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.

>> Learn more about the town of Roxbury

Properties in Roxbury

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24 Ranney Hill Rd, Roxbury, CT 06783

Price$3,500,000

Est. Mortgage: $/month

InternalID L10108738

  • Residential
  • Bedrooms 5
  • Bathroom 10
  • Acres 32.06
  • SqFt 6189

This Shingle Style residence is sited atop 32+ high, private acres to take advantage of the spectacular 270- degree views. Every amenity and finest quality materials. Rooms are generous in scale with high ceilings, elaborate moldings, and wood flooring. The Living Room has a fireplace and 2 sets of French doors that open to an expansive bluestone patio overlooking the heated Gunite pool and stunning views. The kitchen with island, granite counters, cherry cabinets, commercial grade appliances includes 2 sinks and 2 dishwashers and opens to the light-filled family/morning room with its vaulted ceiling, fireplace and French doors. A wood-paneled library. First floor Master with a screened-in porch, tray ceiling, walk-in closet, dressing area and bath with Jacuzzi tub and separate shower. A second main floor bedroom has a full bath and walk-in closet. Second Floor. 3 bedrooms including another Master with large dressing room and 2 baths-one with Jacuzzi tub and separate shower; the other with a marble shower. The other 2 bedrooms have baths en suite. The Finished Lower Level (an additional 3, 822 SF) is very light and opens to the patio surrounding the pool. There is a bath with 2 walk-in showers. A large family room and kids' playroom. A guest suite includes a living room with fireplace. A wet bar adjoins the media room. Plus au pair quarters. There are two 2-car garages separated by a porte-cochere. The landscaped property is composed of 3 separate parcels.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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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24 Ranney Hill Road, Roxbury, CT 06783

Price$3,500,000

Est. Mortgage: $/month

CMLS 99133372

  • Residential
  • Bedrooms 5
  • Acreage 32.06
  • Square Feet 6189

This Shingle Style Residence Is Sited Atop 32+ High, With Spectacular, Private, 270-degree Views. Every Amenity And Finest Quality Materials. Rooms Are Generous In Scale With High Ceilings, Elaborate Moldings, And Wood Flooring. The Landscaped Property Is Composed Of 3 Separate Parcels. Gardens And Blue-stone Patio Surround In Ground Pool. Two Master Suites, 3 Additional En Suite Bedrooms. Comfort And Care With The Right Amount Of Formality Went Into The Kitchen, Family Room, Living Room, Dining Room And Library. Lower Level Has Rec Room, Lounge For Pool With Spa Bath, Au Pair Suite And Media Room With Wet Bar. Too Many Extras To Name. Please See Addendum Remarks

Listing Courtesy of William Pitt Sotheby's

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A Minor Bridge Rd, Roxbury, CT 06783

InternalID L10162543

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Acres 22
  • SqFt 4600

New gorgeous kitchen which opens on to the Falls view! Rarely do such properties come along. Historic 1700's Colonial with direct waterfront on the Roxbury Falls and the provenance of ownership by Geraldine Stutz, Ceo of Henri Bendel, gardens designed by renowned landscape architect Russel Page. Lovingly updated while keeping the interior design of the Geraldine Stutz ownership.The approach to this incredible estate includes six hundred feet of stone walls and two totally private gates. A covered stone patio, perfect for entertaining, opens on to the rushing water of the Falls. A long driveway gated for privacy opens on to perfectly designed and manicured grounds. The former Roxbury post office building saved by Stutz, now acts as an incredible guest house w/ a large stone fireplace, marble bath and kitchen. A fabulously restored 4 room log cabin updated to perfection has been made into a guest house complete with modern kitchen and bath. A gorgeous pond and open lawn with meandering stonewalls wind you through the stunning grounds. The main house offers two stone fireplaces and beautiful brick and pegged floors. Main house and guest houses offer 5 beautiful bedrooms and 6 baths. With the touch of your phone or pad, you can control the sprinkler system, Bose outdoor music system, pool heater, thermostats or alarms. The owner will be afforded total privacy as the property is surrounded by land trust property. Also offered on 8.23 acres at $2, 750, 000. see L10162340

