Litchfield, CT Homes

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  /8

  $299,900 Pending

  • 6 Beds
  • 2 Baths
  • 2,699 Sq Ft

  77 Hubbard St, Winsted, CT 06098

  Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 452-3957

  77 Hubbard St, Winsted, CT 06098
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  /34

  $1,500 - $1,800 per month

  Mill at Still River

  1 - 2 Beds

  101 Whiting St, Winsted, CT 06098

  By far the best place to live in Winsted, Connecticut. Turn of the century construction, every unit overlooks the beautiful Still River, our 700-1000 square-foot one and two bedroom interiors are bright and charming and feature exposed wood beams, 10-foot ceilings, oversized industrial windows, and exposed brick walls. We deliver nature at your door. Our community amenities include same-floor

  101 Whiting St, Winsted, CT 06098
• 

  $292,000 Sold Jul 25, 2025

  • 2,225 Sq Ft
  • $131/SF
  • 42 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1890

  126 Williams Ave, Winsted, CT 06098

  Excellent investment opportunity! This fully occupied two-family home generates a steady $3,300 in monthly rental income. The property has been completely overhauled in the past few years with almost everything updated. It is located in a great neighborhood in walking distance to all the schools in town. Close to playgrounds and the library. The recently painted exterior of this classic home

  Michelle Grant Coldwell Banker Premier Real Estate

  126 Williams Ave, Winsted, CT 06098
• 

  Est $342,236 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,606 Sq Ft

  283 Colebrook Rd, Winsted, CT 06098

  283 Colebrook Rd, Winsted, CT 06098
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  /38

  $1,295,000

  • 3 Beds
  • 3 Baths
  • 2,420 Sq Ft

  722 Lake Dr, Winsted, CT 06098

  Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy

  Joanne Donne The Washington Agency

  722 Lake Dr, Winsted, CT 06098
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  /9

  $850 per month

  • 1 Bed
  • 1 Bath
  • 625 Sq Ft
  • Apartment for Rent

  14 Gay St, Winsted, CT 06098

  First floor one bedroom apartment with off street parking for one car. First month's rent and two month's security if applicable. One year lease required. Walk to shopping, library and restaurants. Great location!

  David Sartirana Northwest CT Realty

  14 Gay St, Winsted, CT 06098
• 

  $1,200,000 Sold Jul 23, 2025

  • 2,407 Sq Ft
  • $499/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1948

  200 Perch Rock Trail, Winsted, CT 06098

  Exceptional Waterfront Living on Highland Lake - Your Dream Home Awaits! Seize this rare opportunity to own a stunning YEAR-ROUND WATERFRONT property on the highly sought-after EAST SIDE of Highland Lake! This turnkey gem is move-in ready and packed with modern features, offering the ultimate retreat for those seeking the serenity and excitement of lake life. Step into an open-concept kitchen and

  Annie Simard LPT Realty

  200 Perch Rock Trail, Winsted, CT 06098
• 

  Est $297,826 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft

  118 E Mountain Ave, Winchester, CT 06098

  118 E Mountain Ave, Winchester, CT 06098
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  /26

  $385,000

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft

  147 Smith Hill Rd, Winsted, CT 06098

  Tucked away on a wooded lot, this meticulously maintained Cape features 4 spacious bedrooms and a full bathroom on each floor. Enjoy watching the birds & other wildlife on the huge rear deck or enjoy the peaceful setting on the enclosed porch. They don't make them like this anymore! The grounds have been lovingly maintained. You will want to move right in.

  SHARON GILSON Northwest CT Realty

  147 Smith Hill Rd, Winsted, CT 06098
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  /14

  $1,450 per month

  Litchfield Heights

  2 Beds

  15 Mountain View Terrace, Winsted, CT 06098

  Litchfield Heights Apartments is nestled quietly in the greenery of the Berkshires. We are situated close to the border of Massachusetts with easy access from Routes 8 & 44. We offer generously sized 1 bedroom flats, and 2 or 3 bedroom Townhouse. Enjoy the ease of maintenance free living when you make Litchfield Heights Apartments your home. Call Litchfield Heights Apartments today for further

  15 Mountain View Terrace, Winsted, CT 06098
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  $862,500 Sold Jul 23, 2025

  • 2,113 Sq Ft
  • $408/SF
  • 61 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1955

  112 Shore Dr, Winsted, CT 06098

  Live like you're on vacation every day! This beautifully updated lakefront home sits directly on the water in Highland Lake's first Bay, offering a level backyard & a private dock just steps from your door. With 50+ feet of direct waterfront and a fenced, low-maintenance yard, this charming year-round home is the perfect blend of comfort, style, & lakefront living. The interior boasts an open

  Nancy Reardon Berkshire Hathaway NE Prop.

