Roxbury CT Luxury Homes for Sale

Find the latest luxury homes for sale in Roxbury, CT. Search through a variety of residential listings to find your new property. Save your favorite listings when you register with us, and you can receive email notifications when new properties match your criteria. Contact us for more information and to schedule a showing.

20 Grassy Hill Rd, Roxbury, CT 06783

Price$1,975,000

Est. Mortgage: $/month

InternalID W10231595

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Acres 3
  • SqFt 9574

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

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

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 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.

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58 Southbury Rd, Roxbury, CT 06783

Price$1,025,999

Est. Mortgage: $/month

InternalID F10228265

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Acres 3.47
  • SqFt 3116

NEW ENERGY EFFICIENT CUSTOM BUILT COLONIAL ON 3+ ACRES OF BEAUTIFUL LANDSCAPED PROPERTY. This 4/3 home has a chefs kitchen featuring custom lighted cabinetry, huge granite island, Viking/Bosch appliances and Wine Cooler. Kitchen flows into dining/ family room w gas fireplace. Sliding doors lead to covered porch with gas connection. Front porch has a wrap around porch. Bonus/media on 2nd floor with grand chandelier. Attached ext 3 car garage w/ storage or work area. Gorgeous Master Ste on first floor with walk in shower and separate tub. Carriage house w/ 3 garage drs, radiant heat/ half bath. RV parking and/or Car Collectors! Carriage house inc'd one bdrm apt on 2nd floor for rental, caretaker, nanny, in-law. Spacious attic and basement.

Listing Courtesy of Keller Williams Realty

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: 3.95% last updated on Apr 27, 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.

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197 Apple Lane, Roxbury, CT 06783

Price$849,000

Est. Mortgage: $/month

CMLS 99185769

  • Residential
  • Bedrooms 4
  • Acreage 11.5
  • Square Feet 3130

Echo Hills Farm. Located On A Lovely Quiet Road Minutes To Great Restaurants And Roxbury Center, This Apple Lane Late 1700's Colonial Farmhouse Was Updated From The Ground Up In The 1980's, It Is Sweetly Sited On 11 Acres Of Level Pasture And Light Woods Complete With Antique Barn, Pond, Stream And Semi-cirular Driveway. There Are 4-bedrooms With 3 Full And 1 Half Baths. A Grand Sunroom And Kitchen Open On To The Blue Stone Patio And Level Lawn With 70's Tennis Court. The Large Open Kitchen Has A See Through Fireplace To The Family Room. Mature Plantings And Flowering Trees Along With Stone Walls Grace The Property.. Energy Efficiency Is Added With Solar Panels For Hot Water And Extra Insulation.

Listing Courtesy of William Pitt Sotheby's

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: 3.95% last updated on Apr 27, 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.

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197 Apple Ln, Roxbury, CT 06783

Price$849,000

Est. Mortgage: $/month

InternalID L10217387

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Acres 11.5
  • SqFt 3130

Echo Hills Farm. Located on a lovely quiet road minutes to great restaurants and Roxbury center, this Apple Lane late 1700's Colonial farmhouse was updated from the ground up in the 1980's, it is sweetly sited on 11 acres of level pasture and light woods complete with Antique Barn, Pond, stream and semi-cirular driveway. There are 4-bedrooms with 3 full and 1 half baths. A grand sunroom and Kitchen open on to the blue stone patio and level lawn with 70's Tennis court. The large open kitchen has a see through fireplace to the family room. Mature plantings and flowering trees along with stone walls grace the property.. Energy efficiency is added with Solar Panels for hot water and extra insulation.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 3.95% last updated on Apr 27, 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.

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81 Rocky Mountain Road, Roxbury, CT 06783

Price$895,000

Est. Mortgage: $/month

CMLS 99184755

  • Residential
  • Bedrooms 4
  • Acreage 6.71
  • Square Feet 4732

Gracious Custom Built Colonial With Far Reaching Views Over Land Trust. The Chef's Kitchen Features Granite Counters And High End Appliances And Opens To A Light Filled Sunroom, Den With Fireplace, And Formal Dining Room. 4 Spacious Bedrooms Each With En-suite Bath. Master Suite Has Dressing Room, Luxury Bath, And A Loft/office With Its Own Balcony. Large Entertaining Room Opens To A Covered Porch And Wrap Around Deck That Spans The Entire Rear Of The Home. High Ceilings Throughout. Large Finished Walk Out Lower Level For Game Room/media Room/gym. Quiet, Private Setting. Walk To Roxbury Playground And Elementary School. A Truly Classic Roxbury Home.