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 Minor Bridge Road, Roxbury, CT 06783

Price$3,100,000

Est. Mortgage: $/month

CMLS 99157760

  • Residential
  • Bedrooms 5
  • Acreage 22
  • Square Feet 4600

Rarely Do Such Properties Come Along! Historic 1700's Colonial With Direct Waterfront On Roxbury Falls And The Provenance Of Ownership By Geraldine Stutz, Ceo Of Henri Bendel With Gardens Designed By Renowned Landscape Architect Russel Page. Lovingly Updated While Keeping The Interior Design Of The Geraldine Stutz Ownership.the Approach Includes 600 Ft Of Stone Walls & 2 Private Gates.the Covered Stone Patio Opens To The Falls. The Main House Is An Historic Treasure With 2 Stone Fireplaces, Beautiful Brick & Pegged Floors. Main House & Guest Houses Offer 5 Bedrooms & 6 Baths. The Former Roxbury Post Office Saved By Stutz, Is An Incredible Guest House & A Restored Log Cabin Is Another Guest House. Gorgeous Pond. Surrounded By Land Trust.

Listing Courtesy of William Pitt Sotheby's

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

102 North St, Roxbury, CT 06783

Price$2,750,000

Est. Mortgage: $/month

InternalID L10167292

  • Residential
  • Bedrooms 6
  • Bathroom 5
  • Acres 21.66
  • SqFt 5204

The “Four Stone Chimney's” of Edgehill Farm, is located in the historic town of Roxbury, Ct., less then 2 hrs from NYC, where Arthur Miller, Marilyn Monroe, Walter Matthau, Dustin Hoffman, Alexander Calder, and many other famous personalities lived and worked. This multi-generational compound is situated on over 21 beautiful landscaped and wooded acres. The stone-walled driveways lead to the main residence, a colonial revival, a 2 br guest house, and a 3 br carriage house which are all equidistant from the natural pond shaped in-ground pool. The barns, silos, and sheds are noted on the Ct. State Registry of Historic Farm Buildings. Dating from 1860, the main house has 6 br., 4.5 baths, 4 fireplaces and has been maintained and updated with the finest materials for the last 50 years by the late Burt Wayne, a noted NY designer. The rooms are all very generous sizes and well proportioned with high ceilings and detailed moldings throughout. A dramatic columned porch runs the entire width of the main house. Both the one level cottage, and the 2 story carriage house with approx, 1455 sq. ft each, have lovely 3 season screened/windowed porches with views of the property. The additional landscaping, orchard, terraces, decks and porches, including a speaker system throughout, lends itself to al fresco entertaining. This stunning country estate or 'Gentleman's Farm' is the perfect residence that could comprise a farm, equestrian property, artists/writers studio, or many ot

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

35 Minor Bridge Rd, Roxbury, CT 06783

Price$2,750,000

Est. Mortgage: $/month

InternalID L10162340

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Acres 8.23
  • SqFt 4600

New gorgeous kitchen which opens on to the Falls view! Rare Historic 1700's Colonial with direct waterfront on the Roxbury Falls with provenance of ownership by Geraldine Stutz, Ceo of Henri Bendel and gardens designed by renowned landscape architect Russel Page. The home has been lovingly updated while keeping the interior design of the Geraldine Stutz ownership. The approach to this incredible estate includes six hundred feet of stone walls and two totally private gates.The covered stone patio, perfect for entertaining, opens on to the rushing water of the Falls. A long driveway gated for privacy opens on to the Russel Page designed, perfectly manicured grounds. The former Roxbury post office building saved by Stutz, acts as an incredible guest house w/ a large stone fireplace, marble bath and kitchen. A fabulously restored 4 room log cabin updated to perfection has been made into a guest house complete with modern kitchen and bath. A gorgeous pond and open lawn with meandering stonewalls wind you through the stunning grounds. The main house is a historic treasure complete with two stone fireplaces and beautiful brick and pegged floors. Main house and guest houses offer 5 beautiful bedrooms and 6 baths. With the touch of your phone or pad, you can control the sprinkler system, Bose outdoor music system, pool heater, thermostats or alarms. The owner will be afforded total privacy as the property is surrounded by land trust property. Also offered on 22+ acres at $3, 100, 00.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