  112 Shore Dr, Winsted, CT 06098
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  Est $43,680 Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098
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  /24

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 2,160 Sq Ft

  181 Torringford St, Winsted, CT 06098

  Charming Colonial on Nearly an Acre! Discover the perfect blend of comfort and space in this 3-bedroom, 1.5-bathroom Colonial home. Situated on almost an acre of flat, usable land, the property features a brand new grand circular driveway and a detached two-car garage. The inviting exterior, with its covered front porch, welcomes you into a home ready for its next chapter. Complete with a

  Michelle Grant Coldwell Banker Premier Real Estate

  181 Torringford St, Winsted, CT 06098
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  /10

  $1,595 per month

  • 4 Beds
  • 1 Bath
  • 1,158 Sq Ft
  • House for Rent

  49 Wetmore Ave Unit 2nd Flr, Winsted, CT 06098

  Spacious 4 bedroom, 2nd floor apartment with a large porch. Washer/dryer hook-up in the unit. Off street parking. Pets considered. Credit and background check required.

  Amanda Balaski Northwest CT Realty

  49 Wetmore Ave Unit 2nd Flr, Winsted, CT 06098
• 

  $370,000 Sold Jul 21, 2025

  • 3,690 Sq Ft
  • $100/SF
  • 6 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1890

  203 Holabird Ave, Winchester Center, CT 06098

  Exceptional Mixed-Use Investment Opportunity Discover the perfect blend of charm, functionality, and income potential at 203 Holabird Avenue in the heart of Winsted, CT. This well-maintained riverfront property features a versatile mixed-use layout with two residential apartments and a dedicated commercial office space, making it ideal for investors or owner-occupants seeking additional income.

  RYAN HORVAY Smith & DeGroat Real Estate

  203 Holabird Ave, Winchester Center, CT 06098
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  Est $107,614 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  11 Gibbs St Unit 6, Winsted, CT 06098

  11 Gibbs St Unit 6, Winsted, CT 06098
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  /35

  $475,000

  • 3 Beds
  • 3 Baths
  • 2,747 Sq Ft

  117 South Rd, Winsted, CT 06098

  Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

  Christina Niziolek William Raveis Real Estate

  117 South Rd, Winsted, CT 06098
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  /20

  $1,000 - $1,450 per month

  Gilbert Clock Apartments

  Studio - 2 Beds

  13 Wallens St, Winsted, CT 06098

  At Gilbert Clock Apartments , our designer-inspired amenities set us apart from the competition. We pride ourselves on providing top-quality apartments outfitted with the everyday amenities you expect as well as luxury amenities to delight your senses and enhance your modern life. Indulge your culinary instincts in your state-of-the-art kitchen, furnished with Beautiful and energy-efficient

  13 Wallens St, Winsted, CT 06098
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  $160,000 Sold Jul 18, 2025

  • 2,914 Sq Ft
  • $55/SF
  • 8 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1947

  100 Norfolk Rd, Winsted, CT 06098

  Endless Potential on 3.7 acres! 4 bedroom and 2 bath cape is a single-family home that was formerly used as a small homestead farm. This home features an open floor plan with soaring 10-foot ceilings on the first floor. The layout is flexible and offers plenty of room to grow. The home is in need of a full rehab and is perfect for investors, DIY enthusiasts, or anyone ready to bring their vision

  Katie Breitkreutz Dave Jones Realty, LLC

  100 Norfolk Rd, Winsted, CT 06098
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  Est $106,508 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  11 Gibbs St Unit 4, Winsted, CT 06098

