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Homes for Sale in Litchfield County CT

Here you'll find the latest residential 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, Roxbury & beyond. 

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102 Melius Warren CT 06754

Price$4,995,000

Est. Mortgage: $/month

MLS Number 170086449

  • Single Family
  • Property Style Antique
  • Bedrooms 7
  • Bathroom 7
  • Acreage 68.4

Historically rich 1799 residence on 89 acs. Cleve Gray, a prominent artist moved here in 1949. Francine du Plessix, the renowned author, joined him when they married in 1957. Their respective studios are on either side of the driveway. The current owner began a total restoration/preservation in 2015: gorgeous kitchen, baths, and new systems (heat, A/C, electric, plumbing). Tennis court. The main house has a living room w/beamed ceiling & fpl, dining room w/fpl, family room w/fpl, and library. The kitchen features high-end appliances/finishes & breakfast nook. Main floor guest suite with fpl & bath. Screened-in porch overlooks the heated swimming pool. 5 BRs, 3 full baths including the master w/fpl, sitting area, dressing room and bath and a den are on the upper level. Wide board floors. One wing houses the original farm office with vaulted ceilings & fpl repurposed as a bar on the main level. Above is a guest apt. with a separate entrance with a living room, kitchen, BR, bath & laundry. The acreage includes gardens, pond, fruit trees. The old barn with silo, Cleve Grey's studio. includes a huge open space with high ceilings and an apt. Across the drive was Mrs. Grey's writing studio. Above the garage is a caretaker's apt with 3 BRs, living room, kitchen and bath. A newly renovated 3-BR guest house lies beyond the main house. The property is 3 parcels: 49+ acs surround the house and outbuildings and 1 parcels across the road of 20.4 acres.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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115 Shearer Washington CT 06793

Price$4,950,000

Est. Mortgage: $/month

MLS Number 170207491

  • Single Family
  • Property Style Barn
  • Bedrooms 2
  • Bathroom 3
  • Acreage 67.19

Modern Barn Living with captivating interior spaces infused with a serene sense history and timelessness. Situated privately on 67+ acres along one of Litchfield County's premier roads, the land is a lovely mix of open pasture, orchard, and mature forestland. The home enjoys breathtaking sunset views and is surrounded by outdoor lounging spaces comprised of bluestone patios, outdoor fireplace, and a heated gunite saltwater pool. The home is anchored by a great room providing expansive living and dining areas and showcases the impressive post-and-beam structure. From here, one is led to a spacious eat-in kitchen featuring custom white oak cabinetry, two inch honed stone countertops, and Subzero and Wolfe appliances as well as a sunken living room with fireplace and heated granite floors. The master bedroom suite, with wide plank floors and exposed beams, is located on the upper level. In addition, a custom temperature controlled wine cellar in the lower level and a loft area overlooking the great room. A detached barn as well as two additional approved building lots allows for future expansion and development possibilities.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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847 & 849 North Goshen CT 06756

Price$4,750,000

Est. Mortgage: $/month

MLS Number L10204033

  • Single Family
  • Property Style Other
  • Bedrooms 5
  • Bathroom 7
  • Acreage 69

Upscale country lodge on almost 70 acres with the ultimate in luxury and all the bells and whistles. Reclaimed antique flooring, massive timbers, incredible stonework, patios, pool, pond with fountain, two bedroom guest house, gentleman's barn, perfect for entertaining, very private.

Listing Courtesy of William Pitt Sotheby's Int. Re

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$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

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: 3.81% last updated on Jul 18, 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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85 Sugar Hill Salisbury CT 06068

Price$4,375,000

Est. Mortgage: $/month

MLS Number L10222566

  • Single Family
  • Property Style Other
  • Bedrooms 6
  • Bathroom 7
  • Acreage 110.84

SUGAR HILL FARM - The lofty elevation of this Loire Valley-inspired Litchfield County estate provides for breathtaking views of the Housatonic River valley and the surrounding countryside. Just up from a majestic waterfall and at the end of a country lane, the Farm's half-mile driveway meanders past open fields, stone walls, a two-acre crystal clear swimming pond and organic orchard as it approaches the courtyard of the French country estate sited on a hundred and eleven acres set in total privacy amidst extensive conservation land. A stunning array of both formal and casual spaces make this substantial home ideal both for family living and entertaining. Dramatic ceiling heights, 5 antique wood burning fireplaces and 14 sets of French doors blend the charm of the Litchfield Hills with the majesty of Sugar Hill Farm. This 6 Bedroom and 4 full and 3 Half Bath home are situated in the West & East wings of the home giving peace & solace to all. Only minutes from the villages of Salisbury, Sharon, Falls Village, Millerton, Wassaic & Great Barrington, MA, yet one has a true sense of oneness with nature high atop Sugar Hill. A Caretaker's House is a full half mile from the main residence while a large barn, workshop, and pond boathouse with dock punctuate this pristine, very special property.

