The Matthews GroupWilliam Raveis

The Matthews Group

Roxbury CT Real Estate

Corn Field in RoxburyTucked away amid the rolling hills on Route 67 is the town of Roxbury. The Mohegan Indians named the area “Shepaug”, which means “rocky water”, for the beautiful, meandering river that cuts through its lowest valleys. The area became Roxbury when it was settled in 1713, and is true to its name considering the abundance of New England fieldstone walls crisscrossing its picturesque, rural landscape. Due to the tranquility of the area, many famous artists, actors, playwrights and more have called the area home, perhaps most notably Marilyn Monroe during the late 1950s.

>> Learn more about the town of RoxburyRoxbury Real Estate for Sale

Properties in Roxbury

Contact The Matthews Group at 860-868-0511 with any questions or to schedule a private tour.

Time Saving Tip: Sign up for a free account to save your favorite listings and get notified when new properties match your criteria.

Click to easily view Roxbury homes, land for sale in Roxbury, houses with land in Roxbury, and luxury homes for sale in Roxbury.

68 Judge Roxbury CT 06783

Roxbury, CT68 Judge

Price$4,250,000

Est. Mortgage: $/month

MLS Number 170400606

  • Single Family
  • Square Feet 10,346
  • Bedrooms 6
  • Bathroom 6
  • Year Built 1995

Rockridge - an exemplary estate by Architectural Digest regular, Ed Cady. Set on 17.5 acres with sweeping, level lawns edged by woodland spilling into over 400 acres of Roxbury Land Trust, the magical setting is just the start. The colonial reproduction home is flanked by two pristinely restored antique barns transformed into architecturally majestic living spaces. Offering over 10,000 SF of custom living space, the 6 BR/6BA home was built with no cap on expense and features hand-built cabinetry, locally forged hardware, Lepage windows/doors, custom sinks and vanities and mechanical systems of the highest level. The kitchen includes concealed SubZero refrigerator and freezer, oversized island and a Diva de Provence range. The great room features a floor to vaulted ceiling height, two stories of windows and one of the home's five FPs. The main suite also highlights majestic, centuries-old hand-hewn beams, oversized windows, built-in cappuccino bar and a FP. Dual dressing rooms and luxury bath (truly spa-like with soaking tub, steam shower and sauna) round out this haven. Lower level includes a wine room, home gym and 1BR guest apartment. Outdoor living with a large bluestone terrace along the back of the home overlooking the lawn and free-form gunite pool and spa. Mechanical details include an irrigation system, generator, lightning protection, central vac, integrated sound system and 8 BR septic. A residence of impeccable stature for an elevated Litchfield County lifestyle.

Listing Courtesy of Compass Connecticut, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

67 Squire Road Roxbury CT 06783

Roxbury, CT67 Squire Road

Price$4,225,000

Est. Mortgage: $/month

MLS Number 170420680

  • Single Family
  • Square Feet 4,371
  • Bedrooms 5
  • Bathroom 3
  • Year Built 1974

Located on one of the most beautiful streets within the idyllic town of Roxbury, CT, this extraordinarily designed and masterfully renovated residence is perfectly situated on almost 11 acres of private land, adjacent to the beautiful Roxbury land-trust, complete with hiking trails and a waterfall. Newly renovated throughout, this residence has a most unique style that combines the best elements of contemporary architecture while retaining the warmth of a New England home. No detail has been overlooked in the design of this home: from tall panes of glass through which light streams into every room, to handcrafted, radiant-heated and artisan-finished white oak floors, to the selectively restored historic wooden post and beams. The intelligent floor plan allows for privacy and seamless indoor-outdoor living whereby one can step onto the beautiful stone patios that overlook the surrounding woods and the stream below, from all the main rooms of the house. The exquisite beauty of nature is ever-present in this one-of-a-kind residence.

