel Rd, Roxbury, CT 06783
    /29

    $1,095,000

    • 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
  • 20 Painter Hill Rd, Roxbury, CT 06783

    $3,495,000 Sold Jan 16, 2025

    • Land
    • 57 Acres
    • $61,112 per Acre
    • 54 Days On Market

    20 Painter Hill Rd, Roxbury, CT 06783

    A New Stone-Wall Lined Private Driveway Leads to this Magnificent Hilltop Parcel. Dotted with Mature Trees & Punctuated by Sweeping Western Views, this is Truly an Estate Quality Offering. This 57+ Acre Property Includes 3 Separate Parcels & Abuts Roxbury Land Trust & Includes a Small Stream & Picturesque Pond. Total Privacy. This Property is a Mere 1.5 Hour Drive to NYC & Accessed off Secondary

    Graham Klemm Klemm Real Estate Inc

    20 Painter Hill Rd, Roxbury, CT 06783
  • 23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    /26

    $1,079,000

    • 4 Beds
    • 3 Baths
    • 1,782 Sq Ft

    23 Painter Hill Rd, Roxbury, CT 06783

    Mint / Move-in Condition! Pristine hilltop home with views on 3 +/- acres. Gorgeous, chic, mint renovation. Open floor plan kitchen/family room with wood-burning fireplace and French doors to a private flagstone patio. Bright and airy living room and dining room. Primary bedroom with vaulted ceilings, balcony and large ensuite renovated bath. Three more bedrooms, 1 full and 1 half bath. Only a

    Peter Klemm Klemm Real Estate Inc

    23 Painter Hill Rd, Roxbury, CT 06783
  • 177 Bacon Rd, Roxbury, CT 06783

    $900,000 Sold Jan 15, 2025

    • 2,450 Sq Ft
    • $367/SF
    • 229 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1985

    177 Bacon Rd, Roxbury, CT 06783

    Newly renovated home in quiet, desirable Roxbury location. New kitchen and baths, wood beams, central air conditioning, roof, paint etc....turn key. Large eat-in kitchen with fireplace, formal dining area, living room with fireplace, den, full bath, mud and laundry rooms all on main level. 3 bedrooms on second floor including large primary suite. 3 full baths in all. Wooden deck off rear of house

    Pels Matthews W. Raveis Lifestyles Realty

    177 Bacon Rd, Roxbury, CT 06783
  • 55 Garnet Rd, Roxbury, CT 06783
    55 Garnet Rd, Roxbury, CT 06783
    55 Garnet Rd, Roxbury, CT 06783
    /38

    $1,400,000

    • 4 Beds
    • 3.5 Baths
    • 4,167 Sq Ft

    55 Garnet Rd, Roxbury, CT 06783

    Welcome Home to this beautiful Estate in the charming Land of Roxbury!! Sprawling kitchen with high end appliances (Wolfe, Sub Zero) cabinets and countertops inluding wine bar with separate sink. Plenty of space for all your family holidays and well planned cocktail parties. This home has two Primary suites. Excellent for weekend guests and possible in laws. Custom built in 2017. 9 Ft ceilings.

    Joe Chemero Coldwell Banker Realty

    55 Garnet Rd, Roxbury, CT 06783
  • 44 Chalybes Rd, Roxbury, CT 06783

    $3,500,000 Sold Jan 09, 2025

    • 4,950 Sq Ft
    • $707/SF
    • 67 Days On Market
    • 4 Beds
    • 6.5 Baths
    • Built 1964

    44 Chalybes Rd, Roxbury, CT 06783

    Tucked Down a Long Private Driveway Less than 1-Min to the Village is this Chic Renovated Colonial with Heated Pool. This Elegant 4+ Bedroom, 6.5 Bath Home Is Very Finely Detailed. Sophisticated Floor-plan Features 2 Main Level Bedrooms including Luxurious Primary Suite with 2 Full Baths, Large Walk-in Closets & a Fireplace. 3 Other en-Suite Bedrooms. Large Country Kitchen with Vaulted Ceiling &

    Carolyn Klemm Klemm Real Estate Inc

    44 Chalybes Rd, Roxbury, CT 06783
  • Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783
    Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783
    Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783
    /12

    $999,000

    • Land
    • 20 Acres
    • $49,627 per Acre

    Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783

    Welcome to Willow Brook Drive! If your dream has been to build your new home in what feels like a Monet painting, this property will make your dream a reality. Here is your chance to have two prime lots of land, together making 20+ acres of endless possibility! With year-round beautiful meadows and enchanting woods, you can have the best of both worlds. Originally cattle pasture, the vast fields

