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The Matthews Group

5 Bedroom Homes in Connecticut

Browse listings for homes with 5 bedrooms in Litchfield County. 

CT Houses for Sale with 5 Bedrooms

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.

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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: 2.8% last updated on Jul 29, 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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141 5 1/2 Mile Road Cornwall CT 06753

MLS Number 170403678

  • Single Family
  • Square Feet 12,373
  • Bedrooms 5
  • Bathroom 7
  • Year Built 1997

Villa Catarina - A grand Tuscan-style estate spectacularly situated on 550+ acres in the heart of Litchfield County offers unparalleled privacy and security as well as magnificent tri-state views of MA, CT and NY. Approached by a long scenic driveway meandering through fields and forests, this unique country compound is introduced by a granite cobbled courtyard, framed by copper beech and fragrant linden trees. The exquisite limestone and stucco Palladian-inspired villa by award-winning architect Thomas Beeby offers superior, commercial grade construction with 5 bedrooms, 4.3 baths and 6 fireplaces. Opening from a dramatic 2-story foyer showcasing a double staircase, the main floor encompasses a formal living and dining room, reception rooms/galleries, a spacious kitchen, library, and study. Gorgeous reclaimed cherry wood floors with radiant heating and 9+ ft high ceilings provide distinctive details. Upstairs, 5 luxurious bedrooms each offer stunning views of the surrounding wooded hillsides. Inviting terraces and formal gardens with dramatic westerly views, along with a Har-Tru tennis court and 6-stall horse barn complete this enchanting property. Peace and tranquility abound with this rare and exceptional offering. Additional acreage available.

Listing Courtesy of Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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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: 2.8% last updated on Jul 29, 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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40/42 Nettleton Hollow Washington CT 06793

MLS Number 170402818

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

"Stone Bridge." The Ultimate Country Estate. Impeccable new construction Shingle and Stone home, set on 31+ private bucolic acres with add'l approved lot, in the 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 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. Magnificent!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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46 June Washington CT 06777

Washington, CT46 June, New Preston

Price$6,750,000

Est. Mortgage: $/month

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: 2.8% last updated on Jul 29, 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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42 Nettleton Hollow 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: 2.8% last updated on Jul 29, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

85 & 83 Scoville Ore Mine Road Salisbury CT 06068

MLS Number 170413936

  • Single Family
  • Square Feet 5,504
  • Bedrooms 5
  • Bathroom 5
  • Year Built 1780

THE TOP OF THE WORLD! There are rare properties that are singularly exceptional - this is one of them. Situated high on the Taconic Range in Salisbury, CT, this must-see family compound looks over the surrounding hills from above. The views to the northeast, east, and southeast embody the spirit of living in the Berkshires. From sunrise to sunset, you can let go of the mundane with just a quick glance at your surroundings, as this homestead is an experience, not just a place. Steeped in history, safe, private, quiet, and serene, Bingham Brook Farm is the home of the Elijah Marshal Barn (1838) and the Josiah Curtis House (1780), both plucked from their original locations and rebuilt on site with concrete foundations in the 1980s. Fields, fences, outbuildings, screened decks, and a pond fit into the natural surroundings like a piece of fine art. This is not for those seeking only the ultra-modern or the contemporary chic. This is for those seeking the epitome of country life in the Litchfield Hills, with panoramic views reminding you to rest, relax, enjoy, and live well... Close to Hotchkiss, Salisbury, Berkshire & Indian Mt. private schools, Great Barrington, MA, Tanglewood, and all the arts and culture the Berkshires have to offer! Please respect the owners privacy and do not drive up the driveway without an appointment.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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67 Squire Road Roxbury CT 06783

Roxbury, CT67 Squire Road

Price$4,225,000

Est. Mortgage: $/month

MLS Number 170420680

  • Single Family
  • Square Feet 4,371
  • Bedrooms 5
  • Bathroom 3
  • Year Built 1974

Located on one of the most beautiful streets within the idyllic town of Roxbury, CT, this extraordinarily designed and masterfully renovated residence is perfectly situated on almost 11 acres of private land, adjacent to the beautiful Roxbury land-trust, complete with hiking trails and a waterfall. Newly renovated throughout, this residence has a most unique style that combines the best elements of contemporary architecture while retaining the warmth of a New England home. No detail has been overlooked in the design of this home: from tall panes of glass through which light streams into every room, to handcrafted, radiant-heated and artisan-finished white oak floors, to the selectively restored historic wooden post and beams. The intelligent floor plan allows for privacy and seamless indoor-outdoor living whereby one can step onto the beautiful stone patios that overlook the surrounding woods and the stream below, from all the main rooms of the house. The exquisite beauty of nature is ever-present in this one-of-a-kind residence.

