26

Roxbury, CT Houses for Sale

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  • 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
  • 262 Tophet Rd, Roxbury, CT 06783
    262 Tophet Rd, Roxbury, CT 06783
    262 Tophet Rd, Roxbury, CT 06783
    /36

    $1,950,000

    • 3 Beds
    • 3.5 Baths
    • 4,458 Sq Ft

    262 Tophet Rd, Roxbury, CT 06783

    A truly magical setting in prime Roxbury location abutting major estates. The barn style home features large newer windows that overlook a spectacular pond. Enjoy the every changing water views with abundant wildlife from every room. Double high ceilings in the main living room are highlighted by library shelving and a field stone fireplace. The renovated kitchen beckons out to the pergola

    Stacey Matthews W. Raveis Lifestyles Realty

    262 Tophet 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
Connecticut Roxbury

Houses for Sale in Roxbury, CT

Why Live in Roxbury

Roxbury, a rural neighborhood in western Connecticut's Litchfield Hills, spans 27 square miles with a population of just over 2,000. Residents appreciate the quiet, low-density living while still being close to urban amenities in nearby towns like Woodbury and Bridgewater. The area is rich in natural beauty, with Hurlburt Park offering a playground, picnic pavilion, and hosting the annual Roxbury Pickin’ and Fiddlin’ Contest. River Road Preserve features a 1.5-mile hiking trail and scenic spots for picnicking and fly-fishing along the Shepaug River. History enthusiasts can explore Mine Hill Preserve, a 19th-century iron-making complex with hiking trails and self-guided tours. 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 18th-century Colonials to modern raised ranches, typically situated on large lots with mature trees. The neighborhood is served by Regional School District Number 12, with highly rated schools like Booth Free School and Shepaug Valley School, and nearby Kent School. While Roxbury lacks extensive commercial activity, residents can visit Roxbury Market & Deli for groceries and meals, or travel 20 miles to Waterbury for more shopping options. Attractions in the area include antique shopping at The Hidden Acorn in Woodbury and the cultural offerings of New York City, accessible by train from Danbury, less than 20 miles away. Crime rates in Roxbury are lower than the national average, contributing to its appeal as a peaceful place to live.
Learn more about living in Roxbury

Home Trends in Roxbury, CT

On average, homes in Roxbury, CT sell after 141 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 4% 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
$488
Number of Homes for Sale
25
Last 12 months Home Sales
47
Months of Supply
6.40
Median List Price
$1,472,500
Median Change From 1st List Price
11%
Median Home Sale Price YoY Change
-4%
How to Buy a Home How to Finance a Home How to Sell a Home

In Roxbury, there are currently 26 houses for sale, offering an array of options for potential buyers. With houses priced between $759,900 to $4,750,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Roxbury is $1,472,500, while the average sale price is $1,351,804, offering insights into the local housing market. On average, houses spend 141 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Roxbury, CT and find the perfect place to call 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.

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