Listing Courtesy of William Raveis Washington

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: 3.95% last updated on Apr 27, 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.

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81 Rocky Mountain Rd, Roxbury, CT 06783

InternalID L10219035

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Acres 6.71
  • SqFt 6274

Gracious custom built colonial with far reaching views over land trust. The chef's kitchen features granite counters and high end appliances and opens to a light filled sunroom, den with fireplace, and formal dining room. 4 spacious bedrooms each with en-suite bath. Master suite has dressing room, luxury bath, and a loft/office with its own balcony. Large entertaining room opens to a covered porch and wrap around deck that spans the entire rear of the home. High ceilings throughout. Large finished walk out lower level for game room/media room/gym. Quiet, private setting. Walk to Roxbury playground and elementary school. A truly classic Roxbury home.

Listing Courtesy of The Matthews Group

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: 3.95% last updated on Apr 27, 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.

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271 South St, Roxbury, CT 06783

Price$1,355,000

Est. Mortgage: $/month

Under Agreement

InternalID L10213771

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Acres 12.26
  • SqFt 4000

Foxcroft Farm is a gated estate comprised of 2 residences, 2 stables w 12 stalls & enclosed bldg for collector cars/equipment on 12+ acres. Main residence, 4000+ sq ft, is completely rebuilt & expanded 1850s colonial w 5-bed/5-bath incl 2 master suites--1 on main floor w Jacuzzi & on 2nd level w sitting rm for nursery; 20x40 gunite pool. Exquisitely renovated w quality & class, the home offers a well-designed living space w oak floors, living rm w north+south views, FP & French doors. Chef's kitchen boasts St Charles custom cabinets, 2 Sub-Zero fridges, 2 dishwashers, Viking range w grill & 2 ovens. High ceiling dining rm w French doors overlooking pool + add'l 4 sets of French doors north & south open to vista of rolling fields & landscaping; private study w fireplace & built-in bookcases. State of art plumbing w pressurized 1000-gal reserve water tank. Basement features locked 100-case wine cellar. Solid brass hardware used throughout; 400AMP w full house generators for both homes. Guesthouse expanded to incl 8 rms+ kitchen, 2 car garage, screen porch+hot tub. Entire parcel enclosed by 4-rail fence w gates suitable for horses/animal pasture/haying & other agricultural uses. There's also an illuminated riding ring. Miles of adjacent trails & nearby Shepaug River plays host to a natural waterfall & old fashion swimming hole permitted for Roxbury residents only. Minutes from historic town of Washington & shopping village of New Preston. Guest house is approximately 28

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 3.95% last updated on Apr 27, 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

89 Flag Swamp Road, Roxbury, CT 06783

Price$1,489,000

Est. Mortgage: $/month

CMLS 99180721

  • Residential
  • Bedrooms 2
  • Acreage 7.78
  • Square Feet 3304

Cady Barn Home With Distant Views! Master Builders Ed Cady Sr And Jr Have Created Some Of New England's Most Iconic Residences. This Rare Opportunity Is The Personal Residence Of Cady Jr. Consisting Of Two Antique Barns From Stone Arabia Ny, The Home Is Rich In Artisanal Details With Exposed Beams, Plaster Walls, And Antique Cypress Flooring. Public Spaces Include A Great Room With Stone Fireplace, A Gourmet Kitchen With Pantry, Beehive Oven, And Custom Cabinetry. Master Suite Includes Two Walk-in Closets, En-suite Bath And Laundry. Currently Configured As A 2br + Sleeping Loft, Easily Expandable To 4br. Set On 7+ Acres With Southern + Western Views. 3-car Garage. Set On A Quiet, Designated Scenic Road, Yet 12 Min To I-84. 90 Min To Nyc.

