Litchfield, CT Homes

• 

  Est $269,184 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  39 Rockwell St, Winsted, CT 06098

  39 Rockwell St, Winsted, CT 06098
• 

  

  

  /4

  $250,000

  • Land
  • 16 Acres
  • $15,723 per Acre

  00 Chapel Rd, Winchester, CT 06098

  Look no further for A Very Private location to build your Dream Home?? On this Lot there is the Hilltop which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester may be the place for you. The access to the Rear lot is though 151 Chapel Rd. property.

  Linda Ganem Borla & Associates Real Estate

  00 Chapel Rd, Winchester, CT 06098
• 

  $495,000 Sold Jun 09, 2025

  • 754 Sq Ft
  • $656/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1911

  704 W Wakefield Blvd, Winsted, CT 06098

  Quintessential New England Lake Cottage! Three season sweet lakefront retreat with charm and character on Highland Lake - one of CT's largest lakes. Waterfront dock, deck offering long views over the lake and plenty of seating for family bbq's. Recently remodeled kitchen, charming livingroom with stone fireplace, hardwood floors, beams, newer windows / sliding doors, half bath and shower lower

  KAREN NEWTON William Pitt Sotheby's Int'l

  704 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $203,980 Not Listed For Sale

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

  111 Riverton Rd Unit 30, Winsted, CT 06098

  111 Riverton Rd Unit 30, Winsted, CT 06098
• 

  

  

  /26

  $1,200,000

  • Land
  • 65 Acres
  • $18,380 per Acre

  257 Torringford St, Winchester, CT 06098

  65+ Acre Property with infrastructure and natural features. Spanning over 65 acres, this private property is accessed via a 5,000 foot driveway and features a mix of open space and wooded terrain. The land is bordered by historic stone walls on both sides, adding character and clear boundary lines. Bonus: 14x40 horse barn, ready for livestock or storage. 24x32 building on a concrete slab,

  Sabrina Janco Century 21 Bay-Mar Realty

  257 Torringford St, Winchester, CT 06098
• 

  $286,000 Sold Jun 09, 2025

  • 1,440 Sq Ft
  • $199/SF
  • 25 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1927

  421 Unity Place, Winsted, CT 06098

  UPDATED | SERENE | CHARMING | 2 LOTS | This Highland Lake retreat is ideal for the 1st time homeowner, getaway retreat or investment opportunity. Nestled in New England's natural beauty, you are sure to enjoy your lush surroundings & stunning views, truly a nature lovers delight. 3+ generous bedrooms, 2 full bathrooms, dining room, fireplaced living room, updated kitchen with stainless

  Michelle Lorenzetti Premier Re Group LLC

  421 Unity Place, Winsted, CT 06098
• 

  Est $278,919 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  36 Charles St, Winsted, CT 06098

  36 Charles St, Winsted, CT 06098
• 

  

  /4

  $44,000

  • Land
  • 0.41 Acre
  • $107,317 per Acre

  130 Alpha Ave, Winsted, CT 06098

  Discover the Perfect Canvas for Your Dream Home in Winchester, Connecticut! This exceptional .41-acre parcel (owner reports closer to .5 ac) combines eight contiguous lots to create a prime opportunity for building your ideal residence. Nestled in the serene surroundings of the Highland Lake neighborhood, the property is lightly wooded with mature, straight-standing hardwoods and features a

  Suzie Larson Turning Point Realty, LLC

  130 Alpha Ave, 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 $452,996 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  43 Spencer St, Winsted, CT 06098

  43 Spencer St, Winsted, CT 06098
• 

  /2

  $39,900

  • Land
  • 0.92 Acre
  • $43,370 per Acre

  256 Colebrook Rd, Winchester Center, CT 06098

  Just under an acre of land and over 100 feet of road frontage available on Colebrook Road!

  Austin Brochu Sullivan Real Estate Inc

  256 Colebrook Rd, Winchester Center, 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
• 

  Est $204,761 Not Listed For Sale

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

  111 Riverton Rd Unit 88, Winsted, CT 06098

  111 Riverton Rd Unit 88, Winsted, CT 06098
• 

  

  /39

  $995,000

  • 4 Beds
  • 2 Baths
  • 3,088 Sq Ft

  469 Platt Hill Rd, Winsted, CT 06098

  HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

  Marshall Cohen Cohen Agency

  469 Platt Hill Rd, 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
• 

  Est $368,832 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  155 West Rd, Winsted, CT 06098

  155 West Rd, Winsted, CT 06098
• 

  

  /3

  $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
• 

  $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
• 

  Est $374,466 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  133 E Wakefield Blvd, Winsted, CT 06098

  133 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /9

  $739,900

  • Land
  • 93 Acres
  • $7,924 per Acre

  0 Old Robertsville Rd, Winchester, CT 06098

  Nestled along a peaceful country road near the Colebrook and Barkhamsted town lines, this breathtaking 93.38-acre parcel embodies the timeless charm of rural New England. Once part of a cherished family farm, the land offers a harmonious blend of rolling meadows, majestic forests, and the gentle, winding presence of the Still River, which meanders through a substantial portion of the property.

  David Sartirana Northwest CT Realty

  0 Old Robertsville Rd, Winchester, CT 06098
• 

  $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
• 

  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
• 

  

  /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
• 

  $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
• 

  Est $287,489 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  107 Peck Rd, Winsted, CT 06098

  107 Peck Rd, Winsted, CT 06098
• 

  

  /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
• 

  $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
• 

  Est $281,144 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
• 

  /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
• 

  $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
• 

  Est $309,415 Not Listed For Sale

  • 5 Beds
  • 2,820 Sq Ft

  204 Gilbert Ave, Winsted, CT 06098

  204 Gilbert Ave, Winsted, CT 06098
• 

  /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
• 

  $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
• 

  Est $288,948 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,294 Sq Ft

  28 Moore Ave, Winsted, CT 06098

  28 Moore Ave, Winsted, CT 06098
• 

  

  /26

  $1,200,000

  • 5 Beds
  • 2.5 Baths
  • 3,307 Sq Ft

  77 Deer Hill Rd, Colebrook, CT 06021

  Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at

  MICHAEL CONLOGUE William Pitt Sotheby's Int'l

  77 Deer Hill Rd, Colebrook, CT 06021
• 

  $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
• 

  Est $218,455 Not Listed For Sale

  • 6 Beds
  • 2,421 Sq Ft

  3 Brookside Ave, Winsted, CT 06098

  3 Brookside Ave, Winsted, CT 06098
• 

  

  /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
• 

  $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
• 

  Est $203,895 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

Showing Results 81 - 120, Page 3 of 18