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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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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
  • Bathroom 11
  • Property Style Contemporary, Modern
  • Bedrooms 5

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: 3.56% last updated on Jan 20, 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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141 5 1/2 Mile Road Cornwall CT 06753

MLS Number 170403678

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

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: 3.56% last updated on Jan 20, 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$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: 3.56% last updated on Jan 20, 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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40/42 Nettleton Hollow Road Washington CT 06793

MLS Number 170402818

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

"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: 3.56% last updated on Jan 20, 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
  • Square Feet 9,800
  • Year Built 2017
  • Bedrooms 5
  • Bathroom 8

"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: 3.56% last updated on Jan 20, 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 June Road Washington CT 06777

MLS Number 170339941

  • Single Family
  • Square Feet 11,000
  • Year Built 2010
  • Bathroom 6
  • Property Style Contemporary

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: 3.56% last updated on Jan 20, 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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30 Laddie Lane Salisbury CT 06039

Salisbury, CT30 Laddie Lane, Lakeville

Price$4,995,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170462772

  • Single Family
  • Square Feet 7,195
  • Bathroom 6
  • Bedrooms 5
  • Property Style Colonial

Georgian Colonial on Private Lane - This dramatic home is located within minutes to town yet, affords dramatic open northwest views of the Taconic Range. A long private driveway leads you to this custom-built home on over 22 acres. Luxury finishes, detailed moldings are noted as you enter the 20ft. high foyer which connects all three levels. The first floor has formal rooms, three wood-burning fireplaces, a gourmet kitchen, pantry, a paneled library, a sunny family room, and a first-floor bedroom suite. The second floor has the master suite with a sitting room, office, walk-in closets, and a double sink bathroom. Three bedrooms and two bathrooms, a laundry room complete the second floor. The lower level is an impressive setting with a media room, full gym, wine room and a guest suite is located above the barn style attached garage. A separate party barn and heated gunite pool complete this wonderful estate.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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264 Painter Hill Road Roxbury CT 06783

Roxbury, CT264 Painter Hill Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number 170461050

  • Single Family
  • Square Feet 4,396
  • Year Built 1792
  • Property Style Cape Cod, Antique
  • Bedrooms 5

Location! Location! Location! This gorgeous antique cape is located in the coveted Painter Hill area of Roxbury. Antique charm abounds. There are 5 bedrooms and 3 full and 2 half baths in the main house. There are also guest quarters above the detached barn/garage. Wide plank wood floors are throughout the home. There are 4 stone fireplaces. There is a gourmet kitchen with a Wolf range and Sub Zero refrigerator and freezer. There is a breakfast area with french doors to the patio. The living room has built ins, a fireplace and opens to a lovely screened porch. The dining room, den and office all have stone fireplaces. The main level primary bedroom is spacious and includes a dressing room, luxurious bath with dual sinks, a soaking tub and shower, as well as french doors to the rear yard. The upper level has 3 bedrooms and a hall bath. There is a private guest suite on the lower level which walks out to the rear yard. There is an in ground gunite pool for your summer pleasure. Painter Hill was named for its scenic beauty and this property will not disappoint. Located under 2 hours from NYC makes this a great weekend getaway or full time home. No weekend showings until further notice.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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201 South Road Winchester CT 06098

Winchester, CT201 South Road

Price$2,900,000

Est. Mortgage: $/month

MLS Number 170416816

  • Single Family
  • Square Feet 4,609
  • Bedrooms 5
  • Property Style Colonial, Chateau
  • Year Built 1997

A totally nature lovers tranquil & serene hidden location. Not visible from access road. 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 15 - 20 acre fenced-in field. Outbuildings include garage with 2-stall horse barn plus hayloft, fenced-in small stone building, storage shed. Expansion potential here as equestrian or other agricultural uses. Potential subdivision. 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: 3.56% last updated on Jan 20, 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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293 Lake Road Warren CT 06777

Warren, CT293 Lake Road

Price$2,745,000

Est. Mortgage: $/month

MLS Number 170167373

  • Single Family
  • Square Feet 6,697
  • Bedrooms 5
  • Bathroom 7
  • Year Built 2000

