and narrow your search. If you have fewer than 200 results, you can save your search.

Litchfield County CT Luxury Homes

Search the latest luxury homes for sale in Litchfield County, CT. The Matthews Group has the knowledge and expertise to help you find the right property. Discover a variety of listings in towns including Washington, Kent, Woodbury & more!

Contact The Matthews Group at 860-868-0511 or online with any questions or to schedule a private tour.

Time Saving Tip: Create a free account to save your favorite listings and get notified when new properties match your criteria.

400 5 1/2 Mile Cornwall CT 06756

Price$19,500,000

Est. Mortgage: $/month

MLS Number L150478

  • Single Family
  • Property Style Other
  • Bedrooms 10
  • Bathroom 15
  • Acreage 450

Behind the elegant gated entrance sits a stunning manor house, the drive is tree lined and meanders by meadows, pastures and stables on either side of the drive*****see additional remarks****** there is a regulation custom gymnasium on lower level w/basketball court, outdoor pool,tennis court,and play court. Also,exercise room with steam rooms and water fountain, elevator. State of the art security system extensively throughout the home,12 foot custom french doors accessing the gardens throughout the first floor. Herringbone floors, custom molding and raised paneling in the trophy room,library, and dining rooms, beautiful loggia with hand painted mural of the property with indoor pool overlooking mature gardens, walk in freezer, top of the line appliances, large elegant foyer with reception room, custom double staircase leading to upper foyer and bedrooms. The 3 car garage is located of the circular front drive and porte cochere. Additional garaging for 3 cars, an office and kennel are located in this area. All stone manor house overlooks the surrounding connecticut foothills. There is also a barn, paddock and pasture as you approach the home. Exquisite. One of a kind.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

141 5 1/2 Mile Cornwall CT 06753

Price$13,500,000

Est. Mortgage: $/month

MLS Number 170164187

  • Single Family
  • Property Style Mediterranean
  • Bedrooms 5
  • Bathroom 7
  • Acreage 1086

This Andreas Palladio inspired villa enjoys breathtaking views and incredible amenities all tastefully designed and set perfectly in a pastoral setting of flourishing fields and lush forest. This rare offering includes over 1,000 acres of both natural and manicured beauty. The drive to the villa starts with a gated entrance that brings you through stately apple orchards, rolling fields, stands of white birch and fern groves. One feels transformed upon entering this palace of tranquility and harmony. Arriving at the granite cobbled main courtyard ringed by copper beech, you are greeted by the home's distinctive limestone and stucco facade highlighted by traditional and more modern Palladian details including a large tripartite window as well as the five-moon phase transit oculus - the homes's identifying feature. Awaiting inside is a two-story grand foyer with a dual floating circular staircase - a design showpiece in itself.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

46 Senff Washington CT 06793

Price$11,950,000

Est. Mortgage: $/month

MLS Number L10157391

  • Single Family
  • Property Style Other
  • Bedrooms 5
  • Bathroom 11
  • Acreage 66.12

Just 90 minutes from NY and minutes to both Washington Depot and Bantam for great dining and shopping, this magnificent modern home designed by Architects Gray and Organschi offers a private and serene setting and is one of the most significant properties in Litchfield County. The award-winning buildings which dot the 70+ acres takes advantage of the gentle hills and 5-acre spring fed swimmable pond. It is an architectural tour de force-- constructed of granite, limestone and Alaskan cedar. The 15,000+ sf Modern home offers 5 bedrooms, 4 full and 5 half baths with an unprecedented amenities of an indoor pool with his and hers changing rooms, squash court, screening room, wine & exercise rooms with swedish sauna. The materials, craftsmanship and fixtures are extraordinary: arched birch slat ceilings, custom mill work, teak window frames, plaster walls, marble baths, sandstone floors, 12 fireplaces and a lead-coated copper roof. A full lighted tennis court with viewing room and guest quarters grace the landscape. The architectural folly with it's 50-seat amphitheater give the highest panoramic views in the area which are some of the best in Litchfield County! A Gate house/Guest house with three bedrooms, kitchen and Living Room greet you at the entry of the property. Gorgeous meadows of indigenous plants, light woods with walking trails, perennial gardens and stone walls grace the 70.7 acres. All within minutes to Washington Depot.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

201-A Millerton Sharon CT 06069

Price$11,850,000

Est. Mortgage: $/month

MLS Number 170116271

  • Single Family
  • Property Style Georgian Colonial
  • Bedrooms 5
  • Bathroom 6
  • Acreage 375.72

Mole's Hill Farm. Minutes from bucolic Sharon, Ct. this English-style estate is a true retreat from today's fast-paced world. Centered by a Manor House filled with understated elegance and a sweeping flair of British style, the estate captures the imagination. Detailed pediments, carved fireplaces, custom millwork and cabinetry are appointed throughout every light-filled room, all perfect for entertaining. The grounds by famed English garden designer Penelope Hobhouse and British architect Sir Anthony Denny combine Edwardian symmetry and style in a hillside setting to breathtaking results. Centered by an obelisk folly, framed by a double allee of zelkovas trees, it is flanked by two formal gardens. One features a walled English garden designed with perennial beds and espaliered fruit trees and a greenhouse. The other features a hornbeam hedged garden surrounding a lap pool and a double pavilion with cabana and guest studio. A Russian dacha is tucked in the woodlands. A tennis court, large barn and three bedroom guest house complete the offering. Additional acreage is available.

