34

Roxbury, CT Homes for Sale

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

    $1,750,000

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

    $2,395,000 Open Sat 11:30AM - 1:30PM

    • 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

    $1,675,000

    • 2 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, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch. Dine or relax on the flagstone terrace next to the heated gunite pool. Mature gardens with

    Peter Klemm Klemm Real Estate Inc

    247 Painter Hill Rd, 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
  • 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
  • 27 Wakelee Rd, Roxbury, CT 06783
    27 Wakelee Rd, Roxbury, CT 06783
    27 Wakelee Rd, Roxbury, CT 06783
    /33

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 2,640 Sq Ft

    27 Wakelee Rd, Roxbury, CT 06783

    Many new renovations in this stunning antique home on a quiet country road. All flat usable land with gorgeous bank barn, gunite pool, Spectacular mature trees, and pond. Town has house listed as 5 bedrooms. The primary bedroom with walk in closet is on the main level. Upstairs is more efficiently used as 2 suites each with walk in closets or offices. Alternately, one of the larger bedrooms could

    Stacey Matthews W. Raveis Lifestyles Realty

    27 Wakelee 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
  • 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
  • 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
    /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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    /26

    $1,095,000

    • 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
  • 11 Hodge Rd, Roxbury, CT 06783
    11 Hodge Rd, Roxbury, CT 06783
    11 Hodge Rd, Roxbury, CT 06783
    /32

    $1,150,000

    • 4 Beds
    • 3 Baths
    • 2,982 Sq Ft

    11 Hodge Rd, Roxbury, CT 06783

    This Circa 1851 Historic house known as 'Mine and Quarry House "in Roxbury, Ct ' Historic and Architectural resource survey is highly significant as the only surviving antique of the mining and quarrying industries. It boarders on 100's of acres of the Roxbury Land trust and enjoys valley views of the Shepaug River. Over time it became a really charming home in a very private and pretty setting

    Karen Casey William Pitt Sotheby's Int'l

    11 Hodge 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
  • 67 Transylvania Rd, Roxbury, CT 06783
    67 Transylvania Rd, Roxbury, CT 06783
    67 Transylvania Rd, Roxbury, CT 06783
    /38

    $1,095,000

    • 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
  • 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
  • 103 Chalybes Rd W, Roxbury, CT 06783
    103 Chalybes Rd W, Roxbury, CT 06783
    103 Chalybes Rd W, Roxbury, CT 06783
    /22

    $2,850,000 New Construction

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

    103 Chalybes Rd W, Roxbury, CT 06783

    TO BE BUILT - Tranquil Luxury on 16 Private Acres in Roxbury, Connecticut. A rare opportunity to create your dream getaway in the heart of lower Litchfield County. Tucked away on 16 secluded acres, this stunning property offers the perfect canvas for your primary, secondary or vacation compound. Choose this beautifully planned 4,777 square foot residence-or bring your own architectural vision to

    Christopher Haggerty Around Town Real Estate LLC

    103 Chalybes Rd W, Roxbury, CT 06783
  • 306 Upper Grassy Hill Rd, Woodbury, CT 06798
    306 Upper Grassy Hill Rd, Woodbury, CT 06798
    306 Upper Grassy Hill Rd, Woodbury, CT 06798
    /40

    $349,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,936 Sq Ft

    306 Upper Grassy Hill Rd, Woodbury, CT 06798

    Your next project starts here at 306 Upper Grassy Hill. Opportunity knocks in the charming town of Woodbury with this 3-bedroom, 2 full bath home packed with potential and ready for its next chapter. Situated on a generous 1.5-acre lot, this property offers plenty of space, privacy, and the chance to build some serious sweat equity. Inside, you'll find hardwood floors, a spacious sunroom

    Shawna Mucherino Coldwell Banker Realty

    306 Upper Grassy Hill Rd, Woodbury, CT 06798
Connecticut Roxbury

Real Estate & Homes for Sale in Roxbury, CT

Why Live in Roxbury

Just a few miles east of Bridgeport, in western Connecticut's Litchfield Hills, sits the town of Roxbury, a rural area spread over 27 square miles with a population just over 2,000. That low population density means that residents here can appear somewhat isolated from the creature comforts associated with urban living, but that’s exactly how they like it. “People move to Roxbury because it’s quiet,” says local Realtor Stephanie Blake of Realty ONE Group Connect. “The rural nature of the town is its real appeal. At the same time, though, it’s c ...

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 $1,640,064.
Are home prices dropping in Roxbury?
Yes, home prices in Roxbury are down 5% in the last 12 months.
How many homes have sold over the last 12 months in Roxbury, CT?
48 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 06488, 06810, 06484, 06010 and 10512.
How much do you need to make to afford a house in Roxbury?
The median home price in Roxbury is $1,379,000. If you put a 20% down payment of $275,800 and had a 30-year fixed mortgage with an interest rate of 6.84%, your estimated principal and interest payment would be $7,220 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $309K 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 135 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 $1,067,500, down 15% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,067,500
Median Single Family Sale Price
$1,232,500
Average Price Per Sq Ft
$477
Number of Homes for Sale
23
Last 12 months Home Sales
48
Months of Supply
5.80
Median List Price
$1,379,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-15%
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