Roxbury CT Real Estate

Corn FieldTucked 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 Roxbury

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, and luxury homes for sale in Roxbury.

r=1-12
11 Farm Roxbury CT 06783

Price$1,195,000

Est. Mortgage: $/month

MLS Number 170182722

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 14.32

"Stone Creek Manor" High Quality Shingle Style home on 14+ private acres in Southern Roxbury. This estate borders 100 acres of protected land. Grand open kitchen with breakfast nook and center island opens on to Great room and private porch.. High quality construction with beautiful mill work and finishes. Gorgeous lush landscaping with fenced raised bed vegetable garden. 3 car garage. Large unfinished basement and attic with space above garage easily offer room to expand ... Minutes to Roxbury Center and easy NYC weekend location, just off Town Line Road. 4 Br, 3.2 baths, hardwood floors, high ceilings, crown moldings, Copper and Arch Shingle roof. 3 porches and open deck offer easy entertaining. French doors, beautiful stone walls and long meandering driveway lead you to the lovely setting complete with two brooks and a truly private location. All this, just minutes to town!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

257 Southbury Roxbury CT 06783

Price$1,150,000

Est. Mortgage: $/month

MLS Number 170212346

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 10.08
  • Square Feet 3,086

Wonderfully private and updated Roxbury compound with four bedroom, four bath mid-century Mediterranean vibe main house offering the convenience of one level living. Secluded and dramatic 10 acre property with park-like grounds that flow from the primary residence and gardens down to the salt pool with expansive stone deck and Guest House. The home's amenities include a chef's kitchen anchored by a Viking Range, Sub Zero and EuroCave Wine cooler. Steam room, covered outdoor grilling/dining area, hot tub, outdoor shower, koi pond and lushly landscaped rock garden are among other lifestyle drivers. Generously sized 2000+ sf Guest/Pool house has additional bedroom, full bath, complete kitchen, open dining/living room, loft and large studio. Within easy reach of farm fresh produce, organics, groceries, prepared foods, fine dining and thousands of acres of preserved land with miles of hiking trails. Barely 10 minutes to I-84 and ~90 minutes from the Big Apple.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

296 Painter Hill Roxbury CT 06783

Price$1,150,000

Est. Mortgage: $/month

MLS Number 170052871

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 4
  • Acreage 4

  One of Roxbury's finest addresses abutting the Alexander Calder estate. This modern farmhouse is a real stunner with an open floor plan, high ceilings and light filled interiors. Its sits high a top Painter Hill and has views across protected land. 5 bedrooms 3.5 baths. Gourmet kitchen with bar stool seating and walk-in pantry. Master suite with spa-like bath room. Spin cycle studio, playroom, media room/office. The tree lined driveway shines with pink blossoms in the Spring. Large barn. Super chic 3 car garage with glass doors.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

18 Minor Bridge Roxbury CT 06783

Price$1,145,000

Est. Mortgage: $/month

MLS Number 170153233

  • Single Family
  • Property Style Colonial, Other
  • Bedrooms 4
  • Bathroom 5
  • Acreage 2.53

Serene and stylish, this classic turnkey residence is beautifully sited in a pastoral setting complete with manicured lawn, boxwood hedges, stone walls, and lofty pines. Set back from the road with a circular driveway, the 4-bedroom/3.2-bath colonial is appointed with timber flooring, roomy interiors, and walls of windows that offer bright spaces throughout. The gourmet kitchen boasts an eating nook, soap stone counters, custom cabinetry, and 6-burner Thermador stove plus grill. Four generous sized bedrooms include a peaceful main floor master suite with a five-piece bathroom with his-and-hers marble vanities, glass shower, large jetted tub overlooking the garden, and a massive dressing room-a clothes lover's dream. The main level also has a large-scale recreation room, a warm family room with stone fireplace, sunny views, and walk-out to the stone entertaining patio with views of the grounds. Enjoy Roxbury summers in your beautiful Gunite pool-the focal point of the 3+-acre lot with perennial gardens and room for outdoor activities. This home has been meticulously cared for & generously loved. See to believe! Other highlights incl a 5-car garage, partially finished basement with an abundance of storage, and an in-ground irrigation system. Total privacy in the very heart of Roxbury Ct. Near town, tennis courts, golf & organic farm stands. Only 90 mins from NYC. This is a property for the person who knows and wants quality, and is ready to move in today.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

32 Judge Roxbury CT 06783

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170165118

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 6.67

Just 90 Minutes from NYC this stone and clapboard home is sited in the highly desirable Golden Harvest are with 270 degree VIEWS over the Shepaug River Valley and hundreds of acres of protected land. Enjoy complete privacy with light filled rooms, floor-to-ceiling windows, vaulted ceilings and a screened porch which overlooks nearby farmland. Enjoy outdoor entertaining with a built in grill on the expansive wrap around deck which overlooks the gorgeous Gunite pool. This architect designed home is set up for easy living with an open concept plan, atrium art gallery space, French doors to the outdoors, and 4 wood burning fireplaces. The family room features a stone fireplace, built-ins, wet bar and opens to the spacious kitchen w/granite counters, new 48 inch gas range and stainless appliances. The master suite features a luxurious master bath and walk in closet. Upstairs, three additional bedrooms overlook the treetop views, while the finished lower level offers more space to gather with a game room, media room and gym.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