Listing Courtesy of Compass Connecticut, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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847 & 849 North Street Goshen CT 06756

Goshen, CT847 & 849 North Street

Price$3,875,000

Est. Mortgage: $/month

MLS Number 170277455

  • Single Family
  • Square Feet 7,886
  • Bedrooms 5
  • Bathroom 7
  • Year Built 2001

Stunning country home designed by and built for owner reminiscent of Utah ski lodge. Impeccable appointments and features on very private 70 acres with crystal clear pond, stream and waterfall. Two bedroom guesthouse and "party barn". Very private and manicured grounds with long driveway entry offering extreme privacy. Reclaimed antique flooring and timbers, extensive stone work interior and exterior. Spectacular master bedroom suite on main level with fireplace, french doors to patio, dressing areas, walk-in closets, spacious master bath. All guest bedrooms oversized and en-suite. Lower level media room theatre quality with wet bar, fabulous wine cellar, fitness room, sauna and game area. Expertly designed, built, and located on one of the most beautiful parcels of land in Litchfield County. A definite "must-see".

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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201 South Road Winchester CT 06098

Winchester, CT201 South Road

Price$3,400,000

Est. Mortgage: $/month

MLS Number 170416816

  • Single Family
  • Square Feet 4,609
  • Bedrooms 5
  • Bathroom 4
  • Year Built 1997

A totally nature lovers tranquil & serene hidden location. First time offered for sale is this personal residence of long time established connecticut commercial builder / contractor. Constructed in 1997, this 4,600 +/- square foot brick & stone chateau style colonial affords the ultimate in privacy on 60 beautiful acres. One-third mile paved & lighted driveway leads to this park-like setting. 10 spacious rooms, offers country kitchen, 5 bedrooms, 3.5 baths, formal living & dining rooms, 3 fireplaces. Multiple open and covered decks / porches. In-ground heated salt water pool. Attractive landscaped grounds, large open fenced-in field. Outbuildings include garage with 2-stall horse barn and hayloft, fenced-in small stone building, storage shed. Expansion potential here as equestrian or other agricultural uses. Country location, yet close by for general retail shopping, medical services. Short distance to lakes, state parks, ski areas.

Listing Courtesy of Cohen Agency

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

25 Painter Ridge Road Washington CT 06793

Washington, CT25 Painter Ridge Road

Price$3,250,000

Est. Mortgage: $/month

MLS Number 170410231

  • Single Family
  • Square Feet 5,875
  • Bedrooms 5
  • Bathroom 7
  • Year Built 1992

Welcome to Sylvan Hill, Washington's most spectacular modern. This internationally acclaimed design by Lester Korzilius was featured in architectural digests in London, Milan, Rome and Tokyo. Complete privacy is yours once you pass through the stone pillars that lead you along the winding drive to this impressive house nestled in the woods. This 5875 sq.ft. structure consists of three circular windowed pavilions with an addition which was added in 2004. There are 5 bedrooms, 5 full and 2 half baths, several options for a home office, a large family room, eat-in kitchen and several other choices for gathering spaces. There is a wine cellar, a greenhouse, a 3-car insulated and heated garage (electric), 3 fireplaces, a pizza oven and an outdoor fireplace/grill. There is approximately 2000 sq.ft. of deck space that features a jacuzzi. There is also a dramatic, circular hallway, a perfect place to display art. This is your chance to own a very special and unique property that truly is itself, a work of art.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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10 Loomarwick Road Washington CT 06777
Pending Continue to Show

MLS Number 170404158

  • Single Family
  • Square Feet 1,330
  • Bedrooms 5
  • Bathroom 4
  • Year Built 1960

LAKE WARAMAUG - A rare opportunity on West Shore Road - 60 ft of private waterfront with dock and spectacular lake views. Just a short walk to the Main Cottage on Loomarwick Rd with 4 bedrooms and 3 full baths. This house features a living room with fireplace, country kitchen with gas range, and a spacious outside entertaining area. The Guest Cottage, formerly an ice house, is the perfect solution for a private home office complete with wifi. There is an open floor plan with kitchen, 1 bedroom and 1 bath. The village of New Preston is just minutes away and events at the Hopkins Vineyard are close by.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.