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.

>> Learn more about the town of Roxbury

Properties in Roxbury

Contact us for more information and to schedule a showing for any real estate below. Save your favorite listings when you create an account with us, and you can get email updates when similar properties are posted.

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

24 Ranney Hill, Roxbury, CT 06783

Price$3,200,000

Est. Mortgage: $/month

MLS Number 170047594

  • Single Family
  • Property Style Other
  • Bedrooms 5
  • Bathroom 10
  • Acreage 22.86

This Shingle Style residence is sited atop 23 high, private acres to take advantage of the spectacular 270- degree views. Every amenity and finest quality materials. Rooms are generous in scale with high ceilings, elaborate moldings, and wood flooring. The Living Room has a fireplace and 2 sets of French doors that open to an expansive bluestone patio overlooking the heated Gunite pool and stunning views. The kitchen with island, granite counters, cherry cabinets, commercial grade appliances includes 2 sinks and 2 dishwashers and opens to the light-filled family/morning room with its vaulted ceiling, fireplace and French doors. A wood-paneled library. First floor Master with a screened-in porch, tray ceiling, walk-in closet, dressing area and bath with Jacuzzi tub and separate shower. A second main floor bedroom has a full bath and walk-in closet. Second Floor. 3 bedrooms including another Master with large dressing room and 2 baths-one with Jacuzzi tub and separate shower; the other with a marble shower. The other 2 bedrooms have baths en suite. The Finished Lower Level is very light and opens to the patio surrounding the pool. There is a bath with 2 walk-in showers. A large family room and playroom. A guest suite includes a living room with fireplace. A wet bar adjoins the media room. Plus au pair quarters. There are two 2-car garages separated by a porte-cochere. The landscaped property is composed of 2 separate parcels.

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

7 Garnet, Roxbury, CT 06783

Price$2,795,000

Est. Mortgage: $/month

MLS Number L10239327

  • Single Family
  • Property Style Barn
  • Bedrooms 5
  • Bathroom 6
  • Acreage 4

Rarely does a property fully embrace New England character with Litchfield Hills Views, Privacy, Salt Water Pool with automatic cover, Spa with seating for 8 and automatic gated entry. Set on a bucolic road in Roxbury, this grand barn style home offers sweeping views across the Hills and open pasture. Rich architectural detail, 4 fireplaces and generous light and bright public spaces with exposed beams, wide board floors, 3 large televisions with surround sound, sonos sound system, in-wall speakers and fully equipped billiard room. The main floor master suite is complete with office/art gallery, dressing room and built-ins, large master bath with tub and walk in shower overlooks gardens, stonewalls, and fruit espalier. An additional 4 bedrooms on the second level, one with large comfortable space to serve as family or guest suite. The kitchen was designed for easy entertaining and opens on to the Great Room with fireplace and features a center island, commercial grade range, Sub-Zero refrigerator, pantry and plenty of cabinetry. The living room offers two sets of french doors to the large deck with pergola for large parties or cozy dinners spent by the fireplace. The lower level with a fully equipped exercise room with Sauna, Workshop or Studio space, a Billiard Room which all open on to the view and bluestone patio and courtyard. The is additional space for a media room. All the amenities required of a Great Estate and just 90 minutes to NYC!

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

27 Apple, Roxbury, CT 06783

Price$2,395,000

Est. Mortgage: $/month

MLS Number 170001362

  • Single Family
  • Property Style Barn
  • Bedrooms 4
  • Bathroom 6
  • Acreage 50.45

Classic Reproduction Barn with all the drama & casual elegance of a Gentleman's Country Estate, in scenic Roxbury, set on a secluded 50+ acres of enchanting wooded venues, perennial gardens, lush lawns, stone terraces, knee walls & meandering stone walks! This Extraordinary expanded barn reproduction adorned with vaulted, beamed ceilings, wide board floors & 4 stone fireplaces offers an array of venues for gathering friends and guests, in the casual ambience of this unique country setting. Retreat from the big city to "Fern Ridge" with a view inspired 36 foot great room showcasing soaring ceilings, beams and intricate custom stone fireplace! The fabulous country kitchen with adjacent hearth room, offers bayed dinette area, fireplace, gas range & subzero with butcher block island to delight any chef! A stylish living room leads through French doors to a 31 foot dining room with stone fireplace & French doors to a stone patio surrounded by English country gardens ; ideal for entertaining indoors to out! Gracious master suite w/fireplace & spa bath, 3 bedrooms w/private baths, expansive screened porch, vintage barn with hayloft, 3 car garage & more! This mecca for outdoor entertaining offers an in ground pool surrounded by lush gardens, patios , basketball court, heliport and adjacent party barn with massive, hand hewn stone fireplaces, kitchenette & full bath! . An exceptional country retreat for those who love the land and the ultimate privacy "Fern Ridge" can offer!