Listing Courtesy of Houlihan/Lawrence

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

44 Briggs Hill Sherman CT 06784

Price$7,999,000

Est. Mortgage: $/month

MLS Number 170110849

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 6
  • Acreage 47.25

S & L Farm is one of the ultimate equestrian properties in the Northeast & certainly among the best in the country. This horse-owners paradise, with unsurpassed views, is owned by an iconic fashion design couple w/over 50 years of experience with horses & building the best of equestrian horse farms across the U.S. The property is being sold with all equipment to run the farm! Every detail has been carefully planned: Beautifully renovated 5 bedroom antique Colonial w/a pool, tennis court & fire pit; 5 car barnwood garage w/Gym & guest quarters above; a 20 stall stable w/wash stalls, grooming stalls, his/hers baths, tack & feed rooms & a lovely lounge/party room on the second level w/views out over the outdoor riding ring. The over-sized outdoor riding ring, surrounded by mature hedges, has state-of-the-art footing, a sprinkler system and un-matched views! There are fenced paddocks ranging in size for all uses- the larger pastures have run-in sheds. The indoor riding ring has custom footing as well. There are an additional 25 stalls surrounding the indoor ring on 3 sides. There is a separate barn building for tractor and equipment storage. A grand prix derby field was created w/every natural jump that a rider will find at the highest level of competition including banks, water jumps, ditches an& a grob. Ride from the farm into the extensive trail system for hours. If a rider has dreams of reaching the Olympics or owning the best, S & L Farm is it! Additional land available.

Listing Courtesy of Douglas Elliman of Connecticut

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

201 Millerton Sharon CT 06069

Price$7,750,000

Est. Mortgage: $/month

MLS Number 170097161

  • Single Family
  • Property Style Georgian Colonial
  • Bedrooms 5
  • Bathroom 6
  • Acreage 95.72

Mole's Hill Farm. Minutes from bucolic Sharon, Ct. this English-style estate is a true retreat from today's fast-paced world. Centered by a Manor House filled with understated elegance and a sweeping flair of British style, the estate captures the imagination. Detailed pediments, carved fireplaces, custom millwork and cabinetry are appointed throughout every light-filled room, all perfect for entertaining. The grounds by famed English garden designer Penelope Hobhouse and British architect Sir Anthony Denny combine Edwardian symmetry and style in a hillside setting to breathtaking results. Centered by an obelisk folly, framed by a double allee of zelkovas trees, it is flanked by two formal gardens. One features a walled English garden designed with perennial beds and espaliered fruit trees and a greenhouse. The other features a hornbeam hedged garden surrounding a lap pool and a double pavilion with cabana and guest studio. A Russian dacha is tucked in the woodlands. A tennis court, large barn and three bedroom guest house complete the offering. Additional land available.

Listing Courtesy of Houlihan/Lawrence

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

34 Burton Road North Canaan CT 06018

Price$6,777,000

Est. Mortgage: $/month

MLS Number 170147826

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 7
  • Acreage 889.8

College Hill Farm - This carefully assembled Nature preserve on 889+ acres with three ten-acre building envelopes offers one of a kind privacy, southwest views, and varied terrain with pond, stream, orchard, open fields and elevated views. The 4 Bedroom home is part of a unique Recreational complex, including regulation softball, squash court, contemporary art studio, connected by an expansive patio with infinity pool, Wisteria covered pergola and Argentine Grill. Natural building materials, including custom-planed & native woodwork as well as custom finishes, join the home's majestic setting with country elegance. Nearby attractions include Norfolk, CT, Infinity Hall & Bistro, swimming at Tobey Pond, Great Mountain Forest, Umpachene Falls, Stockbridge Store, Yale School of Arts & Music, Berkshire Country Store, Ski Butternut, Catamount Ski Area & Aerial Park, Salisbury School, Berkshire School.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Bald Mountain Norfolk CT 06058

Price$6,777,000

Est. Mortgage: $/month

MLS Number 170147909

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 7
  • Acreage 889.8

College Hill Farm - This carefully assembled Nature preserve on 889+ acres with three ten-acre building envelopes offers one of a kind privacy, southwest views, and varied terrain with pond, stream, orchard, open fields and elevated views. The 4 Bedroom home is part of a unique Recreational complex, including regulation softball, squash court, contemporary art studio, connected by an expansive patio with infinity pool, Wisteria covered pergola and Argentine Grill. Natural building materials, including custom-planed & native woodwork as well as custom finishes, join the home's majestic setting with country elegance. Nearby attractions include Norfolk, CT, Infinity Hall & Bistro, swimming at Tobey Pond, Great Mountain Forest, Umpachene Falls, Stockbridge Store, Yale School of Arts & Music, Berkshire Country Store, Ski Butternut, Catamount Ski Area & Aerial Park, Salisbury School, Berkshire School.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

