The Matthews TeamWilliam Raveis

The Matthews Team

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 Team 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.

19 Golden Harvest Road Roxbury CT 06783

Roxbury, CT19 Golden Harvest Road

Price$5,700,000

Est. Mortgage: $/month

MLS Number 170459831

  • Single Family
  • Square Feet 5,808
  • Property Style Colonial, Barn
  • Bedrooms 4
  • Bathroom 6

Perched at one of Roxbury's highest elevations, with hypnotizing views, lies the Golden Harvest homestead of master builder Ed Cady. The compound sits on a 26 acre parcel personally selected for its privacy, elevation and direct adjacency to the Roxbury Land Trust's 450 acre preserve. Using antique timber barn frames from upstate New York, he constructed the buildings that stand today. The main house exudes casual comfort, with hand-hewn beams blending seamlessly with modern finishes. There are five fireplaces in the main home, antique wide-board floors, native Roxbury granite and endless bespoke details that are so distinctively Cady. The spacious kitchen has a separate eating area, pantry and sun-filled greenhouse. The public wing of the home houses the great room, with soaring ceilings, never-ending views and room for both intimate and large-scale entertaining. The upper level houses two primary bedroom suites plus an office that is easily converted to an additional BR. The lower level includes a recreation room and full bath. The 1BR/1.5BA guest house - well separated from the main house - is a jewel with all the same Cady detailing and a deck overlooking the entire Shepaug River Valley. The barn has parking for 3+ additional vehicles and an in-law apartment above. Additional outbuildings give the property a rich historic texture. The craftsmanship and quality here is at the highest level, and the opportunity to own the "King's Castle" comes up only once in a generation.

Listing Courtesy of Compass Connecticut,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

264 Painter Hill Road Roxbury CT 06783

Roxbury, CT264 Painter Hill Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number 170461050

  • Single Family
  • Square Feet 4,396
  • Year Built 1792
  • Property Style Cape Cod, Antique
  • Bedrooms 5

Location! Location! Location! This gorgeous antique cape is located in the coveted Painter Hill area of Roxbury. Antique charm abounds. There are 5 bedrooms and 3 full and 2 half baths in the main house. There are also guest quarters above the detached barn/garage. Wide plank wood floors are throughout the home. There are 4 stone fireplaces. There is a gourmet kitchen with a Wolf range and Sub Zero refrigerator and freezer. There is a breakfast area with french doors to the patio. The living room has built ins, a fireplace and opens to a lovely screened porch. The dining room, den and office all have stone fireplaces. The main level primary bedroom is spacious and includes a dressing room, luxurious bath with dual sinks, a soaking tub and shower, as well as french doors to the rear yard. The upper level has 3 bedrooms and a hall bath. There is a private guest suite on the lower level which walks out to the rear yard. There is an in ground gunite pool for your summer pleasure. Painter Hill was named for its scenic beauty and this property will not disappoint. Located under 2 hours from NYC makes this a great weekend getaway or full time home. No weekend showings until further notice.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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
  • Year Built 1860
  • Bathroom 5

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: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

88 Old Roxbury Road Roxbury CT 06783

Roxbury, CT88 Old Roxbury Road

Price$2,785,000

Est. Mortgage: $/month

MLS Number 170445634

  • Single Family
  • Square Feet 3,623
  • Year Built 1790
  • Bathroom 4
  • Bedrooms 4

