5-Bedroom Homes for Sale in Litchfield County CT

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  /40

  $1,500,000

  • 5 Beds
  • 4.5 Baths
  • 7,490 Sq Ft

  176 Hidden Pond Dr, Watertown, CT 06795

  Experience elevated living in this stunning and fully custom 5-bedroom, 4.5-bath home. Bespoke woodwork throughout; seamlessly blends modern design and welcoming comfort around every corner. As you step inside, the grand staircase sets a tone of elegance that resonates throughout this exceptional residence. The great room draws you in with soaring ceilings, a built-in bar and the first of four

  

  Matthew Egan

  Regency Real Estate, LLC

  (860) 735-3714

  176 Hidden Pond Dr, Watertown, CT 06795
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  /40

  $10,500,000

  • 7 Beds
  • 7 Baths
  • 6,844 Sq Ft

  Unlisted Address

  Magical in every season, Reverie Farm is now available for sale. Located in Warren, CT, Reverie Farm embraces the historical beauty of Litchfield County with impeccable modern upgrades. This much coveted property is comprised of exquisite 7 BR main and guest houses, additional residences, a spectacular historic cow barn repurposed as an art studio along with a vast array of unique barn

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (860) 735-1539

  Unlisted Address
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  /38

  $475,000 Coming Soon

  • 5 Beds
  • 2.5 Baths
  • 2,845 Sq Ft

  245 Guernseytown Rd, Watertown, CT 06795

  Welcome to this spacious and versatile home, ideally situated in one of Watertown's most desirable neighborhoods-just across from the Watertown Golf Club and walking distance to the prestigious Taft School. This expansive 5-bedroom, 2.5-bath residence blends classic design with practical living spaces, ideal for both everyday comfort and entertaining. The main level boasts hardwood flooring

  

  Matthew Egan

  Regency Real Estate, LLC

  (860) 407-6327

  245 Guernseytown Rd, Watertown, CT 06795
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  /30

  $2,000,000

  • 5 Beds
  • 4.5 Baths
  • 7,099 Sq Ft

  6 Claudia Ln, Sharon, CT 06069

  A Regal Sanctuary. Seize the opportunity to own a piece of majesty with this unparalleled castle perched atop a hill, commanding 60+ acres of pristine land. Surrounded by conservancy property, this estate promises uninterrupted tranquility and privacy. As you ascend the private road, the castle's imposing silhouette against the horizon is a prelude to the grandeur within. Boasting expansive

  Alan O'Doherty William Pitt Sotheby's Int'l

  6 Claudia Ln, Sharon, CT 06069
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  /36

  $2,750,000

  • 6 Beds
  • 9 Baths
  • 5,193 Sq Ft

  430 Milton Rd, Goshen, CT 06756

  12-Acre Lakefront- Classic New England Estate. 100 ft. frontage directly on Woodridge Lake, with rights to build a boat dock, deck and cooking area at lake's edge and enjoy water activities and picturesque views. Discover the epitome of charm and grace in this magnificent home with 3 wood-burning fireplaces. 13 total rooms including 7 bedrooms with 7 full & 2 1/2 baths. With two ponds, open

  Peter Klemm Klemm Real Estate Inc

  430 Milton Rd, Goshen, CT 06756
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  /40

  $1,875,000

  • 5 Beds
  • 5 Baths
  • 5,890 Sq Ft

  16 Westmount Rd, Salisbury, CT 06068

  Welcome to your private country retreat-where space, comfort, and opportunity converge. Set on 10 serene acres just five minutes from downtown Salisbury, this 4-bedroom, 3 full and 2 half bath home offers over 5,000 square feet of living space. Ideal for entertaining, the home features a formal living room with a wood-burning fireplace and an oversized kitchen with ample cabinetry, a walk-in

  Tracy Macgowan Elyse Harney Real Estate

  16 Westmount Rd, Salisbury, CT 06068
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  /40

  $2,200,000

  • 5 Beds
  • 3.5 Baths
  • 3,971 Sq Ft

  83 Thomson Rd, Bethlehem, CT 06751

  This STUNNING property is located on a dead end road with 22.90 acres in a "Currier & Ives" setting. It has just gone through an amazing transformation yet still exudes the charm of yesteryear. There are wide board floors and 5 fireplaces. There is a new 1500sf primary bedroom addition with custom closets, luxury bath, heated floors, bonus room and a 3rd laundry room, all with new washer/dryers.

