The Matthews Team

William Raveis Lifestyles Realty

Roxbury CT Real Estate

Corn Field in Roxbury

Nestled amidst the scenic rolling hills on Route 67 lies the quaint town of Roxbury. The Mohegan Indians aptly named the area "Shepaug," which translates to "rocky water" in honor of the stunning, meandering river that winds through its lowest valleys.

Established in 1713, the area was renamed Roxbury and remains true to its name with an abundance of charming New England fieldstone walls crisscrossing its idyllic rural landscape. Its peaceful ambiance has attracted numerous famous artists, actors, playwrights and more over the years - including the iconic Marilyn Monroe who called this serene town home during the late 1950s.

If you're looking for a tranquil retreat away from the hustle and bustle of city life, browse our extensive listings below to explore all available real estate and homes for sale in Roxbury, CT.

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

Properties in Roxbury

Contact the William Raveis Lifestyles Team at 860-868-0511 with any questions or to schedule a private tour.

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79 Wellers Bridge Road Roxbury CT 06783
Coming Soon

MLS Number 170554981

  • Single Family
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,097
  • Acreage 5.9

Charming renovated cottage style home on 5+ acres abutting town land in highly desirable Roxbury. This recently refreshed home features 2-3 bedrooms, two full baths, and a newly renovated kitchen complete with stainless appliances, new cabinetry and windows overlooking a Trex deck and level yard area. The first level offers a primary bedroom with vaulted ceiling, walk-in closet and private access to the deck along with a guest bedroom. A large living room with fireplace, recessed lighting and built-ins flows into the dining room. The dining room with classic slider opens onto a large deck and overlooks the nearby light woods and a small barn that gives plenty of storage along with an under-the-home garage port. The lower level offers a large den or overflow space for guests with a recently renovated full bath and walk out to under home car space. Extras include foyer with pocket door, whole house generator and stonewalls. The opportunity for a perfect weekend getaway or full time living!

Listed by William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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28 Garnet Road Roxbury CT 06783

Roxbury, CT28 Garnet Road

Price$899,000

Est. Mortgage: $/month

Open House

MLS Number 170555572

  • Single Family
  • Next Open House: Sun 03/26 11:00 am. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,301

Totally private tree-top oasis in desirable Roxbury neighborhood. With seasonal long views and sunsets this is a true retreat , a 3 bedroom 3 1/2 bath contemporary home surrounded by the sights and sounds of nature. The expansive two story living/dining room with fireplace has outstanding natural light and an open concept custom kitchen with Bosch appliances. The spacious wrap around deck is ideal for entertaining. Convenient main floor primary bedroom has a renovated en suite bathroom (2019) and direct access to the deck and darling screened-in "teahouse". Perfect spot to add your hot tub! The 2nd floor offers 2 bedrooms, full bath and a cozy loft space for office or media room. Newer carpeting in the fully-finished basement (2020) with in-law suite potential and a full bath. Brand new roof (2020) with top of the line Ultra HD shingles on whole house. Chimney recently repointed in (2018) and sealed (2019). Heating system replaced in 2015 (Budarus G115). New whole house generator and a/c. An inviting woodland paradise for anyone searching for a turn key home. 90 Min to NYC. Close to Roxbury center, Washington Depot and area hiking.

Listed by Rebecca Doh of W. Raveis Lifestyles Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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00 L1 Willow Brook Drive Roxbury CT 06783

MLS Number 170554078

  • Single Family
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 5,508
  • Acreage 10.79

To be built home. Your search ends here! This 6 Bed, 5 Bath, 2 Half Bath home includes an open floor plan with ample storage space. One of the centerpieces of the home, the living room is spacious yet cozy. Ample windows allow for natural light as the space flows through to the dining area and kitchen. The open kitchen features a wall oven, rangetop and large butler's pantry. The center island offers a second seating area and is easily accessible from the double-exposure sliding glass doors that open to the rear deck. With two walk-in closets, an en-suite bathroom and its own terrace, the first-floor primary suite is a modern, sophisticated, and private space. The suite's four large windows allow plenty of natural light. The second floor also has three ample bedrooms with two shared baths and another large ensuite bedroom. Meanwhile, the first floor has a large ensuite guest bedroom. There is also an additional second-floor terrace flex space to relax and enjoy. This spacious new construction, to be built by Welcome Homes in beautiful Roxbury, CT. Welcome Homes makes it easier to build your dream home. The tech-enabled home developer streamlines the entire process and offers guaranteed all-in pricing and a total coverage warranty on the final build. The land can also be purchased separately for $549,000.