Up the long, meandering driveway, you'll find long & clear views of Lake Waramaug & Hopkins Vineyard from this beautiful Colonial home set atop the hillside. This picturesque property includes 16 useable acres (subdividable) with fruit trees, stone walls, mature boxwood garden & perennials. The large chefs kitchen includes a 6 burner dual fuel range & 4 burner gas cooktop in the island, double wall oven, ice maker, wine cooler, large sub zero, dishwasher, 2 garbage disposals, compactor & oversized walk-in pantry w/ built-ins. The Butler's pantry is equipped w/ a dishwasher, sink, custom cabinets & disposal. A beautiful, large screened-in porch & deck is accessible from the DR & kitchen. The FR has 2 story windows on 2 sides, allows you to take in the incredible views. On the opposite wall, there is a paneled FP between built-in bookcases. Flanking the vast foyer is a living room & cozy custom cherry paneled wall & ceiling library accessed through pocket doors. The room is complete w/ a FP & cherry bookcases on either side. The hall leads you to the 3 car attached garage, there you can find a mudroom, laundry room & back staircase leading to the 2nd floor which features 4 bedrooms, 1 of which is quite large & currently used as a studio. The LL features a very large rec. room, family room w/ FP, 1 & 1/2 baths off 2 add'l bedrooms. There is also 10x10 alarmed cement safe room. Mechanicals & ample storage space complete the LL. Close enough to walk the beach. A true must see!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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164 Belden Street Canaan CT 06031

MLS Number 170434011

  • Single Family
  • Square Feet 6,296
  • Bedrooms 5
  • Bathroom 6
  • Year Built 1936

Welcome to your home at "Fox Hollow Farm" located in the New England town of Falls Village. This estate is the perfect escape from city life while still close to renowned restaurants and entertainment like, Lime Rock Park and winter destination, Mohawk Mountain Ski area. As a former hunting lodge, the home has ample space with 5 bedrooms and 6 baths to accommodate your family, friends or staff. Entertain guests with cocktails on the blue stone patio and end with a dinner under the wooden pergola surrounded by foliage. Take a picturesque walk or cross country ski on the moss covered trail around the property. For further relaxation, convert the screened-in pavilion overlooking the pond into a meditation space for your yoga practice. The large barn is awaiting a hobby enthusiast's touch. There are french doors with wrought iron details and wide planked wood floors throughout the home. In addition to the main kitchen, there are two other kitchens for staff use. Work from your home office and use the built-in shelving to display books and collectibles. Gold sconces adorn the walls of the formal dining room and the family room has impressive 30 foot ceilings with exposed beams and a wood fireplace. Upstairs you'll find a recreational room and an enclosed porch flooded with natural light, ideal for an artist studio. The main suite has a fireplace, 2 walk-in closets with a vanity room and Kohler soaking bath tub. Schedule your visit today and marvel at all this home has to offer!

Listing Courtesy of NestSeekers International

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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 Mudge Pond Road Sharon CT 06069

Sharon, CT69 Mudge Pond Road

Price$2,295,000

Est. Mortgage: $/month

MLS Number 170359039

  • Single Family
  • Square Feet 6,000
  • Property Style Barn
  • Bathroom 6
  • Year Built 1990

Waterfront Country Compound - This Mudge Pond Waterfront Converted Dairy Barn is brilliantly renovated. The heart of the house is a Great Room with exposed wooden barn beams and a soaring ceiling, wide board flooring, and a wood-burning fireplace. Enter the stone-columned gate, drive up the allée of weeping cherry trees that leads into this 8.48-acre property. Cherry trees transition to a Concord grape arbor at the entranceway. Abutting Sharon Land Trust guarantees permanent privacy. Main house: 4-5 bedrooms, 4 full bath and 2 half bath, plenty of space for office, exercise or media center, a fabulous indoor swimming pool and Pond views from the kitchen, the Great Room, and 3 bedrooms. Ground-floor Master Suite with fireplace and double French doors to a private patio overlooking the Pond. Huge walk-in closet and master bath with radiant floor heating. Professional Wolf stove with two ovens awaits culinary efforts in the kitchen with its huge seating area and patio. Screened backyard Gazebo, with views in all directions. 100' private lake frontage. This amazing property boasts 2 Guest Houses. The Lake Side Guest House has a full kitchen, living room, bedroom, 2 full baths, and 2 patios with lake views. The Guesthouse on the Land Trust side has 2 bedrooms, a kitchen, a living room, 2 full baths, and a back porch. Convenient to Lakeville, Salisbury, Hotchkiss, IMS and Millerton. Easy access to Metro-North.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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

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 2022 SmartMLS, Inc.