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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51 Judds Bridge Road Roxbury CT 06783

MLS Number 170528318

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,078
  • Acreage 4.69

LOCATION LOCATION! LOCATION! This 4.69 acre peaceful haven of privacy and tranquility is in a neighborhood of million dollar homes. Surrounded by trees and set back from the road, this gem is waiting for your personal touches. Many new updates have been made including new roof, siding, updated main bathroom, flooring, painting and more. A spacious great room with open floor plan greets you as you enter this beauty. There is a separate family room, private and spacious primary suite with full bath (including new bidet) and 3 additional guest bedrooms on the main floor. The lower level is currently being used as office space but could easily be converted to an in-law suite with kitchen, living room, bedroom and full bath. Currently the air conditioning unit is not functioning however all the ductwork is in place. A power outlet in the garage is ready for an EV /Tesla car. A newly fitted backup generator connection and switch for a portable generator are available as well. Must see in person to appreciate the details. Bordered by Moosehorn brook at the north runs a secondary drive to the rear of the house. The foundation of a cabin removed approximately ten years ago can possibly be used to rebuild a small secondary house with a private driveway. Would need approvals of proper Town officials. Stunning westerly views of the open field and the back of Mine Hill offer ever-changing sights, This wildlife playground will never stop filling you with awe of nature.

Listed by Marge Yonika of Finish Line Realty

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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30 Berry Road Roxbury CT 06783

MLS Number 170519061

  • Land
  • Acreage 16.4
  • Zoning Res

Absolutely stunning property located on one of the most beautiful scenic roads an the gateway to Roxbury. Rare opportunity to build in a prime Roxbury location. One of the most beautiful building parcels in Connecticut. 80 minutes to NYC, 5 minutes to the charming town of Bridgewater. Property has significant road frontage on both Minor Bridge and Berry Rd. It's also within walking distance to Lake Lilinonah. Come see this shovel ready parcel and experience what it would be live to live in a picture perfect part of the world. The combination of wooded acres and open pasture is complimented by stone walls and board fence to create what is widely considered to be the most scenic entrance to the town of Roxbury from the west. This building parcel, once the Greyledge Angus Pasture, is comprised of 16+-acres which offer a diversity of topography that is bisected by a scenic stream, new growth woods, and multiple stone walls dating to the 1800s when the entire area was in pasture or used for agriculture. Additional Acrage Available. Exact Property tax TBD

Listed by Jeffrey Phillips and Mark Madonna of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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238 North Street Roxbury CT 06783

Roxbury, CT238 North Street

Price$449,000

Est. Mortgage: $/month

MLS Number 170518529

  • Land
  • Acreage 6.79
  • Zoning res

Rarely available Lot in Roxbury! Magical 6.79 acre lot featuring a majestic stream and spring house, un-touched historic stone walls, gently sloping tree-covered hills and an abundance of pine trees, oaks and maples as your canvas. This masterpiece lot is perfect to build your dream home and to connect with what is important in life. Whether a weekender or full-time resident, the Woods will offer you ultimate privacy with endless possibilities for a simpler place and way of life. Our wonderful architectural team is available to design your one of a kind home or you can bring your own. APPROVED DRIVEWAY PERMIT on FILE. Shown by Owner/Agent.

Listed by Jill Sloane of Brown Harris Stevens

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%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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1 Tamarack Lane Roxbury CT 06783

Roxbury, CT1 Tamarack Lane

Price$1,300,000

Est. Mortgage: $/month

MLS Number 170518421

  • Single Family
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 3,167
  • Acreage 4.5

Fabulous 6-bedroom / 5 ½ bath, barn-style home on 4.5 private acres on a quiet dead-end road with Shepaug River Frontage and a creek. Light and airy interior with soaring ceilings, exposed posts and beams, and floor-to-ceiling windows. Open Living-Dining-Kitchen leads out to a deck. Two first- floor bedrooms with ensuite offices, and full baths. Upstairs there are four more bedrooms - two with ensuite offices and full baths, vaulted ceilings, and skylights and two smaller bedrooms with vaulted ceilings. A charming, lofted room with beautiful views tops off the third floor. Finished, walk-out lower level is currently set-up as a game room with a full bath. Private yet close to the towns of Roxbury and Washington. Rare offering.