Listed by William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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00 L8 Willow Brook Drive Roxbury CT 06783

MLS Number 170554080

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,965
  • Acreage 10

To be built home. This 4BR/4BA colonial is located in beautiful Roxbury, CT. Rich in historical influence, this home embraces traditional colonial design with modern appeal. Classic architecture reinvented through fresh eyes, this home features clean lines, an open floor plan, ornate details, and sleek finishes. This sophisticated new construction is to be built by Welcome. Welcome makes it easier to build your dream home. The tech-enabled luxury home builder streamlines the entire process into three simple steps and offers guaranteed all-in pricing before ever breaking ground and a total coverage warranty on the final build. The living room is one of the centerpieces of the house, easily accessed from the kitchen area or the staircase leading to the second floor. From this space, you are able to enjoy the seamless transition from indoors to outdoors through large, double-exposure sliding glass doors. The kitchen comes fully equipped with high-quality appliances, with the option to upgrade to a beautiful, integrated refrigerator system that fits harmoniously within the custom cabinetry. The kitchen features a large island with ample seating overlooking your living, dining, and outdoor spaces. Positioned at the front of the home, the oversized primary suite's four large windows allow plenty of natural light with an en-suite bathroom featuring double vanities, a floating tub and walk-in shower.

Listed by William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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49 Garnet Road Roxbury CT 06783

Roxbury, CT49 Garnet Road

Price$2,195,000

Est. Mortgage: $/month

MLS Number 170549073

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,693
  • Acreage 4.94

Located in beautiful Litchfield County in the picturesque town of Roxbury, this modern stylish 4 bedroom, 4.5 bathroom home is situated on 5 private, quiet acres, This property offers a fabulous great room with soaring beamed ceiling, an amazing floor to ceiling stone fireplace that is flanked w/2 story windows, walls that are completely lined with glass and French doors that lead to large outdoor entertaining area with wonderful outdoor stone fireplace. Inviting living/dining area w/vaulted ceilings, large stone gas fireplace and opens to the modern high-end kitchen w/cathedral wood lined ceiling, large quartz center island and state of the art appliances. First floor primary bedroom w/Italian stone bath. Upper level has a 2nd primary bedroom suite with stone bath and washer & dryer unit, two additional quest bedrooms, both en-suite with stone baths, Lower level has a large finished area, a great family/rec room. There is also a professionally installed home business grade Ubiquiti UniFi wired and wireless network. All fireplaces are piped for propane. Invisible fencing has also been installed on the property. Only 90 minutes to Manhattan. Totally done and ready to move in!!

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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3 Jonathan Drive Roxbury CT 06783

Roxbury, CT3 Jonathan Drive

Price$445,000

Est. Mortgage: $/month

MLS Number 170551616

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,940
  • Acreage 2.26

Bring your ideas and plan to renovate this contemporary cape. Great upside potential. Western views possible with more clearing. Newly refinished hardwood floors on main level. Kitchen features brand new appliances. 2 main level bedrooms share hall bath. Upstairs is a large suite with 2 rooms, a larger bath, and brand new wall to wall carpeting. The basement is full height and spacious with potential to finish into more living space. 2 car garage. Very convenient location with easy access to Washington, Roxbury, New Milford and Woodbury town centers and amenities.

Listed by Stacey Matthews of W. Raveis Lifestyles Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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48 River Road Roxbury CT 06783

Roxbury, CT48 River Road

Price$860,000

Est. Mortgage: $/month

MLS Number 170548098

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,000
  • Acreage 3.25

This 4 bedroom modern saltbox is surrounded by 3.25 acres of lush lawn and mature trees. Located on historic River Road, walking distance to Shepaug River, River Road Preserve, Roxbury Land Trust, hiking, swimming and fishing. The open floor plan offers multiple living and dining areas, a library with walls of built in bookcases, remodeled half bath and a sunken living room. The bright, kitchen with granite counters, and tile floor is open to a keeping room or music room with wood burning fireplace. The second-floor primary bedroom suite has vaulted ceiling and a Juliet balcony overlooks the side yard and patio. The additional three bedrooms include one en-suite and a 3rd full bath for guests. The back yard is perfect to install your own pool if desired. Enjoy all Roxbury has to offer. A lovely home in a lovely location.