Listing Courtesy of Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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 Platts Hill Newtown CT 06470

Price$3,995,000

Est. Mortgage: $/month

MLS Number 170042641

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 33.11

A once in a generation opportunity to own a very rare & special parcel. This Newtown estate holds a unique place in Connecticut lore. It has an active, licensed 2,400' private airstrip/heliport - hence the property's name, “Flying Ridge”. It is the only remaining private airstrip in Fairfield County, grandfathered since it's original registration in the 1940's, by its original owner, the family of the late Robert Edison Fulton, Jr., an inventor, adventurer, and pilot. The current owner, also an avid aviator, has recently performed renovations and updates creating options for farming, horses, and a unique family compound. This property is truly one of a kind. Tucked away amidst rolling hills on 33 acres, it sits atop a ridge with unspoiled farmland to its east and wetlands to its west. The estate comprises a main house with a 40'x30' cathedral ceiling great room, an airstrip house and observation tower, workshop dwellings and barns. The N-S (35/17) half mile grass runway is suitable for fixed-wing single engine aircraft, as well as helicopters. The property is located 48 nautical miles northeast of Manhattan's lower east side heliport, approximately a 20 minute drive to Waterbury-Oxford airport and 40 minute drive to Westchester County airport, and an hour to Greenwich, Litchfield, and Yale University. Flying Ridge combines these unique commuting advantages with the elegance of country life in an unspoiled, charming rural CT community that has excellent services and schools.

Listing Courtesy of Halstead Real Estate

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$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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12 East Goshen CT 06756

Price$3,995,000

Est. Mortgage: $/month

MLS Number 170168838

  • Single Family
  • Property Style Georgian Colonial
  • Bedrooms 6
  • Bathroom 4
  • Acreage 74.32

BIRDSEY HALL 1802 Classic Brick Federal Georgian on a 74-acre estate offering stunning period detail throughout the main house with over 6000sq.ft. 6 bedrooms, 8 fireplaces, grand private and public rooms with high ceilings in beautifully restored condition. A guest house with garden overlooks endless views of water company land. A second guest house is a converted barn with 5 bedrooms, 2 kitchens, terrace, deck, and views. There is also a 1773 garrison-style homestead with 4 bedrooms and 4 fireplaces. The estate offers tennis courts, inground pool, stone walls, horse paddocks, formal gardens, sweeping lawns, and views. Perfect private or corporate country retreat, horse property, family compound, reception venue all with endless possibilities.

Listing Courtesy of Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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188 Sabbaday Washington CT 06794
Pending

MLS Number 170110677

  • Single Family
  • Property Style Antique
  • Bedrooms 5
  • Bathroom 3
  • Acreage 165.43

Tatetuck Farm, an iconic equestrian estate, has been in the same family for 60 years. It is historically and architecturally significant. 165+ acres located on the east side of a scenic road it is one of the most beautiful 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. Tatetuck Farm evokes a grace and gentility associated with a time gone by. One is embraced by the beauty and peacefulness here. Note: 2 separate parcels. 188, 190 Sabbaday. Specs are for main house only. Taxes, assessments, and acreage have been combined. Also listed with 161 and 193 Sabbaday Lane for $6,495,000. See MLS#L10236930

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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21 Greystone Salisbury CT 06039

MLS Number 170085200

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 5
  • Acreage 33.54

Winding driveway in a pastoral setting with Stonewalls and mature plantings creates an entrance for a nature lovers paradise-as you approach this Iconic Barn Style Architecture with a Luxurious Modern Mix in this 3-Bedroom, 3 Ensuite Bath home with Guesthouse on 33 +/- acres. Take in the breathtaking vistas as soon as you walk in the front door with dramatic views of Lorenzo Pond. Clean lines, soaring ceilings allowing for tremendous light and blends the outside setting into an extension of the home. The texture of Cyprus wood, whitewashed shiplap, soapstone, and bluestone exude the warmth and natural elements of the house that blends in with nature built with exceptional craftsmanship. The Living Room with the walls of windows is so airy and is anchored with 20'foot stone fireplace and built-in bookcases. An Open & flowing floor plan with a beautiful equipped Chef's kitchen opens to a dramatic sunroom highlighting garden, Pond and dining room. Covered outdoor dining along with a large blue stone terrace allows for wonderful entertain with the backdrop of Lorenzo Pond. The 1st floor Master Bedroom and Master bath wing, with walk out private terrace, exudes serenity. Additional 2 bedrooms ensuite on the second floor with Eastern views along with a glass and metal balcony with built-in bookcases overlooking the living room and views providing privacy and space. This farmhouse welcomes both the quiet relaxation along with the ability and space for gracious entertaining.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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184 Fern Litchfield CT 06759

