Litchfield, CT Homes

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  $225,000

  • Land
  • 0.23 Acre
  • $978,261 per Acre

  129 Shore Dr, Winsted, CT 06098

  A RARE OPPORTUNITY on HIGHLAND LAKE! This approved buildable lot is ready and waiting for you to build your dream! Lake life is a great life, make it yours!

  Annie Simard LPT Realty

  129 Shore Dr, Winsted, CT 06098
• 

  $397,000 Sold Jun 04, 2025

  • 1,426 Sq Ft
  • $278/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1989

  323 E Wakefield Blvd, Winsted, CT 06098

  Charming 3-Bedroom Cape in Sought-After Lake Community. Welcome to this beautifully updated 3-bedroom, 2.5-bath Cape nestled in a vibrant lake community offering year-round fun! Enjoy boating, waterskiing, tubing, and all the perks of lake life just steps from your door, with serene water views to enjoy every day. The main level features a bright, inviting living room with hardwood floors and a

  Heather Crabtree Coldwell Banker Realty

  323 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $278,737 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  132 E Lake St, Winsted, CT 06098

  132 E Lake St, Winsted, CT 06098
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  /35

  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
• 

  $314,000 Sold May 30, 2025

  • 1,536 Sq Ft
  • $204/SF
  • 56 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1979

  155 Mathew Rd, Winsted, CT 06098

  Situated on a private road with views of Highland Lake, this beautifully updated home offers a perfect blend of modern comfort and quiet surroundings. Boasting a brand-new roof, siding, windows, as well as new front and back porches this home is ready to go for anyone looking for a great home. Step inside to discover an inviting, light-filled interior with contemporary finishes throughout. The

  Austin Brochu Sullivan Real Estate Inc

  155 Mathew Rd, Winsted, CT 06098
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  Est $280,692 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  107 Peck Rd, Winsted, CT 06098

  107 Peck Rd, Winsted, CT 06098
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  /36

  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
• 

  $250,000 Sold May 30, 2025

  • 2,094 Sq Ft
  • $119/SF
  • 80 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1860

  150 Meadow St, Winsted, CT 06098

  Steeped in history and charm, this 1860-built home offers a blend of classic character and modern updates. With 8 rooms, 4 bedrooms, and 2 baths, this spacious home provides versatile living options. The main level features a kitchen with recent updates, a dining room, a cozy living room, a primary bedroom with an en-suite bath, and a home office. Upstairs, you'll find three bedrooms, a study

  David Sartirana Northwest CT Realty

  150 Meadow St, Winsted, CT 06098
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  Est $272,688 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,490 Sq Ft

  257 Walnut St, Winsted, CT 06098

  257 Walnut St, Winsted, CT 06098
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  /2

  $49,000

  • Land
  • 0.37 Acre
  • $132,432 per Acre

  99 Hubbard St, Winsted, CT 06098

  99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

  David Sartirana Northwest CT Realty

  99 Hubbard St, Winsted, CT 06098
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  $144,000 Sold May 29, 2025

  • 1,768 Sq Ft
  • $81/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1910

  9 Loomis St, Winsted, CT 06098

  ZONING IS TG Regulations are tailored to promote desired development patterns that promote an appropriate transition from rural to town uses. Certain uses are permitted, while others require a Special Permit. Nestled just minutes from Highland Lake and downtown Winchester, 9 Loomis Street presents an excellent opportunity for those seeking a fixer-upper with great potential. This colonial-style

  Kristen Duchene Litchfield County Real Estate

  9 Loomis St, Winsted, CT 06098
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  Est $292,000 Not Listed For Sale

  • 5 Beds
  • 2,820 Sq Ft

  204 Gilbert Ave, Winsted, CT 06098

  204 Gilbert Ave, Winsted, CT 06098
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  /2

  $29,000

  • Land
  • 0.44 Acre
  • $65,909 per Acre

  124 Rockwell St, Winsted, CT 06098

  124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless

  David Sartirana Northwest CT Realty

  124 Rockwell St, Winsted, CT 06098
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  $355,000 Sold May 29, 2025

  • 2,239 Sq Ft
  • $159/SF
  • 46 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  173 Torringford St, Winsted, CT 06098

  Welcome to this beautiful Cape Cod home, offering 2239 square feet of living space. Nestled on a serene 1.79 acre lot, this inviting property provides a perfect blend of comfort and style. Step inside to a generous entry that flows seamlessly into the open living and dining areas, creating an ideal space for both everyday living and entertaining. The huge family room is a true highlight,

  Sandy Fehrs Lamacchia Realty

  173 Torringford St, Winsted, CT 06098
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  Est $280,820 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,294 Sq Ft

  28 Moore Ave, Winsted, CT 06098

  28 Moore Ave, Winsted, CT 06098
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  /39

  $950,000

  • 14 Beds
  • 7 Baths
  • 4,860 Sq Ft

  175 N Main St, Winsted, CT 06098

  Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail) in Winsted with anchor tenant Noli's Restaurant (Rent $2,266 w 3% increase/year) w over 20 years in business! Pride of Ownership is evident with Capital Improvements made by the current owners, including: new water heaters, heating zones, electrical

  Ryan Rea Berkshire Hathaway NE Prop.

