Litchfield, CT Homes

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  $400,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,209 Sq Ft

  110 Rugg Brook Rd, Winsted, CT 06098

  Wow! Check out this beautiful, modern, colonial built in 1998 with over 2,000 square feet on 3+ level acres with an inground pool and an attached garage. Enjoy the comfortable feel and the beautiful hardwood floors, vaulted ceiling in the primary bedroom suite. With views of Winchester Club Pond this is the perfect location for peace and quiet.

  Michelle Grant Coldwell Banker Premier Real Estate

  110 Rugg Brook Rd, Winsted, CT 06098
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  /19

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 834 Sq Ft
  • Townhouse for Rent

  141 Boyd St, Winchester, CT 06098

  Stop by and check out this charming duplex style rental close to the highland beach public boat launch and Holland beach . You can buy a beach pass at Townhall for lots of summer fun . This unit features a covered front porch that enters you into a cozy living room with recessed lighting , wood floors and a fireplace mantel . The kitchen has been remodeled with stainless appliances, refrigerator,

  Mary Mary LeBlanc Realty

  141 Boyd St, Winchester, CT 06098
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  $325,000 Sold Jul 17, 2025

  • 1,849 Sq Ft
  • $176/SF
  • 40 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1956

  284 Gilbert Ave, Winsted, CT 06098

  Welcome to 284 Gilbert Avenue-a charming 4-bedroom Cape that combines efficient updates with inviting living spaces. Approximately 1,849 sq ft of sun-splashed interiors begin with a spacious eat-in kitchen featuring generous cabinetry, a dining area, and sliders that open to an elevated deck-perfect for grilling while enjoying the privacy of the beautifully manicured backyard. The main level also

  David Sartirana Northwest CT Realty

  284 Gilbert Ave, Winsted, CT 06098
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  Est $395,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  111 Mundry Rd, Torrington, CT 06790

  111 Mundry Rd, Torrington, CT 06790
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  /27

  $375,000

  • 3 Beds
  • 3,660 Sq Ft

  57 Main St, Winsted, CT 06098

  Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

  Stacy LaQuerre Regall Realty, LLC

  57 Main St, Winsted, CT 06098
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  /11

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Townhouse for Rent

  188 E Lake St, Winsted, CT 06098

  Welcome to our beautiful lakeside apartment! 2 bedroom/1 Bath. Situated on the picturesque shores of Highland Lake, this fully renovated and furnished apartment offers stunning views and serenity. The apartment features a spacious living area, a fully equipped kitchen, huge primary bedroom with lake views, dedicated office space and in unit laundry. Whether you are looking for a peaceful

  Annie Simard LPT Realty

  188 E Lake St, Winsted, CT 06098
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  $282,000 Sold Jul 16, 2025

  • 2,470 Sq Ft
  • $114/SF
  • 10 Days On Market

  • 5 Beds
  • 1.5 Baths
  • Built 1890

  88 Strong Terrace, Winsted, CT 06098

  This solid 5-bedroom colonial in Winsted has been in the same hands for over 40 years and been well taken care of the whole time. With almost 2,500 square feet there's plenty of space for whatever you need, whether it's family, guests, or just room to spread out. Inside, you'll find large living and dining areas, good-sized bedrooms, and lots of natural light. If you're looking for space,

  Austin Brochu Sullivan Real Estate Inc

  88 Strong Terrace, Winsted, CT 06098
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  Est $256,206 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft

  139 Boyd St, Winsted, CT 06098

  139 Boyd St, Winsted, CT 06098
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  $259,900

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  179 Gilbert Ave, Winsted, CT 06098

  Welcome to 179 Gilbert Avenue! This charming Ranch-style home offers a total of over 1,700 square feet of comfortable living space, with 1,144 sq ft on the main level featuring a cozy living room, an eat-in kitchen, full bathroom, and three bedrooms. The finished lower level adds approximately 600 sq ft and provides great flexibility with a spacious family room, a second full bath, and an

  David Sartirana Northwest CT Realty

  179 Gilbert Ave, Winsted, CT 06098
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  $120,000 Sold Jul 08, 2025

  • 570 Sq Ft
  • $211/SF
  • 3 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1984

  11 Gibbs St Unit 7, Winsted, CT 06098

  Welcome to easy, one-level living in this rarely available unit at Gilbert Commons! This well-maintained 1 bedroom, 1 full bathroom condo offers approximately 570 square feet of comfortable living space with plenty of natural light and privacy. Inside, you'll find a spacious living room, a well-appointed kitchen with generous cabinet storage, and your own dedicated laundry room. The modest

