Roxbury CT Real Estate

Corn FieldTucked 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 Roxbury

Properties in Roxbury

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18 Falls Roxbury CT 06783

Price$4,500,000

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

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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

Price$3,250,000

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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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7 Garnet Roxbury CT 06783

Price$2,695,000

Est. Mortgage: $/month

MLS Number L10239327

  • Single Family
  • Property Style Barn
  • Bedrooms 5
  • Bathroom 6
  • Acreage 4

Views, views... Rarely does a property fully embrace New England character with Litchfield Hills Views, Privacy, Salt Water Pool with automatic cover, Spa with seating for 8 and automatic gated entry. Set on a bucolic road in Roxbury, this grand barn style home offers sweeping views across the Hills and open pasture. Rich architectural detail, 4 fireplaces and generous light and bright public spaces with exposed beams, wide board floors, 3 large televisions with surround sound, sonos sound system, in-wall speakers and fully equipped billiard room. The main floor master suite is complete with office/art gallery, dressing room and built-ins, large master bath with tub and walk in shower overlooks gardens, stonewalls, and fruit espalier. An additional 4 bedrooms on the second level, one with large comfortable space to serve as family or guest suite. The kitchen was designed for easy entertaining and opens on to the Great Room with fireplace and features a center island, commercial grade range, Sub-Zero refrigerator, pantry and plenty of cabinetry. The living room offers two sets of french doors to the large deck with pergola for large parties or cozy dinners spent by the fireplace. The lower level with a fully equipped exercise room with Sauna, Workshop or Studio space, a Billiard Room which all open on to the view and bluestone patio and courtyard. The is additional space for a media room. All the amenities required of a Great Estate and just 90 minutes to NYC!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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 Painter Hill Roxbury CT 06783

MLS Number 170241553

  • Single Family
  • Property Style Antique, Farm House
  • Bedrooms 5
  • Bathroom 4
  • Acreage 11.36

Originally homesteaded in the 1800's, the current 12-acre estate was once part of a 222-acre farmstead and is historically significant as one of few Roxbury properties that remained in the family of the original owners for 150+ years. The original English bank barn stands at the south of the property comprised of a c.1872 main residence, guest house, gunite pool, screened pool folly, 2 orchards, and dining patio. Fully renovated in 2015, the stunning estate is located in a whisper-quiet setting with western exposure at the top of Painter Hill. A formal dining room is wrapped in windows offering sunset views and direct access to dining patio. Adjacent is a formal living room with fireplace as its focal point. Opposite is a family room, and quietly set apart from the main living space is a 1st floor Master Suite with screened porch, walk-in closet, and 5-piece marble bath w/ dual sinks, free-standing soaking tub & separate shower. The 1-bed guesthouse is ideal for guests' extended stays, a caretaker's house or as an onsite rental income opportunity. It offers a full eat-in kitchen with double SubZero and appliances/finishes keeping with the quality of the main house. There's a half bath and an ensuite bedroom on the main level, while the upper level comprises a media room with two sleeping coves. Both main & guest house have cedar shake roofing with copper seams and gutters. Owners have plans that envisions combining the barns into a residence with spectacular Western views.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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 Wakelee Roxbury CT 06783

Price$1,695,000

Est. Mortgage: $/month

MLS Number 170176589

  • Single Family
  • Property Style A-Frame
  • Bedrooms 4
  • Bathroom 4
  • Acreage 25.2

TO BE BUILT. "The Woods" has arrived! Custom 2200-3500 sq foot home on beautiful 25.2 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. Surrounded by the Roxbury Land Trust on one side, 1 Wakelee Road is a stunning property featuring the Battle Swamp Brook running through it, 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

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%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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

Price$1,600,000

Est. Mortgage: $/month

MLS Number 170226904

  • Single Family
  • Bedrooms 5
  • Bathroom 9
  • Acreage 3
  • Square Feet 8,875

Welcome to beautiful 20 Grassy Hill Road located in Roxbury, Connecticut! From the moment you turn onto the scenic, equestrian road that leads to this stunning home, lush lawns and impeccably maintained grounds will have you feeling right at home! As you set foot through the grand front entrance you'll notice the beautiful staircase, gorgeous hardwood floors & colossal ceilings, a magnificent, open floor plan & enormous picture windows with an exceptional view from every angle - stone backsplash, gorgeous stone countertops and an abundance of space are amongst the first luxuries to catch your attention when you enter the kitchen. This spectacular home is an entertainers dream. From the impeccable flagstone patio, to the sprawling 3-acre lawn, you would be hard-pressed to find a more exquisite property to entertain. The enormous master suite includes beautiful ensuite, large walk-in closet with built-ins & giant soaker tub! Look no further than the basement for an abundance of space that could be used as an additional living space, home entertainment room or could be used as a home-based business! Not enough perks? Here are a few more: Horse Barn on property, gorgeous & mature landscape, home office/art studio(separate structure), in-law suite, three-car garage, freshly painted inside and out, commercial construction that is second to none, close proximity to town, & much more! Don't miss your chance to live in one of the nicest homes that Roxbury currently has to offer!

