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The Matthews Group

Roxbury CT Homes for Sale

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Houses for Sale in Roxbury

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67 Squire Road Roxbury CT 06783

Roxbury, CT67 Squire Road

Price$4,225,000

Est. Mortgage: $/month

MLS Number 170420680

  • Single Family
  • Square Feet 4,371
  • Bedrooms 5
  • Bathroom 3
  • Year Built 1974

Located on one of the most beautiful streets within the idyllic town of Roxbury, CT, this extraordinarily designed and masterfully renovated residence is perfectly situated on almost 11 acres of private land, adjacent to the beautiful Roxbury land-trust, complete with hiking trails and a waterfall. Newly renovated throughout, this residence has a most unique style that combines the best elements of contemporary architecture while retaining the warmth of a New England home. No detail has been overlooked in the design of this home: from tall panes of glass through which light streams into every room, to handcrafted, radiant-heated and artisan-finished white oak floors, to the selectively restored historic wooden post and beams. The intelligent floor plan allows for privacy and seamless indoor-outdoor living whereby one can step onto the beautiful stone patios that overlook the surrounding woods and the stream below, from all the main rooms of the house. The exquisite beauty of nature is ever-present in this one-of-a-kind residence.

Listing Courtesy of Compass Connecticut,LLC

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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142 East Flag Swamp Road Roxbury CT 06783

Roxbury, CT142 East Flag Swamp Road

Price$2,950,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170404703

  • Single Family
  • Square Feet 4,544
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1995

Welcome to Laurelwood - a country home like no other. Set on nearly 100 acres of pristine, untouched land, this residence is a jewel. Modern design elements such as walls of glass and soaring ceilings work in harmony with warmer interior materials like wood and native stones. Built of the finest materials, and maintained impeccably, the home has a gracious layout with large public spaces interspersed with smaller, more intimate moments. The kitchen offers warm wood cabinetry, SubZero and Miele appliances, and a dining area with a FP and views to the pond. A new deck expands the kitchen area to the outdoors. The LR is cozy with a FP. 4BRs provide plenty of private space. Baths are luxuriously appointed with Waterworks tile and fixtures, and the master bath has a spacious soaking tub. Sheltering in place is a joy at Laurelwood, as the home provides a separate office that anchors one end of the home and features a vaulted ceiling and walls of glass. Another incredible space is the home gym - no need to leave in order to stay fit. Rounding out the offering are top of the line mechanicals including two new, multi-zone HVAC systems, two separate attached garages that provide a total 4+ car covered parking, a whole-house generator and a separate utility barn which houses the heavy equipment to keep the estate running smoothly. This equipment is available for sale outside of escrow. All of this magical solitude, yet moments to everything and only 90 minutes from Manhattan.

Listing Courtesy of Compass Connecticut,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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36 Clover Knolls Roxbury CT 06783

Roxbury, CT36 Clover Knolls

Price$2,925,000

Est. Mortgage: $/month

MLS Number 170418676

  • Single Family
  • Square Feet 3,050
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1987

Clover Knolls - 129 acres of natural beauty in one of Roxbury's most storied and treasured corners. Offering a variety of Connecticut's best landscapes including sun-kissed farm pastures with distant views, lovingly tended mature forest, a sparkling spring-fed pond and open sweeping lawn around the contemporary home, few locations in Litchfield County evoke such emotion, inspiration and sense of place. Offered for the first time in nearly forty years, this special property is ready for its next chapter and presents a multitude of possibilities. There are multiple building parcels allowing for the construction of a larger main residence, separate dwellings for a single-owner compound, or for subdivision. The current 2BR residence is set on a perfect spot with views to the pond and further distant views beyond and was built with a beautifully warm and simple design aesthetic reminiscent of Frank Lloyd Wright. Construction of a larger, main residence at a higher elevation could leave the existing home as a guest house, pool/tennis house, etc. The property is largely held in tax-benefitting status and the forest is under a forestry management plan which keeps the woods healthy and maximizes their attractiveness for humans and wildlife alike. This truly magical land sits in the heart of Litchfield County's desirable Roxbury/Washington region, less than two hours from Manhattan but a world away. Taxes and assessment listed are for all five parcels.

Listing Courtesy of Compass Connecticut,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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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
  • Bathroom 5
  • Year Built 1860

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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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
  • Bedrooms 4
  • 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: 3.05% last updated on Oct 14, 2021
* 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 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
  • Year Built 1815
  • Bedrooms 5

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: 3.05% last updated on Oct 14, 2021
* 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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17 Berry Road Roxbury CT 06783
Pending Continue to Show

MLS Number 170401685

  • Single Family
  • Square Feet 6,936
  • Bedrooms 3
  • Bathroom 1
  • Year Built 2007

Concept Plans and builder available immediately! The 7,000±-square-foot Barn/Farm Office, associated buildings and paddocks were constructed by the current owner in 2007. The Barn is sited on an elevated position to ensure views and access to the breeze emanating from the Shepaug River Valley. The design of the building(s) borrows from the Judds Bridge Farm in Roxbury. It utilizes a clapboard design, 12-over-12 mullioned windows, cedar shake roof, and copper gutters, while integrating leading HVAC and water technology as well as eco-friendly solar panels. While the buildings are currently utilized for commercial purposes, the Barn was designed to be easily converted into a substantial residence with the addition of five evenly spaced dormers on the second floor of the barn which would align with the six-foot-tall windows on the ground floor to allow for the creation of up to five en suite bedrooms. The Barn site is comprised of 25± acres and surrounded by stone walls, pasture, and horse or cattle/sheep turn-outs designed by the owner. Additional adjacent land is also available. The Tractor Barns and Haylofts located behind the Barn can be repurposed as a conventional garage and storage space, or additional living quarters to accommodate a car collection and/or staff.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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114 Town Line Road Roxbury CT 06783