  David Sartirana Northwest CT Realty

  11 Gibbs St Unit 7, Winsted, CT 06098
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  Est $259,507 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  174 Wallens St Unit D3, Winsted, CT 06098

  174 Wallens St Unit D3, Winsted, CT 06098
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  /20

  $259,900

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  22 Curtice St, Winsted, CT 06098

  Step into timeless elegance with this beautifully updated colonial-style home, where classic charm meets modern convenience. Gleaming hardwood floors flow seamlessly throughout the main living areas, creating a warm and inviting atmosphere. The fully renovated kitchen is a chef's dream, featuring premium finishes, sleek countertops, and top-of-the-line appliances. Upstairs, you'll find spacious

  Terence Dominick Complete Real Estate

  22 Curtice St, Winsted, CT 06098
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  $314,000 Sold Jul 03, 2025

  • 1,480 Sq Ft
  • $212/SF
  • 64 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  150 Mathew Rd, Winsted, CT 06098

  Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, lake rights. 6,500 watt whole house generator. 8x12 shed with power, 35 Amp out side outlet for camper, working chimney for wood stove on lower level, ASSUMABLE MORTGAGE!

  Josh Dionne Commercial Services Realty

  150 Mathew Rd, Winsted, CT 06098
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  Est $238,522 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  174 Wallens St Unit D2, Winsted, CT 06098

  174 Wallens St Unit D2, Winsted, CT 06098
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  /32

  $349,900

  • 5 Beds
  • 2 Baths
  • 2,531 Sq Ft

  41 Lovely St, Winsted, CT 06098

  Highest and Best by Wednesday at 1 pm. Lovely 2 family home on a side street ,not far from Highland lake, parks, town hall, restaurants and shopping . The home is in move in condition and features updated ,fully applianced kitchens & updated baths, wood floors and Vinyl windows.The 1st floor features 6 rooms , 3 bedrooms and 1 bath with access to the basement. The second floor features 5 rooms ,

  Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
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  $225,000 Sold Jul 03, 2025

  • 1,612 Sq Ft
  • $140/SF
  • 166 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1900

  39 Baker St, Winsted, CT 06098

  Wonderful opportunity to own a 2 family with a newer 2 car garage. Home has gas heat. Wood floors thru out, in need of refinishing. Updated cabinets in kitchens; in need of flooring and appliances. Units each have their own heat and laundry hook ups. Wonderful front covered porches. Private back deck 12x12. Thermal paned windows thru out. Property in need of cosmetic updates, TLC. Subject to

  Christine Hunter Hunter Real Estate, LLC

  39 Baker St, Winsted, CT 06098
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  Est $240,771 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit D1, Winsted, CT 06098

  174 Wallens St Unit D1, Winsted, CT 06098
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  /34

  $314,900

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft

  107 Old Rd N, Winchester, CT 06098

  Completely Updated Raised Ranch on a Peaceful, Secluded Lot in Winsted! Escape the noise and discover this beautifully updated Raised Ranch, set on a private 0.78-acre lot in the quiet town of Winsted. Surrounded by nature and tucked away in a serene setting, this home offers the perfect balance of indoor comfort and outdoor living. Inside, you'll love the bright, open layout and thoughtful

  Jill Rubino Century 21 AllPoints Realty

  107 Old Rd N, Winchester, CT 06098
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  $1,575,000 Sold Jun 30, 2025

  • 2,687 Sq Ft
  • $586/SF
  • 316 Days On Market

  • 7 Beds
  • 4 Baths
  • Built 1890

  508 W Wakefield Blvd, Winsted, CT 06098

  Welcome to Strong Island, a waterfront retreat on Highland Lake. The clean waters of Highland Lake in the town of Winchester in Litchfield County surround this 1.6 acres island. History abounds for this property as the original house dates back to 1890. There were significant alterations made in 1920 that added several rooms, a boat house, a barn and porch. Babe Ruth made several trips to Strong

  Pierre Moran William Pitt Sotheby's Int'l

  508 W Wakefield Blvd, Winsted, CT 06098
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  Est $284,322 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  174 Wallens St Unit C3, Winsted, CT 06098

  174 Wallens St Unit C3, Winsted, CT 06098
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  /10

  $235,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  130 Stanton Ave, Winsted, CT 06098