  175 N Main St, Winsted, CT 06098
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  $279,000 Sold May 19, 2025

  • 1,101 Sq Ft
  • $253/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1956

  56 Lakeview Rd, Winsted, CT 06098

  Don't miss this 3 bedroom Ranch with a 2 car attached garage and an amazing view of Highland Lake - very close proximity to state boat launch and public beach. Some TLC will be well worth the effort here! Roof (2019), heating system (November 2017), and central air!

  Tony Goia The Washington Agency

  56 Lakeview Rd, Winsted, CT 06098
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  Est $219,315 Not Listed For Sale

  • 6 Beds
  • 2,421 Sq Ft

  3 Brookside Ave, Winsted, CT 06098

  3 Brookside Ave, Winsted, CT 06098
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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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  $320,000 Sold May 16, 2025

  • 1,509 Sq Ft
  • $212/SF
  • 29 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  47 Moore Ave, Winsted, CT 06098

  Nestled in the charming town of Winchester, Connecticut, this beautifully remodeled ranch home offers the perfect blend of modern elegance and cozy comfort. Boasting four spacious bedrooms and seven total rooms, this residence features hardwood floors throughout and a thoughtfully updated galley kitchen that will inspire your inner chef. Gorgeous granite counters and new appliances, with a quaint

  Suzie Larson Turning Point Realty, LLC

  47 Moore Ave, Winsted, CT 06098
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  Est $202,157 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  111 Riverton Rd Unit 66, Winsted, CT 06098

  111 Riverton Rd Unit 66, Winsted, CT 06098
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  /5

  $295,000

  • Land
  • 51 Acres
  • $5,784 per Acre

  393 Winchester Rd, Winsted, CT 06098

  WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

  Tom McGowan Elyse Harney Real Estate

  393 Winchester Rd, Winsted, CT 06098
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  $8,000 Sold May 16, 2025

  • 980 Sq Ft
  • $8/SF
  • 44 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  104 Norfolk Rd, Winsted, CT 06098

  An opportunity for redevelopment! This bungalow-style home, situated on a 0.50-acre lot along State-maintained Route 44, is beyond salvageable and will require demolition. Offering 980 sq. ft. of living space with 5 rooms, including 2 bedrooms and 1 full bath, the property is in unsafe condition and there will be no access granted due to structural concerns. While located in a rural setting, it

  David Sartirana Northwest CT Realty

  104 Norfolk Rd, Winsted, CT 06098
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  Est $206,610 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  45 Beach St, Winsted, CT 06098

  45 Beach St, Winsted, CT 06098
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  /2

  $69,000

  • Land
  • 2.00 Acres
  • $34,500 per Acre

  503 N Main St, Winsted, CT 06098

  Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

  Charles Albertario William Raveis Real Estate

  503 N Main St, Winsted, CT 06098
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  $190,000 Sold May 15, 2025

  • 1,848 Sq Ft
  • $103/SF
  • 20 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1905

  154 Wallens St, Winsted, CT 06098

  Investors & Owner Occupants, schedule your appointment NOW!!! Come view this 2-family home, price to sell!!! Located near all amenities! Seller is motivated, bring all offers!!!

  Adam Devine Dorrance Realty

  154 Wallens St, Winsted, CT 06098
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  Est $411,593 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,313 Sq Ft

  193 Spencer Hill Rd, Winsted, CT 06098

  193 Spencer Hill Rd, Winsted, CT 06098
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  /2

  $749,900

  • 7 Beds
  • 3 Baths
  • 3,486 Sq Ft

  39 S Main St, Winsted, CT 06098

  THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

  RYAN HORVAY Smith & DeGroat Real Estate

  39 S Main St, Winsted, CT 06098
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  $379,000 Sold May 09, 2025

  • 1,531 Sq Ft
  • $248/SF
  • 90 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  244 Colebrook Rd, Winsted, CT 06098

  Welcome to 244 Colebrook Road, a beautifully renovated home that perfectly blends modern upgrades with timeless charm. Move-in ready, this home features thoughtful updates designed to suit all your lifestyle needs. Virtually staged. The first floor opens to a formal living room that seamlessly connects to a gourmet kitchen, outfitted with all-new appliances and a large quartz island seating

  Carol York For Sale By Owner Connecticut

  244 Colebrook Rd, Winsted, CT 06098
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  Est $249,398 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  234 Oak St, Winsted, CT 06098

