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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 more!

Contact us for more information and to schedule a showing for any real estate below. Save your favorite listings when you create an account with us, and you can get email updates when similar properties are posted.

390 Town St, Cornwall, CT 06796

Price$2,485,000

Est. Mortgage: $/month

InternalID L10216225

  • Residential
  • Bedrooms 4
  • Bathroom 8
  • Acres 13.57
  • SqFt 6800

A HOME YOU DREAM ABOUT - Complete privacy, unparalleled views & superior architecture. A spacious and versatile open-concept floor plan creates an indulgent home that seamlessly transitions between indoor and outdoor spaces; accentuating its premier location. Four en suite Bedrooms, including a generous Master Bedroom Suite, Indoor Pool, Music Room, Exercise Studio with Sauna, Screened Porch, 8-Bay Garage and quality craftsmanship complete the luxurious intermingling of spaces throughout this home. An expansive multi-tier deck abuts the tranquility of a stone water feature, all overlooking Western views of the Catskill Mountains. The home is a scenic drive from the shopping and entertainment in Kent, Litchfield, and the Southern Berkshires. Cornwall itself is home to great local skiing at Mohawk Ski Area, hiking, biking and gorgeous views at Mohawk State Forest, scenic Cream Hill Lake, incredible Housatonic River fly fishing, quaint boutique shopping at J. McLaughlin, The Wishhouse, etc… & the famous Cornwall Covered Bridge.

Listing Courtesy of Elyse Harney Real Estate

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.16% last updated on Feb 23, 2017
* 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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37 Oak Ridge Dr, Newtown, CT 06470

Price$1,289,000

Est. Mortgage: $/month

InternalID F10212850

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Acres 2.47
  • SqFt 5810

Understated classicism - be prepared to be surprised as this home unfolds before you. Designed with supreme thoughtfulness and crafted by a master, the quality and detail is outstanding. Nothing but the best selections, materials and workmanship have been utilized. This home was conscientiously built with low VOC materials before it became the vogue, i.e. solid wood doors and floors. 4 en suite family bedrooms, a 5th bedroom with nearby full bath for guests or au pair. The windows and transoms alone are amazing. A family TV gathering room plus a cathedral bonus room with wall of bench storage plus a sunny breakfast room. Add to that an exercise room, a Home Theater with 12 recliners and a Hockey Rink in the lower level! Gorgeously landscaped grounds with extensive stonework, a private usable yard, stone walls, oversized patio, firepit, and inground pool. The 'barn' has 2 more garages and a walk-up loft plus a heated area. Privately located in a neighborhood near the Easton line. Simply stunning.

Listing Courtesy of Flagpole Realty Inc

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: 4.16% last updated on Feb 23, 2017
* 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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, Norfolk, CT 06058

Price$1,675,000

Est. Mortgage: $/month

InternalID L10214656

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Acres 2.41
  • SqFt 2866

Roof Tree - on the shores of Doolittle Lake. Originally an Alfredo Taylor day camp dating from the 1930's, the house has been expanded, renovated and fully winterized for year round use. The original structure is now an enchanting 20' x 30' living/dining room with a handsome hand-built stone fireplace, leaded glass windows, cathedral ceiling and wide board floor. Glass doors bring in the lake view and lead to the stone terrace. The expansive entry hall (once the south-facing stone terrace) features its own whimsical stone fireplace. A more modern family/living room (22' x 18") has lots of windows, 9' ceilings, wood floor, wood stove, dining area and connects to the kitchen as well as the lakeside terrace and the south-side sun-catch terrace. There are 3 large bedrooms each with full bath. 2, 866 square feet of living space on 2.4 lakeside acres.

Listing Courtesy of Betsy Little Real Estate LLC

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: 4.16% last updated on Feb 23, 2017
* 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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108 Anderson Rd, Kent, CT 06757

Price$1,695,000

Est. Mortgage: $/month

InternalID L10214978

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Acres 23.92
  • SqFt 4082

One of the most desirable properties in Kent! Located close to Lake Waramaug this 11 room home with attached enclosed 30' heated pool is perfectly sited on 23 private acres taking full advantage of the views of meadows, pond, and mountains. The property is enhanced by perennial plantings, evergreens, berry bushes, and flowering shrubs and trees. Generous windows fill the spacious rooms with light and enhance the beauty of the wood floors. The great room features a wood burning fireplace with built-in cabinets and bookshelves on each side and is open to the dining area. A deck overs the pond and the great room opens to a screened-in porch. The master bedroom with a full bathroom and walk-in closet is conveniently located on the first floor. Originally built for author, cartoonist, sculptor and illustrator William Steig this 4 bedroom home also includes an office, delightful sitting room, and spacious family room that opens to the patio. With acres of meadows and the pond this sensational property is perfectly suited for horses. Whether walking the meadows, sitting or fishing at the pond stocked with sunfish and small mouth bass, or playing lawn games you'll relax at this exceptional property. The open floor plan, screened porch, deck, and enclosed heated pool are perfect for entertaining or simply enjoying the tranquil views and privacy.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 4.16% last updated on Feb 23, 2017
* 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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28 Jefferson Hill Rd S, Litchfield, CT 06759

