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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18 Falls Roxbury CT 06783

Roxbury, CT18 Falls Road

Price$4,300,000

Est. Mortgage: $/month

MLS Number 170216895

  • Single Family
  • Property Style Colonial
  • Bedrooms 6
  • Bathroom 7
  • Acreage 9.64

Stunning Compound with 200 +/- feet of Shepaug River frontage, this property simply has it all! Long private gated driveway & flat usable open land. Fish from your own back yard! 5-6 bedroom main house w/ gourmet eat-in kitchen opening to vaulted family room w/ cupola. Main & 2nd floor master bedrooms, finished lower level with gym, sauna, and meticulous storage areas. Attached in-law apartment with full kitchen. Large covered porch, French doors from every room leading to multiple terraces & professionally landacaped gardens. 2 car attached garage. Gunite Pool & Jacuzzi with oversized blue stone terrace. Glorious fully outfitted Pool/Guest House with full kitchen, bath, changing rooms, pergola & outdoor fireplace. Uber chic Party Barn/game room w/ guest room, 1.5 baths, full kitchen, vaulted ceiling, double sided stone fireplace & 1 car garage. Generator. Completely Luxurious Perfection!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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110 Town Line Roxbury CT 06783

Roxbury, CT110 Town Line Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 170316576

  • Land
  • Acreage 78

78± 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 multiple new build site 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 on 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. Almost a 1/2 mile of road frontage, with views south and east, one of the highest elevations in Roxbury on the most scenic roads

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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110 & 114 Town Line Roxbury CT 06783

Roxbury, CT110 & 114 Town Line Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 170316596

  • Single Family
  • Property Style Colonial, Farm House
  • Bedrooms 7
  • Bathroom 1
  • Acreage 78

78± 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 multiple new build site 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 on 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. Additional land may be available

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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 Tophet Roxbury CT 06783

Roxbury, CT53 Tophet Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 170219302

  • Single Family
  • Bedrooms 4
  • Bathroom 7
  • Acreage 9.57
  • Square Feet 7,451

Located about 85 miles from Manhattan, this marvelous country estate provides quiet privacy and tranquil surroundings, tucked into the Roxbury Land Trust on two sides. An impeccable Roxbury manor looks out over nine level park-like manicured acres with mature landscaping, colorful and fragrant perennial flowers and plantings. Picturesque patios, decks and stone walkways abound, a curved stone staircase leads to the heated outside pool and a small pond add to the prestigious setting. Recent high-end expansion and upgrades provide easy living as a vogueish home for a weekend and Summer retreat or a grand primary residence! Walk in to discover the elegant upscale surroundings that provide hints of New England yet, are elegantly bright and open. A brilliant great room exudes the beauty of the outside environment through three walls of glass. Central to the house is an impressive dining room, providing a great space for a grand banquet. The well-equipped Kitchen, bright and open has a wonderful large breakfast nook opening into a side foyer. On this main level you will also find a spacious master suite and comfortable office with two walls of windows and a fireplace. Downstairs there is a large room for possible use as a gym or theater room. Also find a lengthy indoor gunite lap pool complete with a full bath, an automatic cover to retain heat and a slider leading out to the gardens...continued in the Addendum...

Listing Courtesy of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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8 Mallory Roxbury CT 06783

Roxbury, CT8 Mallory Road

Price$2,595,000

Est. Mortgage: $/month

MLS Number 170322768

  • Single Family
  • Bedrooms 6
  • Bathroom 9
  • Acreage 6.05
  • Square Feet 6,400

The very best of everything under 90 minutes from NYC. Exquisite Georgian Colonial set on 6+ picturesque acres offering panoramic views and western sunsets in gorgeous southern Roxbury setting. Large wood paneled "ELEVATOR" with access to all floors. 6 bedrooms in the main house and 2-3 bedrooms for guests in the Carriage house. Heated saltwater gunite pool. Impeccable craftsmanship with custom millwork throughout together with handcrafted baseboards, three fireplaces, and a unique paneled library. Living room with herringbone hardwood floors, french doors that lead out from the dining room to a beautiful veranda overlooking the grounds with long-reaching views of the Litchfield hills. The lower level with fireplace offers a large family room, office, a full kitchen, and an additional bedroom or gym with a full bath. 4 bay garage plus 2 added bays in the 2 story barn suitable for use as a craft or artist's studio with separate utilities. Carriage house with a soaring ceiling in the living room, full kitchen, and a private screened porch that overlooks and surrounds the pool with private fencing and gorgeous mature garden. Also, a large rear deck with BBQ overlooking the lovely grounds ideal for entertaining family and friends