  Sharon McGuire William Pitt Sotheby's Int'l

  83 Thomson Rd, Bethlehem, CT 06751
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  /33

  $3,995,000

  • 6 Beds
  • 5.5 Baths
  • 6,121 Sq Ft

  79 Hilltop Rd, Sharon, CT 06069

  1880's perfection, a true rare find in the heart of Sharon, CT. Magnificent seven bedroom, 5.5 bath estate, beautifully preserved and situated on a sprawling 4-acre lot with a pool. Large eat-in kitchen with massive center island. Screen porch overlooking the pool with beautiful hilltop views. 79 Hilltop masterfully combines historic charm with modern luxury, offering you the best of both

  Carolyn Morrison William Pitt Sotheby's Int'l

  79 Hilltop Rd, Sharon, CT 06069
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  /40

  $3,400,000

  • 7 Beds
  • 6.5 Baths
  • 4,824 Sq Ft

  Unlisted Address

  Elegant Torrington House sits on the site of what was once known as Cobble Hill Farm on a total of 95.5 acres along Old Goshen Road in Norfolk, CT. The grand 1805 Colonial with its large rooms, high ceilings and multiple original details including triple-hung windows, wide board floors and carved stone fireplaces surrounds and mantles, was moved years ago from the Torrington area to the original

  Betsy Little Betsy Little Real Estate LLC

  Unlisted Address
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  /39

  $2,745,000

  • 6 Beds
  • 3 Baths
  • 4,380 Sq Ft

  12 Popple Swamp Rd, Cornwall Bridge, CT 06754

  A rare and storied offering, the Colonel Dwight Wellington Pierce Farmstead is a distinguished circa 1830 Greek Revival residence listed on the State Registry of Historic Places. Perched on a rise with views of mountains, conserved land, and state forest, it blends heritage, natural beauty, and modern comfort. Spanning over 4,300 square feet, the main house features original moldings, wide-plank

  William Melnick Elyse Harney Real Estate

  12 Popple Swamp Rd, Cornwall Bridge, CT 06754
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  /40

  $4,199,000

  • 8 Beds
  • 9.5 Baths
  • 10,516 Sq Ft

  184 Fern Ave, Litchfield, CT 06759

  Come see this remarkably private property a stone's throw from the center of Litchfield. This stately home was built in 1992 and boasts over 10,000 s/f of finished space. The grounds are professionally landscaped and have a beautiful patio, pool and greenhouse. There are 8 bedrooms and 13 bathrooms along with a powder room . The sunny , modern, large eat-in kitchen open onto a patio, which

  Florence DeDampierre W. Raveis Lifestyles Realty

  184 Fern Ave, Litchfield, CT 06759
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  /39

  $1,995,000

  • 5 Beds
  • 2.5 Baths
  • 3,425 Sq Ft

  56 Sharon Rd, Lakeville, CT 06039

  This distinguished 1880s Victorian residence in the heart of Lakeville village offers a masterful blend of period craftsmanship and contemporary luxury on 2.5 private acres. Located moments from both the town green and Lakeville Lake, this meticulously restored 5-bedroom estate presents refined living in one of Litchfield County's most sought-after locations. The welcoming wrap-around covered

  Elyse Morris Elyse Harney Real Estate

  56 Sharon Rd, Lakeville, CT 06039
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  /40

  $1,595,000

  • 5 Beds
  • 2 Baths
  • 3,693 Sq Ft

  424 E Wakefield Blvd, Winsted, CT 06098

  Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

  KAREN NEWTON William Pitt Sotheby's Int'l

  424 E Wakefield Blvd, Winsted, CT 06098
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  /35

  $2,195,000

  • 5 Beds
  • 6 Baths
  • 5,113 Sq Ft

  88 Rucum Rd, Roxbury, CT 06783

  Located in picturesque Roxbury, CT-nestled in southern Litchfield County and under two hours from New York City-this exquisite barn-style residence offers the perfect blend of rustic charm and modern luxury. Set on 8 sprawling acres, the property features an expansive lawn, beautifully curated specimen plantings, and a sparkling pool with integrated spa-ideal for both relaxation and entertaining.