    Ryan Bollard William Pitt Sotheby's Int'l

    Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783
  • 76 Davenport Rd, Roxbury, CT 06783

    $1,240,000 Sold Dec 30, 2024

    • 2,445 Sq Ft
    • $507/SF
    • 392 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1989

    76 Davenport Rd, Roxbury, CT 06783

    Magically enchanting, nestled, literally, into a private Roxbury hillside, this unique "bermed earth shelter home" of stone, stucco and slate overlooks nearly 8 acres of professionally landscaped grounds, a gunite pool, stone patios, seasonal views and an active year round stream. The approach over the bridge, along a gentle sloping winding driveway opens to a lush, intimate setting of mature

    GRACE FRANJOLA Berkshire Hathaway NE Prop.

    76 Davenport Rd, Roxbury, CT 06783
  • 238 North St, Roxbury, CT 06783
    238 North St, Roxbury, CT 06783
    238 North St, Roxbury, CT 06783
    /22

    $479,000

    • Land
    • 7 Acres
    • $70,545 per Acre

    238 North St, Roxbury, CT 06783

    DRIVEWAY NOW UNDER Construction! Engineering APPROVED-Permit on File. Rarely available Lot in Roxbury! Magical 6.79 acre lot featuring a majestic stream and spring house, un-touched historic stone walls, gently sloping tree-covered hills and an abundance of pine trees, oaks and maples as your canvas. This masterpiece lot is perfect to build your dream home and to connect with what is important

    Jill Sloane Brown Harris Stevens

    238 North St, Roxbury, CT 06783
  • 68 Carriage Ln, Roxbury, CT 06783

    $865,000 Sold Dec 23, 2024

    • 4,102 Sq Ft
    • $211/SF
    • 129 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2004

    68 Carriage Ln, Roxbury, CT 06783

    Absolute peaceful, quiet and private Paradise with views and endless Possibilities. Immerse yourself in tranquility with this custom-built 5 bedroom Cape Cod estate boasting 900 feet of private frontage and captivating seasonal vistas. This expansive property offers the ultimate in privacy and flexibility, perfect for multigenerational living, entertaining, or simply enjoying the peace and quiet.

    Kathryn Clair William Pitt Sotheby's Int'l

    68 Carriage Ln, Roxbury, CT 06783
  • 307 North St, Roxbury, CT 06783
    307 North St, Roxbury, CT 06783
    307 North St, Roxbury, CT 06783
    /6

    $234,900

    • Land
    • 3.00 Acres
    • $78,300 per Acre

    307 North St, Roxbury, CT 06783

    Peaceful wooded lot to build your weekend or forever home! Driveway has been roughed in and leads to the building site set back well from the road. Beautiful outcroppings, mature hardwoods, antique stone walls all set in a private rolling terrain. Survey, perc test and soil survey are available. Close to Washington and Roxbury centers makes this the perfect place to call home.90 minutes to NYC

    Sindy Butkus Klemm Real Estate Inc

    307 North St, Roxbury, CT 06783
  • 15 E Woods Rd, Roxbury, CT 06783

    $1,600,000 Sold Dec 23, 2024

    • 5,477 Sq Ft
    • $292/SF
    • 189 Days On Market
    • 7 Beds
    • 4.5 Baths
    • Built 1976

    15 E Woods Rd, Roxbury, CT 06783

    Family compound on 30+/- high acres with long driveway to 7-bedroom, 4 1/2 bathroom contemporary main house with easy indoor/outdoor living. Vaulted living/dining with fireplace & sliders to deck. Eat-in Kitchen. First floor primary bedroom suite with fireplace & sliders to deck. Den with fireplace & sliders. Vaulted family room with fireplace. Game room. 3-car attached garage. Separate

    Peter Klemm Klemm Real Estate Inc

    15 E Woods Rd, Roxbury, CT 06783
  • 179 South St, Roxbury, CT 06783
    179 South St, Roxbury, CT 06783
    179 South St, Roxbury, CT 06783
    /16

    $1,275,000

    • Land
    • 13 Acres
    • $100,078 per Acre

    179 South St, Roxbury, CT 06783

    Own a Piece of Roxbury History! This exceptional 12.7-acre property boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. 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