188 Sabbaday Washington CT 06794

MLS Number L10236930

  • Single Family
  • Property Style Antique
  • Bedrooms 5
  • Bathroom 3
  • Acreage 219.52

Tatetuck Farm, an iconic equestrian estate, has been in the same family for 60 years. It is historically and architecturally significant. On 219 acres located on both the east and west sides of a scenic road it is one of the most expansive properties ever available in Washington. The main house is considered to be one of the finest Federal-style Colonials in the area with 5 bedrooms, 4 fireplaces, a stone terrace overlooking spectacular grounds: stone and rail fencing, gardens, pool, pond, pastures, and woodlands. The pool, uniquely shaped as a quadrant, has a pool house with fireplace, kitchenette, dressing room and bath. A 2 bedroom guest house has a finished basement and garage. Three horse barns (combined total of 18 stalls) are surrounded by verdant pastures and riding ring. 131 acres is in an agricultural conservation easement to Steep Rock Land Trust. On the west side of the road are two houses and a large 15 stall barn. Both properties have 2 bedrooms and can be used as rental, caretaker or guest houses. Much of this land abuts the Hidden Valley portion of Steep Rock. Tatetuck Farm evokes a grace and gentility associated with a time gone by. One is embraced by the beauty and peacefulness here. Note: 4 separate parcels. 188, 190, 161 & 193 Sabbaday. Specs are for main house only. Taxes, assessments, and acreage have been combined. Also listed on 165.43 acres for $3,995,000. See MLS#170110677

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Norfolk CT 06058

Price$6,495,000

Est. Mortgage: $/month

MLS Number L152330

  • Single Family
  • Property Style Colonial
  • Bedrooms 9
  • Bathroom 7
  • Acreage 550

Yale farm some of New England's most astounding views, pasture, woods, ponds, brooks, and privacy. Colonial revival house in need of restoration, charming cabin, extensive barn, plus... The land has several subdivided parcels, each with stunning views. There are so many attributes and features they must be seen.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

42 Nettleton Hollow Washington CT 06793

MLS Number 170072482

  • Single Family
  • Bedrooms 5
  • Bathroom 8
  • Acreage 22.55
  • Square Feet 9,800

"Stone Bridge." The Ultimate Country Estate. Impeccable new construction Shingle and Stone home, set on 22+ private bucolic acres in the highly desirable Nettleton Hollow area in Washington, CT. Architect-designed and built by HOBI Award Winning, Corbo Associates, this 8300+ sq ft, with additional finished 1350 ft on the lower level is graced with 5 bedroom suites including first and second floor master suites and state of the art easy care systems, heated gunite pool and pond. The public spaces open on to terrace and patio space to bring the outdoors in. Garaging for 3 car via porte cochere to a second garage. Privately set off the the road with a meandering driveway and overlooking a nearby pond, the elegant and comfortable spaces throughout flow from house to patio and pool. Soaring ceilings and glass bring the outside into every room. Sprawling spaces for easy entertaining with 7 fireplaces, elevator, library, home theater, game room, wine cellar and tasting room, sound dampened walls, generator, central vacuum, home technology system with security system. A top of the line kitchen is the center of the home with an additional butler's kitchen for entertaining. Top rated construction and energy efficiency, using state of the art geothermal heating and cooling system and Cat 6 audio wiring for sound, data and internet. The manicured grounds, mature plantings and stonework were professionally planned and include an irrigation system. Additional land available. Magnificent!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

124 Lake New Fairfield CT 06812

Price$5,900,000

Est. Mortgage: $/month

MLS Number 170152829

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 6
  • Acreage 0.64

"Artreehoose" Premier Candlewood Isle Waterfront Modern. This Ultra chic home was designed by renowned architectural firm, Della Valle Bernheimer using only the finest materials including Monumental sliding glass panels which wrap the 20 ft high living room space and opens to a covered patio, bringing the feeling of the outside, to the interior spaces. Phantom screening for media viewing creates a luxurious outdoor entertaining space, insect-free, to enjoy the views of the lake or open air dining. The magnificent Schiffini kitchen with walnut veneer and stainless steel center island overlooks the gorgeous sweeping views of Candlewood Lake and western sunsets. Walk out to the outdoor entertaining space equipped with outdoor kitchen with built-in grill, pizza oven and storage and enjoy all there is to offer in the lake lifestyle with sandy beach, dock and magnificent stone hot tub. A Grand Living room is the heart of the home with soaring ceiling and two floating staircases which lead to the second story master suite, two additional en suite bedrooms and a state of the art media room with additional half bath and wet bar. Additional features included Flamed bluestone floors with radiant heating throughout, State of the art home automation system allowing control of music, lighting, security and temp from one location. The Candlewood Isle Clubhouse offers tennis courts, marina, basketball, bocce, children's and social. This is Lake living at it's best!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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.