  234 Oak St, Winsted, CT 06098
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  /2

  $23,900

  • Land
  • 0.15 Acre
  • $159,333 per Acre

  48 Bridge St, Winsted, CT 06098

  Nestled just steps from downtown, this .15-acre lot offers a fantastic opportunity in a highly convenient location. The property is fairly level and provides easy access to shopping, restaurants, The Gilson Theater, and Little Red Barn Brewery. With city water and sewer available, this lot is ready for your vision. Whether you're looking to build or invest, this prime spot puts you right in the

  David Sartirana Northwest CT Realty

  48 Bridge St, Winsted, CT 06098
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  $160,000 Sold May 07, 2025

  • 992 Sq Ft
  • $161/SF
  • 37 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  37 Riveredge Dr Unit 37, Winsted, CT 06098

  Enjoy the private and peaceful setting of Still River right from your bedroom window or private patio all the while being close to the many amenities offered in town. Inside this well-maintained condo you'll find an abundance of natural light flowing in every room, a bright slider opening up to your own patio, all new paint throughout, lots of storage and durable like-new flooring on the main and

  Erin Ruwet Century 21 AllPoints Realty

  37 Riveredge Dr Unit 37, Winsted, CT 06098
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  Est $139,000 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 734 Sq Ft

  110 E Mountain Ave, Winsted, CT 06098

  110 E Mountain Ave, Winsted, CT 06098
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  /2

  $23,900

  • Land
  • 0.22 Acre
  • $108,636 per Acre

  19 Hill St, Winsted, CT 06098

  Located on a lightly traveled side street, this .22-acre lot offers a peaceful getaway with easy access to downtown. The property features a flat area at the street before gently sloping upward, creating a unique setting for potential future use. City water and sewer are available in the street, but buyers should conduct their own due diligence regarding buildability. Whether you're looking for a

  David Sartirana Northwest CT Realty

  19 Hill St, Winsted, CT 06098
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  $269,000 Sold May 05, 2025

  • 1,175 Sq Ft
  • $229/SF
  • 35 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1880

  39 Finn St, Winsted, CT 06098

  Fabulous Opportunity to own in the Highland lake community. Walking distance to both beaches and boat launch. This adorable3-4 bedroom home has new hardwood floors thru out the first floor, has been freshly painted, new fridge and stove, roof only 2 yrs old, thermal paned windows. Large storage shed. Open concept with a living room/dining room combo. Large area for gardening and ready to move

  Christine Hunter Hunter Real Estate, LLC

  39 Finn St, Winsted, CT 06098
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  Est $267,978 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,582 Sq Ft

  24 Union St, Winsted, CT 06098

  24 Union St, Winsted, CT 06098
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  /21

  $245,000 Pending

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

  174 Wallens St Unit D3, Winsted, CT 06098

  SELDOM AVAILABLE 2 BR MOVE IN CONDITION RANCH AT THE CLOCMAKERS HILL ADULT COMMUNITY FOR 55 AND OVER.SPECIAL END UNIT WITH LOTS OF SUNNY WINDOWS-COVERED FRONT PORCH AND ATTACHED GARAGE-CAIR GAS-HIGH CEILINGS-HICKORY KITCHEN CABINETS WITH CORIAN COUNTERS-REMODELED BATHS -GAS FIREPLACED LIVING ROOM OPEN TO FORMAL DINING ROOM WITH LOTS OF SUNNY WINDOWS-MASTER BEDROOM WITH WALKIN CLOSET AND FULL

  Mary New Berkshire Hathaway NE Prop.

  174 Wallens St Unit D3, Winsted, CT 06098
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  $70,000 Sold May 01, 2025

  • 2,016 Sq Ft
  • $35/SF
  • 18 Days On Market

  • 5 Beds
  • Built 1800

  50-52 Cottage St, Winchester, CT 06098

  Investor Special! This four-level, two-family property at 50-52 Cottage St. was previously prepared for demolition but may still hold potential for the right investor. A complete rehab or possible teardown, this property is being sold as-is and will require vision, expertise, and cash-no financing will qualify. Whether you're looking for a full-scale renovation project or a lot for future

  David Sartirana Northwest CT Realty

  50-52 Cottage St, Winchester, CT 06098
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  Est $235,284 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit C7, Winsted, CT 06098

  174 Wallens St Unit C7, Winsted, CT 06098
• 

  

  /40

  $1,699,500 Pending

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft

  538 Wheelers Point, Winsted, CT 06098

  Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360' direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunning kitchen for folks who cook, charming diningroom with bar and window seat overlooking the waterfront, and spacious

  KAREN NEWTON William Pitt Sotheby's Int'l

  538 Wheelers Point, Winsted, CT 06098

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