Litchfield County CT Luxury Homes

Search the latest luxury homes for sale in Litchfield County, CT. Discover a variety of beautiful luxury real estate listings.

Luxury Homes for Sale in CT

Contact The Matthews Group at 860-868-0511 or online with any questions or to schedule a private tour. Our team has the knowledge and expertise to help you find the right property.

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

View by Town
Bethlehem | Bridgewater | Cornwall | Goshen | Kent | Litchfield | Morris | New Milford | Roxbury | Sharon | Sherman | Warren | Washington | Woodbury

328 Calkinstown Sharon CT 06069

Sharon, CT328 Calkinstown Road

Price$12,650,000

Est. Mortgage: $/month

Pending

MLS Number 170304779

  • Single Family
  • Property Style Other
  • Bedrooms 6
  • Bathroom 9
  • Acreage 34.51

EXTRAORDINARY CUSTOM-BUILT HOME - This beautifully appointed Stone Federal-style home with the best views in the county, featuring extraordinary craftsmanship and architectural details is now for sale in Sharon CT. With 8,400 square feet plus 1500 square feet in the lower level and 13 Rooms, including six wood-burning fireplaces, a chef's kitchen opening to a family room and dining area, elegant living & formal dining rooms and library with reclaimed and restored 300-year-old paneling, this home is incomparable in style and quality. The master bedroom suite consists of a luxurious master bath, master sitting room as well as two walk-in closets. Four en suite bedrooms and a family room complete the second floor. The third floor offers an additional en suite bedroom. The screening room, wine cellar & exercise room are contained in the lower level. A 4-car heated garage and a bluestone patio complete this home. With plenty of room for a pool, guest house, or tennis court and beautifully sited on 35 acres amongst stone walls and professional landscaping, this home is a timeless treasure, built for everyday living.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

36 Herrick Sharon CT 06069

Sharon, CT36 Herrick Road

Price$11,995,000

Est. Mortgage: $/month

MLS Number 170294995

  • Single Family
  • Bedrooms 11
  • Bathroom 13
  • Acreage 51.3
  • Square Feet 14,541

Herrick House & the Granary Art Gallery - The Former Estate of Art Collector Melva Bucksbaum. This Magnificent Estate is an Art Collectors Paradise. The Main house, originally built in the 1920's was completely renovated in 2007-2008 with top-quality craftsmanship throughout. The property consists of 7 buildings to include the main residence, a guest home, a caretaker's house with storage facility with security office above, pool with pool house and library, large utility garage, completely renovated log cabin and a state-of-the-art Museum called the “Granary”, all located on 51.08 acres in scenic Sharon, Connecticut. The Granary, is a 14,000 sq. ft. art gallery that offers 4 gallery viewing rooms, storage vaults, FE25 "clean agent" fire suppression system to protect the artwork, expansive security system, video surveillance, glass art transport elevator, commercial-grade geothermal heating system, water bug system, humidity system to keep art in its natural state with a regulated alarm system. The Granary is temperature controlled, so it could also be converted to be used for a wine collector, vehicle gallery, etc. This beautiful property offers stone entrances with automatic gates, stone walls, country gravel driveways, professionally manicured landscaping, apple orchard and fruit-bearing trees, chef's herb & vegetable garden, courtyard with lighted flagstone walking paths, meadows with rolling fields and untouched land to maintain its natural beauty. Very Special Property!

Listing Courtesy of Neumann Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

400 5 1/2 Mile Cornwall CT 06756

Cornwall, CT400 5 1/2 Mile Road

Price$11,950,000

Est. Mortgage: $/month

MLS Number L150478

  • Single Family
  • Property Style Georgian Colonial
  • Bedrooms 10
  • Bathroom 15
  • Acreage 100