  Pels Matthews W. Raveis Lifestyles Realty

  88 Rucum Rd, Roxbury, CT 06783
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  /16

  $1,649,000

  • 5 Beds
  • 4 Baths
  • 3,676 Sq Ft

  51 Senff Rd, Washington, CT 06793

  Pristine 5-bedroom private home on scenic dirt road ideal for walking, jogging and biking. Magnificent design with 2 gas fireplaces, 2 over-sized wood decks overlooking the heated pool surrounded by endless summer hydrangea and 3 acres of lawns. The perfect location minutes from the center of Washington, the Mayflower and Winvian Inns & Spas.

  Peter Klemm Klemm Real Estate Inc

  51 Senff Rd, Washington, CT 06793
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  /40

  $1,950,000

  • 5 Beds
  • 6 Baths
  • 7,413 Sq Ft

  39 Quanopaug Trail, Woodbury, CT 06798

  Exceptionally constructed contemporary set on almost 9 acres with a beautiful view of distant hilltops. Both the house and the outdoor spaces are truly impressive, perfect for entertaining and nature lovers. With over 7,500 sq ft, the home is spacious with exposed beams, an abundance of windows and many updates & upgrades. The public rooms are open and airy encompassing the kitchen, dining and

  Maria Taylor Klemm Real Estate Inc

  39 Quanopaug Trail, Woodbury, CT 06798
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  /40

  $2,199,000

  • 9 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  431 W Wakefield Blvd, Winsted, CT 06098

  This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
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  /26

  $1,784,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,220 Sq Ft

  2 Pickett Rd, Roxbury, CT 06783

  NEW CONSTRUCTION. WELCOME TO YOUR DREAM HOME! This stunning new construction colonial farmhouse boasts modern elegance and top-of-the-line finishes throughout. Featuring 5 spacious bedrooms and 3.5 luxurious bathrooms, this home offers ample space for comfortable living. The open concept living area is perfect for entertaining, with a gourmet kitchen that includes high-end stainless-steel

  Michael Lissack The Virtual Realty Group

  2 Pickett Rd, Roxbury, CT 06783
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  /40

  $389,000

  • 6 Beds
  • 4 Baths
  • 2,898 Sq Ft

  579 Main St, New Hartford, CT 06057

  2 family home in New Hartford! Own a piece of history with this iconic double Cape (circa 1804) in the heart of New Hartford. Spanning 2,898 sq. ft., this 12-room, 5-bedroom, 4-bathroom home blends antique charm with endless customization possibilities. Key Features: 2 units! Timeless Design: Original wide chestnut floors, built-ins, and four fireplaces, including a bake oven and wood stove.

  Suzie Larson Turning Point Realty, LLC

  579 Main St, New Hartford, CT 06057
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  /40

  $650,000

  • 5 Beds
  • 5 Baths
  • 4,797 Sq Ft

  25 Jefferson Dr, New Milford, CT 06776

  This oversized 5-bedroom, 3-full, 2-half-bath home is situated on a quiet cul-de-sac with a level backyard. The inviting entryway fills the home with natural light, setting the tone for the open-concept floor plan, perfect for entertaining. The newly renovated kitchen features granite countertops, a center island, shaker-style cabinets, and stainless steel appliances, seamlessly connecting to the

  Kim Kendall Keller Williams Realty

  25 Jefferson Dr, New Milford, CT 06776
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  /32

  $625,000

  • 5 Beds
  • 2 Baths
  • 2,326 Sq Ft

  Unlisted Address

  Beautiful & Private 1.7 Acre setting for this Spacious 4 Bedrm. Colonial, 1st floor Large Bedroom Suite with full bath. Also on Main Level: 12x14, Den/office or work-out room. Kitchen with Corian countertops, blt.In Ovens, fireplace & breakfast bar over-looking gorgeous backyard with Slate Patio, Stone Walls & private view. Adjacent to Kitchen is: 15x13 Family Room or informal Dining with custom

