Roxbury CT Luxury Homes for Sale

Find the latest luxury homes for sale in Roxbury, CT. Search through a variety of residential listings to find your new property. Save your favorite listings when you register with us, and you can receive email notifications when new properties match your criteria. Contact us for more information and to schedule a showing.

18 Ranney Hill, Roxbury, CT 06783

Price$1,099,000

Est. Mortgage: $/month

MLS Number 170091589

  • Single Family
  • Property Style Other
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.49

New construction by Master Craftsman on 5.49 acre lot in beautiful Roxbury. This beautiful home is located close to town center on a quiet country road. This 4 bedroom, 3.5 bath, 3226 square foot shingle style home is built with the finest workmanship as well as the finest materials. The gourmet kitchen is amazing and features a center island and a stone fireplace. Thermador appliances include a 6 burner gas cooktop, a wall oven, built in microwave, a warming drawer, dishwasher and a refrigerator. All appliances have custom cabinetry that match the hand crafted cabinets. The open floor plan features a large open area that can be set up as a living room/dining room combination or a variety of different ways as your life style dictates. There is a lovely sun room off the kitchen. There is a mud room area coming in from the garage and a half bath close by. The upper floor includes a lovely master suite with walk 2 in closets and a luxurious master bath with soaking tub, dual sinks and a tiled shower. There are 3 additional bedrooms, 1 en-suite and 2 share a hall bath. There are beautiful wood floors throughout and the beams used are from trees that were on the property. The house sits up high with season mountain views. It is gently sloping with a level area with plenty of room for that soccer game. In the rear of the house is a blue stone patio with a site for a pool close by. Located within 90 minutes of NYC makes this a great second home or a full time home! Taxes TBD

Listing Courtesy of William Pitt Sotheby's Int'l

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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: 4.57% last updated on Jun 21, 2018
* 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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139 Transylvania, Roxbury, CT 06783

Price$819,000

Est. Mortgage: $/month

MLS Number 170090237

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 2.25

After a meticulous restoration this stunning stone manor home will impress the most discerning buyer! Setback on a bucolic road seamlessly blends original detail with crisp modern finishes. Enjoy a roaring fire in the original "stone" room with vaulted ceilings and gleaming espresso hardwood floors. The eat in kitchen is every chef's dream, featuring leathered granite counters, a carrera marble center island, and professional stainless steel appliances. The dining room can easily sit 20 for the quintessential party. Dine/Entertain al fresco on one of the 3 magnificent outdoor spaces including an impressive bluestone center courtyard. Measuring over 600 sq. ft. (included in total) you can watch the latest films in your media/entertainment/game room. Three impeccable bedrooms, 2+marble spa like baths, architectural lighting throughout. The latest security system, HVAC systems and mechanicals complete this stunner. A private location yet within close proximity to dining, nightlife, shopping and major highways make this an incredible opportunity. Available designer furnished.

Listing Courtesy of William Raveis Real Estate

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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: 4.57% last updated on Jun 21, 2018
* 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

Price$1,590,000

Est. Mortgage: $/month

MLS Number 170084675

  • Single Family
  • Property Style European, Other
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.85

90 minutes from NYC with beautiful sunset lake views. Sophisticated and lavish hideaway that reflects that magical merging of creativity and architecture. Once you see it, you'll want to own it. Fully remodeled in 2016, the 4,000+ sq/ft custom home is a masterwork of design and craftsmanship. Every detail was carefully selected and quality crafted. Highlights include a custom Neff kitchen, Perrin and Rowe fixtures, exquisite Klaff baths, stone and Cherrywood flooring, solid mahogany doors, Marvin windows with wood shudders, stone fireplace-all capped beneath an intricate hand-split cedar shingle roof. Living is easy in this tucked-away home with perfect westerly views that look down on the 50-acre Wright's pond and a beautiful lush valley accented by stone walls. Plenty of natural light and sprawling entertaining spaces flow inside and out-to the viewing patio with hand-cut stone, to the stunning infinity pool and spa, to the cascading waterfall beyond. Additional amenities include: Sonos sound system; steam shower with spa; spacious Master Suite with balcony overlooking the park-like grounds, mountaintop viewing platform, fire-pit, terraced golf putt, and irrigation system. Set far back from the road with tons of privacy on rare waterfront land, this offers resort style living in the highly desirable town of Roxbury Ct, close to restaurants and shopping.

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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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104A Botsford Hill, Roxbury, CT 06783

Price$1,175,000

Est. Mortgage: $/month

MLS Number 170082685

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 2
  • Bathroom 2
  • Acreage 16

Great opportunity to own 16 acres of open land in one of the prime locations in Roxbury . Offering a five room two bedroom Cape house with Living room with fireplace. Three barns, one with a Club room offering a fireplace and kitchen. Open lush fields plus long views. Prime location.

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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

Price$2,100,000

Est. Mortgage: $/month

MLS Number 170084060

  • Single Family
  • Property Style Contemporary
  • Bedrooms 5
  • Bathroom 6
  • Acreage 22.7

Overlooking a majestic, commanding view, positioned on nearly 23 acres of meadow, fenced in paddocks and four stall barn, this 5,000 sq. ft. custom built, brick contemporary proudly enjoys western sunsets in a most desirable Roxbury location with frontage on both Two Rod Highway and Painter Ridge, framed by impressive stone walls and mature landscaping. The handsomely fenced paddocks and four stall horse barn with tack room, 2nd story hay loft and farm equipment storage, supplies this active horse farm with modern amenities for the novice or experienced horse enthusiast. The pool and hot tub / garden room provide a relaxing respite from your ride when not lounging on the private patios, taking in the views. Interior features include two fireplaces, a wet bar in the family room, five bedrooms en suite (includes a separate in law apartment), partially finished basement, updated mechanicals, newer roof, custom cabinetry and an open, airy environment are dominated by soaring ceilings. Lovingly cared for by one owner, this 1988 homestead is poised for a 2018 freshening, suitable for the sensibilities of the most discerning buyers.Note: Acreage includes 17.65 acres at 88 Painter Ridge (taxes $11,336) and contiguous 5.1 acre parcel at 53 Two Rod Highway (with taxes of $1,725) in Washington. Rare opportunity.

