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The Matthews Group

Litchfield County CT Waterfront Homes

Search the latest waterfront 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!

Find Waterfront Homes for Sale in CT

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400 5 1/2 Mile Road Cornwall CT 06753

Cornwall, CT400 5 1/2 Mile Road

Price$16,450,000

Est. Mortgage: $/month

MLS Number 170366275

  • Single Family
  • Square Feet 18,000
  • Bedrooms 10
  • Bathroom 15
  • Year Built 1992

This extraordinary estate with a beautiful Georgian Federal-style home was designed by the American architect Allan Greenberg for world-renowned tennis legend Ivan Lendl. Ride through the gates passing horse paddocks, a barn, and up a long and meandering driveway to the impeccable stone house. Enter the first floor passing a grand staircase to a light-bathed main floor with virtually every room boasting French doors to beautiful gardens and patios. A wood-paneled library, spacious living room, formal dining room, and family room, all with fireplaces and wide plank oak floors, as well as a trophy room/office and an eat-in chef's kitchen with state-of-the-art appliances and butler's pantry complete the 1st level. The primary bedroom suite with 2 oversized walk-through closets, a sitting room, and a luxurious oversized bathroom accompanies an office with a paladin window, a children's library, and 3 additional ensuite bedrooms on the 2nd floor. The third floor has 5 en-suite bedrooms. Additional indoor amenities include an indoor pool adjoining two locker rooms, a sauna, a workout room, and a full-sized gymnasium. Outside there is a heated gunite pool with a cabana, tennis court, and play court. The attached 3 bay garage is complemented by a 3 bay detached garage with office space on the second floor. All of this, overlooking the Connecticut foothills.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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57 Mount Tom Road Salisbury CT 06068

MLS Number 170352914

  • Single Family
  • Square Feet 22,282
  • Year Built 2002
  • Property Style Colonial
  • Bathroom 14

Incomparable Country Estate - The country estate of legendary producers Thomas Miller and Robert Boyett is now available for sale in Salisbury Connecticut. Meticulously designed by Acheson Doyle Partners, beautifully landscaped and finished with the finest materials, the 9-bedroom main house is on more than 470 pristine acres and boasts unparalleled western views of the Berkshire Mountain Range. The entrance hall, with a grand staircase, opens to a dramatic 39-foot-long formal dining space with a soaring 32-foot-tall (3 stories) glass atrium ceiling. Several living spaces on the main floor including a light-filled 47-foot great room, a handsome library as well as a spacious living room compliment an exceptionally appointed designer quality chef's kitchen with a large butler's pantry and views of the formal gardens and orchard. There are two primary bedrooms, both with luxuriously appointed ensuite primary bathrooms, dressing rooms, and french doors to outdoor deck space with exceptional views. The Roof Deck surrounding the Atrium glass skylight has 360-degree views of Mt. Tom, Bear Mountain, and the Berkshire Mountain range. In addition to a 3-bedroom (1900 square foot) Caretaker's Cottage, the property also includes an Expansive Outdoor Pool, a Spa (seats 15), Tennis Court, a Barn with Property Office, a Warehouse, and Art Storage Building. Finally, a rustic log cabin on the highest point of the property has the best views of the Twin Lakes in the county.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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46C Senff Road Washington CT 06793

Washington, CT46C Senff Road

Price$11,950,000

Est. Mortgage: $/month

MLS Number 170391895

  • Single Family
  • Square Feet 18,811
  • Bedrooms 5
  • Bathroom 11
  • Year Built 2002

Designed by architectural firm Gray Organschi - Il Poggio delivers on a vision many desire, few will accomplish. As you enter from a quiet country road, a modernist form rises from the hillside as the promise of serene relaxation, active endeavours, intimate gatherings, and memorable events unfolds. Walls of glass enhanced by the natural beauty of wood and stone frame unobstructed views of the landscape from every room. One level down you'll find the indoor activity center with a saltwater pool, hot tub, sauna, showers, squash court, movie theatre, family room, and game room. Venture outdoors to clip herbs from the kitchen garden, start seedlings in the greenhouse, practice yoga on the balconies. Follow the custom crafted foot bridge to the private spring fed pond. Swim or paddle a canoe on the pond, play tennis on the lighted courts, or tinker in the hobby barn. Stroll to the edge of the hillside to “the folly” - reminiscent of a Roman amphitheatre where family and renowned musicians have performed. Explore 106+ acres of Il Poggio before retiring with a glass of wine from the cellar in front of one of many fireplaces. Enjoy gatherings in the grand kitchen overlooking views of the pond or relax in one of five en-suite bedrooms with spa inspired baths in the main house - four with a wood burning fireplace. With a three bedroom guest house, and bunks for four in the grass-roofed tennis house there's room for many to stay in this enclave unlike any other in the Litchfield Hills.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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564 Undermountain Road Salisbury CT 06068