  Kathleen Logan Kathy Logan Real Estate

  Unlisted Address
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  /40

  $375,000

  • 6 Beds
  • 2 Baths
  • 1,862 Sq Ft

  91 Cutler St, Watertown, CT 06795

  This home boasts 6 bedrooms! 2 on the first floor and 4 on the second. All hardwood floors and brand new paint throughout. Walls, ceilings, doors and trim. Just needs a few cosmetic updates to make this shine. The pool is great in this summer heat! It is heated so you can get a few extra months a year. The location is very convienient. You can walk into town. Gas, shopping, restaurants, church,

  Stacey Costanzo eXp Realty

  91 Cutler St, Watertown, CT 06795
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  /40

  $849,900

  • 5 Beds
  • 3.5 Baths
  • 4,414 Sq Ft

  21 Hidden Pond Dr, Watertown, CT 06795

  Welcome to this Majestic Colonial home, nestled on a picturesque 1.92-acre lot in one of Watertown's most coveted neighborhoods. With 4,414 square feet of meticulously maintained living space, this home offers the perfect blend of elegance, comfort, and functionality. As you enter, you'll be greeted by a spacious and bright foyer that flows into a variety of inviting living areas. The heart of

  Robert Disapio Dave Jones Realty, LLC

  21 Hidden Pond Dr, Watertown, CT 06795
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  /39

  $347,900

  • 5 Beds
  • 3.5 Baths
  • 3,476 Sq Ft

  49 Chestnut Ave, Torrington, CT 06790

  Investors & homeowners take note! Great opportunity to own a versatile property. Live in one unit and rent the other to offset mortgage costs! Each unit features a spacious layout with an eat-in kitchen, formal dining room, and formal living room, all highlighted by hardwood floors. The second unit offers flexibility with 3-4 bedrooms and additional attic space-perfect for a home office, guest

  MARCO MONROY The Washington Agency

  49 Chestnut Ave, Torrington, CT 06790
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  /40

  $9,850,000

  • 7 Beds
  • 8 Baths
  • 9,200 Sq Ft

  Unlisted Address

  Butternut Brook House: Litchfield Hills Estate with Pond, Pool & Guest Homes - Butternut Brook House is a luxurious Litchfield County estate nestled in the heart of the Litchfield Hills, offering a rare combination of privacy, sophistication, and natural beauty. Set on over 36 acres of pristine Connecticut countryside, this stunning property features sweeping western views, a private pond,

  Elyse Morris Elyse Harney Real Estate

  Unlisted Address
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  /34

  $529,000

  • 5 Beds
  • 3 Baths
  • 2,315 Sq Ft

  172 Bentley Cir, Goshen, CT 06756

  This spacious Raised Ranch located in Woodridge Lake is ready for its next owner! Meticulously maintained, this ranch is easy lake community living with 5 total bedrooms and 3 full bathrooms. The main level features a living room with vaulted ceilings and a cozy fireplace that opens onto the front deck overlooking the sloping property and pond! The kitchen features a large island with seating

  Ted Murphy E.J. Murphy Realty

  172 Bentley Cir, Goshen, CT 06756
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  /3

  $339,900

  • 6 Beds
  • 3 Baths
  • 2,600 Sq Ft

  393 S Main St, Torrington, CT 06790

  Three family property, centrally located, comprised of two separate structures. Great potential. Needs work but worth the effort. Long term tenants in place (month to month) and wish to stay. Paved, easy to care for lot. Inquire for details. Access limited. Square footage approximate 1250 and 1350. Property sold as is.

