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The Matthews Team

Roxbury CT Real Estate

Corn Field in RoxburyTucked 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 RoxburyRoxbury Real Estate for Sale

Properties in Roxbury

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264 Painter Hill Road Roxbury CT 06783

MLS Number 170498741

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 3,823
  • Acreage 5.99

A renovated antique gem located in one of the most picturesque areas of Roxbury. Surrounded by tranquil grounds and close to pristine public lands, the John Lewis Homestead (1780) exemplifies the art of marrying the old and new. Over the years, the original homestead has been expanded, restored, remodeled, and renovated. The home's tasteful renovation created bright rooms throughout and a well-situated gunite pool. The newer light-filled section seamlessly flows into the original structure, which maintains vintage features reminiscent of a time of quiet contentment and has three original stone fireplaces, exposed beams, and wide flooring. The current layout provides space for a formal dining room, den, and study, as well as three bedrooms and a full bath upstairs. The grand living room has a large fireplace, antique beams, built-in bookshelves, and a screened-in porch overlooking the pool. The adjacent primary bedroom has exposed beams, french doors, a dressing room and luxury bath with a jacuzzi tub and Waterworks fixtures. The large eat-in kitchen includes a large kitchen island, Wolf range, and Subzero fridge. The walk-out lower level includes a bedroom and bath with french doors leading to the pool. The detached garage has guest quarters with vaulted ceilings, a full bath and kitchenette. You'll love the magical grounds with specimen trees, mature plantings, and exposed granite, all less than two hours from New York City.

Listed by Maria Taylor of Klemm Real Estate Inc

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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$2,695,000

Est. Mortgage: $/month

MLS Number 170422197

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 5,204
  • Acreage 21.66

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 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!

Listed by Kathryn Clair and Kathryn Clair Bassett of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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$2,675,000

Est. Mortgage: $/month

MLS Number 170484416

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 3,050
  • Acreage 129.04

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 3BR 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.

Listed by Rick Distel and Jeffrey Phillips of Compass Connecticut,LLC

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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$2,275,000

Est. Mortgage: $/month

MLS Number 170414483

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,000
  • Acreage 18

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!

Listed by Kathryn Clair and Kathryn Clair Bassett of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 2,640
  • Acreage 8.01

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.

Listed by Karen Silk of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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6 Painter Hill Road Roxbury CT 06783
Under Agreement

MLS Number 170486070

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,816
  • Acreage 6.03

One of early Roxbury's fabulous beauties! This well-preserved, late nineteenth-century Victorian Farmhouse has been lovingly maintained over the years, featuring modern renovations with appreciation and sensitivity to original detail. Huge, bright country kitchen, made for easy entertaining, is the central gathering place. Marble center island open to four directional views of the gardens, stone patio & walls, large blue stone screened porch and in-ground gunite pool. Adjoining, relaxed, yet formal, dining room has original Italianate bay windows and doors. Welcoming front and back parlor rooms feature wrap-around veranda and screened bluestone porch. Three period fireplaces. Three generous sized bedrooms on the second floor; main suite has a large closet room and a two room bath. Three story Country Carpenters Bank Barn with 4+ parking places. Also included, #8 Painter Hill. a four-room cottage, at a distance, planted out and private to main house with its own driveway. An income producing property since 1986. Stunning and private setting. The six acre protected property is adjacent, on two sides, to Roxbury's historic farms. Other two sides border major estates. Features a brook, land dotted with stately old growth Sugar Maples, conifers and open land. Walk to Maple Bank farm stand, Roxbury Market and houses of worship. A very special country estate 90 minutes from NYC. Quick closing possible. Agent/Owner.

Listed by Cecelia Santillo of Klemm Real Estate Inc

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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154 Baker Road Roxbury CT 06783

Roxbury, CT154 Baker Road, Mine Hill

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170502416

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,368
  • Acreage 2.45

This amazing unique property offers so many options and opportunities. It is business zoned and set on a beautiful level 2.45 acre lot. The main house is currently used as a sculpture art studio, residence and rental unit. The commercial grade kitchen is every cook's desire, from the 6 burner Vulcan gas stove to the enormous center island to the 3 bay sink and loads of storage. The kitchen overlooks a sunroom with radiant heated floors and a private perfectly level side yard. Stepping into the living room graced with beamed ceiling, 2 stone fireplaces you enjoy the embrace of history. A formal dining room with it's own fireplace is currently used as a 1st fl bedroom. A tiled full bath finishes the main level. Upstairs you are welcomed to a grand cathedral loft with wide chestnut beams and gorgeous wide plank floors. Three spacious bedrooms, one with a full bath & walk-in closet along with another full bath with laundry finish this side of the home. There is a 2nd floor apartment with a separate entrance that offers a spacious living rm/kitchen combo, bedroom and full bath. Now onto the cathedral log home that was built in 1994, it offers a wonderful escape from a busy lifestyle. You will enjoy a bright and airy open floor plan overlooking an inviting wrap-around deck, 1 bedroom, a full bath and a 2 car garage with room to tinker. This amazing property in Roxbury's charming business zone offers endless opportunities.

