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The Matthews Team

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 Team 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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141 5 1/2 Mile Road Cornwall CT 06753

MLS Number 170403678

  • Single Family
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 12,373
  • Acreage 550

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.

Listed by Joseph Barbieri and Diana Bisselle of Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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$9,900,000

Est. Mortgage: $/month

MLS Number 170496156

  • Single Family
  • Bedrooms 5
  • Bathroom 11
  • Square Feet 18,811
  • Acreage 106

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.

Listed by Kathryn Clair and Kathryn C Bassett of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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130 Taconic Road Salisbury CT 06068

MLS Number 170487337

  • Single Family
  • Bedrooms 5
  • Bathroom 9
  • Square Feet 11,224
  • Acreage 41

Exceptional Estate with Western Views, Pool, and Pond - An outstanding Twin Lakes area home privately sited on one of the premiere roads in Salisbury, CT with a legacy property designed by the World-Renowned Landscape Architect Dan Kiley. Gorgeous Main House suited for entertaining with 5 Bedrooms, 8 Full Baths and 3 Half Baths, soaring Living Room ceiling, formal Dining Room, Library, Eat-in Kitchen, Family Room, Playroom with Kitchen, Gym, Indoor Pool, central air conditioning, generator, Pond with dock, Har-tru Tennis Court, Basketball Half-Court - all facing magnificent western Views. On +/-41 gorgeous acres. Additionally featured is a beautiful, newly renovated 2-Bedroom 2-Full Bath Guest House with central air and a private stone Terrace and Garden, and a Gate House with a spectacular Office with fireplace, a multi-car Garage, and one-Bedroom Apartment. A magnificent Estate in the Northwest Corner of Connecticut just minutes from The White Hart Inn, and the lakes, hiking, restaurants, and shopping of Salisbury, CT, Millerton, NY, and the Southern Berkshires. Spectacular! Property being offered on +/-41 acres - pending sub-division approval. Adjusted Assessment and Taxes TBD

Listed by Juliet Moore and Elyse Harney Morris of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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$8,200,000

Est. Mortgage: $/month

MLS Number 170406828

  • Single Family
  • Bedrooms 5
  • Bathroom 11
  • Square Feet 18,811
  • Acreage 70.7

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.

Listed by Kathryn Clair and Kathryn C Bassett of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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Washington CT 06777

Washington, CT, New Preston

Price$7,500,000

Est. Mortgage: $/month

MLS Number 170497262

  • Single Family
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 9,000
  • Acreage 21.65

Rarely does such a front row center seat become available! Perched high atop Gunn Hill in New Preston, this extraordinary 22 acre estate has panoramic views of Lake Waramaug & the Hills of Kent and Warren. Its commanding position captures breathtaking sunrises, sunsets, and starry nights. Recently built and lightly used, the classic shingle style residence is spacious indeed - 9,000 sq ft of living space accessing 1700 sq ft of mahogany deck & blue stone terraces. The park-like grounds are magical, featuring gardens, a 40'x20' heated swimming pool, rolling manicured hills with meandering pathways by ancient stone walls, birch tree forests and remains of an old quarry. A Portico leads to a spacious foyer with a Powder Room and Coat Room nearby and a formal Dining Room featuring a lighted hip ceiling and corner Club door to a butler's pantry with standing bar-sink. The foyer and exquisite stairway open to the spacious Living Room with coffered ceiling, FP, custom cabinetry with window seat. Glass doors open to the enormous terrace. The Primary Bedroom Suite also has a door to the terrace, a seating area, dual dressing rooms and a luxurious spa bathroom with radiant heated marble tile floors. The Cherry paneled Library w/FP and the family Dining/open plan Kitchen have many windows and access to the terrace. The kitchen is a dream with walls of cabinets and windows, a breakfast bar, an island with prep-sink and Sub-Zero and Wolf appliances. SEE ADDENDUM

Listed by Roger Saucy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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 Road Washington CT 06793

MLS Number 170382809

  • Single Family
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 9,800
  • Acreage 22.55

"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!

