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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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: 3.68% last updated on Dec 5, 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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18 Falls Roxbury CT 06783

Roxbury, CT18 Falls Road

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: 3.68% last updated on Dec 5, 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

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: 3.68% last updated on Dec 5, 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: 3.68% last updated on Dec 5, 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

Roxbury, CT1 Wakelee Road

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: 3.68% last updated on Dec 5, 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

Roxbury, CT20 Grassy Hill Road

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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$
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$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

Roxbury, CT143 Tophet Road

Price$1,575,000

Est. Mortgage: $/month

MLS Number 170173659

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

A gracious country farmhouse for all four seasons. 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: 3.68% last updated on Dec 5, 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

Roxbury, CT271 South Street

Price$1,295,000

Est. Mortgage: $/month

MLS Number 170140845

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

GENTELMAN'S FARM! 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 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: 3.68% last updated on Dec 5, 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

Roxbury, CT257 Southbury Road

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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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25 Highmeadow Roxbury CT 06783

Roxbury, CT25 Highmeadow Lane

Price$1,050,000

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: 3.68% last updated on Dec 5, 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 Southbury Roxbury CT 06783

Roxbury, CT53 Southbury Road

Price$999,999

Est. Mortgage: $/month

MLS Number 170172388

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

Fairy-Tales do come true in this whimsical custom stone cottage overlooking a large private lily pond. The long circular driveway meanders around a 30 foot rock outcropping to a charming European style enclave. A custom Klaff kitchen features top quality appliances, mahogany inlaid Neff Cabinets and opens to a breakfast nook with magical water views. The home includes custom arched mahogany doors, Marvin windows, wood shutters and a hand carved banister which enhances the sweeping staircase. Spectacular custom baths include a clawfoot tub, steam shower, TV and jetted tub. The hand split cedar shingle roof mirrors thatching, giving the home an English Cotswolds' feel. As you step outdoors you will enjoy the expansive lawns, stunning gardens, stonewalls and the ever present pond views. Take a swim in the glass mosaic/Gunite infinity pool with over-sized spill over Jacuzzi. Irrigation system assures you a lush healthy lawn. This home is a year round water lover's paradise perfect for fishing, canoeing, paddle boarding and ice skating. Step into your own Thomas Kincaid painting with 21st century amenities. This one of a kind home is not your typical cookie cutter colonial, come see this unique property for yourself. Seller relocating and motivated, bring all offers.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

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: 3.68% last updated on Dec 5, 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.