Listed by BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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238 North Street Roxbury CT 06783

Roxbury, CT238 North Street

Price$415,000

Est. Mortgage: $/month

MLS Number 170543254

  • Land
  • Acreage 6.79
  • Zoning res

Rarely available Lot in Roxbury! Magical 6.79 acre lot featuring a majestic stream and spring house, un-touched historic stone walls, gently sloping tree-covered hills and an abundance of pine trees, oaks and maples as your canvas. This masterpiece lot is perfect to build your dream home and to connect with what is important in life. Whether a weekender or full-time resident, the Woods will offer you ultimate privacy with endless possibilities for a simpler place and way of life. Our wonderful architectural team is available to design your one of a kind home or you can bring your own. APPROVED DRIVEWAY PERMIT on FILE. Shown by Owner/Agent.

Listed by Brown Harris Stevens

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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92 Hemlock Road Roxbury CT 06783
Pending Continue to Show

MLS Number 170543648

  • Land
  • Acreage 3.03
  • Zoning A&C

Cleared and open 3-acre lot on a quiet town road in Roxbury. Soil testing has been done for a 4-bedroom home without an engineered septic system. Driveway permit is approved, and this lot is ready to build on with easy access. Hemlock is an unpaved town road, not far from town and a private area.

Listed by Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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8 Evergreen Drive Roxbury CT 06783

MLS Number 170541618

  • Land
  • Acreage 3.39
  • Zoning C

Great location for this approved 3.4 acre lot located on a private cul-de-sac directly across from the Shepaug River and Mine Hill. This is one of the last undeveloped lots in the subdivision. Ideal upper location on this lot to build a home that has a view of Litchfield Hills and the Shepaug Valley yet is private from the other already built homes. Septic plan and percolation tests have been completed and suitable for a 4 bedroom home. Great area of $500K to $700K homes!

Listed by Weichert REALTORS Briotti Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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72 Welton Road Roxbury CT 06783

Roxbury, CT72 Welton Road, Tophet

Price$1,595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 170539824

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,758
  • Acreage 20

Quintessential and wonderful Hone on 20+- acres on BOTH SIDES OF DIRT ROAD. 14.61 ac with the house and directly across the street, 5.39 ac of raw land. Privacy and every amenity! updated 3 yrs ago. Entranceway where you can put a coat on, Living room with fireplace, eat in kitchen, with all amenities and fireplace and dining room with built in hutches and a fireplace. A Den/Library with built-ins and a half bath, and the primary bedroom suite complete the first floor. There are three bedrooms and a bath upstairs. Outside, there are numerous places to contemplate nature with a patio off the kitchen, a lovely pool area and extensive grounds. A primary location, this setting is one of the best!

Listed by William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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44 South Street Roxbury CT 06783

Roxbury, CT44 South Street

Price$2,195,000

Est. Mortgage: $/month

MLS Number 170537959

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,450
  • Acreage 6.17

Josiah Bronson House. Consummate Connecticut 1792 Antique colonial estate, renovated to serve today's lifestyle while keeping all the charm of it's historic roots. Once a retreat to writer Manfred Lee of Ellery Queen fame and later used in film shoots, this estate sits between two ponds and overlooks 6 level acres of meadow, perennial gardens and heated pool area. The 3 bedroom main house and 1 bedroom guest space with living room, separate 725 ft studio barn features old barn beams from historic barn once on the property, for office/gathering/game room. An antique Ice house and rustic potting grace the garden areas. There is a recently built three bay barn garage with gym area. The heated pool, skating pond, perennial gardens, stone walls, brick and stone terraces all add to the feel of yesteryear. The first floor of the main house offers a luxurious high end kitchen with pantry and center island, an open Living room, Sun room, great room and library. Additional features are wood shingle roof, mature gardens. Set in the heart of Roxbury, close to hiking trails, Hurlbut park and Minor Memorial Library. - Private pool area with an adjacent outdoor shower.

Listed by William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 23, 2023
* 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.

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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 2023 SmartMLS, Inc.