Listed by Kathryn Clair and Kathryn C Bassett of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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72 Upper Church Hill Road Washington CT 06794

MLS Number 170483937

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,754
  • Acreage 6.65

Four Corners Farm. At the very top of the hills with forever views, a beautiful open flat property. An original 1850's Col farmhouse, with an 1800s schoolhouse addition, plus a late 1800's tobacco barn addition. All masterfully integrated, renovated & restored by a famous Interior Designer. Published triple-mint home in move-in condition. Mindful of the character & personality of an antique home, and considerate of the contemporary needs of a modern family. Open flow & light spaces, for entertaining & for extended family needs. Primary bedrm suite w/sitting room, dressing room, his/hers baths, all ensuite. Five/Six bedrms, 5 ½ all new baths. Antique light fixtures sourced from Paris, along with re-purposed original wide plank flrs. Two/three home offices/playrooms, plus a large family room w/full bath (or ground-flr master). All new Kitchen with style-appropriate custom cabinetry, matched Italian quartz counters, English brass fixtures, Wolf, SubZero, Bosch appliances. Architectural lighting throughout kitchen, breakfast & dining rooms, and an adjacent Dish Room/Butler pantry. All new Inground heated salt-water pool & spa, and pergola integrated with the guest/pool-house/studio with full bath, gym, full kitchen. Antique 7000 sqft barns, repurposed into storage rms, utilities & equipment, plus 4-car garages. Spectacular views, sunsets & sunrises. Highlighted in Cottages and Gardens! Go to: https://www.cottagesgardens.com/step-inside-a-vintage-farmhouse-in-litchfield-county/

Listed by Maria Taylor and Carolyn Klemm of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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69 Beaver Dam Road Salisbury CT 06068

MLS Number 170496182

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,589
  • Acreage 3.93

Magnificent 1929 Estate Salisbury CT - Classic Mediterranean Revival set on almost 4 beautifully landscaped acres with specimen trees and expansive views. A private driveway with lush landscaping welcomes visitors to the cobblestone courtyard. Updated and expanded in keeping with its rich architectural history, this meticulously maintained five-bedroom five-bathroom home includes a primary wing with its own sitting room with a wood-burning fireplace and a private terrace overlooking the gardens. The home features a formal living room with fireplace, bright and modern gourmet kitchen, garden room overlooking a gunite pool, dining room, and a multi-purpose room off the kitchen. A private apartment is on the lower level with its own entrance. Connected by the courtyard is the carriage barn/guest house with a one-bedroom apartment and 3 bay garage. This extraordinary home is located in the prestigious Taconic section of Salisbury, CT., within biking distance to Twin Lakes and walking distance to the Appalachian Trail.

Listed by Thomas Callahan of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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135 Interlaken Road Salisbury CT 06039
Under Agreement

MLS Number 170485963

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,226
  • Acreage 1.3

Thoughtfully renovated and seductively designed Lakeville lakefront home with 5 bedrooms and 4 full baths. The main living level is a mix of open and private spaces, the materials and colors are functional and utterly simple. The design evokes a classic lake feel that has been delicately and deliberately imagined for the current lakefront lifestyle; as designed by Amie Weitzman Design. The main floor has access to both an open deck and screened-in porch. There are two wood-burning fireplaces one in the main floor living/dining area and one in the office/den. There are lake views from many of the home's rooms, and the sweeping and inviting lawn and garden bring one to the lake and your own dock and swim raft. Minutes to Salisbury, Millerton, Hotchkiss, and IMS.