c.1790/1800 Colonial-Federal-style farmhouse located on a whisper-quiet and unpaved scenic country road in one of the most desirable areas of Roxbury. The character-loaded 3-story clapboard house is sited on a perfectly level 23+- acre property that includes a 19th century former smokehouse, and a historically significant English U-shaped barn, open pastures and paddocks, a stream running along the west boundary to the pond, and pine forest to the northeast. The property is accented by fieldstone walls and abuts Roxbury Land Trust, offering privacy within walking distance to nature preserves and trails. Located a mere 90 miles from NYC you will feel a world away in this renovated antique home with its sophisticated feel and a sense of history as you note many lovely period details throughout. These include exposed hand-hewn beams, original hardwood flooring, four wood-burning fireplaces, and oversized 12-over-12 windows that allow natural light to bathe each room. The interior features a central fireplace surrounded by public rooms, including a formal dining room, library/sitting room, and formal living room. The country kitchen, complete with designer appliances and butler's pantry, is located off the formal dining room in its own wing with cathedral ceiling. The kitchen opens to an informal dining area and keeping room that is flooded with natural light thanks to skylights and five sets of glass sliders that open to the gardens.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave 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
  • Property Style Cape Cod, Farm House
  • 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: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

27 Wakelee Road Roxbury CT 06783

Roxbury, CT27 Wakelee Road

Price$2,200,000

Est. Mortgage: $/month

MLS Number 170443960

  • Single Family
  • Square Feet 2,640
  • Bathroom 3
  • Bedrooms 5
  • Year Built 1815

Location, Historic, Architectural and Iconic. Rarely does such a superb property come to market. Located on one of the most beautiful country roads in Roxbury. This circa 1840's Greek Revival type is perfectly sited to catch the sun, thus many of the rooms are bathed in light. The rooms are centered around the period fireplace. The front rooms consist of a generous formal dining room and handsome library with fireplace. The cook's kitchen with center island and its abundance of windows, patio access, and post and beam construction is open to the main living areas of the home. This is an extraordinary space for easy entertaining. Ceiling are 9' 6” with wide board floors, architectural details reflecting the period, and a sense of historic integrity. The main level primary bedroom is en-suite and has its own wing with all amenities and complete privacy. Also on the main level is powder room and laundry. Upstairs there are four additional bedrooms (one with a fireplace) and a large bathroom. The land, consisting of eight acres, is level and mostly open meadow providing pollinator pathways. An in-ground pool, a tennis court, a pond, a significant historic English Bank barn, established gardens, all amenities which create country living to perfection. The property is adjacent to Roxbury Land Trust. There have been thoughtful additions over the years combining architectural integrity with gracious modern living.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

11 Falls Road Roxbury CT 06783

Roxbury, CT11 Falls Road

Price$1,795,000

Est. Mortgage: $/month

MLS Number 170460589

  • Single Family
  • Square Feet 3,722
  • Bedrooms 4
  • Year Built 2022
  • Property Style Colonial, Antique

New construction w/ authentic details & an open layout. Set on 3± flat acres with possible pool site, the 4BR/4.5 bath is finished in clapboard w/cedar shake roofing & sited on a quiet country road. Main fl has an open great room w/ chef's kitchen, FP, and French drs leading to stone patio. The formal living rm has a 2nd FP & lots of space for entertaining. The formal dining rm is spacious enough to comfortably host large dinner parties. The 2nd fl primary suite is fitted with a FP, walk-in closet, marble bath& dual sink, soaking tub & glass shwr. There's also 2 guest BRs & 2 full baths--one en suite. 3rd fl with full height ceilings, offers a 4th BR, separate flex room, full bath & storage closet. Custom touches are incorporated throughout the home to create the sense it has been on site for a century. The Bertazzoni oven & gas stove, the carbon-grey velvet quartz kitchen countertops, & white oak herringbone pattern flooring are just a few of the home's distinctive features. Add'l amenities include: detached 2-car garage w/ cedar board siding, cedar shake roofing & hand forged door hinges; an automated whole-house generator; zoned air conditioning; a hot water system that uses the most recent heat pump technology, and a wide-open basement for additional storage. Done to perfection with taste and style, the 3,600±-square-foot home was designed as plug-and-play living for the voguish couple looking for a weekend/summer retreat or an indulgent primary residence.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

114 Town Line Road Roxbury CT 06783

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: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

114 Town Line Road Roxbury CT 06783

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: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