  Douglas Yeomans Higgins Group Bedford Square

  393 S Main St, Torrington, CT 06790
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  /40

  $685,000

  • 5 Beds
  • 3.5 Baths
  • 3,488 Sq Ft

  68 High St, New Hartford, CT 06057

  This is the one you have been waiting for! Perched atop a gentle hill, this exquisite move-in ready home offers stunning panoramic views and is just a short walk to the heart of New Hartford. A rare find in this area, this five bedroom, three and a half bath Colonial is connected to public water and public sewer. Step through the front door and be impressed by an inviting open floor plan. To the

  Ann-Marie Rossley Berkshire Hathaway NE Prop.

  68 High St, New Hartford, CT 06057
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  /6

  $449,900

  • 7 Beds
  • 5 Baths
  • 3,178 Sq Ft

  908 Main St, Torrington, CT 06790

  Come and checkout this Oversized 3 family property! Large open units with washer/dryer hookups in each unit. Large parking area along with a nicely manicured yard area! This one wont last long! Great investment opportunity whether you live in one unit and rent out the other two, or rent the whole building! May be possible to convert to a 4 Family Residence, Buyer/Agent must do their own due

  Brian Barbosa (Broker) Brian Barbosa (Broker)

  908 Main St, Torrington, CT 06790
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  /28

  $1,095,000

  • 5 Beds
  • 4.5 Baths
  • 4,116 Sq Ft

  89 Iron Ore Hill Rd, Bridgewater, CT 06752

  This spacious Colonial is perfectly set on 2+ acres adjacent to a nature preserve with hiking trails. The sought-after neighborhood includes dock rights on Lake Lillanonah for boating, waterskiing, kayaking, swimming. The kitchen was renovated about 10 years ago. Its center island and bar area open to the family room and dining room. The formal living room can also be used as a media room and

  Stacey Matthews W. Raveis Lifestyles Realty

  89 Iron Ore Hill Rd, Bridgewater, CT 06752
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  /31

  $334,900

  • 5 Beds
  • 2 Baths
  • 1,257 Sq Ft

  54 Greenridge Rd, Torrington, CT 06790

  Welcome to 54 Greenridge, a beautifully maintained 4-bedroom, 2-bath Cape tucked away on a quiet dead-end street in Torrington's east end. Set on a lovely piece of property, this home blends charm, comfort, and thoughtful updates throughout. The heart of the home is the remodeled kitchen (2021), featuring granite countertops, stainless steel appliances, and a cozy breakfast nook that catches the

  Pascale Nejaime William Pitt Sotheby's Int'l

  54 Greenridge Rd, Torrington, CT 06790
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  /38

  $5,995,000

  • 7 Beds
  • 8.5 Baths
  • 6,351 Sq Ft

  85 W Church Hill Rd, Washington Depot, CT 06794

  Stunning uber luxe retreat built to the highest standards in premier location. 7 bedrooms, 8 Full and 1 half Waterworks bathrooms. Long driveway. Combined Living/Dining with wood burning fireplace, steel French doors to outdoor stone terrace. Eat-in Kitchen. Enclosed screened porch with fireplace. Library/Home Office with vaulted ceiling, antique beams, built-in bookshelves and wood burning

  Peter Klemm Klemm Real Estate Inc

  85 W Church Hill Rd, Washington Depot, CT 06794
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  /37

  $799,000

  • 6 Beds
  • 3.5 Baths
  • 5,072 Sq Ft

  21 South Rd, Harwinton, CT 06791

  A Rare Country Estate with New York Elegance - Just Minutes from Litchfield! Step into timeless charm and modern comfort at 21 South Road, a rare 4+ acre estate located in Harwinton's prestigious Historic District. Less than 2 hours from Manhattan and minutes from Litchfield center, this refined country retreat offers an ideal escape for discerning buyers seeking peace, privacy, and

  Penelope Woodford Coldwell Banker Realty

  21 South Rd, Harwinton, CT 06791
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  /27

  $599,900

  • 5 Beds
  • 2 Baths
  • 2,925 Sq Ft

  61 Park Lane Rd, New Milford, CT 06776

  This One Is Just Right! Step into the charm of this Progressive Era beautiful 2-family home set on 1+ acre in New Milford's flexible B1 zone. With over 2,600 sq ft of living space, this property offers income potential, character, and room to grow. The main level unit features 3 bedrooms, 1 bath, soaring 9' ceilings, an eat-in kitchen, spacious rooms, basement access, and a gorgeous wraparound