Listed by Elyse Harney Morris and John Panzer of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

64 Hammertown Road Salisbury CT 06068

MLS Number 170492210

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 5,061
  • Acreage 12.42

New offering! 12+ acres, including an additional building lot with breathtaking views! - This comprehensively and thoughtfully renovated 5-Bedroom, 4-Bath home sits prominently upon 5+ acres in the heart of Salisbury, CT. Careful craftsmanship gracefully brings together the breathtaking setting with natural materials and thoughtful details creating unmatched depth and warmth. A large Kitchen, Dining, and Family Room are at the heart of the home and all overlook the surrounding mountain range, opening to a mahogany sunset deck. A wood-burning fireplace in the Living Room and back-covered porch enjoy sunrises from the east. A Mudroom Entry at the back of the home includes a Full Bath, custom benches, a pantry, and Laundry Room. French doors open to the three-season Screened Porch and a beautifully fabricated blackened steel ladder and banister lead to a loft that features reclaimed wood flooring and wallboard. The first-floor bedroom Suite is flooded with sunshine and sits at the front of the home. The Second floor boasts 3 bedrooms that share a Hall Bath and an oversized Primary Suite with stunning views, a dressing room, and a private third-floor loft. The primary bath includes a steam shower, double vanity, and soaking tub overlooking the surrounding farmland. The third loft space at the front of the home serves as a great Bonus or Recreation Room and highlights the history of the home with massive chestnut beams and reclaimed wooden flooring.

Listed by Holly M Leibrock and Elyse Harney Morris of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

264 Painter Hill Road Roxbury CT 06783

MLS Number 170498741

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 3,823
  • Acreage 5.99

A renovated antique gem located in one of the most picturesque areas of Roxbury. Surrounded by tranquil grounds and close to pristine public lands, the John Lewis Homestead (1780) exemplifies the art of marrying the old and new. Over the years, the original homestead has been expanded, restored, remodeled, and renovated. The home's tasteful renovation created bright rooms throughout and a well-situated gunite pool. The newer light-filled section seamlessly flows into the original structure, which maintains vintage features reminiscent of a time of quiet contentment and has three original stone fireplaces, exposed beams, and wide flooring. The current layout provides space for a formal dining room, den, and study, as well as three bedrooms and a full bath upstairs. The grand living room has a large fireplace, antique beams, built-in bookshelves, and a screened-in porch overlooking the pool. The adjacent primary bedroom has exposed beams, french doors, a dressing room and luxury bath with a jacuzzi tub and Waterworks fixtures. The large eat-in kitchen includes a large kitchen island, Wolf range, and Subzero fridge. The walk-out lower level includes a bedroom and bath with french doors leading to the pool. The detached garage has guest quarters with vaulted ceilings, a full bath and kitchenette. You'll love the magical grounds with specimen trees, mature plantings, and exposed granite, all less than two hours from New York City.

Listed by Maria Taylor of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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 Tichnor Road Sharon CT 06069

Sharon, CT37 Tichnor Road

Price$3,500,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170497220

  • Single Family
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 4,438
  • Acreage 16.94

This spectacular picturesque retreat is Immaculately built with impeccable attention to detail and quality. The owner was not only building his dream home but creating a masterpiece. Every decision made was with AAA+ excellence! Spacious rooms with custom detail throughout make for comfortable living and a beautiful indoor/outdoor flow overlooking the unparalleled eastern mountain views. A central Great Room with timber frame beams and soaring ceilings, combines the Living Room with a floor to ceiling stone wood-burning Fireplace, Dining Area, and Kitchen- all of which open to an expansive Covered Porch. This main level also includes a half bath, mudroom, and laundry room. There are Five EnSuite Bedrooms, included on the main level is a Primary Suite with a walk-out porch. A half story up is a second Primary 1,000 sq foot Suite with mountain views. The second floor has a den with outstanding mountain views and 2 additional ensuite bedrooms each with a walk-out porch. The Lower Level includes a Recreational Room with a second stone wood-burning fireplace, a 5th EnSuite bedroom with a walk-out, a Bar, a Game room, and a Half Bath, as well as French Doors that opens to the backyard toward the Eastern Mohawk Mountain View. Completing this amazing house is an attached 3-car garage with radiant heated floors and top-of-the-line Carriage doors. This Impressive home is only a few months away from completion with many of the materials either in place or on order.

Listed by Liza C Reiss and Elyse Harney Morris of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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