    Kathryn Clair William Pitt Sotheby's Int'l

    179 South St, Roxbury, CT 06783
  • 44 Baker Rd, Roxbury, CT 06783

    $550,000 Sold Dec 09, 2024

    • 2,501 Sq Ft
    • $220/SF
    • 182 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1962

    44 Baker Rd, Roxbury, CT 06783

    Enchanted Garden. New to the market after 25 years is this charming 4-5 bedroom home on two magnificent park-like acres with a seasonal view. The first-floor layout includes a living room with fireplace, dining room, kitchen, great room with vaulted ceiling, wood burning stove and sliders out to the deck and pergola covered with hanging hydrangea, powder room, laundry room and a comfortable size

    Judith Auchincloss Klemm Real Estate Inc

    44 Baker Rd, Roxbury, CT 06783
  • 11 Ravenrock, Roxbury, CT 06783
    11 Ravenrock, Roxbury, CT 06783
    11 Ravenrock, Roxbury, CT 06783
    /35

    $4,750,000

    • 4 Beds
    • 5.5 Baths
    • 7,063 Sq Ft

    11 Ravenrock, Roxbury, CT 06783

    A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in the beautiful Litchfield Hills with spectacular views that go on for miles. This property includes a four bedroom, five and a half bath main residence, in ground heated Gunite pool, tennis court, one-bedroom caretaker's apartment over a 3-bay garage, two bedroom guest apartment and greenhouse. This compound

    Maria Taylor Klemm Real Estate Inc

    11 Ravenrock, Roxbury, CT 06783
  • Lot 1 Willow Brook Dr, Roxbury, CT 06783

    $480,000 Sold Nov 26, 2024

    • Land
    • 11 Acres
    • $44,486 per Acre
    • 101 Days On Market

    Lot 1 Willow Brook Dr, Roxbury, CT 06783

    Welcome to your new private paradise, Willow Brook Dr! Enjoy the pristine meadows, woodlands, and breathtaking westerly views atop this private road. Situated in the "Good Hill" neighborhood of Roxbury, CT, you will find endless nature preserves to explore, all just minutes away. Abundant restaurants, groceries, and amenities all easily accessible. Truly, the quintessential New England

    Ryan Bollard William Pitt Sotheby's Int'l

    Lot 1 Willow Brook Dr, Roxbury, CT 06783
  • 0 Wellers Bridge Rd, Roxbury, CT 06783
    0 Wellers Bridge Rd, Roxbury, CT 06783
    0 Wellers Bridge Rd, Roxbury, CT 06783
    /21

    $464,000

    • Land
    • 25 Acres
    • $18,553 per Acre

    0 Wellers Bridge Rd, Roxbury, CT 06783

    Approved building lot with a completed survey and site plans, including wetland delineation and a forthcoming report. This 25.01-acre wooded oasis in Roxbury, located just half a mile from scenic Route 67, offers a tranquil and private retreat in the heart of historic Roxbury. With 250 feet of road frontage on Wellers Bridge Rd, this property is a prime opportunity for those looking to build a

    David Hughes Century 21 AllPoints Realty

    0 Wellers Bridge Rd, Roxbury, CT 06783
  • 27 Mine Hill Rd, Roxbury, CT 06783

    $1,085,000 Sold Nov 25, 2024

    • 2,265 Sq Ft
    • $479/SF
    • 86 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1974

    27 Mine Hill Rd, Roxbury, CT 06783

    Quintessential Roxbury Cape with detached studio space across from 300+ acres of Roxbury Land Trust and hiking. Enjoy modern amenities and unparalleled privacy in this serene setting with abundant windows and French doors that fill the space with natural light. Step inside to an open floor plan through an entry featuring custom built-ins and stone flooring, leading to a living room and dining

    Kathryn Bassett William Pitt Sotheby's Int'l

    27 Mine Hill Rd, Roxbury, CT 06783
  • 0 Good Hill Rd, Roxbury, CT 06783
    0 Good Hill Rd, Roxbury, CT 06783
    /2

    $985,000

    • Land
    • 66 Acres
    • $14,972 per Acre

    0 Good Hill Rd, Roxbury, CT 06783

    Large parcel of raw land offering a unique opportunity. This 66 acre parcel fronts two well connected roads, ensuring ease of access and flexibility in planning. With some clearing it offers easterly views of the rolling landscape and morning sunrises, making the parcel perfect for a large estate or residential compound. Roxbury is in southern Litchfield County with a population of less than

    Sindy Butkus Klemm Real Estate Inc

    0 Good Hill Rd, Roxbury, CT 06783

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