Salisbury, CT564 Undermountain Road

Price$11,890,000

Est. Mortgage: $/month

MLS Number 170394617

  • Single Family
  • Square Feet 5,850
  • Bedrooms 11
  • Bathroom 6
  • Year Built 1880

Manor House plus 11 Additional Buildings - This spectacular 85+/- acre property is a destination Educational Center. It offers a magnificent 1880 Manor House, with spectacular distant Views, a Pond, and 11 additional buildings which house an Auditorium, Group Meeting Areas, Breakout Private Offices, a Fitness Center, Pondside Cottage, huge Dining Hall with Commercial Kitchen, and accommodations in over 56 Guest Rooms. The land is made up of 70+/- acres in the Southern Berkshires and 15+/- abutting acres in Salisbury, CT - the entire CT side runs along Sage's Ravine. There are walking trails throughout the land and access to the Appalachian Trail. You will be smitten by this property and totally taken with the possibilities. Note: Details and taxes are only for the Main House which is on the Massachusetts side of the property. Please ask for details for all of the 12 buildings and the total property.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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132 Curtiss Road Warren CT 06777

Warren, CT132 Curtiss Road

Price$10,000,000

Est. Mortgage: $/month

MLS Number 170418353

  • Single Family
  • Square Feet 3,372
  • Bedrooms 3
  • Bathroom 4
  • Year Built 1820

Step back in time at Lost Acre Farm to one of the last great opportunities to own over 100 acres of unencumbered land overlooking Lake Waramaug, CT's most beautiful and protected lake. The property is located at one of the highest spots in the area and along a dead end road abutting state land and major estates. The 3 bedroom existing main house has exquisite southwestern lake views, terraces, gardens, mature fruit/specimen trees, multiple guest houses, large equestrian barn, pool with pool house and a pond with waterfall. The 3 charming guest cottages can be restored for living while the main house undergoes renovation or you build anew. The total acreage is 114.64 acres currently divided into 4 parcels. Further subdivision and conservation potential is possible as there is significant road frontage. Percolation testing would need to be done by buyers. Under 2 hours to NYC. 10 minutes to chic village centers of New Preston, Washington, Kent, Litchfield, Warren. Access to Lake Waramaug at the Warren Town beach just a 2 minute drive down the street. Nearby country clubs offer golf, beach and tennis. 20 minutes to Mohawk Mountain for skiing. Taxes reflect all 4 parcels, much of land in PA 490.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Road Washington CT 06793

Washington, CT46 Senff Road

Price$9,950,000

Est. Mortgage: $/month

MLS Number 170406828

  • Single Family
  • Square Feet 18,811
  • Bedrooms 5
  • Bathroom 11
  • Year Built 2002

Designed by architectural firm Gray Organschi - Il Poggio delivers on a vision many desire, few will accomplish. As you enter from a quiet country road, a modernist form rises from the hillside as the promise of serene relaxation, active endeavours, intimate gatherings, and memorable events unfolds. Walls of glass enhanced by the natural beauty of wood and stone frame unobstructed views of the landscape from every room. One level down you'll find the indoor activity center with a saltwater pool, hot tub, sauna, showers, squash court, movie theatre, family room, and game room. Venture outdoors to clip herbs from the kitchen garden, start seedlings in the greenhouse, practice yoga on the balconies. Follow the custom crafted foot bridge to the private spring fed pond. Swim or paddle a canoe on the pond, play tennis on the lighted courts, or tinker in the hobby barn. Stroll to the edge of the hillside to “the folly” - reminiscent of a Roman amphitheatre where family and renowned musicians have performed. Explore 70 acres of Il Poggio before retiring with a glass of wine from the cellar in front of one of many fireplaces. Enjoy gatherings in the grand kitchen overlooking views of the pond or relax in one of five en-suite bedrooms with spa inspired baths in the main house - four with a wood burning fireplace. With a three bedroom guest house, and bunks for four in the grass-roofed tennis house there's room for many to stay in this enclave unlike any other in the Litchfield Hills.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

40/42 Nettleton Hollow Road Washington CT 06793

MLS Number 170402818

  • Single Family
  • Square Feet 11,776
  • Bathroom 8
  • Bedrooms 5
  • Year Built 2017

"Stone Bridge." The Ultimate Country Estate. Impeccable new Shingle and Stone home, set on 31+ private bucolic acres with add'l approved lot, in highly desirable Nettleton Hollow area in Washington. 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 cars 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 professionally planned grounds with mature plantings and stonework include an irrigation system and 1,000 ft of road frontage. Magnificent!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