  11 Gibbs St Unit 4, Winsted, CT 06098
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  /37

  $515,000

  • 5 Beds
  • 4 Baths
  • 5,016 Sq Ft

  55 Walnut St, Winsted, CT 06098

  Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

  David Sartirana Northwest CT Realty

  55 Walnut St, Winsted, CT 06098
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  /18

  $1,350 per month

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

  23 Allen St, Winsted, CT 06098

  Discover your new home in this delightful 2-bedroom, 1-bathroom apartment offering 1,100 square feet of thoughtfully designed living space. Located on a peaceful dead-end road in a quiet neighborhood, this unit combines comfort, convenience, and charm in a prime location close to amenities. Step into an inviting open-concept living and dining area, accentuated by coffered ceilings that add a

  Jeffrey Liskin Northwest CT Realty

  23 Allen St, Winsted, CT 06098
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  $208,900 Sold Jul 18, 2025

  • 1,200 Sq Ft
  • $174/SF
  • 131 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1875

  39 Orchard St, Winsted, CT 06098

  Back on the market, buyer's financing fell through. Welcome to this beautifully updated 3-bedroom, 1.5-bath colonial in the heart of Winsted! This home seamlessly blends classic charm with modern conveniences, featuring a spacious layout, abundant natural light, and stylish updates throughout. The inviting living room offers a cozy atmosphere perfect for gatherings. The updated kitchen boasts

  Michael J Flaherty Jr Sullivan Real Estate Inc

  39 Orchard St, Winsted, CT 06098
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  Est $252,175 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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  /40

  $419,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,105 Sq Ft

  17 Woodland Ave, Winsted, CT 06098

  Beautiful 3 bedroom updated colonial walking distance to Highland lake beach.Large eat in kitchen with granite counter tops,center island,bar area ,spacious sitting area with antique cooking stove that burns wood creates good heat.Living room with hardwood floors,fireplace and built ins.Nice patio off kitchen,yard is landscaped with fountains.2 car garage.This home is in great condition and wont

  Vincent DeVico Showcase Realty, Inc.

  17 Woodland Ave, Winsted, CT 06098
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  /24

  $1,650 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  23 Wetmore Ave Unit 2, Winsted, CT 06098

  Available 8-1-25. Immaculate second floor unit, recently renovated, super clean and bright. Quiet second floor, spacious layout. 2 bedroom, hardwood floors and tile throughout. Pet may be considered. Washer and Dryer in unit. All newer appliances, gas range. Off street parking. Private enclosed second floor back porch and private enclosed front porch. Small water and sewer fee per person.

  Suzie Larson Turning Point Realty, LLC

  23 Wetmore Ave Unit 2, Winsted, 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 $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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  /32

  $425,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,086 Sq Ft

  50 Lakeview Rd, Winsted, CT 06098

  Located just a short stroll from Holland Beach and only a 3-minute drive to the public boat launch, this charming Colonial offers the perfect blend of comfort, convenience, and year-round recreation. Nestled on a level corner lot in a well-established neighborhood, this home invites you to enjoy all the amenities of Connecticut's second-largest lake - from kayaking and boating to lakeside walks

  Paula Nelson William Raveis Real Estate

  50 Lakeview Rd, Winsted, CT 06098
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  /5

  $1,145 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  174 Main St Unit A, Winsted, CT 06098

  One bedroom apartment on the first floor. Large kitchen and a recently remodeled bath. Washer/dryer can be added in the unit for an additional $75 per month. Pets considered. First month and two months security, if applicable. Credit and background check required.

  Amanda Balaski Northwest CT Realty

  174 Main St Unit A, 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 $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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  /39

  $559,999 Pending

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

  144 Marshall St, Winsted, CT 06098

  Welcome to your own private paradise! Nestled on an incredible 55 acres, this one-of-a-kind property offers peace, privacy, and the perfect blend of comfort and outdoor adventure. Featuring a ranch-style layout with 3 bedrooms and 2 full baths, this home is ideal for easy one-level living. Step inside to find hardwood floors throughout and three cozy fireplaces that bring warmth and character to

  Monica Palmerie RE/MAX RISE

  144 Marshall St, 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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  $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
• 

  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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  /28

  $380,000 Under Contract

  • 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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  /9

  $1,400 per month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Property for Rent

  936 Main St Unit 7, Winchester, CT 06098

  Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance to the property is being changed and will be much nicer than now. This is the final phase. Beautiful free standing ranch style homes, 2 bedroom with 2 baths available as well as an attached entrance enclosed porch. This is the only house available, all others are rented to good

  Michael Block Building Blocks LLC

  936 Main St Unit 7, Winchester, CT 06098
• 

  $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
• 

  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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