MLS Number 170385553

  • Single Family
  • Square Feet 2,228
  • Bathroom 1
  • Bedrooms 7
  • 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: 3.05% last updated on Oct 14, 2021
* 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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12 Church Street Roxbury CT 06783

MLS Number 170436101

  • Single Family
  • Square Feet 5,105
  • Bedrooms 6
  • Bathroom 4
  • Year Built 1740

Located in the center of the Village Green, on a ley line between the 3 colonial churches this exceptional horse property with its 1740/1790 circa Georgian colonial has two bridges that cross over its brook to the Meadows and it's own beautiful pond to enjoy. One area built in 1740 with a central fireplace, the rest of the house built in 1790 with two working fireplaces. Historically significant due to architecture and original Smith family that owned the property. US senator Nathan Smith and his wife Sarah McCracken Smith were the original owners. His brother was US representative, state congressman and state senator Nathaniel Smith and his wife Rebecca Benedict Smith lived nearby in Woodbury; and he also served on the state Supreme Court. They were the uncles of US congressman Truman Smith, who served as a US representative and US senator. All three men were lawyers educated at Yale and were judges practicing in Litchfield County. Historic trees include a 400 year old maple tree and a 300 year old sycamore tree. Various fruit, flowering trees. +A studio apartment. Barn built around 1800 with 4 horse stalls, sink, cold running water and its own well. Also a 30×24×14 foot open barn for shelter on 2 acres of horse pasture with fencing & a round pen. All construction in the house and barn is Chestnut, with original nails, Peg and post- construction. Chestnut floors throughout the house with a front Palladian window, Gracian columns on front & side. Outdoor pen 10x20x5' Tax7471.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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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. Enjoy all Roxbury has to offer. This bucolic town features low taxes and so much natural beauty.

Listing Courtesy of BHGRE Bannon & Hebert

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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14 Old Boston Post Drive Roxbury CT 06783

Roxbury, CT14 Old Boston Post Drive

Price$1,195,000

Est. Mortgage: $/month

MLS Number 170442716

  • Single Family
  • Square Feet 2,826
  • Bedrooms 3
  • Bathroom 4
  • Year Built 1984

Western Views from this impeccably maintained Contemporary Acorn Deck House which was designed to bring the outdoors in. The deck overlooks distant foothills and enjoys great sunsets! It is all about the outdoors with an in ground pool, screened porch, horse barn, fenced pasture and paddocks set off a long driveway for great privacy, yet minutes to Roxbury Center. A separate 3 acre lot is included with office or studio space, the former use as veterinary practice, which fronts on Southbury Road. The post and beam home was designed with an open concept floor plan and the quality is felt throughout, with solid mahoghany doors, double thermal pane windows and mahoghany sliders. The cook's kitchen with center island and German made Tesla cabinetry, looks out on to the updated deck with Feeney cable railings and out to the western views. A first floor bedroom with full bath for guests or master suite and two additional bedrooms make this an easy home to entertain and work from home. A loft reading room or office overlooks the first floor and out to western views. A lower level family room and gym round out the space. The raised bed summer gardens, perennial plantings and 40+ evergreen trees, comprised of Norway spruce, Douglas fir and White pine trees are a gardeners delight. There is a three stall horse barn and 5 bay shed barn with pasture. Located on a town maintained gravel road and nearby the historic Boston Post Road!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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82 Transylvania Road Roxbury CT 06783

Roxbury, CT82 Transylvania Road

Price$1,150,000

Est. Mortgage: $/month

MLS Number 170395038

  • Single Family
  • Square Feet 4,062
  • Bathroom 3
  • Property Style Colonial
  • Bedrooms 4

Secluded 21+ acre retreat on a quiet road in Roxbury, Connecticut. This sophisticated 4000 square-foot colonial sitting in its serene location with privacy surrounding you has exquisite millwork throughout. Designed and detailed for fine living. Kitchen features granite counters, granite backsplash, double wall ovens, subzero refrigerator, natural cherry cabinets and 10 foot ceilings throughout. The beams in the great room give you a marvelous 36×26 square-foot room. The formal library/office has pocket doors for privacy. Formal dining room. Two laundry rooms. Foyer chandelier has electric key to lower for cleaning. Lighting package. Central air, central vac. Master suite has large master bath, two person shower, Jacuzzi for two and a large walk-in closet. Oversize three car garage with workshop space. Basement with 10 foot ceilings also for your exercise area and workshop space. 40×16 foot deck. Large enclosed sunporch. With a babbling brook that runs across the property. Possible equestrian just add a barn. 4 thermostats for heating control. Two 330 gallon oil tanks. 10 foot ceilings throughout the home including the basement. 40x16 Party Deck. Lot is Sub dividable. Minutes from town center. All near Parks, trails, river, lake, Private schools and medical facilities. 90 min to NYC, NJ, Boston.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 2021 SmartMLS, Inc.