The Matthews Team

William Raveis Lifestyles Realty

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
Pending Continue to Show

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: 5.22% last updated on Aug 11, 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$2,525,000

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: 5.22% last updated on Aug 11, 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$2,495,000

Est. Mortgage: $/month

Pending Continue to Show

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 C Bassett of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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 C Bassett of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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$1,925,000

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: 5.22% last updated on Aug 11, 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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101 South Street Roxbury CT 06783

Roxbury, CT101 South Street

Price$1,899,999

Est. Mortgage: $/month

Open House

MLS Number 170507607

  • Single Family
  • Next Open House: Sun 08/21 11:30 am. to 12:30 pm.
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 5,439

Nestled in the quiet community of Roxbury a long private driveway leads to a stunning contemporary home. Built on just over 38 acres this home offers a private escape with hiking trails, pond and stream. The custom built residence offers an open first-floor plan including a custom kitchen with family room, bar, dining room, living room and den. The second floor includes 3 bedrooms 2 bathrooms and a large primary suite with attached dressing room, office and en-suite bathroom. The walk out basement offers a full wine cellar and rec room with ample room for a home gym or office. Over the two car garage an additional in-law suite with bathroom is available for all of your visiting guests.

Listed by Samantha Kelley of Tranzon Auction Properties

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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80 Rocky Mountain Road Roxbury CT 06783

Roxbury, CT80 Rocky Mountain Road

Price$1,795,000

Est. Mortgage: $/month

MLS Number 170505049

  • Single Family
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 5,801
  • Acreage 14.29

Stunning Roxbury home with western views, five bedrooms, gunite pool, three car garage and barn on 14+ acres abutting land trust. Beautifully built shingle style home with fabulous architectural details. Enter via an expansive living room with beamed ceiling, stone fireplace and French doors that spill out to a wisteria covered stone patio with western views. The custom kitchen features marble countertops, copper farmer's sink, sub-zero fridge and freezer, dual wall ovens and butler's pantry all of which open out to a vast bluestone patio overlooking perennial gardens, rock outcroppings and gunite pool. The dedicated dining room sits just off the kitchen, highlights include a stone fireplace and bespoke barreled ceiling. On the second floor you will find a laundry room and three bedrooms each with an en-suite bath. Wake to western views in the primary bedroom which includes dual closets and sizable bath with soaking tub and shower. On the third floor, enjoy two large bedrooms with a shared full bath. A sizable bonus room above the garage features custom-built ins and full bath - ideal for office, play or distinct guest area. An incredibly private setting with close proximity to Roxbury Land Trust preserves and Apple Lane Park.

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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
Open House

MLS Number 170485345

  • Single Family
  • Next Open House: Sat 08/13 11:00 am. to 1:30 pm.
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,941

This renovated gem is 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 a perfect daily living layout with an 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 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.

Listed by Derek Greene of The Greene Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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: 5.22% last updated on Aug 11, 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

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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53 Southbury Road Roxbury CT 06783

Roxbury, CT53 Southbury Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170509415

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,405
  • Acreage 5.85

A long circular drive leads you to this uniquely styled waterfront property that blends whimsy, sophistication, beauty, and function. The exterior of the home is welcoming with a stone and wood façade, a thatched inspired roof made of hand-hewn split cedar shingles, a maple leaf shaped copper roof detail, stonewalls and walkway. A mix of high quality and yet fun details can be found throughout the house. There is hand carved Mahogany banister as you enter, Cherry wood with brick inlay floor, stone accent walls in kitchen and bath, Mahogany arched doorways and a custom Neff kitchen with Mahogany inlaid cabinetry and copper farm sink. There are 4 floors of living space with the formal living room, dining room with custom wet bar, kitchen, family room with stone fireplace and half bath on the main level. The second level includes two bedrooms, full bath, and the primary bedroom with private balcony, two walk-in closets and full bath. A circular stairway leads to third level with small loft and office and lower level includes laundry, office with built-ins and a media room. Peaceful, private, and perfectly placed, you can enjoy the gorgeous sunsets over Lee's pond from almost every room. There are two Roxbury granite patios and tiered level lawns. Make this your own private sanctuary and enjoy the wildlife, sights and sounds of the Litchfield Hills.

Listed by Maria Taylor and Carolyn Klemm of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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