Listing Courtesy of Lasko Real Estate, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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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143 Tophet Roxbury CT 06783

Price$1,575,000

Est. Mortgage: $/month

MLS Number 170173659

  • Single Family
  • Property Style Colonial, Farm House
  • Bedrooms 4
  • Bathroom 6
  • Acreage 4.01

Gracious country farmhouse. Resort grade salt water, heated pool and spa with rolling ridgeline views across a vast tract of protected land. Located along one of Roxbury's most coveted stretches, the property is nestled within an 800+ acre greenbelt of farmed and undisturbed land trust. The home is an open space design with 8 foot+ ceilings , detailed millwork and oversized window banks throughout, overflowing with natural light. Four en suite generous bedrooms. Excellent mechanical systems, including a Quietsource 27K generator. Peaceful and private, yet within easy reach of area recreational activities, farm stands, organic groceries, restaurants and boutiques. If you desire a luxurious, updated country home surrounded by natural beauty, come take a look. Agent Owner.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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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271 South Roxbury CT 06783

Price$1,295,000

Est. Mortgage: $/month

MLS Number 170140845

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 5
  • Acreage 12.26

Fabulous Gated Compound comprised of 2 Residences, 2 stables with 12 stalls and equipment barn all on 12+ beautiful, level, fenced in acres. The main house is an 1850's antique that has been lovingly restored. Master bedroom on the main level as well as one on the upper level. The gourmet eat in kitchen features custom cabinets and hi-end appliances. There are beautiful hardwood floors and 2 fireplaces, 1 in the living/dining room and 1 in the office adjacent to the main floor master. The family room overlooks a beautiful in ground pool. There is a room once a wine cellar in the basement. Many sets of french doors open to the lovely landscaped property, right out of a Currier & Ives painting. The 2800 sq ft guest house has 4 bedrooms, 2.5 baths and a lovely living/dining room, kitchen, office, family room, sun room and deck. There is 400 amp service with full house back up generators for both houses. The 12+ acre property is fenced for horses, (or other animals) with open pastures and an illuminated riding ring. Enjoy all the art and culture the area has to offer as well as many thousands of acres of land trust for your hiking and out door activities. Roxbury Falls is an old fashioned swimming hole close by for Roxbury residents use only. Enjoy the town centers of Woodbury, Washington, New Preston and Kent which are all close by with antique shops, boutiques, art galleries and great restaurants. 90 minutes to Manhattan makes this a great weekend as well as a full time home!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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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257 Southbury Roxbury CT 06783

Price$1,150,000

Est. Mortgage: $/month

MLS Number 170212346

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 10.08
  • Square Feet 3,086

Wonderfully private and updated Roxbury compound with four bedroom, four bath mid-century Mediterranean vibe main house offering the convenience of one level living. Secluded and dramatic 10 acre property with park-like grounds that flow from the primary residence and gardens down to the salt pool with expansive stone deck and Guest House. The home's amenities include a chef's kitchen anchored by a Viking Range, Sub Zero and EuroCave Wine cooler. Steam room, covered outdoor grilling/dining area, hot tub, outdoor shower, koi pond and lushly landscaped rock garden are among other lifestyle drivers. Generously sized 2000+ sf Guest/Pool house has additional bedroom, full bath, complete kitchen, open dining/living room, loft and large studio. Within easy reach of farm fresh produce, organics, groceries, prepared foods, fine dining and thousands of acres of preserved land with miles of hiking trails. Barely 10 minutes to I-84 and ~90 minutes from the Big Apple.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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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32 Judge Roxbury CT 06783

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170165118

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 6.67

Just 90 Minutes from NYC this stone and clapboard home is sited in the highly desirable Golden Harvest area with 270 degree VIEWS over the Shepaug River Valley and hundreds of acres of protected land. Enjoy complete privacy with light filled rooms, floor-to-ceiling windows, vaulted ceilings and a screened porch which overlooks nearby farmland. Enjoy outdoor entertaining with a built in grill on the expansive wrap around deck which overlooks the gorgeous Gunite pool. This architect designed home is set up for easy living with an open concept plan, atrium art gallery space, French doors to the outdoors, and 4 wood burning fireplaces. The family room features a stone fireplace, built-ins, wet bar and opens to the spacious kitchen w/granite counters, new 48 inch gas range and stainless appliances. The master suite features a luxurious master bath and walk in closet. Upstairs, three additional bedrooms overlook the treetop views, while the finished lower level offers more space to gather with a game room, media room and gym.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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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296 Painter Hill Roxbury CT 06783

Price$1,050,000

Est. Mortgage: $/month

MLS Number 170052871

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

  One of Roxbury's finest addresses abutting the Alexander Calder estate. This modern farmhouse is a real stunner with an open floor plan, high ceilings and light filled interiors. Its sits high a top Painter Hill and has views across protected land. 5 bedrooms 3.5 baths. Gourmet kitchen with bar stool seating and walk-in pantry. Master suite with spa-like bath room. Spin cycle studio, playroom, media room/office. The tree lined driveway shines with pink blossoms in the Spring. Large barn. Super chic 3 car garage with glass doors.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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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35 Gold Mine Roxbury CT 06783

Price$1,050,000

Est. Mortgage: $/month

MLS Number 170206198

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 15.01

Exceptional example of Frank Lloyd Wright-Inspired mid-century modern architecture built of steel & stone offers a unique combination of character & features that would be hard to replicate at any price. Nestled in the hills of Roxbury on a 15-acre lot, the 6,000-sqft residence blends organically into the rolling landscape at the top of a long graveled drive along which are two spring-fed ponds. Light-filled interior contains a formal entry with chestnut paneled bar area w fireplace, spacious living room with alcove sunroom and natural stone fireplace, formal living room, kitchen, 1st fl en-suite master w garden access, 4-room in-law apt w kitchenette & separate entry with foyer. Second level has large master suite with a balcony & a sky-lit exercise room. A 2nd spacious bedroom has living room-like feel with enough room to accommodate a king size bed & generous sitting area. Additional rooms incl office/library with built-in bookshelves, first-floor laundry room & bonus room. Oak flooring and cedar closets throughout. The property has great view potential with some clearing, and sports a flagstone patio for entertaining or relaxation, a cedar-fenced vegetable garden, mature plantings, two water fountains, and a detached 4-car garage.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 2019
* 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.