Winchester, CT Homes

• 

  $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
• 

  Est $382,562 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,615 Sq Ft

  161 Spencer St, Winsted, CT 06098

  161 Spencer St, Winsted, CT 06098
• 

  

  

  /35

  $279,923 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  39 Orchard St, Winsted, CT 06098

  Seller is working on final details. Welcome to your dream home, 39 Orchard st ! This beautifully updated colonial offers the ideal combination of timeless architecture and contemporary comfort, all situated on a fantastic private lot. As you step inside, you are greeted by the warm glow of refinished hardwood floors, The living room is inviting and bright, leading you into a dining area perfect

  Dayris Del Castillo eRealty Advisors, Inc.

  39 Orchard St, Winsted, CT 06098
• 

  $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
• 

  Est $276,289 Not Listed For Sale

  • 3 Beds
  • 1,766 Sq Ft

  87 Wetmore Ave, Winsted, CT 06098

  87 Wetmore Ave, Winsted, CT 06098
• 

  

  /32

  $949,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,131 Sq Ft

  43 E Lake St, Winsted, CT 06098

  Enjoy beautiful sunsets from the large composite deck of this year-round, westerly facing, 4 bedroom, 3 full bath, waterfront home. The peaceful location in Hurlbut cove in first bay allows for kayaking and swimming without the usual boat traffic on Highland Lake. A sandy wading area for little ones is next to the maintenance free aluminum boat dock. There are hardwood floors throughout the

  Keith Meyer Northwest CT Realty

  43 E Lake St, Winsted, 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 $206,857 Not Listed For Sale

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

  111 Riverton Rd Unit 52, Winsted, CT 06098

  111 Riverton Rd Unit 52, Winsted, CT 06098
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  /34

  $285,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,880 Sq Ft

  101 Norfolk Rd, Winsted, CT 06098

  Beautifully updated Raised- Ranch retreat on 1.33 wooded acres! Nestled in a serene, natural setting yet conveniently close to local amenities. When you enter the home you will find two generous sized rooms with new vinyl plank flooring, fresh paint & a mini split as well as a spacious storage/utility room with laundry. The main floor includes the living room with a stone accent wall & great

  Jackie Desmarais Showcase Realty, Inc.

  101 Norfolk Rd, Winsted, 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 $307,959 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 954 Sq Ft

  155 Alpha Ave, Winsted, CT 06098

  155 Alpha Ave, Winsted, CT 06098
• 

  

  /21

  $150,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 635 Sq Ft

  38 Riveredge Dr Unit 38, Winsted, CT 06098

  End Unit Ranch-Style Condo - Winchester. Discover privacy and convenience in this well-maintained one-level end unit nestled in the foothills of the Berkshire Mountains. Offering an open-concept layout, this ranch-style condo features a spacious living room, dining area, kitchen, large bedroom, full bathroom with in-unit laundry, & excellent closet space. While the condo would benefit from

  Suzie Larson Turning Point Realty, LLC

  38 Riveredge Dr Unit 38, 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 $309,782 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,114 Sq Ft

  136 Glendale Ave, Winsted, CT 06098

  136 Glendale Ave, Winsted, CT 06098
• 

  

  /27

  $235,000 Under Contract

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit H1, Winsted, CT 06098

  Discover effortless living in this inviting home at the sought-after Clockmaker's Hill community. The thoughtfully designed open floor plan creates seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining room, perfect for hosting friends and family. The sun-drenched kitchen features a convenient breakfast bar for casual dining and morning coffee. The

  Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, 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
• 

  Est $596,703 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  732 W Wakefield Blvd, Winsted, CT 06098

  732 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /10

  $225,000 Under Contract

  • 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
• 

  $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 $262,285 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  152 Pratt St, Winsted, CT 06098

  152 Pratt St, 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 $255,676 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,109 Sq Ft

  27 Benton St, Winsted, CT 06098

  27 Benton St, Winsted, 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 $608,368 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,032 Sq Ft

  233 Colebrook Rd, Winsted, CT 06098

  233 Colebrook Rd, 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 $221,244 Not Listed For Sale

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

  111 Riverton Rd Unit 10, Winsted, CT 06098

  111 Riverton Rd Unit 10, 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 $287,228 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,006 Sq Ft

  98 Meadow St, Winsted, CT 06098

  98 Meadow 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 $1,202,198 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,320 Sq Ft

  630 E Wakefield Blvd, Winsted, CT 06098

  630 E Wakefield Blvd, 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 $266,691 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,054 Sq Ft

  185 N Main St, Winsted, CT 06098

  185 N Main St, Winsted, CT 06098
• 

  $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 $489,750 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  213 Spencer Hill Rd, Winsted, CT 06098

  213 Spencer Hill Rd, 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 $276,991 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,430 Sq Ft

  107 Lake St, Winsted, CT 06098

  107 Lake St, Winsted, CT 06098
• 

  $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
• 

  Est $266,295 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,594 Sq Ft

  181 Stanton Ave, Winsted, CT 06098

  181 Stanton Ave, Winsted, CT 06098
• 

  $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
• 

  Est $247,509 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  10 Hurlbut St, Winsted, CT 06098

  10 Hurlbut St, Winsted, CT 06098

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