38

Roxbury, CT Homes for Sale

Section Image
  • 85 Good Hill Rd, Roxbury, CT 06783
    85 Good Hill Rd, Roxbury, CT 06783
    85 Good Hill Rd, Roxbury, CT 06783
    /33

    $1,680,000

    • 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 William Pitt Sotheby's Int'l

    85 Good Hill Rd, Roxbury, CT 06783
  • 88 Rucum Rd, Roxbury, CT 06783
    88 Rucum Rd, Roxbury, CT 06783
    88 Rucum Rd, Roxbury, CT 06783
    /35

    $2,195,000

    • 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
  • 143 Tophet Rd, Roxbury, CT 06783
    143 Tophet Rd, Roxbury, CT 06783
    143 Tophet Rd, Roxbury, CT 06783
    /40

    $2,395,000

    • 4 Beds
    • 5.5 Baths
    • 5,848 Sq Ft

    143 Tophet Rd, Roxbury, CT 06783

    Located along one of Roxbury's most coveted stretches, this property is nestled among an 800+ acre greenbelt of farmland and conserved land with plentiful hiking trails. The open floor plan is designed with 9 foot+ ceilings, detailed millwork and oversized windows which infuse the interiors with natural light. The main level features a show stopping kitchen open to the dinning and media rooms.

    Stacey Matthews W. Raveis Lifestyles Realty

    143 Tophet Rd, Roxbury, CT 06783
  • 67 Botsford Hill Rd, Roxbury, CT 06783
    67 Botsford Hill Rd, Roxbury, CT 06783
    67 Botsford Hill Rd, Roxbury, CT 06783
    /29

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 4,800 Sq Ft

    67 Botsford Hill Rd, Roxbury, CT 06783

    Discover the appeal of this Swedish inspired shingle-style beauty with light and modern finishes throughout. It's nestled into 41+ ultra-private acres on a picturesque country road. Enter the front door into the two-story foyer which flows into the vaulted ceiling living room with lots of glass, adobe fireplace and easy access to the tucked away library with floor to ceiling bookshelves. The

    Maria Taylor Klemm Real Estate Inc

    67 Botsford Hill Rd, Roxbury, CT 06783
  • 45 Moosehorn Rd, Roxbury, CT 06783
    45 Moosehorn Rd, Roxbury, CT 06783
    45 Moosehorn Rd, Roxbury, CT 06783
    /22

    $1,995,000

    • 4 Beds
    • 3.5 Baths
    • 4,517 Sq Ft

    45 Moosehorn Rd, Roxbury, CT 06783

    Pristine 4+ bedroom large (4,517 sq. ft.) private home on a scenic dirt road - perfect for walking, jogging and biking surrounded by Moosehorn Land Preserve and country estates. Magnificent design incorporating picturesque country views, over-sized living room, dining room for 12+, chef's kitchen, vaulted ceilings, hardwood floors and two gas fireplaces. Heated pool surrounded by endless summer

    Peter Klemm Klemm Real Estate Inc

    45 Moosehorn Rd, Roxbury, CT 06783
  • 247 Painter Hill Rd, Roxbury, CT 06783
    247 Painter Hill Rd, Roxbury, CT 06783
    247 Painter Hill Rd, Roxbury, CT 06783
    /21

    $1,649,000

    • 3 Beds
    • 4 Baths
    • 2,396 Sq Ft

    247 Painter Hill Rd, Roxbury, CT 06783

    Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by Roxbury's best historic estate neighborhood, farms and homes of artists, actors and writers. Magnificent open floor plan with 2-3 bedrooms on main floor, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch and another bedroom in finished lower level. Dine or relax on the flagstone

    Peter Klemm Klemm Real Estate Inc

    247 Painter Hill Rd, Roxbury, CT 06783
  • 253 Tophet Rd, Roxbury, CT 06783
    253 Tophet Rd, Roxbury, CT 06783
    253 Tophet Rd, Roxbury, CT 06783
    /33

    $1,649,000

    • 4 Beds
    • 3.5 Baths
    • 2,437 Sq Ft

    253 Tophet Rd, Roxbury, CT 06783

    Quintessential CT Mini- Estate of 2 Homes! Top restoration of 3-Bedroom/2.5 bath Victorian plus a Guest House with giant stunning, heated, saltwater pool, 2nd small spa pool and wonderful stone terraces and open lawns. Historic Pool House Rental Income: $50,000-$100,000 per year. Perfect for generational living as both the Main House and the Pool House have their own pools, driveways and garages.