Listed by Peter Klemm of Klemm Real Estate Inc

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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3 Tamarack Lane Roxbury CT 06783

Roxbury, CT3 Tamarack Lane

Price$3,250,000

Est. Mortgage: $/month

MLS Number 170518422

  • Single Family
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 7,821
  • Acreage 13.06

Rarely available Riverfront Estate with sprawling Post-and-Beam, Shingle-style Main House, gorgeous free-form pool with pool house, tennis/basketball court, guest/caretaker's cottage, barn with paddock on 13 +/- acres of rolling open meadows, level lawns, landscaped gardens and vegetable gardens with substantial frontage on the Shepaug River set along a private dead-end lane. Main house has three-four bedrooms and four full and two half baths. Great Room with towering 21 +/- ft. Cathedral ceilings, fireplace, a loft, beams, and French doors to a centrally located brick terrace overlooking the stunning open meadows. Large eat-in kitchen with Fieldstone Fireplace and pantry. Formal Dining Room with walls of windows. First-floor Primary Suite with office, walk-in closet, French Doors to the terrace and ensuite bath with over-sized shower. Originally an Artist's Studio, currently serves as a family room with ensuite bedroom upstairs and separate entrance. Large Media/Music Room connects to another private ensuite bedroom with private entrance. Enormous Bonus Room has many possibilities and is currently a workshop and gym with attached green house. Central AC, Full-house generator, and four-car garage. Rare private oasis yet close to Towns of Washington and Roxbury. Under two hours to NYC. Must see!

Listed by Peter Klemm of Klemm Real Estate Inc

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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: 6.49% last updated on Dec 1, 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$1,295,000

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: 6.49% last updated on Dec 1, 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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92 Hemlock Road Roxbury CT 06783

Roxbury, CT92 Hemlock Road

Price$299,000

Est. Mortgage: $/month

MLS Number 170502501

  • Land
  • Acreage 3.03
  • Zoning A&C

Approved and cleared 3 acre lot located on a quiet town road in Roxbury. Approved for a 4 bedroom home with a standard (not engineered) septic. Located on a gravel road in a area of fine homes. Driveway approval in place and the parcel is cleared.

Listed by Timothy G Tierney of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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200 North Street Roxbury CT 06783

Roxbury, CT200 North Street

Price$569,000

Est. Mortgage: $/month

MLS Number 170498394

  • Land
  • Acreage 8.64
  • Zoning Res

There are lots and then there are magical, special, unparalleled lots, steeped in history where you can actually feel and hear the terrain singing to you. The woods roxbury is such a place as evidenced by our recent sales. This is the last available lot from phase ii, (lot #1) and it must be seen and heard to understand how your future heirloom home will be cherished. This 8.64 acre lot features un-touched historic stone walls, a beautiful stream flowing, gently sloping tree-covered hills and an abundance of ferns, pine trees, oaks and maples as your canvas. The home site is absolutely flat and perfect! This masterpiece lot is ideal to build your dream home and to connect with what is important in life. Whether a weekender or full-time resident, the woods will offer you ultimate privacy with endless possibilities for a simpler place and way of life. Our wonderful architectural team is available to design your one of a kind home or you can bring your own. Shown by owner/agent.

Listed by Jill Sloane of Brown Harris Stevens

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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 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 ideal 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. Relax on a large West facing renovated brick terrace with captivating seasonal views. The first floor has a versatile layout with three flex 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. We have estimates the pool and the garage. 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: 6.49% last updated on Dec 1, 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
Pending Continue to Show

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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268 Southbury Road Roxbury CT 06783

Roxbury, CT268 Southbury Road

Price$149,900

Est. Mortgage: $/month

MLS Number 170469195

  • Land
  • Acreage 11.1
  • Zoning C

A must-see 11+ acre approved building lot with a large pond and level house location! Come build your dream home and obtain instant equity in this charming town in Litchfield County. Close to restaurants, beautiful hiking trails, and less than 2 hours from Manhattan. Just 10 minutes from three town centers and shopping. The house site sits up off the road and overlooks the pond area. Easy access and walking to the house site through the existing old driveway bed. The lot includes an existing well.

Listed by Rhya B Szymansky of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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