244 North Street Roxbury CT 06783

Roxbury, CT244 North Street

Price$1,395,000

Est. Mortgage: $/month

MLS Number 170460156

  • Single Family
  • Square Feet 1,815
  • Bathroom 3
  • Year Built 2022
  • Property Style Contemporary

Beautiful approved 6.94 acre Lot and house location, with approved driveway and permits in place, with a waterfall and brook running through. This is a special piece of land abutting 10.61 acres of gorgeous open space located in the storied town of Roxbury CT, a consummate NYC weekender town. Our home, designed by renowned architect Hugh Sullivan of Bennett Sullivan Associates, Inc., can be built with modern touches such as walls of windows, black metal roof, and sleek touches, or remain a more traditional design, the choice is yours. At 1815 SF, this flexible loft home features extra high 11 foot ceilings throughout and dramatic 16.8 foot vaulted ceiling in the living room with Wittus shaker stove. There is an open chefs kitchen with Viking, Miele and Sub-zero appliances and sintered stone counter tops. Dining and living rooms are side by side for easy entertaining. The 3rd bedroom makes a great guest room or home office for the perfect full time or weekend getaway. A solarium and an all-season room leading out to a large deck make it easy to enjoy the ever changing views of the woods. There is also a detached garage and circular paved drive. Other specs include Control 4 system, Simpli-safe security system, Andersen 400 windows and Generac generator. The picturesque lot features un-touched historic stone walls and an abundance of pine trees, oaks and maples as your canvas. A masterpiece, perfect to build your dream home. Shown by private appointment. Owner/Agent.

Listing Courtesy of Brown Harris Stevens

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

53 Southbury Road Roxbury CT 06783

Roxbury, CT53 Southbury Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170453042

  • Single Family
  • Square Feet 4,758
  • Bathroom 4
  • Bedrooms 4
  • Property Style Colonial, Tudor

Welcome to your very own storybook cottage! Your fairytale home awaits with custom details that will WOW you!The hand split cedar roof is one of the first things you will notice along with maple leaf shaped copper roof detail. As you enter the foyer you will notice a sweeping staircase made of rich mahogany, custom arched doors and hardwood floors. A house made for entertaining, the floor plan allows for guests to flow seamlessly from to room with plenty of access to enjoy the views of the surrounding beauty. The gourmet custom mahogany eat in kitchen offers high end appliances, a copper farmhouse sink and a breakfast area. A stunning stone fireplace is the focal point of the dining room with plenty of space for guests. Upstairs you will find a master bedroom with a private balcony overlooking the backyard and custom steam shower as well as double walk in closets. Wander through the garden path to the backyard overlooking a private pond with views of the most gorgeous sunsets. An in ground heated gunite pool with built in spa and swim up bar makes this home the perfect year round retreat. This home has some much to offer including a brand new whole house generator finished basement and a flexible floorplan to suit your lifestyle. Come fall in love!

Listing Courtesy of Family Realty Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

48 River Road Roxbury CT 06783

Roxbury, CT48 River Road

Price$1,195,000

Est. Mortgage: $/month

MLS Number 170428914

  • Single Family
  • Square Feet 3,000
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1982

As you enter the meandering drive you will feel the peace of the natural surroundings envelope you. 3.25 acres of lush lawn and mature trees. This contemporary saltbox is the perfect backdrop for your art and eclectic furnishings. From the foyer, you enter the library where walls of built-in bookcases greet you. The open floor plan with multiple living and dining areas including a patio, deck with awning. The bright, kitchen with upscale appliances, granite counters, and tile floor is perfect for the chef in the family. Keeping room or music room with fireplace is open to the kitchen. The second floor features 4 bedrooms including a master suite with vaulted ceiling and Juliet balcony overlooking the side yard and patio. The remaining three bedrooms include one en-suite and a 3rd full bath for guests. Walk to the Roxbury land trust, or swim in the River. The back yard is perfect to install your own pool if desired. Enjoy all Roxbury has to offer. This bucolic town features low taxes and so much natural beauty.

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave 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 2022 SmartMLS, Inc.