InternalID L10208373

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Acres 77.54
  • SqFt 4903

Bucolic and serene setting surrounds this architecturally designed 5000 sq.ft. country home. 77+ acre estate includes fruit trees, fenced pastures, stone walls, and woods. The property has barns, studio/office, shade garden with native stone, and garaging for 8 vehicles. This is a rare opportunity for quiet country living with close proximity to Litchfield Center. Travel from NYC is 90min. Possible subdivision. Agent/Owner

Listing Courtesy of The Matthews Group

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: 4.16% last updated on Feb 23, 2017
* 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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299 Ashpohtag Rd, Norfolk, CT 06058

Price$2,950,000

Est. Mortgage: $/month

InternalID L10214835

  • Residential
  • Bedrooms 6
  • Bathroom 6
  • Acres 12.9
  • SqFt 9758

Roughland Estate. Located on 12 bucolic acres in southern Berkshires with stone walls, fields and pond, owners purchased original c. 1800s farmhouse as respite from urban living in NYC and LA and demands of career in entertainment business. Couple carefully renovated existing barn creating modern, architectural masterpiece to accommodate large family and entertaining lifestyle. Every aspect of exterior design considered - especially the stone silo connecting original barn structure to new construction, mirroring tower atop Norfolk's iconic Haystack Mt. Interiors by POESIS Design boast custom engineered spiraling iron staircase, original cut stone, walnut floors, soaring windows, exposed steel beams, porches. Main floor public spaces include sleek Boffi chef's kitchen, a combination living and dining area with stone fireplace and built-in modern shelving, media room, and music/dance studio with wet bar. Private upper floors offer a master suite with dressing room, living space with stone fireplace, full bath and balcony - as well as four additional bedrooms. Chic office space perched in tower with 360 degree views. Lower level includes one bdrm studio apartment, game room. Light filled interior pool and spa wing with steam shower, sauna and full bath. Outdoor seating and screened gazebo. Guest house is original farmhouse. Truly unique aesthetic marrying timeless, rustic original barn with modern, industrial design. Nearby Toby Pond, Yale Music School, Infinity Music Hall.

Listing Courtesy of The Matthews Group

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: 4.16% last updated on Feb 23, 2017
* 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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185 Goodhouse Road, Litchfield, CT 06759

InternalID L10214793

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Acres 5
  • SqFt 5537

WATERFRONT SPLENDOR in Litchfield offering more than 5, 000 square feet of incredible design and detail reminiscent of a French country manor. This spectacular home sits on 5 acres with frontage on Hidden Pond and has gorgeous water views from most rooms. Bold interior architectural design, detailed moldings, wainscoting, and coffered and tray ceilings are just a few of the special features. A well-planned kitchen with high end appliances from Miele, Wolf and U-line make entertaining a pleasure. Large stone patio with fire pit. Extensive exterior lighting on front of dwelling and terraces. Several sound systems throughout interior and exterior of home. First floor MBR. Second (rear) staircase from laundry area and garage. Detached 4-car garage/barn with upper level is perfect for hobbyist and for storing equipment. Professionally landscaped grounds by Litchfield Horticultural Center. Hidden Pond is a 9-acre private pond accessible only by owners in Litchfield Family Estates. Detailed specification sheet is available upon request. Please view all photos in this listing to gain a true appreciation for this incredible Litchfield waterfront home. Adjacent 2-acre building lot also available for purchase.