  Step right into effortless living with this charming 2bedroom ranch-style home, nestled right in town and wrapped in durable, lowmaintenance vinyl siding. As you approach, you'll appreciate the tidy curb appeal and generous driveway-perfect for guests or extra vehicles. Inside, an open concept living and dining area welcomes you with abundant natural light and easy flow, ideal for both everyday

  David D'Amore Northwest CT Realty

  130 Stanton Ave, Winsted, CT 06098
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  $950,000 Sold Jun 27, 2025

  • 3,216 Sq Ft
  • $295/SF
  • 55 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2008

  355 W Lake St, Winsted, CT 06098

  Sweeping Views, Exceptional Craftsmanship, and Lake Life at Its Finest.Set on a rare half-acre double lot across from Highland Lake, this custom-built 5-6 bedroom home offers panoramic views over First Bay and deeded dock access just steps from your front door-perfectly positioned beside Holland Beach for the ultimate lake lifestyle. Thoughtfully designed and meticulously maintained, the home

  David Sartirana Northwest CT Realty

  355 W Lake St, Winsted, CT 06098
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  Est $1,149,509 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,963 Sq Ft

  411 W Wakefield Blvd, Winsted, CT 06098

  411 W Wakefield Blvd, Winsted, CT 06098
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  /9

  $222,500

  • 3 Beds
  • 1.5 Baths
  • 976 Sq Ft

  1 Hamill Dr, Winsted, CT 06098

  Good bones! Good location! Good opportunity! Every room in this home needs your touch! Great opportunity to build sweat equity if your handy and can do some of the work yourself! The yard also needs work. Present homeowner envisioned bringing in some fill to grade the yard back behind the home. Right now it drops off and so only a little around the house is usable. It could be nice! So if your

  Nancy Bard Bard Real Estate, LLC

  1 Hamill Dr, Winsted, CT 06098
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  $157,500 Sold Jun 26, 2025

  • 992 Sq Ft
  • $159/SF
  • 3 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  19 Riveredge Dr Unit 19, Winsted, CT 06098

  Don't miss your chance to own this beautiful Riveredge condo as these condos go under contract within hours! In the kitchen you will find brand new Stainless Steel appliances as well as brand new cupboards and counters! Freshly painted throughout and new carpet on stairs and second floor. Also, a brand new water tank has been installed! Nothing for you to do but move your belongings in and enjoy

  Maria Smith KW Legacy Partners

  19 Riveredge Dr Unit 19, Winsted, CT 06098
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  Est $294,172 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, Winsted, CT 06098
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  /19

  $287,750

  • 4 Beds
  • 1 Bath
  • 1,492 Sq Ft

  12 Cherry St, Winsted, CT 06098

  This Home is Modern day updates Meets Old World Charm...The Updated Kitchen offers granite counter tops, custom cabinetry, tile flooring, and a pantry with Washer/ dryer hookups for convenience.. You'll find a formal dining room with hardwood floors, A main level bedroom, large living room with French doors and open stair case that leads to the upstairs.. Also on the Main level you'll find a

  Sue MCGHEE The Washington Agency

  12 Cherry St, Winsted, CT 06098
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  $269,900 Sold Jun 25, 2025

  • 1,424 Sq Ft
  • $190/SF
  • 31 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1948

  115 Stanton Ave, Winsted, CT 06098

  Step inside this charming Cape Cod style home as you walk in the front door your in a large living room with wood floors, big picture window and lots of sunshine and seasonal views. The kitchen is bright and sunny and has room for a large table. The master bedroom is also on the main level and features double closets and wood floors. The full bath is also on this level . There is a cozy sunroom

  Mary Mary LeBlanc Realty

  115 Stanton Ave, Winsted, CT 06098
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  Est $621,496 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,318 Sq Ft

  715 W Wakefield Blvd, Winsted, CT 06098

  715 W Wakefield Blvd, Winsted, CT 06098
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  /14

  $224,900

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft

  99 Norfolk Rd, Winsted, CT 06098

  99 Norfolk Rd, Winsted CT - Opportunity Knocks! This cute 3-bedroom Cape sits proudly on 1.3 acres and is ready for its next chapter! With vinyl siding, replacement windows, and a lovely setting perched high up from the road, the bones are here-now it just needs your vision. For those seeking an investment opportunity or ready to roll up their sleeves and bring this gem back to life, this could