Listing Courtesy of Berkshire Hathaway NE Prop.

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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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30 Highmeadow, Roxbury, CT 06783

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170083109

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 20.3

Beautiful Estate,20+ level Acre Property In Lovely Roxbury. Horse Property Or Nature Lovers Paradise ,Open W/ Views, also Some Lightly Wooded Land W/ A Trail For Horses, Hiking, Atv's, Many Barns, Also Party Barn ,Many More Amenities. Renovated 4-stall barn 80 ft. long with a workshop and room for tractor or golf carts or cars. New 5-stall barn 60 ft by 25 ft under construction. A one of a kind property with mountain views. An outdoor wood furnace for saving on oil. New fencing with 5 large turn outs. Beautiful home with very high ceilings and well built construction through out. was renovated down to the studs in 1999. A almost new swim spa. A new whole house generator. This is a must see house.

Listing Courtesy of Hegarty & Co Real Estate

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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 Davenport, Roxbury, CT 06783

Price$1,025,000

Est. Mortgage: $/month

MLS Number 170060161

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 3
  • Bathroom 3
  • Acreage 4.12

Charming renovated 1840's getaway in northern Roxbury. 3 bedrooms in main house, separate 1 bedroom guest house. Pool, brook, waterfall and fabulous gardens. Magical setting located between Roxbury town center and Washington Green just 5 minutes in either direction. Fabulous rear terrace overlooking brook and waterfall. Very special.

Listing Courtesy of William Raveis Real Estate

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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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182 Painter Hill, Roxbury, CT 06783

Price$1,195,000

Est. Mortgage: $/month

MLS Number 170056829

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 7.81

Painter Hill Views. Perched at one of Roxbury's highest elevations, this immaculate home was designed to take full advantage of the sweeping views of the Litchfield Hills. This pristine Painter Hill residence offers western sunsets and is sited in the highly desirable Painter Hill area of Roxbury. Privately situated, this meticulously maintained 3 bedroom home is complete with in-ground pool and just under 8 acres of open pasture and woodlands. The renovated high end kitchen is equipped with center island, Sub Zero refrigerator and Viking Range, along with updated baths throughout. The Open concept floor plan with two-story great room and stone fireplace, allows for easy entertaining with flow from kitchen to Great Room and then out to the terrace which overlooks the pool, mature gardens and fenced pasture. Other amenities are hardwood floors, high ceilings, a wrap around porch, mud room, an over-sized three bay garage and loft style second floor den. There is a third level finished space for game room, office or den. A Litchfield Hills Treasure!

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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$1,249,000

Est. Mortgage: $/month

MLS Number 170051962

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 6.67
  • Square Feet 5,436

Just 90 Minutes from NY! Architecturally Stunning Estate in the desirable Golden Harvest Area of Roxbury. The hilltop setting with 280 degree views of the Shepaug River Valley offer a quiet and private oasis with gorgeous heated gunite pool with bluestone terrace overlooking views of foothills and nearby farmland. This architect-designed stone and clapboard home is set up for easy living with open concept plan and soaring ceilings. The 4 wood burning fireplaces, floor to ceiling windows, french doors to outside entertaining space complete with built-in grill. The screened porch overlooks the pool and stone outcroppings, ledge and Laurel. The lighted driveway meanders into the private setting. The grand foyer opens on to the living room with soaring ceiling, grand fireplace and a cozy dining room with fireplace. The heart of the living space is the great room with stone fireplace which is open to the updated kitchen with custom cabinetry, granite counters, 48 inch gas range with convection and stainless appliances. The master is on the first level and there are 3 additional bedrooms on the upper level. The lower level is finished with space for a game room, media room or gym. All the luxury, with the ease of modern living!

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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$1,550,000

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

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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$1,749,000

Est. Mortgage: $/month

MLS Number 170051574

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

If clean country living, comfort and privacy are what you are looking for, then you will find it here. This turnkey home is located along one of Roxbury's most coveted rural stretches, sitting amidst an 800+ acre greenbelt of land trust property. Come and unwind in a bucolic setting with a luxurious salt water pool and spa, lush landscaping and long mountain views to the southwest. The house features an open space design concept with high ceilings and oversized window banks, filling it with natural light. All four bedrooms are generously sized and en suite. Enjoy walking, hiking, bicycle rides or snowshoeing along abundant country roads and trails. Perfectly positioned to visit the local farm stands, organic groceries, restaurants and boutiques in the area. Ready to move in! Agent Owner.

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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

24 Ranney Hill, Roxbury, CT 06783

Price$3,200,000

Est. Mortgage: $/month

MLS Number 170047594

  • Single Family
  • Property Style Other
  • Bedrooms 5
  • Bathroom 10
  • Acreage 22.86

This Shingle Style residence is sited atop 23 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 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 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 2 separate parcels.

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->Name}

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: 4.57% last updated on Jun 21, 2018
* 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.