102 North Street, Roxbury, CT 06783

Price$2,750,000

Est. Mortgage: $/month

CMLS 99159788

  • Residential
  • Bedrooms 6
  • Acreage 21.66
  • Square Feet 5204

The “four Stone Chimney's” Of Edgehill Farm, Is Located In The Historic Town Of Roxbury, Ct., Less Then 2 Hours From Nyc. Edgehill Farm Is An Exquisite Family Compound Consisting Of 3 Homes. The Main House Is 5200 Sq Ft Colonial Revival With 6 Bedrooms And 4.5 Baths And Features Many Oversized And Beautiful Proportioned Rooms. Four Stone Chimneys And Four Formal Fireplaces Appoint The Home. The Cottage Is A Lovely 1 Story 1450 Sq Ft Ranch With 2 Bedrooms And 2 Baths. The Carriage House Is A 2 Story 1455 Sq Ft Home With 3 Bedrooms And 2 Baths. The Property Is On 21.66 Acres Borders Beautifully Landscaped Grounds, In Ground Pool And Patios.

Listing Courtesy of William Pitt Sotheby's

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

35 Minor Bridge Road, Roxbury, CT 06783

Price$2,750,000

Est. Mortgage: $/month

CMLS 99157746

  • Residential
  • Bedrooms 5
  • Acreage 8.23
  • Square Feet 4600

Gorgeous New Kitchen Opens To The Falls View! Historic 1700's Colonial With Direct Waterfront On Roxbury Falls And The Provenance Of Ownership By Geraldine Stutz, Ceo Of Henri Bendel And Garden Design By Renowned Landscape Architect Russel Page. Lovingly Updated While Keeping The Interior Design Of The Geraldine Stutz Ownership.the Approach Includes 600 Ft Of Stone Walls & 2 Private Gates.the Covered Stone Patio Opens To The Falls. The Main House Is An Historic Treasure With 2 Stone Fireplaces, Beautiful Brick & Pegged Floors. Main House & Guest Houses Offer 5 Bedrooms & 6 Baths. The Former Roxbury Post Office Saved By Stutz, Is An Incredible Guest House & A Restored Log Cabin Is Another Guest House. Gorgeous Pond. Surrounded By Land Trust.

Listing Courtesy of William Pitt Sotheby's

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

85 Painter Ridge Rd, Roxbury, CT 06783

InternalID L10157947

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Acres 46
  • SqFt 13209

Set on over 45 pastoral acres with dramatic westerly views, this larger-than-life barn with 20 ft ceilings offers a serene and inspirational setting for all creatives: painters, sculptures, writers, photographers, performers, etc. Masterfully renovated from the ground up, the ~13K-square-foot barn has been transformed into a smart, loft-style contemporary living space. Enormous light-filled living room with western facing walls of glass and wood burning fireplace; 3 ensuite bedrooms, professional kitchen with tumbled stone flooring and wood burning pizza oven, large office area, den, upper level ~6K+ sq/ft semi-finished studio space. Renovated with radiant-heated slate flooring throughout main level, 80 new custom historic architectural windows and over 7K square feet of reclaimed redwood, chestnut and cypress. All radiant heat, central air conditioning and lighting runs off Lutron system controlled on your smart phone. Large steel doors open to stone patio with open fields, orchards and views of distant rolling hills. The perfect urban sophisticate escape, ideal for artist residency, film and theater production, photography or recording studio, dance or yoga studio, etc. Land is suitable for animal pastures or other agriculture uses. Minutes to the charming historic town of Washington, just 90 minutes from NYC. Included in sale is second parcel of 6.7 acres with Washington address on South St.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