  Todd Sargent Coldwell Banker Realty

  61 Park Lane Rd, New Milford, CT 06776
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  /29

  $349,900

  • 6 Beds
  • 2 Baths
  • 2,357 Sq Ft

  114 Pulaski St, Torrington, CT 06790

  Well maintained 2 family home features large apartments with laundry hook-ups in each unit. First floor has 2 bedrooms, 1 bath, large open living room/dining area, and eat-in kitchen. 2nd floor has 2 bedrooms on main level and fully finished walk up attic with two more bedrooms, large living room/dining area. Both units have laundry hook-ups in unit, front and side porches and off street parking.

  Mary Mary LeBlanc Realty

  114 Pulaski St, Torrington, CT 06790
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  /40

  $995,000 Open Sun 12PM - 2PM

  • 5 Beds
  • 3.5 Baths
  • 3,752 Sq Ft

  11 College Hill Rd, Canaan, CT 06018

  Welcome to Owls Nest - a peaceful and private retreat tucked away on over 5 acres in the hills of Canaan in the foothills of the Berkshires. This beautifully maintained colonial offers 4 bedrooms, 3.5 bathrooms, and timeless charm throughout. Upstairs, all bedrooms feature hardwood floors, while the main level boasts 2 wood-burning fireplaces, a spacious living room, a formal dining room, and a

  Dave Jones Dave Jones Realty, LLC

  11 College Hill Rd, Canaan, CT 06018
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  /36

  $425,000

  • 7 Beds
  • 4 Baths
  • 2,648 Sq Ft

  238 E Main St, Torrington, CT 06790

  Don't miss this excellent opportunity to own a fully rented 4-unit multifamily property offering solid returns and long-term stability. This well-maintained building includes a diverse mix of units: 1x1BR, 1x1BR+Office Room, 1x2BR+Office room, 1x3BR+Office room; two of the units are equipped with in-unit laundry hook-ups, and current washer/dryer units are tenant-owned. All apartments are

  Jessica Chavez Turning Point Realty, LLC

  238 E Main St, Torrington, CT 06790
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  /40

  $1,335,000

  • 5 Beds
  • 6 Baths
  • 6,201 Sq Ft

  325 Woodbury Rd, Watertown, CT 06795

  Own a grand architectural gem. This 1926 Georgian Revival slate-roofed brick mansion is impeccably restored to 21st century high standards with 3.33 professionally landscaped acres, a natural pond, specimen trees and gunite pool tucked into flourishing gardens having a hundred year's growth under the loving hands of avid gardeners, all breathtaking to behold. Known as The Lilley House, built for

  GRACE FRANJOLA Berkshire Hathaway NE Prop.

  325 Woodbury Rd, Watertown, CT 06795
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  /17

  $759,900

  • 7 Beds
  • 4 Baths
  • 2,940 Sq Ft

  8 Southbury Rd, Roxbury, CT 06783

  Wonderful opportunity to live in the heart of prestigious Roxbury in Litchfield County. Well preserved antique colonial filled with charm. Updates include kitchen, baths and open living area leading to primary bedroom. Brand new septic, 4 car garage with storage above and period outbuildings including a barn. Washer and dryer are located on the main level, upstairs bedrooms offer privacy for

  Lisa Titcomb William Pitt Sotheby's Int'l

  8 Southbury Rd, Roxbury, CT 06783
• 

  

  /40

  $1,349,000

  • 5 Beds
  • 3.5 Baths
  • 3,432 Sq Ft

  118 South St, Litchfield, CT 06759

  LOCATED IN THE HEART OF HISTORIC LITCHFIELD on one of the town's most celebrated streets, this historic South Street residence offers a rare opportunity to own a piece of Connecticut's past. Known as the Huntington-Andrews House, this c.1800 home was once the residence of Charles B. Andrews-Connecticut's only Governor to later serve as Chief Justice-making it a true local landmark. SET AMONG

  Beverly Mosch William Pitt Sotheby's Int'l

  118 South St, Litchfield, CT 06759

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