Listed by Pam Famiglietti of William Raveis Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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4 Painter Ridge Road Roxbury CT 06783

MLS Number 170485345

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,941
  • Acreage 3.95

This soon-to-be-finished gem is being remodeled in the bucolic Painter Hill district of Roxbury near Washington CT. This is a must-see property full of character, privacy and seasonal views! All of the needed updates are done! Imagine entering the home through a sunlit vestibule. To the right, there is an impeccable entertaining room with a lofty barn wood trussed cathedral ceiling. To the left is an ideal daily living layout with open dining, living room, and fully renovated gourmet kitchen well-appointed with new Dacor appliances and quartz countertops. The second-floor Primary suite is luxurious with a cathedral ceiling, walk-in closets and new bath with a large soaking tub and walk-in shower. Enjoy relaxing on a large West facing renovated brick terrace with captivating seasonal views. The first floor has a versatile layout with three additional rooms, which could accommodate a first-floor bedroom suite, separate offices and a gym, or suit to your use. The large one-car garage is detached. Town approvals exist for a future two car attached garage and tree clearing for a possible pool area. Don't miss this rare opportunity to live in a one of a kind house in Roxbury. Make your appointment now this home will go fast.

Listed by Derek Greene of The Greene Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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202 North Street Roxbury CT 06783

Roxbury, CT202 North Street

Price$1,479,000

Est. Mortgage: $/month

MLS Number 170504263

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,815
  • Acreage 8.64

Beautiful approved 8.64 acre Lot and house location, with a magical brook running through it. Located in the storied town of Roxbury CT, a consummate NYC weekender town. Our home, designed by renowned architect Hugh Sullivan of Bennett Sullivan Associates, Inc., can be built with modern touches such as walls of windows, black metal roof, and sleek touches, or remain a more traditional design, the choice is yours. At 1815 SF, this flexible loft home features extra high 11 foot ceilings throughout and dramatic 16.8 foot vaulted ceiling in the living room with Wittus shaker stove. There is an open chefs kitchen with Viking, Miele and Sub-zero appliances and sintered stone counter tops. Dining and living rooms are side by side for easy entertaining. The 3rd bedroom makes a great guest room or home office for the perfect full time or weekend getaway. A solarium and an all-season room leading out to a large deck make it easy to enjoy the ever changing views of the woods. There is also a detached garage and circular paved drive. Other specs include Control 4 system, Simpli-safe security system, Andersen 400 windows and Generac generator. The picturesque lot features un-touched historic stone walls and an abundance of pine trees, oaks and maples as your canvas. A masterpiece, perfect to build your dream home. This special home can be modified to suit your needs/desires both inside and out. LOT can also be sold without house design. Shown by private appointment. Owner/Agent.

Listed by Jill Sloane of Brown Harris Stevens

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$
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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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167 Tophet Road Roxbury CT 06783

Roxbury, CT167 Tophet Road, Tophet

Price$1,389,000

Est. Mortgage: $/month

MLS Number 170500757

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 4,040
  • Acreage 8.7

Located just 90 min from NYC, this stunning contemporary ranch is situated on 8.7 acres of lush green land & a large spring-fed pond, perfect for swimming, boating & fishing. (Marilyn Monroe was a resident of Roxbury from 1956-61 & swam in this pond.) Gorgeous blue stone patios, mature perennial gardens, impressive stonewalls, & a large green meadow, perfect for gardening or vineyards, grace the property. Over 4k sf on two levels, large custom kitchen with Sub-Zero fridge, 6-burner gas range, Corian countertops, center island & vaulted ceiling with skylights. The living room has a wall of windows & a double-sided wood fireplace. The family room has many windows & plenty of space to relax & unwind. Walk out to the upper patio from the family room to experience the beauty of the surroundings. There's 3 bedrooms & 2.5 baths on the main level. The primary bedroom is luxurious with cream toned walls & thick carpeting, walls of windows, abundant closet space, & a beautiful en-suite with a jetted tub, a radiant heated floor & glass enclosed double walk-in shower. The finished, lower level is the perfect setup & includes an office, a lower family room, spa & shower. A functional green house with access to a 2-3 vehicle, attached, heated garage, and a large, rustic, 3-bay barn - the perfect woodshop, artist's studio, or storage area. This home features oil heat, CAIR & a whole house generator. Take a scenic tour through this beautiful country home. You will not be disappointed!

Listed by Rebecca Zandvliet of Coldwell Banker Realty 2000

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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 170476208

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,656
  • Acreage 4.16

This 1790-hipped roof home has a balanced, symmetrical facade in keeping with the late Georgian style. Differentiating from your typical colonial are the notable decorative details such as the gable, which crowns the shallow central projection, and the wooden quoins, which give texture to the outer edges. Centrally located on the historic green of Roxbury, this home is among those that the merchant elite of the Post Revolutionary period commissioned. Equally historical are the trees on the property, some dating further back than the construction itself. Large maples, sycamores, and willows lovingly accentuate the beauty of this treasured part of town. The home's front entrance is flanked by a formal living room on the left and a large dining room on the right, both with fireplaces and original carpentry details. The rear of the home comprises three sections; a short back hall to the left, which leads to a first-floor bedroom, en suite, and kitchenette; a central eat-in kitchen overlooking the backyard, and the original undated portion to the right offering a den and mudroom space. The home's historical character is revealed in details such as the horsehair plaster, a material that expands and contracts with the seasons, giving the house a life-like quality. Typical of the more intimate spaces of bygone eras are the lovely seating nooks like the one that sits atop the central staircase.

Listed by Michael Caporizzo of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4,062
  • Acreage 21.07

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.

Listed by Beatriz Conroy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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