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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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400 5 1/2 Mile Cornwall CT 06756

Cornwall, CT400 5 1/2 Mile Road

Price$17,500,000

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 a 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 off 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. Land located in both Cornwall and Goshen. Exquisite. One of a kind.

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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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

$
$
%
$/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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141 5 1/2 Mile Cornwall CT 06753

Cornwall, CT141 5 1/2 Mile Road

Price$13,500,000

Est. Mortgage: $/month

MLS Number 170164187

  • Single Family
  • Property Style Mediterranean
  • Bedrooms 5
  • Bathroom 8
  • Acreage 1086

This Andrea 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 property which exudes 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. 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: 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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201-A Millerton Sharon CT 06069

Sharon, CT201-A Millerton Road

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: 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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46 Senff Washington CT 06793

Washington, CT46 Senff Road

Price$9,950,000

Est. Mortgage: $/month

MLS Number L10157391

  • Single Family
  • Property Style Other
  • Bedrooms 5
  • Bathroom 11
  • Acreage 70.07

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: 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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201 Millerton Sharon CT 06069

Sharon, CT201 Millerton Road

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: 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

46 June Washington CT 06777

MLS Number 170228944

  • Single Family
  • Property Style Contemporary
  • Bedrooms 5
  • Bathroom 6
  • Acreage 31.36

The Pinnacle - Brilliantly designed home on 30+ acres affording complete privacy and jaw dropping views overlooking Lake Waramaug. This environmentally conscious masterpiece features a durable hand-cut sandstone exterior, sustainably sourced mahogany woodwork displayed throughout, and a state-of-the-art geothermal heating & cooling system. From every room care was taken to seamlessly blend indoor space with the outdoors. Property includes 100' of frontage on CT's premier lake complete with parking, picnic area, pebble beachfront and boat dock. The home's first floor features a great room with a vaulted ceiling anchored by an impressive stone fireplace with marvelous views afforded by a wall of windows. The chef's kitchen includes a butler & service pantries, eating nook, as well as large lounge area with fireplace making it a tremendous space to entertain. In addition, a formal dining room and library round out this floor. A custom floating staircase leads one upstairs which includes the master bedroom suite complete with fireplace and spacious bath with soaking tub and rain shower. Included on this level are a guest suite with private bath and sitting room, two additional bedrooms both en suite, and a home office. The lower level has limestone floors with radiant heat, a home theater, a dedicated Full Swing golf simulator room, spacious lounge with fireplace, billiard room with wet bar, gym, and a wine cellar with 1,000+ bottle capacity.

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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333 Montevideo Avon CT 06001

Avon, CT333 Montevideo Road

Price$5,900,000

Est. Mortgage: $/month

MLS Number 170231312

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Acreage 116
  • Square Feet 7,964

Most Unique Property for Nature lovers! Abington Estates sits on 116 acres with 4 homes, 3 barns, a 12 acres swimming pond, boathouse, dock, raft. All homes are very well maintained and occupied. The main house (#333) is understated elegance built in 1991 in a contemporary brick and steel Adirondack style. It has 7964 sq ft with 10 rooms, 4BR/3full/2halfbaths/ 500 sq ft art studio, 5 fireplaces, partly finished basement with sauna, 3 car garage. Sitting on a grassy knoll it enjoys glorious sunset views to the west and serene water views to the east. The 3 cottages, #221, #295 and #379 are all located on the ridge and are rented and support 70% of the property tax. #221, The Parsonage is located directly across from the 3 Victorian Barns has 1350 sq ft with 2 br/1.1ba. Stone House, #295 built in 1900 in art deco style is 2888 sq ft with 2-3 /2 ba, updated stainless kitchen, 4 fireplaces. The North Cottage is 1002 sq ft with 2br/2 baths. All appliances convey with the property. Most of the acreage has been classified forest land for over 10 years. Land abuts Heublein Tower park and MDC property. Wild life abounds! Tenants have been long term having lived there for 3 to over 25 years. See attachments for floor plans. Ask agent for floor plans and about development opportunities.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/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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48 Porter Salisbury CT 06039

MLS Number 170246265

  • Single Family
  • Property Style Other
  • Bedrooms 7
  • Bathroom 9
  • Acreage 20.92

48 Porter Street, known as Porter House, is situated in one of Lakeville, CT premier locations. The spectacular compound is perched high on a hill offering idyllic countryside vistas with rolling lawns and southwesterly views of Lakeville's pristine lake. Experience complete privacy on this beautifully manicured property while enjoying easy proximity to Lakeville's vibrant village filled with shopping, dining, sailing, and all the surrounding year-round amenities Litchfield County has to offer. Inside, soaring ceiling in the majestic entry foyer opens to beautiful custom wood paneled walls throughout the expansive yet intimate home. All of the first floor great rooms are filled with natural light and feature views out to the surrounding landscaped terraces, covered porches and secret gardens. The second floor features seven bedroom suites and a media room. With a flowing floor plan, offering superior design and meticulously maintained grounds, this property has consistently been a coveted successful summer rental.

Listing Courtesy of Houlihan/Lawrence

$
$
%
$/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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102 Melius Warren CT 06754

Warren, CT102 Melius Road

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

$
$
%
$/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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7 Arrow Point Warren CT 06777

Warren, CT7 Arrow Point Road

Price$4,995,000

Est. Mortgage: $/month

MLS Number 170172029

  • Single Family
  • Property Style Colonial, Other
  • Bedrooms 4
  • Bathroom 6
  • Acreage 1.35

Rare Direct Waterfront - This Classic New England Shingle Style home is set on Connecticut's 2nd largest lake with its own private beach and dock. The house is perfectly sited and is designed to connect one with the outdoors with expansive windows and french doors that offer perfect views year-round. The large level lawn and spectacular gardens are there for sport or restoration. There is also an outdoor shower to rinse off after a swim in the lake. Enter the house through the main foyer and you'll be struck by the views to the lake and the quality of this home. The main level features a modern living plan with an open kitchen, living and dining area. The living area is anchored by an impressive fieldstone fireplace and opens to a lovely screened porch with its own fireplace. The kitchen is fully outfitted with double islands, farmhouse and prep sinks, breakfast bar, honed stone countertops, Subzero refrigerator, Wolf range and a butler's pantry with wine cooler. The dining area sits directly in front of a large window and has two built in hutches and access to the terrace. Rounding out the first floor is a handsome wood paneled den with fireplace and a first-floor bedroom suite complete with a full bath and private outdoor access.

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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847 & 849 North Goshen CT 06756

Goshen, CT847 & 849 North Street

Price$4,500,000

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

$
$
%
$/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.

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.