Listing Courtesy of Compass Connecticut, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

36 Clover Knolls Roxbury CT 06783

Roxbury, CT36 Clover Knolls

Price$3,300,000

Est. Mortgage: $/month

MLS Number 170418676

  • Single Family
  • Square Feet 3,050
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1987

Clover Knolls - 129 acres of natural beauty in one of Roxbury's most storied and treasured corners. Offering a variety of Connecticut's best landscapes including sun-kissed farm pastures with distant views, lovingly tended mature forest, a sparkling spring-fed pond and open sweeping lawn around the contemporary home, few locations in Litchfield County evoke such emotion, inspiration and sense of place. Offered for the first time in nearly forty years, this special property is ready for its next chapter and presents a multitude of possibilities. There are multiple building parcels allowing for the construction of a larger main residence, separate dwellings for a single-owner compound, or for subdivision. The current 2BR residence is set on a perfect spot with views to the pond and further distant views beyond and was built with a beautifully warm and simple design aesthetic reminiscent of Frank Lloyd Wright. Construction of a larger, main residence at a higher elevation could leave the existing home as a guest house, pool/tennis house, etc. The property is largely held in tax-benefitting status and the forest is under a forestry management plan which keeps the woods healthy and maximizes their attractiveness for humans and wildlife alike. This truly magical land sits in the heart of Litchfield County's desirable Roxbury/Washington region, less than two hours from Manhattan but a world away. Taxes and assessment listed are for all five parcels.

Listing Courtesy of Compass Connecticut, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

142 East Flag Swamp Road Roxbury CT 06783

Roxbury, CT142 East Flag Swamp Road

Price$3,250,000

Est. Mortgage: $/month

MLS Number 170404703

  • Single Family
  • Square Feet 4,544
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1995

Welcome to Laurelwood - a country home like no other. Set on nearly 100 acres of pristine, untouched land, this residence is a jewel. Modern design elements such as walls of glass and soaring ceilings work in harmony with warmer interior materials like wood and native stones. Built of the finest materials, and maintained impeccably, the home has a gracious layout with large public spaces interspersed with smaller, more intimate moments. The kitchen offers warm wood cabinetry, SubZero and Miele appliances, and a dining area with a FP and views to the pond. A new deck expands the kitchen area to the outdoors. The LR is cozy with a FP. 4BRs provide plenty of private space. Baths are luxuriously appointed with Waterworks tile and fixtures, and the master bath has a spacious soaking tub. Sheltering in place is a joy at Laurelwood, as the home provides a separate office that anchors one end of the home and features a vaulted ceiling and walls of glass. Another incredible space is the home gym - no need to leave in order to stay fit. Rounding out the offering are top of the line mechanicals including two new, multi-zone HVAC systems, two separate attached garages that provide a total 4+ car covered parking, a whole-house generator and a separate utility barn which houses the heavy equipment to keep the estate running smoothly. This equipment is available for sale outside of escrow. All of this magical solitude, yet moments to everything and only 90 minutes from Manhattan.

Listing Courtesy of Compass Connecticut, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

102 North Street Roxbury CT 06783

Roxbury, CT102 North Street

Price$2,895,000

Est. Mortgage: $/month

MLS Number 170422197

  • Single Family
  • Square Feet 5,204
  • Bedrooms 6
  • Bathroom 5
  • Year Built 1860

Magnificent Compound. "Four Stone Chimneys" of Edgehill Farm, updated by noted NYC designer, the late Burt Wayne, is located just 90 minutes from NYC. Set on over 21 acres of open meadow, gardens and stone terraces in the historic town of Roxbury where Arthur Miller, Marilyn Monroe, Walter Mathau, Alexander Calder, William Styron, among many other artists and writers perfected their craft, is the perfect getaway! This 1860's Colonial Revival Estate with 6 bedrooms in the Main house, 4.5 baths and 4 fireplaces, has been lovingly maintained and updated with the finest materials. Enjoy your guests with a 3 bedroom carriage house and an additional 2 bedroom guest house surrounding a natural shaped in-ground pool, sumptuous gardens and brick terrace. The rooms are a generous size with high ceilings and detailed moldings throughout. A dramatic columned front porch runs the entire length of the main house. The guest houses, each with 1450 feet, have 4 season porches and overlook Orchard, Christmas Tree Farm and Pine grove. The barns and silos are noted on the Connecticut State Registry of Historic Farm Buildings. A stone walled driveway leads you into the heart of the this stunning "Gentleman or Gentlewomans' farm" and is the perfect residence for an equestrian, artist or writer!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Lot A South Street Roxbury CT 06783

