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.

83 Squire, Roxbury, CT 06783

Price$1,050,000

Est. Mortgage: $/month

MLS Number 170013352

  • Single Family
  • Property Style Antique
  • Bedrooms 3
  • Bathroom 4
  • Acreage 2.58

Hampshire House - The weekend home Hollywood would create. Authentic c1760 saltbox - a sea captain's house in New Hampshire which was lovingly dismantled and moved to Roxbury where it was rebuilt on a new foundation with all modern mechanicals and comforts. This antique rivals homes twice the price and exudes charm and character with 3 ensuite BRs, 5 fireplaces, original hardwood floors, original wood wall paneling, exposed wood beams and vaulted ceilings. Keeping room with original built-in buttery, resplendent master suite with fireplace and just-renovated bath featuring Carrara marble and classic subway tile, dining room which features Roxbury granite hearth, cozy den, and a chef's kitchen appointed with top-of-the-line appliances. Walkout garden level presents a surprise suite complete with family room and fireplace, sunny bedroom and full bath - this is absolutely perfect space for friends from the city, visiting family, or even a nanny. The south-facing garden level features a wall of French doors opening to a spacious bluestone terrace. The professionally landscaped gardens are awash in color all season, with mature hydrangea, peony, clematis and boxwood. The grounds are private and enchanting, with a pond, small stream and striking frontage on roaring Jack's Brook. This piece of Heaven sits on one of Litchfield County's most storied roads amidst some of the area's most notable estates. Located just 90 min from Manhattan, this is truly a home where memories are made.

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

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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: 3.92% last updated on Jul 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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42 Squire, Roxbury, CT 06783

Price$949,000

Est. Mortgage: $/month

MLS Number 170007397

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 4
  • Bathroom 5
  • Acreage 6.5

Beautifully Renovated Squire Road 1860 Estate complete with Pool, Tennis Court, 4 br Colonial plus two additional bedrooms in the guest house, 3 full baths in main house and 2 additional baths in guest house, 2 level Studio/Gameroom/Pool House with full bath and deck overlooking pool and brook. Open land with frontage on Little Jack's Brook, mature plantings, short walk to Land Trust. antique wide board floors, a/c, stone walls. Minutes from town. A Gem!

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

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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: 3.92% last updated on Jul 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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27 Apple, Roxbury, CT 06783

Price$2,500,000

Est. Mortgage: $/month

MLS Number 170001362

  • Single Family
  • Property Style Barn, Other
  • 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

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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: 3.92% last updated on Jul 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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257 Good Hill, Roxbury, CT 06783

Price$1,150,000

Est. Mortgage: $/month

MLS Number 170000890

  • Single Family
  • Property Style Farm House
  • Bedrooms 4
  • Bathroom 4
  • Acreage 4.67

ROXBURY RETREAT - Sophisticated - Country Chic eyebrow-cape Farmhouse on just under 5 private lush park-like acres surrounded by protected land in the heart of historic Roxbury, CT. The spacious, open light-filled interior presents with 4 Bedrooms 3 full and 1 half Baths. The public and private rooms are filled with period detail, two fireplaces and state of the art amenities. Every room is an entity unto itself with accoutrements - Chef's Kitchen with fireplace, wide board flooring, first floor Master with marble Bath, finished lower level. The exterior affords expansive outdoor living with a stunning heated gunite spa, stone fire pit, pergola with room for a pool and tennis courts and is perfect for intimate or large gatherings. Just over two hours from New York or Boston.

Listing Courtesy of Elyse Harney Real Estate

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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: 3.92% last updated on Jul 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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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 become available that so fully embraces New England character with Litchfield Hills views, Privacy, Pool/Spa, Gated entry- updates that create perfection. Set on a bucolic road in Roxbury, this grand barn style home offers sweeping views across the Hills and open pasture. Impeccably maintained interiors, which are rich in architectural detail, 4 fireplaces and generous public spaces which are light and bright with exposed beams and wide board floors offer views from most every room. The main floor master overlooks high views, gardens and light woods. The grounds are graced with mature perennial gardens, stonewalls, and fruit espalier. The kitchen was designed for avid cooking and entertaining and features a center island, commercial grade range, Sub-Zero refrigerator, pantry and plenty of cabinetry. The living room opens on to the large deck for easy entertaining with the Kitchen/Great Room area for large parties or cozy dinners spent by the fireplace. A fabulous porch spans the view over the gardens, pool and Hills. A first level master suite is complete with Bath, dressing room, large closet and an Office or Art Gallery. An additional 4 bedrooms on the second level, offer comfortable space for family or guests. The lower level with Gym and Sauna, Workshop or Studio space, a Family/Billiard Room all open on to the view and stone patio. There is additional space for a media room. All the amenities required of a Great Estate.. just 90 minutes to NYC!

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

{$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: 3.92% last updated on Jul 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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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: 3.92% last updated on Jul 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, Roxbury, CT 06783

Price$895,000

Est. Mortgage: $/month

Pending

MLS Number 99184755

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 6
  • Acreage 6.71

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 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: 3.92% last updated on Jul 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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89 Flag Swamp, Roxbury, CT 06783

Price$1,489,000

Est. Mortgage: $/month

MLS Number 99180721

  • Single Family
  • Property Style Barn
  • Bedrooms 2
  • Bathroom 3
  • Acreage 7.78

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

{$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: 3.92% last updated on Jul 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, Roxbury, CT 06783

Price$1,895,000

Est. Mortgage: $/month

MLS Number L10211179

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

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 and the Lilly Preserve that comprises a large portion of this home's view. The house 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

{$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: 3.92% last updated on Jul 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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53 Southbury, Roxbury, CT 06783

Price$1,950,000

Est. Mortgage: $/month

MLS Number L10210056

  • Single Family
  • Property Style Colonial, Tudor
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.85

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

{$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: 3.92% last updated on Jul 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, Roxbury, CT 06783

Price$999,999

Est. Mortgage: $/month

MLS Number 99171965

  • Single Family
  • Property Style Barn, Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.47

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

{$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: 3.92% last updated on Jul 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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15 Old Boston Post, Roxbury, CT 06783

Price$1,295,000

Est. Mortgage: $/month

MLS Number 99124604

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 7
  • Acreage 4.15

Set back in a private Roxbury enclave sits this stylish and expansive country home. The great room is the star here, a truly spectacular space for entertaining with double height stone fireplace, enormous windows on 3 sides, and a large fully equipped bar. The kitchen is newly renovated and offers every possible amenity including a large center island for gathering and a breakfast nook/sunroom. Other features include: gym, playroom, large office with full ethernet connectivity and separate entrance, wine closet, Jacuzzi, custom woodwork, generator, outdoor shower, sound system with 15 zones, digital phone system. Plenty of flat land with views, mature trees, and custom tree house! Pool site proven

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: 3.92% last updated on Jul 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

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.