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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88 Painter Ridge Roxbury CT 06783

Roxbury, CT88 Painter Ridge Road

Price$1,850,000

Est. Mortgage: $/month

MLS Number 170302692

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 6
  • Acreage 22.75

Premier Roxbury Location! Immaculate contemporary home on 22+ acres with a premier 5 stall horse barn which includes a heated wash stall, tack room with laundry, bath and a storage garage with drive in, drive out for your horse trailer. There is a full second floor for hay that could possibly be converted to staff quarters. The fields have fenced paddocks. A lovely property with frontage on 2 roads for possible subdivision. The home is lovely with a great floor plan. The kitchen has all hi-end appliances and looks out to the back terrace and the swimming pool with cabana. The formal dining room and living room has beautiful wood floor. The living room adjoins a screened porch with a hot tub that also looks out at the pool area. Upstairs there is a lovely Master Bedroom Suite with a fireplace, french doors to an upper deck overlooking the pool, walk in closets and a master bath with dual sinks, stall shower and a soaking tub. There are 2 other en-suite bedrooms on this level as well as a laundry room. The lower level has a large game room. There is an in-law apartment accessed from the mud room off the kitchen. It is on the second floor and has a living/dining room combo, kitchen, full bath and a bedroom. There is also an upper deck with access from the living room. The 3 car attached garage gives plenty of room for your cars. Any additional farm equipment will fit in the barn. There is also an additional shed near the barn. The house faces west with amazing sunsets and views!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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77 Tophet Roxbury CT 06783

Roxbury, CT77 Tophet Road, Tophet

Price$1,695,000

Est. Mortgage: $/month

MLS Number 170304364

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 3.05

A pea pebble, circular drive leads to this lovely nantucket-style cedar-shingled colonial on one of Roxbury's most coveted roads. The graceful foyer welcomes you to a dramatic two-story living room with a fireplace and coffered ceiling and wall to wall windows overlooking the mahogany deck, blue stone patio and English gardens. This builder's own luxury home has a main level master suite with grand master bath, large walk-in customized closet, library with fireplace, butternut cabinetry and herringbone floors. There is a large eat-in chef's kitchen with floor to ceiling windows, Viking fridge and stove, a butler's pantry and a comfy four-seasons sunroom. . A formal dining room, laundry room and mudroom with powder room complete the first floor. The many french doors, decks and patios invite you to enjoy outside living. The property is surrounded on 3 sides by Widmark land preserve, guaranteeing your privacy. The custom touches are plentiful including custom millwork, wide-board oak flooring and venetian plaster walls and ceiling. The second floor balustrade overlooks the living room, flanked by bookshelves and includes a sitting area with entry to an outdoor balcony. There are 3 more bedrooms, each with its own full bath as well as an office and a large bonus room.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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20 Grassy Hill Roxbury CT 06783

Roxbury, CT20 Grassy Hill Road

Price$1,549,000

Est. Mortgage: $/month

MLS Number 170296059

  • Single Family
  • Property Style Contemporary, Barn
  • Bedrooms 5
  • Bathroom 9
  • Acreage 3

Set on a Gorgeous Scenic Country Equestrian road. Contemporary with high ceilings, Open Floor Plan and Light everywhere from the grand window! Lush lawn and pasture with Horse Barn. Impeccably maintained grounds. The front entrance opens to a grand staircase with colossal ceilings, Hardwood floors and enormous picture windows with an exceptional view from every room - The open kitchen offers gorgeous stone countertops and backsplash with island for easy entertaining. From the impeccable flagstone patio, to the sprawling 3-acre lawn. An enormous master suite includes beautiful en suite, large walk-in closet with built-ins & giant soaking tub! The lower level is complete with an abundance of space that could be used as an additional living space, home entertainment room or home based business! Other amenities..Horse Barn, gorgeous & mature landscaping, home office/art studio(separate structure), in-law suite, three-car garage, freshly painted inside and out, close proximity to town, & much more!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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53 Southbury Roxbury CT 06783

