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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Town Line Roxbury CT 06783

Roxbury, CTTown Line Road

Price$16,000,000

Est. Mortgage: $/month

MLS Number 170254324

  • Single Family
  • Property Style Colonial
  • Bedrooms 10
  • Bathroom 10
  • Acreage 320

Greyledge Estate - one of the largest and most spectacularly situated properties in Litchfield County - is available for acquisition for the first time, in its entirety. In the event no transaction is effected by January 31, 2020, each parcel and any associated view sheds will be offered for sale individually, in a sequence to be determined. Greyledge Estate sits at the gateway to the Litchfield Hills, a popular and growing second home market defined by community and rural tranquility, that is only 80 miles from New York City. The Estate is one of the most spectacularly situated properties in Litchfield County in that it occupies an elevated position on a picturesque ridge running along the border of Bridgewater and Roxbury, Connecticut. The 320±-acre property is comprised of contiguous land parcels that are bordered by over 500 acres of perpetually protected Land Trust property to the north and to the east of the estate. Greyledge Estate is further differentiated by its scale and scarcity as it is one of the largest parcels of unencumbered, prime land in Western Connecticut. The property offers a rare combination of near 360-degree views to the horizon, multiple elevated build sites, more than 100 acres of farm fields, woods, and approximately 25,000 square feet of beautifully maintained homes and out-buildings. The purchaser can maximize the value of the existing land by reconfiguring select parcels and performing lot line adjustments with neighboring properties

Listing Courtesy of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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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

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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$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: 3.33% last updated on Apr 9, 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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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: 3.33% last updated on Apr 9, 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$2,100,000

Est. Mortgage: $/month

MLS Number 170265819

  • Land
  • Acreage 48.4

This prime, unencumbered build site offers exceptional unobstructed eastern and southeastern views from a picturesque ridge running along the border of Bridgewater and Roxbury, Connecticut. More land available.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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114 Town Line Roxbury CT 06783

Roxbury, CT114 Town Line Road

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170265806

  • Single Family
  • Property Style Colonial
  • Bedrooms 7
  • Bathroom 1
  • Acreage 30.3

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 new build 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 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.

Listing Courtesy of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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294 Painter Hill Roxbury CT 06783

Roxbury, CT294 Painter Hill Road

Price$1,325,000

Est. Mortgage: $/month

MLS Number 170274512

  • Single Family
  • Property Style Colonial, Farm House
  • Bedrooms 3
  • Bathroom 5
  • Acreage 4.52

Impeccable hilltop farmhouse offers privacy & 270 views on most picturesque ridge in Roxbury. Essentially rebuilt in 2016 the top-to-bottom reno spared no expense w/ white oak flooring & beamed ceilings throughout, Carrara marble counters, all BRs en suite, designer appliances, new electrical/HVAC/new plumbing/mechanicals, heated 16x32 gunite pool & full house generator. The 3,300-sqft home offers gourmet kitchen w/ farmer's sink, marble island w/ seating + storage, Subzero & Bosch appliances, instant hot water & dining area. The kitchen is accented w/ reclaimed wood beams & opens to living rm offering ample entertaining space, or taking in the views, or relaxing by the handmade herringbone-brick fireplace. Also on main level off entry foyer is a formal dining rm, powder rm & library/overflow bedroom. Master suite on the 2nd level provides washer dryer, walk-in closet, marble bath w/ dual sink, soaking tub & glass shower & hillside views. Opposite is the 2nd en suite guest BR w/ full bath. Lower level storage & a large rm for use as a theater/media rm. A 3rd rm houses mechanicals. Set on 5 acres of sloping lawn, the house is set back far from a little country road at the end of a long driveway. Full house generator, detached 2 car garage & clean energy efficient propane heat & central air. Walking distance to property are miles of picturesque riding trails & the nearby Shepaug River plays host to a natural waterfall & an old fashion swimming hole for residents only.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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271 South Roxbury CT 06783

Roxbury, CT271 South Street

Price$1,295,000

Est. Mortgage: $/month

MLS Number 170140845

  • Single Family
  • Property Style Colonial
  • Bedrooms 8
  • Bathroom 7
  • Acreage 12.26

GENTELMAN'S FARM! FABULOUS GATED COMPOUND! Comprised of 2 Residences, 2 stables with 14 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 are 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. Low taxes! 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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$1,250,000

Est. Mortgage: $/month

MLS Number 170281260

  • Single Family
  • Property Style A-Frame
  • Bedrooms 3
  • Bathroom 4
  • Acreage 4.09

TO BE BUILT. "The Woods" has arrived! Custom 2200-3500 sq foot home on beautiful 4.09 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

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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25 Highmeadow Roxbury CT 06783

Roxbury, CT25 Highmeadow Lane

Price$985,000

Est. Mortgage: $/month

MLS Number 170234250

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 27.87

If you love horses you'll love this property! Main property has 17.31 acres PLUS there is an additional 10.56 lot that comes with the house that abuts the subject property. Some pastures have been fenced in this house is ready for horses with an 8 stall barn completely outfitted for boarding horses. The barn has a 980sq ft living unit above it for the caretaker. In addition there is a 3 bay garage/barn and four additional out buildings for storage for animals/chickens etc. A small pond also enhances this property! This house is located on a cul-de-sac and is very private. The main house was freshly painted with new carpets, new granite counter and high-end appliances. The huge family room steps out to a huge deck over looking the pastures and the valley, the walk out basement is fully finished with bathroom and fireplace. Only minutes to Rt84 and Rt 90. Make this your country get a way! - To help visualize this home's floorplan and to highlight its potential, virtual furnishings may have been added to photos found in this listing.

Listing Courtesy of Aspen Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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32 Judge Roxbury CT 06783

Roxbury, CT32 Judge Road

Price$950,000

Est. Mortgage: $/month

MLS Number 170165118

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

This stone and clapboard home is sited in the highly desirable Golden Harvest area with 270 degree seasonal 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. Walk to miles of hiking trails. Just 90 minutes to NYC.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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51 Mine Hill Roxbury CT 06783

MLS Number 170286329

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.73

Country living in a small rural town right out of Currier & Ives! This lovely 4 bedroom, 3.5 bath home is set on a 2.73 acre lot on a gravel road, directly across from land trust with miles of hiking trails. There is an in ground, gunite pool for your summer enjoyment. Come in from the 2 car garage to the mud room. The antique home has had many updates and has a very cozy feel with a fireplace in the dining area off the kitchen. There is a large great room with a vaulted ceiling, beams and an additional fireplace for those cozy nights. The updated kitchen is bright and cheerful with lots of light. There is a full bath on the main floor as well as a half bath. The master bedroom suite is on the upper level with a lovely full bath and a walk in closet. There are three other bedrooms on this level as well a another full bath. Enjoy the areas farm to table restaurants, farmers markets, country fairs and art exhibits. There are many outdoor activities with the areas thousands of acres of land trust with hiking trails, lakes and rivers for fishing and kayaking. There are ski areas close by also. Located only 90 minutes from NYC, this would be a great weekend escape as well as a full time home.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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.