Listing Courtesy of Coldwell Banker Residential Brokerage

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

8 Mallory, Roxbury, CT 06783

Price$2,175,000

Est. Mortgage: $/month

MLS Number 170043492

  • Single Family
  • Bedrooms 6
  • Bathroom 9
  • Acreage 6.05
  • Square Feet 6,400

Exquisite Georgian Home ... ELEVATOR access on all floors, set on 6+ picturesque acres offering panoramic views and western sunsets in gorgeous southern Roxbury Setting. 6 Bedroom home with elevator and a 2 bedroom carriage house. Saltwater gunite pool. Impeccable craftsmanship. Paneled Library. Living room with herringbone hardwood floors, french doors out from Dining Room out to Cover porch and views. 4 Bay garage plus 2 bay garage in Barn. Separate Carriage House for guests with soaring ceiling in the living room, full kitchen and private patio. Saltwater pool. Lower level space offers media room/family room, office and additional bedroom and full bath. Screened in porch overlooks pool.

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

46 Southbury, Roxbury, CT 06783

Price$2,100,000

Est. Mortgage: $/month

Pending

MLS Number 170055846

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 56.24

Roxbury Luxury Cottage-Style. Long winding gated driveway leads to this 3 bedroom main house + studio guest house. Both are renovated to the highest standards, with top-of-the-line everything. Kitchen opens to great room with fireplace, breakfast nook with banquette seating, and media room. Large screened dining pavilion with wrap around terrace and built-in fire pit. Entertain all Summer at the salt water mountain-top pool/jacuzzi with views, cabana and outdoor fireplace. Spectacular gardens are irrigated with a separate well and a 16 zone system. Large wildflower fields, over 50 acres of trails for walking, biking or horses. Generator, sauna, Control4 home automation system, potential conservation easement available. Possibility for barn and horses, extra building lot included. All within 1.5 hours to NYC!

Listing Courtesy of William Raveis Real Estate

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

88 Painter Ridge, Roxbury, CT 06783

Price$2,100,000

Est. Mortgage: $/month

MLS Number 170084060

  • Single Family
  • Property Style Contemporary
  • Bedrooms 5
  • Bathroom 6
  • Acreage 22.7

Overlooking a majestic, commanding view, positioned on nearly 23 acres of meadow, fenced in paddocks and four stall barn, this 5,000 sq. ft. custom built, brick contemporary proudly enjoys western sunsets in a most desirable Roxbury location with frontage on both Two Rod Highway and Painter Ridge, framed by impressive stone walls and mature landscaping. The handsomely fenced paddocks and four stall horse barn with tack room, 2nd story hay loft and farm equipment storage, supplies this active horse farm with modern amenities for the novice or experienced horse enthusiast. The pool and hot tub / garden room provide a relaxing respite from your ride when not lounging on the private patios, taking in the views. Interior features include two fireplaces, a wet bar in the family room, five bedrooms en suite (includes a separate in law apartment), partially finished basement, updated mechanicals, newer roof, custom cabinetry and an open, airy environment are dominated by soaring ceilings. Lovingly cared for by one owner, this 1988 homestead is poised for a 2018 freshening, suitable for the sensibilities of the most discerning buyers.Note: Acreage includes 17.65 acres at 88 Painter Ridge (taxes $11,336) and contiguous 5.1 acre parcel at 53 Two Rod Highway (with taxes of $1,725) in Washington. Rare opportunity.

Listing Courtesy of Berkshire Hathaway NE Prop.

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

36 Southbury, Roxbury, CT 06783

Price$1,995,000

Est. Mortgage: $/month

MLS Number 170041786

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 6
  • Acreage 5.01

A 21st century Colonial that captures the grandeur of much older estates but includes all the amenities and features that are befitting today's lifestyle. Generously proportioned rooms, 5 fireplaces, fabulous kitchen/great room, crown moldings, hardwood floors, wainscoting, finest appliances, fixtures and finishes, heated pool on 5 landscaped acres. The elegant 2-story entry halls leads to the living room with fireplace, dining room with fireplace and coffered ceiling, the kitchen/great room featuring a beamed vaulted ceiling, center island, granite counters, high-end appliances, and eat-in area. French doors open to a screened-in porch. A main floor master suite has a fireplace, tray ceiling, walk-in closets, and luxurious master bath with soaking tub, separate shower, two sinks and W.C. There are two additional en suite bedrooms on the second level as well as a laundry room. A separate staircase leads to the game room/loft/office above the garage with a separate bedroom and full bath. The finished lower level has a family room with fireplace, bar, wine cellar, office /bedroom and full bath. French doors from this level access a covered porch and the pool. Outdoor living space includes an open blue stone patio, a covered porch with stunning views, a balcony, and the screened-in porch overlooking the pool. Other features: Attached 3-bay garage, an automatic pool cover, 3 furnaces, generator, central air-conditioning, security system, newly-painted exterior.