42 Nettleton Hollow Road Washington CT 06793

MLS Number 170382809

  • Single Family
  • Square Feet 9,800
  • Bedrooms 5
  • Bathroom 8
  • Year Built 2017

"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: 3.05% last updated on Oct 14, 2021
* 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 June Road Washington CT 06777

MLS Number 170339941

  • Single Family
  • Square Feet 11,000
  • Bedrooms 5
  • Bathroom 6
  • Year Built 2010

Modern Hilltop Retreat - 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: 3.05% last updated on Oct 14, 2021
* 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 Road Avon CT 06001

Avon, CT333 Montevideo Road

Price$5,995,000

Est. Mortgage: $/month

MLS Number 170441863

  • Single Family
  • Square Feet 6,964
  • Bedrooms 4
  • Year Built 1989
  • Bathroom 5

This historic 115-acre estate has a private 12-acre lake entirely on the property and sits on Talcott Mountain at the highest point in Avon CT. With sweeping majestic views of the Farmington Valley and the foothills of the Berkshire Mountains, Montevideo is simply magnificent! The main residence, rebuilt in 1991, is situated around mature trees and affords eastern views of the lake and western views of the valley. In addition to the 7900 square foot main residence, the property has three houses ranging in size from 1,000 - 2,000 square feet, three Victorian-era barns, a boathouse, a dock, and a floating wood raft. Originally established in the early 19th century, the property has been home to only three families since 1890. Daniel Wadsworth, a well-known arts patron, originally developed the property. Many historic figures have enjoyed Montevideo. Hudson River Valley School artist Thomas Cole created several paintings from the estate. Mark Twain enjoyed swimming in the property's lake. Teddy Roosevelt would stop by for visits on his way to nearby Hueblein Tower. Today the same beauty that attracted some of history's luminaries still exists. Montevideo easily could function as a personal vacation property, a corporate retreat, or a recreational compound with a private music and art studio.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

7 Arrow Point Road Warren CT 06777

Warren, CT7 Arrow Point Road

Price$5,500,000

Est. Mortgage: $/month

MLS Number 170436422

  • Single Family
  • Square Feet 6,974
  • Bedrooms 4
  • Bathroom 6
  • Year Built 2006

Unique opportunity to own fabulous shingle style house with direct frontage on Lake Waramaug with private dock and walk in beach area. Generous yard in both front and rear of house. Mature landscaping with fruit trees and lake irrigation system. Built to very high standards in 2006-7 with 4 en-suite bedrooms, open kitchen, dining and living rooms all with lake views. First floor guest room, office, screened porch with fireplace, mudroom, laundry and outdoor shower. Bluestone patio with built in grill. Second level includes 2 room primary suite with lake views, walk in closet, fireplace and balcony, two additional en-suite bedrooms and game room. Finished attic flex space on third floor. Walk out lower level includes gym, wine cellar, storage and unfinished area ready for your imagination. Both an attached 2 car garage and separate stand alone 2 bay barn with walk up space above. Generator and basketball complete this incredibly rare offering.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

10 Evans Passway Morris CT 06763

Morris, CT10 Evans Passway, Lakeside

Price$4,500,000

Est. Mortgage: $/month

MLS Number 170398186

  • Single Family
  • Square Feet 8,700
  • Bedrooms 4
  • Bathroom 7
  • Year Built 2003

Stunning waterfront residence on Connecticut's largest natural lake, Bantam. This 8700 SF, 16 room stone and shingle home boasts views from every room as well as the rooftop bar, multiple balconies and terraces. This home is perfect for entertaining with a full kitchen outside with DCS appliances, pizza oven, dining on stone patio or upper level balcony, lounging area with TV, Gunite infinity hot tub/pool, terrace with fire pit, dock & beach area. The main living space has an open floor plan with endless lake views, chef's kitchen with top of the line appliances, butler's pantry, dining area with access to balcony, formal dining room with fireplace and sitting area with fireplace. There are two master suites, one on the main level and one upstairs. Both have fireplaces and sitting areas (one with a Japanese shower room). There are two additional en suite bedrooms and beautiful murals hand painted throughout. This one of a kind home has it all with a movie theater with high def projector, cigar and wine room, spacious rec room with pool table/games, bar & great room with retro kitchen, spa with steam shower & sauna and easy elevator access to every floor. More features include Sonos sound system, irrigation system, waterfall in entrance, generator, propane radiant heat, central air, central vac, electric car powering station, two outbuildings/garages, laundry on each floor, dry cleaner, security system, and more! A MUST SEE! Just 90 miles from NYC. Shown by private appt.

Listing Courtesy of Brown Harris Stevens

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

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