  Lisa McCarthy Coldwell Banker Realty

  99 Norfolk Rd, Winsted, CT 06098
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  $860,000 Sold Jun 24, 2025

  • 3,016 Sq Ft
  • $285/SF
  • 90 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1956

  399 Colebrook Rd, Colebrook, CT 06021

  HILLTOP COMFORT IN COLEBROOK - Welcome home and put those cares aside in this meticulously maintained Country Colonial, a home transformed in the 1990's with a seamless conversion from a single level house to a spacious two level home. The 10.15 acres includes two additional building lots, a spring fed pond, apple trees, stone walls, gardens that delight in any season, and a wonderful patio that

  David Taylor Elyse Harney Real Estate

  399 Colebrook Rd, Colebrook, CT 06021
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  Est $277,579 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
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  /28

  $300,000

  • 4 Beds
  • 1 Bath
  • 1,978 Sq Ft

  279 Pratt St, Winsted, CT 06098

  Perched atop Pratt Street in Winsted, this traditional farmhouse offers a peaceful retreat on a generous 1.75-acre lot. Tucked away from the hustle and bustle, the property provides a quiet sanctuary surrounded by nature, perfect for those yearning to live out their farming dreams. The home itself features a classic farmhouse charm with inviting living spaces. You'll find warm hardwood floors

  Michelle Grant Coldwell Banker Premier Real Estate

  279 Pratt St, Winsted, CT 06098
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  $113,000 Sold Jun 23, 2025

  • 570 Sq Ft
  • $198/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1985

  11 Gibbs St Unit 9, Winsted, CT 06098

  Welcome to easy, one-level living in this rarely available first-floor end unit at Gilbert Commons! This well-maintained 1 bedroom, 1 full bathroom condo offers approximately 570 square feet of comfortable living space with plenty of natural light and privacy. Inside, you'll find a spacious living room, a well-appointed kitchen with generous cabinet storage, and your own dedicated laundry room.

  David Sartirana Northwest CT Realty

  11 Gibbs St Unit 9, Winsted, CT 06098
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  Est $178,009 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  17 Front St, Winsted, CT 06098

  17 Front St, Winsted, CT 06098
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  /39

  $779,900

  • 3 Beds
  • 3.5 Baths
  • 4,953 Sq Ft

  111 South Rd, Winsted, CT 06098

  Perched up higher than the rest with sweeping views up a private driveway in beautiful Winchester Center you'll find this custom built 4,953 sq ft Colonial nestled in on 3.97 serene & bucolic acres. For the car enthusiasts, you'll see a 3 bay garage that can fit up to at least 7 cars if lifts are installed including a bonus 2 car tandem garage within the 3 bays. Plenty of room for oversized

  Dawn Rousseau Showcase Realty, Inc.

  111 South Rd, Winsted, CT 06098
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  $460,000 Sold Jun 20, 2025

  • 3,021 Sq Ft
  • $152/SF
  • 128 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1875

  288 Torringford St, Winsted, CT 06098

  Welcome to this charming four-bedroom antique home that is beautifully renovated to blend timeless character with modern comforts. As you step inside you'll be greeted by the warmth of refinished hardwood floors and an inviting living room featuring a cozy fireplace and built-in bookcases perfect for relaxing or entertaining. The heart of the home is the brand-new kitchen boasting sleek granite

  Mark Porriello RE/MAX Right Choice

  288 Torringford St, Winsted, CT 06098
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  Est $441,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  319 Taylor Brook Rd, Winsted, CT 06098

  319 Taylor Brook Rd, Winsted, CT 06098
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  $850,000

  • Land
  • 116 Acres
  • $7,296 per Acre

  82 Riverton Rd, Colebrook, CT 06021

  Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

  Suzie Larson Turning Point Realty, LLC

  82 Riverton Rd, Colebrook, CT 06021
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  $280,000 Sold Jun 16, 2025

  • 1,424 Sq Ft
  • $197/SF
  • 110 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  174 Boyd St, Winsted, CT 06098

  A charming house located 2 blocks from highland lake. This 3 bedroom, 1 large full bath is move-in ready. The dining room has a beautiful built in, the 3 large windows allowing for natural light to brighten the room. Off of the dining room is a nice family room. The kitchen is large and spacious and off the kitchen in the back is a lovely sunroom with a fireplace (natural gas) that has sliders

  Margaret Alexson Elyse Harney Real Estate

  174 Boyd St, Winsted, CT 06098

Showing Results 41 - 80, Page 2 of 18