Price$3,600,000

Est. Mortgage: $/month

MLS Number 170206376

  • Single Family
  • Property Style Colonial, Other
  • Bedrooms 8
  • Bathroom 13
  • Acreage 18.4

One of Litchfield's finest estates presents this lovely sprawling 18.4 private acres guarded w/a stone gated entrance. This grand center hall Colonial proudly perched overlooking stunning views of a park-like setting of stonewalls, heated saltwater Gunite pool, hot tub, expansive Bluestone patios & decks, 2 bedrm guest house, greenhouse & backed by Topsmead state forest & boarders a land trust. Inside, soaring ceilings & 2-story balcony foyer w/cascading staircase lure you in to admire the extensive master craftsmanship, architectural design & breathtaking masonry throughout! Gourmet kitchen w/top of the line apls, inviting LR & formal DR crowned w/FP's, library & FR w/custom built-ins, conveniently located laundry-rm round out the 1st flr. Home hosts 9.4Baths, 8+bedrms one of which is the master suite w/FP, sitting area, sunrm & exquisite spa-like marble bath retreat! 1st flr also offers access to the finished 3rd flr & finished walkout LL w/exercise-rm, wine cellar, 2-½ baths, walk-in steam shower, 2nd kit. & crowned w/a masterful stone wood-burning FP! 6 car heated garage w/room for you to add lifts allowing for 12cars! 7-zones for heating/cooling, whole house generator & MORE! Private setting yet only moments into town. Come & explore the wonders of Litchfield county w/its many wine vineyards, nature parks/fine dining/shopping. Easily access NY, MA, RI & Bradly Intl Airport. Space to add a helipad for convenience in travel. The sale of this home includes an additional lot

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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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168 Taconic Salisbury CT 06068

Price$3,500,000

Est. Mortgage: $/month

MLS Number 170143519

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 6
  • Bathroom 6
  • Acreage 61.09

Rare offering of restored 1880 Shingle Style on 60+ acres, with equestrian facilities in a superb location. Expansive lawns, gardens, woodlands, trails, meadows, orchard, pond, Moore Brook, pool. The residence has been meticulously expanded and improved to retain classic elements while enhancing it with new systems. Wrap-around front porch. Entry hall with stairway, living room with fpl, dining room. The kitchen features a soapstone island, farm sink, fine appliances, tin ceiling and access to the terrace & porch. A dining area separates the kitchen and family room with fpl & doors to screened-in porch and terrace. Stunning western views. Second level: The master suite has a fpl, 2 walk-in closets, porch, bath w/tub & steam shower. 3 more BRs and 2 baths, study and laundry room. Third level: 2 BRs, 1 bath and storage area. A media room and half bath are in the lower level. Extraordinary details: moldings, antique mantels, wide plank flooring, 9' ceilings, fluted board window and door casings, custom light fixtures. Updated systems include Hydro-air heat, central air, water softener, full-house generator, security. Garage with 3 bays and second floor. Stable/Garage with 3 stalls, wash stall, feed, room, tack room, hayloft, half bath and 2 garage bays & second floor. Surrounded by paddocks, dressage ring, a cross-country course, grass jump field. A cabin with woodstove and screened-in sleeping porch is sited in the wooded portion of the property.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

158/154 Shortwoods New Fairfield CT 06812

MLS Number 170213663

  • Single Family
  • Property Style Contemporary
  • Bedrooms 6
  • Bathroom 7
  • Acreage 16.01

Dramatic craftsman style contemporary on 16 acres (with potential to subdivide) set high for unparalleled views of Candlewood Lake and Squantz Pond, plus bordered by Pootatuck State Forest for complete privacy. Ultimate resort lifestyle home including 10,218 sf on 3 levels with 6 BR, 6/1 baths, plus htd gunite pool; golf green complete with sand traps and 3 tee boxes; full size basketball court; tennis court; multiple stone patios; built-in grill; extraordinary landscaping w/irrigation; and breathtaking sunrise and sunsets from nearly every room. Custom built plus continuous expansion/renovation under the direction of award winning architect, Sean O'Kane, with the highest attention to detail inside/out including: 5 gas fireplaces; state of the art kitchen remodel featuring twin SubZeros, Wolf 6 burner gas range/double ovens, custom cabinetry, colossal island with bar seating, and magnificent stone counters; MBR suite with double bths including one with steam shower & radiant htd floor; LR w/planked ceiling and wet bar; DR with curved wall of windows; fully equipped gym with timbered ceiling; FR with built-in entertainment system and vaulted mosaic mural tile ceiling; lower level with radiant htd floors, expansive media and game rooms, climate controlled wine cellar, plus guest suite w/steam shower; 4 car garages; central vac; 45KW generator; 13 in-room iPads; plus 4 wells/7 hot water tanks and filtration. Negotiable option to purchase nearly all furnishings and gym equipment.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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

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.