    Peter Klemm Klemm Real Estate Inc

    253 Tophet Rd, Roxbury, CT 06783
  • 32 Grassy Hill Rd, Roxbury, CT 06783
    32 Grassy Hill Rd, Roxbury, CT 06783
    32 Grassy Hill Rd, Roxbury, CT 06783
    /39

    $2,395,000

    • 4 Beds
    • 5 Baths
    • 4,728 Sq Ft

    32 Grassy Hill Rd, Roxbury, CT 06783

    Roxbury dream home with forever views. Tucked away down a gracious drive off a bucolic town road this quintessential Georgian welcomes you home and envelopes you in calm and comfort. Arrival at the motor court provides the first glimpse of a western view that stretches from Roxbury as far as the eye can see, giving an immediate sense of place. The home, unabashedly radiant in its sunny yellow

    Rick Distel Compass Connecticut, LLC

    32 Grassy Hill Rd, Roxbury, CT 06783
  • 2 Pickett Rd, Roxbury, CT 06783
    2 Pickett Rd, Roxbury, CT 06783
    2 Pickett Rd, Roxbury, CT 06783
    /26

    $1,784,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,220 Sq Ft

    2 Pickett Rd, Roxbury, CT 06783

    NEW CONSTRUCTION. WELCOME TO YOUR DREAM HOME! This stunning new construction colonial farmhouse boasts modern elegance and top-of-the-line finishes throughout. Featuring 5 spacious bedrooms and 3.5 luxurious bathrooms, this home offers ample space for comfortable living. The open concept living area is perfect for entertaining, with a gourmet kitchen that includes high-end stainless-steel

    Michael Lissack The Virtual Realty Group

    2 Pickett Rd, Roxbury, CT 06783
  • 99 Carriage Ln, Roxbury, CT 06783
    99 Carriage Ln, Roxbury, CT 06783
    99 Carriage Ln, Roxbury, CT 06783
    /4

    $1,735,000 Coming Soon

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

    99 Carriage Ln, Roxbury, CT 06783

    Welcome to this beautifully maintained 4-bedroom, 2.5-bath home, nestled in a serene and peaceful location-perfect for those seeking comfort and tranquility. Step inside to a spacious open-concept living and dining area, ideal for hosting gatherings and entertaining with ease. The modern kitchen features state-of-the-art appliances, ample counter space, and generous storage-making it a dream for

    Debra Tricarico Houlihan Lawrence

    99 Carriage Ln, Roxbury, CT 06783
  • 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

    • 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
  • 67 Transylvania Rd, Roxbury, CT 06783
    67 Transylvania Rd, Roxbury, CT 06783
    67 Transylvania Rd, Roxbury, CT 06783
    /39

    $1,049,000

    • 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
  • 88 Hemlock Rd, Roxbury, CT 06783
    88 Hemlock Rd, Roxbury, CT 06783
    88 Hemlock Rd, Roxbury, CT 06783
    /27

    $1,495,000

    • 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
  • 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
  • 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
  • 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
  • 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
  • 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 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    /27

    $1,549,000

    • 4 Beds
    • 3.5 Baths
    • 2,716 Sq Ft

    33 Sentry Hill Rd, Roxbury, CT 06783

    Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room,

    Peter Klemm Klemm Real Estate Inc

    33 Sentry Hill Rd, Roxbury, CT 06783
  • 18 Tunnel Rd, Roxbury, CT 06783
    18 Tunnel Rd, Roxbury, CT 06783
    18 Tunnel Rd, Roxbury, CT 06783
    /29

    $1,129,000

    • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 81 Chalybes Rd W, Roxbury, CT 06783
    81 Chalybes Rd W, Roxbury, CT 06783
    81 Chalybes Rd W, Roxbury, CT 06783
    /40

    $2,200,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,677 Sq Ft

    81 Chalybes Rd W, Roxbury, CT 06783

    TO BE BUILT - A New Classic by Connecticut Residential. Here's your chance to create something truly special in the heart of lower Litchfield County. Tucked away on over 4 private acres in picturesque Roxbury, this proposed home by Connecticut Residential blends timeless Colonial charm with modern-day comfort-thoughtfully designed for today's lifestyle while honoring traditional New England