Roxbury, CTLot A South Street

Price$2,695,000

Est. Mortgage: $/month

MLS Number 170414483

  • Single Family
  • Square Feet 4,000
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2021

To Be Built, just 90 minutes from NYC! Beautiful 18 Acre lot with High Foothill and pastoral views, light woods and abutting Roxbury Land Trust for great hiking, surrounding the property. Private setting with Driveway in, stone outcroppings and mountain laurel abound. Ready to build your private magnificent estate. Located in the sought-after Squire Road area of Roxbury, just minutes from town and great access to NYC and an easy, down-county commuting location!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

32 Grassy Hill Road Roxbury CT 06783

Roxbury, CT32 Grassy Hill Road

Price$2,300,000

Est. Mortgage: $/month

MLS Number 170396074

  • Single Family
  • Square Feet 4,728
  • Bedrooms 4
  • Bathroom 5
  • Year Built 2001

This custom built Georgian with stylish corner quoins lends an air of quiet sophistication to this rural setting. Come and relax in this very private home which sits at the crest of a large open field with dramatic western views. Perfect potential for animals or creating a farm. Gourmet kitchen with bright breakfast nook that overlooks the property. Butler's pantry leads into formal dining room with views. Formal living room, Media Room and Library complete the first floor. Crown moldings, French doors and hardwood floors enhance the luxurious feel. The second floor features a spacious master bedroom with views and 2 addl bedrooms with a jack and jill bath. The 4th bedroom is part of the apartment/office above the garage and up a separate staircase. Perfect for guest, in-laws, nanny or a home office. The basement is large and full height is offers potential for finishing into a game room, gym, movie room etc. Generator.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

114 Town Line Roxbury CT 06783

Roxbury, CT114 Town Line, Mine Hill

Price$1,800,000

Est. Mortgage: $/month

MLS Number 170405991

  • Land
  • MLS Status Active
  • Acreage 41
  • Waterfront
  • Zoning C

Unencumbered acres* comprising antique Dickinson Dairy House, sheds, and Greyledge Flag Barn. The land offers rare potential either as a renovation opportunity or as a new build given the dramatic vistas of the Shepaug River Valley afforded by the elevation and 240-degree views. The Dickinson Dairy House (aka the Seruphas Ward House c. 1845) is a vernacular farmhouse influenced by the Greek Revival style. It is composed of an early 19th-century center hall building and a recessed kitchen wing to the south with a full English basement at the rear. The Dairy House provides an interesting perspective how country builders at this time integrated both colonial and Greek Revival styles in Litchfield County. The home has not been occupied since the current owner purchased the property and it requires extensive renovation. Located to the south of the house is the Greyledge Barn -- constructed in 1996 and built of weathered siding from a barn in Indiana to replicate the look and aesthetic of a calving barn of similar size that used to occupy the rocky promontory that defines Greyledge Farm and the Estate. The barn is now used primarily for vehicle and equipment storage; however, it can be easily repurposed as it has a poured concrete floor, excellent natural light, and the structural integrity of a new building. View shed restrictions apply. Survey in process. Exact acreage TBD.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

17 Berry Road Roxbury CT 06783

MLS Number 170401685

  • Single Family
  • Square Feet 6,936
  • Bedrooms 3
  • Bathroom 1
  • Year Built 2007

