The Matthews Team

William Raveis Lifestyles Realty

5 Bedroom Homes in Connecticut

Browse listings for homes with 5 bedrooms in Litchfield County. 

CT Houses for Sale with 5 Bedrooms

Contact the William Raveis Lifestyles 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 1000

Villa Catarina - A grand Tuscan-style estate spectacularly situated on 1,000+ 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.

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

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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Cornwall Hollow Road Cornwall CT 06753

MLS Number 170516051

  • 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, 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. Inviting terraces and formal gardens with dramatic westerly views of the surrounding wooded hillsides, along with a Har-Tru tennis court complete this enchanting property. Peace and tranquility abound with this rare and exceptional offering. Additional acreage available: see listing for 141 5 1/2 Mile Rd, Cornwall.

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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, 6 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: 5.22% last updated on Aug 11, 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$8,200,000

Est. Mortgage: $/month

MLS Number 170496156

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

$1,700,000 Price Adjustment with 106+/- Acres! Designed by Gray Organschi Architecture - 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 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 wood burning fireplaces and spa inspired baths. Along 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

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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: 5.22% last updated on Aug 11, 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 24.88

"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

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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36 Whitford Road Sharon CT 06069

Sharon, CT36 Whitford Road

Price$4,995,000

Est. Mortgage: $/month

MLS Number 170506671

  • Single Family
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5,070
  • Acreage 11.65

Exceptional home on 11.65 private acres with breathtaking western views. Large windows take full advantage of the view in the living room and kitchen. Enjoy the Chef's Kitchen with sophisticated design, a Marble-topped center island, stainless steel appliances, both gas and induction cooktops, an extra-wide sink, double ovens, and dishwashers for easy cleanup. Enjoy multiple dining options, al fresco on the deck, casual in the kitchen, or formal in the main dining room, each with its own appeal. Next to the kitchen, is a rustic and casual living space with a wood plank vaulted ceiling, stone hearth, and chimney. Other first-floor rooms include a library/office with built-in bookcases and a main floor bedroom with a shared full-sized bath. On the second floor, you'll find the primary suite with large windows, a walk-in closet, and a full bath. The lower level has great entertaining space with a mini-kitchen, wine storage, gathering space, large bedroom, changing rooms, and full bath. A french door provides quick access to the lounge area and pool. The attached guest house has a covered breezy-way and includes a gym/studio, full bath, bedroom, and private entrance. Professionally landscaped this property is truly special with beautiful plantings and specimen Pear trees. The heated gunite pool has a lovely grass surround and a pool house with an outdoor kitchen. Other features include a gated entry, a pond with a fountain, and cascading water feature.

Listed by Elyse Harney Morris and Tracy Macgowan of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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
Under Agreement

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: 5.22% last updated on Aug 11, 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
Pending Continue to Show

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: 5.22% last updated on Aug 11, 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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79 Roxbury Road Washington CT 06793

Washington, CT79 Roxbury Road

Price$3,250,000

Est. Mortgage: $/month

MLS Number 170486078

  • Single Family
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 4,990
  • Acreage 4.72

Boar House is an extraordinary property set on 4.72 acres bordering Steeprock Preserve. Redesigned and expanded by noted neoclassical Charleston architect, Randolph Martz, this spacious and elegant house offers 5 bedrooms, 5 1/2 baths & over 4,900 sq ft of living space. Both the formal living and dining rooms are impressive with high ceilings, fireplaces and floor to ceiling windows. The renovated gourmet chef's eat-in kitchen includes a large work area , honed granite counters and SubZero and Viking appliances. The kitchen enjoys the view of the tranquil setting of the formal gardens through multiple picture windows. Just around the corner is the charming library/family room with window seat and wetbar. The first of two main floor bedrooms has a full bath, walk-in closet and French doors to the private deck. The second bedroom has built-ins and full bath. The primary bedroom is privately located on the second floor and has a fireplace, marble bath, and large dressing room. There are two additional ensuite bedrooms on the second level. Through a separate exterior entrance is a detached finished space including office & entertainment area and full bath. There is an audio system and a whole house generator. The grounds are magnificent with in ground heated pool, professionally designed gardens, brick & bluestone walkways, stonewalls, terrace with pergola and a fabulous playhouse tucked in the woods. 2 hours from NYC. NE Home Mag - https://www.nehomemag.com/dressed-to-impress/

Listed by Maria Taylor of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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6 Milton Road Goshen CT 06756

MLS Number 170508713

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,222
  • Acreage 3.31

WATERFRONT: This lake house plan gives you loads of outdoor spaces to enjoy luxury waterfront living on large private lake in the Litchfield hills. The exterior has a combination of shake siding, wood beams, and large windows giving it great curb appeal. Two 2-car garage connected to the house by a massive covered deck that wraps all the way around the rear of the house. Just inside the home, you'll walk into a large entry with a soaring cathedral ceiling that flows into the great room. The great room is warmed by a fireplace with built-in bookshelves. The kitchen and dining room are open to the great room. The kitchen includes a large walk-in pantry and a large island with a snack bar. Behind the kitchen, you will find a wonderful pocket office with a desk. On the left side of the home, you'll find 2 bedrooms. The primary bedroom includes a large bathroom with dual vanities, a wet room, an enclosed toilet, and a huge walk-in closet. Bedroom 2 has access to its own bathroom as well. Lower level offers 2,072 square feet including theater room with a raised seating platform, a rec area, 3 additional bedrooms, an additional family room, and a mudroom with a bathroom that allows you to shower on your way in from the water. A lake bar on the backside of the garage opens up to the waterfront for your outdoor entertainment. Take a boat from your private dock - waterski, fish, or motor down to the clubhouse facilities to play tennis or get lunch on the beach.

Listed by Karen Newton and Stephen M Drezen of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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17 Judea Cemetery Road Washington CT 06793

Washington, CT17 Judea Cemetery Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 170513597

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 3,950
  • Acreage 10.2

NEW PRICE $2.995M. Full of history, character, grace & charm from the Revolutionary war thru the Civil War (lore has it that it was part of the Underground Railroad) to today Apple Lane Farm has taken its place in Washington as one of the premier properties. Occupying a coveted location w/ land on both sides of the road & complete w/ a guest barn & an APT over the garage the main house shines like a jewel. A spacious entry hall w/ the original large FP opens the way to the paneled library, powder room, LR & screened porch. The formal DR to the left of the center hall leads into the KIT, butler's pantry, small office & back entrance. The graceful staircase splits at the landing leading to the master BR suite & guest room on one wing & 2 other guest BRS & baths plus laundry room on the other wing, additionally there is a small BR on the 3rd floor. There are many original features from the 5 FPS to the magnificent hardwood wide board floors, french doors, crown molding & so much more. The guest barn house holds its own w/ 3 BRS & 3.5 baths plus a stunning stone FP & generous sized great room for living & dining. There is also a beautiful tennis court to enjoy & a pool site that can afford the buyer an opportunity to design their own pool. Basically owned by only 2 families for the last 200 years w/ a brief foray by entrepreneur George Soros here is your opportunity to share in a unique property. Listing Includes 17, 18 & 22 Judea Cemetery Road.

Listed by Judith Auchincloss of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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