Roxbury, CT53 Southbury Road

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170295710

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

Discover a flawless connection between the tranquil outdoors to indoor living with this bold sun-filled property. Perched on 5.85 acres of secluded park-like land with impeccable landscaping, this unique Tudor-style dream is located in a world of its own with celebrated elegance and starry nights - a true fairytale. 53 Southbury offers 4 expansive bedrooms, a private circular driveway, a hand-split cedar single roof, Marvin windows w/ custom shutters, and more custom designs throughout. Spring & Summer with loved ones will be one to remember w/ a remarkable in-ground heated gunite pool w/ spillover spa, perfect for both splashing around and relaxing w/ an added bonus of the custom waterfall! Walk-in to the grand entrance to see custom arched mahogany doors, sweeping staircase & rich hardwood floors. The living area flows effortlessly into the large dining room, perfect for entertaining. Friends & family will all enjoy the stone & mahogany Neff kitchen w/ spacious breakfast nook overlooking the private pond and access to your large outdoor deck! Master bedroom suite shines with a private outlook, ensuite w/ tub & custom steam shower w/ waterproof television. This wonderous property also has a full basement complete with washer/dryer, and a large rec space perfect for a home theater, playroom, or more. A true visionary retreat offering superb pond fishing, canoeing, kayaking, and memories that will forever be cherished- come see why this outstanding delight is perfect for you!

Listing Courtesy of Executive Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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 Roxbury CT 06783

Roxbury, CT101 South Street

Price$1,495,000

Est. Mortgage: $/month

MLS Number 170306375

  • Single Family
  • Property Style Contemporary
  • Bedrooms 6
  • Bathroom 6
  • Acreage 38.05

Live in your own nature preserve! Enjoy complete privacy down long driveway where this striking home is set in the middle of 38+/- lush acres. The back deck looks out to rushing brook, pond, waterfall and gorgeous rocky outcroppings. The kitchen opens to the family room with wrap around windows and a dramatic circular fireplace around which all the activity of the room rotates. Upstairs, there are 4 bedrooms and 3 baths, the master having its own office area or dressing room. There is an additional 2 bedroom apartment over the garage which makes a great in-law suite or private offices for a perfect work at home scenario. The finished basement features a playroom, exercise room and an amazing 3,600 bottle wine cellar.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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11 Farm Roxbury CT 06783

Roxbury, CT11 Farm Road

Price$1,400,000

Est. Mortgage: $/month

MLS Number 170317525

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 14.32

Spacious Shingle-Style home with complete privacy bordered by 100 acres of protected land. Large open kitchen with breakfast nook and center island. Every room on the main floor has access to the outdoors with huge windows and multiple porches. Main floor separate office with doors for privacy. Unfinished room on second floor could be a second office if needed. Quality construction throughout - hardwood floors, high ceilings, crown moldings, beautiful mill work, copper & architectural shingle roofing. Two brooks, gorgeous landscaping and a raised, fenced vegetable garden. 3 car garage with separate lead with large unfinished attic that could be guest apt. Unfinished basement has high ceilings and walls of windows. Perfect for finishing into game room and gym. 10 minutes to Washington or the New Milford Greens. House generator in place.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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206 North Roxbury CT 06783

Roxbury, CT206 North Street

Price$1,295,000

Est. Mortgage: $/month

MLS Number 170281260

  • Single Family
  • Property Style A-Frame
  • Bedrooms 3
  • Bathroom 4
  • Acreage 26.7

TO BE BUILT. "The Woods" has arrived! Custom 2200-3500 sq foot home on beautiful 26.7 acre lot. Constructed of the finest materials by local craftsmen dedicated to perfection, this home is a work of art. The design of the home fits the topography of the land, creating minimal disruption to the natural surroundings. Due to extensive use of locally-sourced natural materials, homes seamlessly blend into the canopied gently-sloping hillside. With an array of interior material options, and additional upgrades, each home can be customized to your specific tastes and whimsical desires and can be as large as 4100 sq ft or more. In addition, homes can be further customized by working directly with the architect. This stunning home-site features un-touched historic stone walls and an abundance of pine trees, oaks and maples for ultimate privacy. Jill Sloane Owner/Agent.

Listing Courtesy of Halstead Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.