85 Painter Ridge Road, Roxbury, CT 06783

Price$2,500,000

Est. Mortgage: $/month

CMLS 99156100

  • Residential
  • Bedrooms 3
  • Acreage 39.25
  • Square Feet 5376

45+ Acres, Westerly Views, Repurposed Dairy Barn W 20' Ceilings Offers Beautiful Setting For All Creatives. Masterfully Renovated W Light-filled Living Room + Western Walls Of Glass + Fp; 3 Ensuite Brs, Prof Kitchen W Tumbled Stone Floor + Wood Burning Pizza Oven, Office, Den, Upper Level ~6k+ Sq/ft Studio Space. Radiant-heated Slate Flooring Throughout Main Level, 80 New Custom Windows, 7k+ Sq/ft Reclaimed Woods. All Climate And Lighting Runs Off Lutron System Controlled Via Smart Phone. Large Steel Doors Open To Patio W Open Fields, Orchards & Views Of Rolling Hills. Perfect Urban Escape, Ideal For Artist Residency, Film And Theater Production/photography/recording Studio/dance/yoga, Etc. 2nd ~6 Acre Parcel Incl W Washington Address

Listing Courtesy of William Pitt Sotheby's

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

32 Highmeadow Ln, Roxbury, CT 06783

Price$2,499,000

Est. Mortgage: $/month

InternalID F10151164

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Acres 42
  • SqFt 4728

One of a kind equestrian property on 42 gorgeous mountain top acres tucked into the Litchfield Hills. The property offers a serene setting, beautiful views, privacy and convenient access to area restaurants, amenities and I-84. Classic 3BR 2 ½ Bath Farmhouse Colonial with one-bedroom apartment or Au-Pair suite blends perfectly into the landscape, encompassing the sweeping lawns, open meadow, 4 grass paddocks, Four stall Barn, and 220'x140' professional riding ring. Enjoy the morning sun and gorgeous views from your front porch or the shade from mid-day sun on rear patio overlooking paddocks & barn. Approvals in place for perfectly designed 145'x36' 20 stall barn with 200'x100' indoor riding ring and additional 4BR home. This is a property that must be seen to be appreciated.

Listing Courtesy of ReMax Experience, LLC

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

32 Highmeadow Lane, Roxbury, CT 06783

Price$2,499,000

Est. Mortgage: $/month

CMLS 99152851

  • Residential
  • Bedrooms 4
  • Acreage 42
  • Square Feet 4728

One Of A Kind Equestrian Property On 42 Gorgeous Mountain Top Acres Tucked Into The Litchfield Hills. The Property Offers A Serene Setting, Beautiful Views, Privacy & Convenient Access To Area Restaurants, Amenities And I-84. Classic 3br 2 ½ Bath Farmhouse Colonial W/ 1br Apartment Blends Perfectly Into The Landscape, Encompassing The Sweeping Lawns, Open Meadow, 4 Grass Paddocks, Four Stall Barn, And 220'x140' Professional Riding Ring. Enjoy The Morning Sun And Gorgeous Views From Your Front Porch Or The Shade From Mid-day Sun On Rear Patio Overlooking Paddocks & Barn. Approvals In Place For Perfectly Designed 145'x36' 20 Stall Barn W/ 200'x100' Indoor Riding Ring & Additional 4br Home. This Property That Must Be Seen To Be

Listing Courtesy of ReMax Experience, LLC

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* 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 A VisitAsk A QuestionMore Details

  © 2017 Greater Fairfield County CMLS, Inc. All rights reserved.

The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of the Greater Fairfield County CMLS, Inc. Real estate listings held by brokerage firms other than The Matthews Group are marked with either the “IDX Detail Logo” or the "IDX Thumbnail Logo” (a little black house surrounding the letters “IDX”) and detailed information about them includes the name of the listing broker.