Listing Courtesy of Murphy E J Realty

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: 4.16% last updated on Feb 23, 2017
* 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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31 Stuart Rd, Bridgewater, CT 06752

InternalID L10214641

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Acres 4.9
  • SqFt 4511

Impressive 5 bedroom home set back from road on almost 5 lightly wooded acres amidst stonewalls and wildflower gardens with spectacular pool and patio area. Inviting wrap around porch and attractive turret greet you. Traditional grandeur awaits inside with formal areas, spacious family room, stone Romford fireplaces, teak wood floors throughout and a true cook's kitchen with all the amenities, including granite, handcrafted tile work, gas range and custom cabinets. Master suite features fireplace and luxurious marble and onyx bath. Stunning pool retreat with spa, hot tub, impressive stone waterfall, stone patio, 2 firepit areas &pool house. Seasonal western views, true oasis from everyday life.Custom built w/high-end materials throughout.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 4.16% last updated on Feb 23, 2017
* 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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89 West Hyerdale Dr, Goshen, CT 06756

Price$2,995,000

Est. Mortgage: $/month

Pending

InternalID L10213942

  • Residential
  • Bedrooms 6
  • Bathroom 5
  • Acres 1.73
  • SqFt 6700

Waterfront Classic Lakehouse Adirondack style with exposed beams, soaring ceilings, chestnut floors, chef's kitchen, master suite with fireplace on main level. Singularly unique 1.75 acre private, South-facing peninsula overlooking Woodridge Lake with 450+ feet waterfront on lake and river. Custom designed and built with utmost quality. Lower level family / game room with wet bar, stone fireplace, walk-out to stone patio with fireplace. Guest suite with private bath and sauna, custom built "Bunk room" over garage with built-in beds! Screened porch and open mahogany deck overlooking lake. Ultimate home for entertaining and relaxing on Connecticut's cleanest private lake.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 4.16% last updated on Feb 23, 2017
* 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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, Goshen, CT 06756

Price$1,795,000

Est. Mortgage: $/month

InternalID L10213720

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Acres 139.69
  • SqFt 4561

Spectacular post and beam construction on 140 Goshen acres. 3 Bedrooms and 3.5 bathrooms in main house with open floor plan. Sun room, screen porch with wood burning fireplace and stone terraces to enjoy the view over some of the properties meadows. Kitchen and baths all finished to perfection. Guest house / barn with heated garaging for 10 cars. Many trails throughout the property and a number of large open hay pastures. Very convenient to Mohawk Mtn skiing, Lime Rock Park for racing, Norfolk for music and Litchfield Green for shopping and dining. Fabulous gardens and grounds with large estates and state lands around.

Listing Courtesy of The Matthews Group

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: 4.16% last updated on Feb 23, 2017
* 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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36 Red Horse Hl, Sharon, CT 06069

Price$2,300,000

Est. Mortgage: $/month

InternalID L10204893

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Acres 7.25
  • SqFt 5000

RENOVATED TO PERFECTION! Stylish and sleek 5000+/- square foot Smart Home on private and quiet 7+ acres! Light filled with high ceilings and pastoral views, this 5 bedroom, 3.5 bath home features a gorgeous new gourmet kitchen with eating area and family room leading to the deck and screened porch. Both the spacious living room and library have wood burning fireplaces. There is a luxurious master suite on the first floor with french doors to it's own patio. There is also an upstairs master suite plus 3 more bedrooms or possible studio space. Top quality finishes throughout. All new systems, new windows, new doors, new siding, new roof, radiant heat, A/C - no stone left unturned. An attached 2 car garage completes this beautiful and welcoming home.

Listing Courtesy of Best & Cavallaro

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: 4.16% last updated on Feb 23, 2017
* 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 North St, Litchfield, CT 06759

Price$1,195,000

Est. Mortgage: $/month

Under Agreement

InternalID L10213201

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Acres 2.02
  • SqFt 6189

This historically significant residence is a beautiful example of the Greek Revival style. Records kept by Litchfield Historical Society indicate it was built in 1829-30. It is known as the Charles S. Webb House. The home has been expanded and modernized while preserving the fine original architectural details. The design of the fanlight in the cornice is echoed to dramatic effect in the enlarged fanlights that adorn the tops of windows and French Doors throughout the main residence and the charming guesthouse. Beyond the welcoming foyer are the living room with fireplace, dining room with fireplace, and the extraordinary great room/kitchen. The Great room has a fireplace and 2 sets of French doors opening to the bluestone terrace overlooking the pool, guesthouse and manicured grounds. The kitchen features high-end appliances, prep and clean-up areas, 2 sinks, 2 wine coolers, custom cabinetry and pantry. The eat-in area has a vaulted ceiling and huge windows. On the second level are 3 en suite bedrooms and an exquisite paneled library/den. The master bedroom has a luxurious bath with heated floors, marble counters, soaking tub & separate shower. The laundry room is located on this level. Beyond the pool is the 900 SF guesthouse which reflects the style of the main residence. The 2-story living room has French Doors on three sides, 3 large fanlights, a kitchen, loft bedroom and full bath. The two landscaped acres have been meticulously maintained.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 4.16% last updated on Feb 23, 2017
* 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