Listing Courtesy of William Pitt Sotheby's

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: 3.95% last updated on Apr 27, 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

89 Flag Swamp Rd, Roxbury, CT 06783

Price$1,489,000

Est. Mortgage: $/month

InternalID L10212415

  • Residential
  • Bedrooms 2
  • Bathroom 3
  • Acres 7.78
  • SqFt 3304

CADY BARN HOME WITH DISTANT VIEWS! Master Builders Ed Cady Sr and Jr have created some of New England's most iconic residences. This rare opportunity is the personal residence of Cady Jr. Consisting of two antique barns from Stone Arabia NY, the home is rich in artisanal details with exposed beams, plaster walls, and antique cypress flooring. Public spaces include a great room with stone fireplace, a gourmet kitchen with pantry, beehive oven, and custom cabinetry. Master suite includes two walk-in closets, en-suite bath and laundry. Currently configured as a 2BR + sleeping loft, easily expandable to 4BR. Set on 7+ acres with southern + western views. 3-car garage. Set on a quiet, designated scenic road, yet 12 min to I-84. 90 min to NYC.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 3.95% last updated on Apr 27, 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.

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143 Tophet Road, Roxbury, CT 06783

Price$1,995,000

Est. Mortgage: $/month

CMLS 99181078

  • Residential
  • Bedrooms 4
  • Acreage 4.01
  • Square Feet 5527

Location, Quality + Style Merge Seamlessly To Create This Unique Property Nestled Amidst Estates Of Luminaries Past And Present. 750+ Acres Of Protected Land Are Within Walking Distance, Including The Matthau Preserve Directly Across The Street. The Home Is Open And Bright With Multiple Large Window Banks + French Doors. The Open Concept Main Floor Flows Effortlessly For Entertaining Featuring Detailed Millwork Throughout. On The 2nd Floor Three Bedroom Suites Share An Open Living Space; The Generous Master Has A Gas Fireplace. A Fourth Bedroom Suite Occupies The Entire 3rd Floor. No Detail Overlooked: Chef's Kitchen. Mahogany Deck + Porch. Luxurious Salt Scott Pool With Spa. Generator. Privacy, Tranquility + Distant Southwestern Views.

Listing Courtesy of William Pitt Sotheby's

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: 3.95% last updated on Apr 27, 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 Rd, Roxbury, CT 06783

Price$1,995,000

Est. Mortgage: $/month

InternalID L10211179

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Acres 4.01
  • SqFt 5527

Location, quality and style merge seamlessly to create this unique property nestled amidst estates of luminaries past and present. 750+ acres of protected land are within walking distance, including the Matthau preserve directly across the street. The home is open and bright with multiple large window banks and french doors. The open concept main floor flows effortlessly for entertaining featuring detailed millwork throughout. On the 2nd floor three bedroom suites share an open living space; the generous master has a gas fireplace. A fourth bedroom suite occupies the entire 3rd floor. No detail overlooked: Chef's kitchen. Mahogany deck and porch. Luxurious salt Scott Pool with spa. Generator. Privacy, tranquility and distant southwestern views.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 3.95% last updated on Apr 27, 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 Road, Roxbury, CT 06783

Price$1,995,000

Est. Mortgage: $/month

InternalID L10210056

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Acres 5.85
  • SqFt 4400

Almost Famous! Introducing this magical waterfront fairy-tale style custom stone cottage. Drive down the long private driveway to meet your serene world class views and waterfront setting. All custom baths including steam shower with TV and spa. Enjoy the open custom mahogany and stone Neff kitchen. Cherry, stone and brick floors meander through the house. The home includes custom arched mahogany doors and Marvin windows with wood shutters. As you step outdoors relish the 6 acres encompassing stunning gardens and stonewalls.The hand split cedar shingle roof mirrors that of a thatched roof giving the home an English Cotswolds feel. Take a swim in the incredible custom glass mosaic gunite infinity pool with an infinity spa overlooking the 50 acre pond. Escape to the mountain top and enjoy the seating area with the fire-pit while watching the sunset. Irrigation system assures you a lush healthy lawn. Water lover's paradise. Modern amenities with captivating views reminiscent of impressionist painter Claude Monet's Giverney water lily garden. Also include on this estate like property is a terraced golf putt, a granite rock climbing wall and a grand 30 ft. waterfall comprised of local Roxbury Granite. Truly no expense spared on this perfectly charming sophisticated storybook property. A must see property located in desirable Roxbury CT.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 3.95% last updated on Apr 27, 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

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The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of the Greater Fairfield County CMLS, Inc. Real estate listings held by brokerage firms other than The Matthews Group are marked with either the “IDX Detail Logo” or the "IDX Thumbnail Logo” (a little black house surrounding the letters “IDX”) and detailed information about them includes the name of the listing broker.