35 Gold Mine Roxbury CT 06783

Price$1,050,000

Est. Mortgage: $/month

MLS Number 170206198

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 15.01

Exceptional example of Frank Lloyd Wright-Inspired mid-century modern architecture built of steel & stone offers a unique combination of character & features that would be hard to replicate at any price. Nestled in the hills of Roxbury on a 15-acre lot, the 6,000-sqft residence blends organically into the rolling landscape at the top of a long graveled drive along which are two spring-fed ponds. Light-filled interior contains a formal entry with chestnut paneled bar area w fireplace, spacious living room with alcove sunroom and natural stone fireplace, formal living room, kitchen, 1st fl en-suite master w garden access, 4-room in-law apt w kitchenette & separate entry with foyer. Second level has large master suite with a balcony & a sky-lit exercise room. A 2nd spacious bedroom has living room-like feel with enough room to accommodate a king size bed & generous sitting area. Additional rooms incl office/library with built-in bookshelves, first-floor laundry room & bonus room. Oak flooring and cedar closets throughout. The property has great view potential with some clearing, and sports a flagstone patio for entertaining or relaxation, a cedar-fenced vegetable garden, mature plantings, two water fountains, and a detached 4-car garage.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

51 Mine Hill Roxbury CT 06783

Price$995,000

Est. Mortgage: $/month

MLS Number 170120213

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.73

Charming antique with many updates. 4 bedrooms 3 full baths includes large Master with walk-in closet and vaulted ceilings. Family room with vaulted ceiling and exposed hand hewn beams. Open kitchen walks out to brick terrace and looks out over the pond with water lilies. Newly renovated mud room. Gunite pool with blue stone terrace and pergola. Walk down the street to miles of trails at Roxbury Land Trust. Great central location with easy access to Bridgewater, Roxbury, Washington and New Milford.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

126 Squire Roxbury CT 06783

Price$849,000

Est. Mortgage: $/month

MLS Number 170183378

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 3
  • Acreage 18.83

NEW PRICE! Surrounded by substantial properties this custom built contemporary home offers a private 18 acre setting in a special Roxbury location. The house is immaculate with an open floor plan and abundant natural light. There are 4 bedrooms, 2.5 baths, a kitchen with center island, Jenn-Air range and cherry cabinets, maple flooring on the main level and a two story living room with fireplace. The master bathroom has been recently renovated with all new fixtures, new vanity with double sinks, spacious shower and radiant heated floor. The lower walk-out level has a family room with wood burning fireplace, a laundry room and an office. A deck and a patio provide additional space for outdoor living overlooking the low maintenance grounds. There is an attached 2 car garage and a separate, heated 3 car garage with finished space above. A quiet, peaceful location only minutes from town.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

10 High Meadow Roxbury CT 06783

Price$795,000

Est. Mortgage: $/month

MLS Number 170198602

  • Land
  • Acreage 19.82

Gorgeous approved building lot tucked away in a private hilltop setting. Mostly level and rolling property that also provides view potential to the east and west. Beautiful location to build the home of your dreams on 19+ acres in a great Roxbury location. Convenient to all area dining, shopping and short drive to I-84. Roxbury is a beautiful town with low taxes!!

Listing Courtesy of ReMax Experience, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

72 Wellers Bridge Roxbury CT 06783

Price$775,000

Est. Mortgage: $/month

MLS Number 170208021

  • Single Family
  • Property Style Antique
  • Bedrooms 4
  • Bathroom 4
  • Acreage 4.28

Ultimate Charm in this 1790 farm house. House features original wide plank chestnut floors, exposed beams and three fireplaces. Also enjoy the first floor master suite with his & her marble baths & dressing room. Kitchen has custom milled cabinetry & professional appliances. For outdoor enjoyment the property has an in-ground gunite pool, patio, terrace, beautiful gardens and beautiful old stonewalls. Truly a one of a kind vintage New England colonial! New Metal Roof not yet pictured.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

205 Apple Roxbury CT 06783

Price$750,000

Est. Mortgage: $/month

MLS Number 170131689

  • Single Family
  • Property Style Cape Cod, Farm House
  • Bedrooms 4
  • Bathroom 4
  • Acreage 3.17

Beautifully renovated shingle style cape in a pastoral Roxbury setting, just across from Tierney Preserve for great hiking, streams and nature paths. With it's 3+ acres, western views and gorgeous sunsets, this home has it all. It is expansive, featuring 4 bedrooms, 3.5 baths, as well as potential guest suite/in-law apartment. Set on idyllic Apple Lane, the home takes advantage of the gorgeous grounds with sun room and stone patio open to western and southern views, with large windows throughout. The Updated Kitchen and Master bath make this home easy to move in and begin living. Retreat to the country, in classic style, just minutes away from Roxbury Center!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

116 Wellers Bridge Roxbury CT 06783

Price$749,000

Est. Mortgage: $/month

MLS Number L10155237

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 4
  • Acreage 3.29

One level living! Spectacular mid-century modern home with floor to ceiling windows, high ceilings, exposed beams, hardwood floors. Great for entertaining. Grand Living Room and Great Room with french doors which open to patio and overlooks heated gunite pool and stone patio. Separate building with Studio/gym/office. Garden Conservatory Room, magnificent sunsets, countless updates throughout, Stone walls. Outdoor shower and cabana. Cast Iron Wood stove. Low Taxes. Minutes from town!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.