This exquisite Georgian Federal was built by the highly noted Amerian Architect, Allan Greenberg; one of the leading classical architects of the twenty-first century, also known as New Classical Architecture. Behind the elegant gated entrance sits stunning Hillhouse, located on 100 acres, the drive is tree-lined and meanders by meadows, pastures, and all just 10 minutes from Litchfield Center and under 2 hours from NYC. **see additional remarks** There is a regulation custom gymnasium on the lower level with basketball court, tennis court, play court all leading to the outdoor pool and cabana. Overlooking the mature gardens you'll find a luxurious & sunny indoor gunite pool with a hand-painted mural of the property and surrounding hillside; located off the exercise room, complete with steam rooms, dressing rooms, water fountain & elevator. State of the art security system can be found extensively throughout the home, 12-foot custom French doors accessing the gardens throughout the first floor. Wide oak plank floors, custom molding and raised paneling in the trophy room, library, and dining rooms. You'll find top of the line appliances in the kitchen, an elegant foyer with reception room, a beautiful loggia, a custom wide 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 & kennel are located in this area. All stone manor house overlooks the Connecticut foothills.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

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: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

46 Senff Washington CT 06793

Washington, CT46 Senff Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number L10157391

  • Single Family
  • Property Style Other
  • Bedrooms 5
  • Bathroom 11
  • Acreage 56.06

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 56+ 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: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

125 AB TOWNLINE ROAD Bridgewater CT 06783

MLS Number 170301831

  • Single Family
  • Property Style Colonial
  • Bedrooms 10
  • Bathroom 10
  • Acreage 52.9

Greyledge Estate sits at the gateway to the Litchfield Hills, only 80 miles from New York City. It 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. Set back in privacy on 52.9± acres, the historically significant C.1820 center-hall clapboard colonial is comprised of 10 bedrooms (4 with fireplaces), multiple living rooms, reception rooms, breezeways lined with French doors, 2 outdoor terraces, a library, office, 9 fireplaces, a chef's kitchen, tack room, and a dramatic candle-lit dining room that can comfortably accommodate seated dinners for 24 people. The Pool House is comprised of a combined living/dining room with a fireplace, a full kitchen, two changing rooms, two full baths, and two large bedrooms. It is located approximately 100 yards from the Main House, affording both an attractive visual landmark as well as an alternative living venue for privacy or large gatherings of weekend guests. The Estate also includes a 20-acre elevated build site comprised of primarily open pasture with 360-degree views. The land can be subdivided from the main parcel without sacrificing privacy, though it is currently not available for purchase independent of the Main House.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

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: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

1 Glen Brook Farm Sherman CT 06784

MLS Number 170279944

  • Single Family
  • Property Style Contemporary
  • Bedrooms 6
  • Bathroom 7
  • Acreage 75

75 acres of verdant fields and woods with breathtaking views, Sherman CT, Additional acres available upon request @ $8.5M asking. THE RESIDENCE: Perched atop the sprawling grounds is a newly constructed, modern loft farm residence whose exterior and interior architecture marry elegantly a sophisticated home and the surrounding pastorale outdoors. Soaring cathedral ceilings, floor to ceiling picture windows that perfectly frame the sublime country vista outside, and the abundance of natural stone, wood and steel finishes throughout the interior lend this 7,000 sq. ft.mansion its bucolic atmosphere, airiness and warmth. The home consists of six luxurious bedrooms, seven sumptuous full marble baths, a recreation/family room, and a theater room. The open floor plan allows unencumbered flow between the double-height living room, the spacious dining, and a handsome, modern, gourmet kitchen with custom walnut millwork, Miele appliances, exquisite yellow marble peninsula and granite countertop. The 7” wide-floors and trim are made of white oak. Enormous sliding glass walls in the great room and main level bedroom open onto the Grand Terrace on the main level, while the glass walls of two bedrooms &the recreation room on the lower level provide access to a lower level terrace. All overlook the grand lawn with breathtaking open countryside views, and the resplendent stable and quaint modular staff quarters in the periphery. Taxes roughly $20,000 annually

Listing Courtesy of Classiques Modernes Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

333 Montevideo Avon CT 06001

Avon, CT333 Montevideo Road

Price$5,900,000

Est. Mortgage: $/month

MLS Number 170287728

  • Single Family
  • Bedrooms 4
  • Bathroom 6
  • Acreage 116
  • Square Feet 7,964