    Christopher Haggerty Around Town Real Estate LLC

    81 Chalybes Rd W, Roxbury, CT 06783
  • 85 Chalybes Rd W, Roxbury, CT 06783
    85 Chalybes Rd W, Roxbury, CT 06783
    85 Chalybes Rd W, Roxbury, CT 06783
    /35

    $2,950,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 4,071 Sq Ft

    85 Chalybes Rd W, Roxbury, CT 06783

    TO BE BUILT - A Home by CORBO! A rare opportunity to build your dream home on over 6 private acres in Roxbury, CT-one of lower Litchfield County's most sought-after towns. This award-winning Colonial reproduction pairs timeless architecture with modern craftsmanship and is ideally positioned for western exposure and unforgettable sunsets (subject to tree clearing and final siting). Choose this

    Christopher Haggerty Around Town Real Estate LLC

    85 Chalybes Rd W, Roxbury, CT 06783
  • 103 Chalybes Rd W, Roxbury, CT 06783
    103 Chalybes Rd W, Roxbury, CT 06783
    103 Chalybes Rd W, Roxbury, CT 06783
    /37

    $2,850,000 New Construction

    • 5 Beds
    • 7 Baths
    • 4,777 Sq Ft

    103 Chalybes Rd W, Roxbury, CT 06783

    TO BE BUILT - A Home by CORBO! Tranquil luxury on 16 private acres in Roxbury, CT-an exceptional opportunity to bring your dream home to life in the heart of lower Litchfield County. Set well back from the road and oriented for western exposure, this stunning property offers sweeping views (subject to tree clearing and final siting) and the ultimate in privacy. Choose this thoughtfully designed

    Christopher Haggerty Around Town Real Estate LLC

    103 Chalybes Rd W, 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 Open Sun 12PM - 2PM

    • 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
Connecticut Roxbury

Real Estate & Homes for Sale in Roxbury, CT

Why Live in Roxbury

Roxbury, CT, located in the Litchfield Hills just east of Bridgeport, offers a rural lifestyle with nearby urban amenities. Spanning 27 square miles with a population of over 2,000, Roxbury is known for its quiet, undeveloped landscape. Residents enjoy outdoor attractions like Hurlburt Park, which hosts the annual Roxbury Pickin’ and Fiddlin’ Contest, and River Road Preserve, ideal for hiking and fly-fishing. History enthusiasts can explore Mine Hill Preserve, featuring remnants of a 19th-century iron-making complex and extensive hiking trails. Adjacent to Mine Hill is the Kelsey Museum and Sculpture Garden, showcasing works by Sterett-Gittings Kelsey, and the Mine Hill Distillery, where visitors can sample locally distilled spirits. Homes in Roxbury range from raised ranch-style houses to historic Colonial homes, often situated on large lots with mature trees. The town is served by Regional School District Number 12, with highly rated Booth Free School and Shepaug Valley School, along with the nearby Kent School. While Roxbury lacks extensive commercial activity, residents can visit the Roxbury Market & Deli for groceries and meals, or travel 20 miles to Waterbury for more shopping options. For a broader shopping experience, New York City is accessible by train from Danbury, less than 20 miles south.
Learn more about living in Roxbury

Frequently Asked Questions

What is the average home price in Roxbury, CT?
Homes for sale in Roxbury, CT have an average home price of $1,681,987.
How many homes have sold over the last 12 months in Roxbury, CT?
49 homes have sold in Roxbury, CT over the last 12 months.
What are the most popular zip codes in Roxbury, CT?
The most popular zip codes in Roxbury, CT include 06783, 06798, 06752, 06793 and 06776.
How much do you need to make to afford a house in Roxbury?
The median home price in Roxbury is $1,472,500. If you put a 20% down payment of $294,500 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $7,620 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $327K a year to afford the median home price in Roxbury.
How are the schools in Roxbury, CT?
Roxbury, CT has highly rated public and private schools. Some of the best schools in Roxbury based on Niche Grades are Booth Free School, Pomperaug Regional High School and Shepaug Valley School. Browse all the schools in Roxbury, CT to learn more.

Home Trends in Roxbury, CT

On average, homes in Roxbury, CT sell after 136 days on the market compared to the national average of 50 days. The median sale price for homes in Roxbury, CT over the last 12 months is $1,200,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,200,000
Median Single Family Sale Price
$1,300,000
Average Price Per Sq Ft
$484
Number of Homes for Sale
29
Last 12 months Home Sales
49
Months of Supply
7.10
Median List Price
$1,472,500
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group