Concept Plans and builder available immediately! The 7,000±-square-foot Barn/Farm Office, associated buildings and paddocks were constructed by the current owner in 2007. The Barn is sited on an elevated position to ensure views and access to the breeze emanating from the Shepaug River Valley. The design of the building(s) borrows from the Judds Bridge Farm in Roxbury. It utilizes a clapboard design, 12-over-12 mullioned windows, cedar shake roof, and copper gutters, while integrating leading HVAC and water technology as well as eco-friendly solar panels. While the buildings are currently utilized for commercial purposes, the Barn was designed to be easily converted into a substantial residence with the addition of five evenly spaced dormers on the second floor of the barn which would align with the six-foot-tall windows on the ground floor to allow for the creation of up to five en suite bedrooms. The Barn site is comprised of 25± acres and surrounded by stone walls, pasture, and horse or cattle/sheep turn-outs designed by the owner. Additional adjacent land is also available. The Tractor Barns and Haylofts located behind the Barn can be repurposed as a conventional garage and storage space, or additional living quarters to accommodate a car collection and/or staff.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

17 Berry Road Roxbury CT 06783

MLS Number 170405968

  • Land
  • MLS Status Active
  • Acreage 25
  • Zoning RR3

Concept Plans and builder available immediately! The 7,000±-square-foot Barn/Farm Office, associated buildings and paddocks were constructed by the current owner in 2007. The Barn is sited on an elevated position to ensure views and access to the breeze emanating from the Shepaug River Valley. The design of the building(s) borrows from the Judds Bridge Farm in Roxbury. It utilizes a clapboard design, 12-over-12 mullioned windows, cedar shake roof, and copper gutters, while integrating leading HVAC and water technology as well as eco-friendly solar panels. While the buildings are currently utilized for commercial purposes, the Barn was designed to be easily converted into a substantial residence with the addition of five evenly spaced dormers on the second floor of the barn which would align with the six-foot-tall windows on the ground floor to allow for the creation of up to five en suite bedrooms. The Barn site is comprised of 25± acres and surrounded by stone walls, pasture, and horse or cattle/sheep turn-outs designed by the owner. Additional adjacent land is also available. The Tractor Barns and Haylofts located behind the Barn can be repurposed as a conventional garage and storage space, or additional living quarters to accommodate a car collection and/or staff.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

114 Town Line Roxbury CT 06783

Roxbury, CT114 Town Line, Mine Hill

Price$1,800,000

Est. Mortgage: $/month

MLS Number 170385553

  • Single Family
  • Square Feet 2,228
  • Bedrooms 7
  • Bathroom 1
  • Year Built 1880

Unencumbered acres* comprising antique Dickinson Dairy House, sheds, and Greyledge Flag Barn. The land offers rare potential either as a renovation opportunity or as a new build given the dramatic vistas of the Shepaug River Valley afforded by the elevation and 240-degree views. The Dickinson Dairy House (aka the Seruphas Ward House c. 1845) is a vernacular farmhouse influenced by the Greek Revival style. It is composed of an early 19th-century center hall building and a recessed kitchen wing to the south with a full English basement at the rear. The Dairy House provides an interesting perspective how country builders at this time integrated both colonial and Greek Revival styles in Litchfield County. The home has not been occupied since the current owner purchased the property and it requires extensive renovation. Located to the south of the house is the Greyledge Barn -- constructed in 1996 and built of weathered siding from a barn in Indiana to replicate the look and aesthetic of a calving barn of similar size that used to occupy the rocky promontory that defines Greyledge Farm and the Estate. The barn is now used primarily for vehicle and equipment storage; however, it can be easily repurposed as it has a poured concrete floor, excellent natural light, and the structural integrity of a new building. View shed restrictions apply. Survey in process. Exact acreage TBD.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

26 Judge Road Roxbury CT 06783

Roxbury, CT26 Judge Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170394482

  • Single Family
  • Square Feet 3,118
  • Bedrooms 4
  • Bathroom 6
  • Year Built 1991

A rare opportunity to own a special country home with pool and guest apartment. The main house has 10 rooms and a flexible floor plan - 3+ bedrooms and additional rooms for overflow guests or home offices. The separate 2 car garage/barn has an apartment on the second floor with 1.5 baths. Set back from a quiet town road, the property has lovely mature gardens and beautiful outdoor living spaces including a covered front porch, a patio with pergola and a deck with pastoral views. There is a recently added heated fiberglass inground pool. A quiet Roxbury location close to the Bridgewater town line and only 90 min to NYC.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.