Most Unique Safe Harbor Property for Nature lovers! Abington Estates is a family compound which sits on 116 acres with 4 homes, 3 barns, a 12 acre swimming and fishing pond, boathouse, dock, and 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/4 full/2 halfbaths/ 500 sq ft creative space 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 4 br/2ba. Stone House, #295 built in 1900 in art deco style is 2888 sq ft with 2-3 br /2 ba, updated stainless kitchen, 4 fireplaces. The North Cottage is 1002 sq ft with 3 br/2 baths. All appliances convey with the properties. 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. See attachments for floor plans. Ask agent for floor plans and about development opportunities. 2 hours to Boston or NY, 10 min to shops and restaurants. A country setting yet close to town for home deliveries, too!

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

85 Davis Kent CT 06785

Kent, CT85 Davis Road, South Kent

Price$5,900,000

Est. Mortgage: $/month

MLS Number 170307657

  • Single Family
  • Property Style Chateau, European
  • Bedrooms 4
  • Bathroom 5
  • Acreage 13.25

Elegant, contemporary, private compound Designed by renowned architect and interior designer, Robert Couturier, "Dover House" is set against the stunning backdrop of North Spectacle Lake in South Kent. A picturesque driveway leads to a magnificent 1710 guesthouse. The Extensive, formal, published gardens designed by Miranda Brooks beautifully offsets the Gunite pool house and the two square pavilion main house with a pyramid-style roof. The formal dining room is featured in The Finest Rooms in America by Thomas Jayne. Each room enjoys remarkable style and detail with either views of the lake or gardens. From the library steps to the water's edge. A unique two-car garage completes this private setting. Dover House is a true escape to beauty and nature. 14+/- acres abutting land trust and views of this pristine lake.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

96 Romford Washington CT 06794

MLS Number 170330745

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 46.97

Private Helipad & Landing Strip on a magical hilltop setting in Washington, CT. This secluded 50 acre estate includes an elegantly renovated Colonial with 4 bedrooms/4 bathrooms, luxurious master suite, gourmet kitchen and windows galore to take in the extraordinary distant views. The long driveway winds through a myriad of colorful flowering trees past deep, pristine ponds with an island. Imagine living here to witness the fall foliage turn throughout the river valley and across the distant hills. Property features a heliport and airstrip with hangar for your private plane, providing quick and easy access from your backyard to NYC, or to the Cape islands and the Hamptons in 45 minutes! Enjoy sunrise to sunset views on your private oasis conveniently located just mins to town center.

Listing Courtesy of Compass Connecticut, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk A QuestionMore Details

Lot 3 and 4 Milton Rd Goshen CT 06756

MLS Number 170325448

  • Single Family
  • Property Style Farm House, Modern
  • Bedrooms 6
  • Bathroom 8
  • Acreage 6

Set between open pastures & wooded privacy, dawns a brand new Litchfield County classic. Beautifully situated on the largest plot of land overlooking the prestigious and private Woodridge Lake, this “to be built” estate from an award winning builder will feature exceptional detail and gorgeous waterfront views from every room! The property is just over 6 ac. with nearly 500 ft of private direct water frontage. This 7,800 sfs mart-home features stunning high-end finishes, multiple fireplaces, interiors with dramatic shiplap paneling, sleek trim work, and built-ins throughout. The home will have 11 rooms, 6BR, 6 full baths, 2 half baths, and a spacious 1st floor master bedroom suite w/ walk in closets, and a spa like bath all with high end finishes. A state-of-the-art kitchen with inset furniture grade cabinetry and built-in kitchen banquette will flow into a grand vaulted family room with walls of glass facing the water. Covered wrap around porches lead to a stunning patio w/ inground gunite pool overlooking the lake. Exterior finishes include James Hardie fiber cement siding, custom PVC exterior trim, gorgeous red cedar porch ceilings, and lead coated copper gutters. Color scheme for windows and siding will be determined with buyer as well as many of the exemplary finishes in the house. LOT CAN ALSO BE PURCHASED SEPARATELY FOR $1,800,000.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 TourAsk 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.