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

143 Tophet, Roxbury, CT 06783

Price$1,749,000

Est. Mortgage: $/month

MLS Number 170051574

  • Single Family
  • Property Style Colonial, Farm House
  • Bedrooms 4
  • Bathroom 6
  • Acreage 4.01

If clean country living, comfort and privacy are what you are looking for, then you will find it here. This turnkey home is located along one of Roxbury's most coveted rural stretches, sitting amidst an 800+ acre greenbelt of land trust property. Come and unwind in a bucolic setting with a luxurious salt water pool and spa, lush landscaping and long mountain views to the southwest. The house features an open space design concept with high ceilings and oversized window banks, filling it with natural light. All four bedrooms are generously sized and en suite. Enjoy walking, hiking, bicycle rides or snowshoeing along abundant country roads and trails. Perfectly positioned to visit the local farm stands, organic groceries, restaurants and boutiques in the area. Ready to move in! Agent Owner.

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

49 Garnet, Roxbury, CT 06783

Price$1,650,000

Est. Mortgage: $/month

MLS Number 99167565

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 4.94

Located in the idyllic town of Roxbury, this totally renovated home with every attention to detail. Situated on 5 quiet park like acres, this property offers wonderful privacy. Fabulous great room has a soaring beamed ceiling, 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 and stone fireplace. Living/dining room has vaulted ceiling, stone fireplace and opens to the gourmet kitchen w/cathedral wood ceiling, large quarts center island and state of the art appliances. First floor master bedroom w/Italian stone bath. Upper level has three additional bedroom all en suite. Only 90 minutes to Manhattan. A must see!!

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

20 Grassy Hill, Roxbury, CT 06783

Price$1,599,000

Est. Mortgage: $/month

MLS Number W10231595

  • Single Family
  • Bedrooms 5
  • Bathroom 6
  • Acreage 3
  • Square Feet 9,574

Gracious equestrian estate with breathtaking views. Three private acres of prime Roxbury property. Wonderful open floor plan with endless possibilities. Expansive Corsi designer kitchen with top of the line appointments, eat-in area, large living room with tons of light and large fireplace. Impressive stone entry. Well designed window walls capturing the amazing views throughout the home. Entertain all summer with heated Gunite pool, fountain, spa and pavilion. Finished garden level is home to private cigar and wine rooms. Solid concrete construction. Lovely 4 stall stable, paddock and room to expand. Artist studio just a short walk from the bluestone terrace. Convenient location for commuters and nature enthusiasts alike.

Listing Courtesy of The Heritage Group, LLC

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

53 Southbury, Roxbury, CT 06783

Price$1,590,000

Est. Mortgage: $/month

MLS Number 170084675

  • Single Family
  • Property Style European, Other
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.85

90 minutes from NYC with beautiful sunset lake views. Sophisticated and lavish hideaway that reflects that magical merging of creativity and architecture. Once you see it, you'll want to own it. Fully remodeled in 2016, the 4,000+ sq/ft custom home is a masterwork of design and craftsmanship. Every detail was carefully selected and quality crafted. Highlights include a custom Neff kitchen, Perrin and Rowe fixtures, exquisite Klaff baths, stone and Cherrywood flooring, solid mahogany doors, Marvin windows with wood shudders, stone fireplace-all capped beneath an intricate hand-split cedar shingle roof. Living is easy in this tucked-away home with perfect westerly views that look down on the 50-acre Wright's pond and a beautiful lush valley accented by stone walls. Plenty of natural light and sprawling entertaining spaces flow inside and out-to the viewing patio with hand-cut stone, to the stunning infinity pool and spa, to the cascading waterfall beyond. Additional amenities include: Sonos sound system; steam shower with spa; spacious Master Suite with balcony overlooking the park-like grounds, mountaintop viewing platform, fire-pit, terraced golf putt, and irrigation system. Set far back from the road with tons of privacy on rare waterfront land, this offers resort style living in the highly desirable town of Roxbury Ct, close to restaurants and shopping.

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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$1,550,000

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

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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.