Winsted, CT Homes

• 

  Est $393,408 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
• 

  

  

  /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
• 

  $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
• 

  Est $292,010 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
• 

  

  

  /36

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,736 Sq Ft

  38 Upland Rd, Winsted, CT 06098

  Estate Owned 3 to 4 Bedroom Colonial in Immaculate Move In Condition! Tucked away on a quiet street but within walking distance of Schools, Medical Facilities and Shopping. Special features include a huge cedar closet, Hardwood floors throughout the entire house, bay windows, 24' x 14' Family Room with Propane Gas Stove and an Oversized Full Bath The Master Bedroom features its own office.

  Holly Blinkoff Cohen Agency

  38 Upland Rd, 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
• 

  Est $288,537 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  107 Peck Rd, Winsted, CT 06098

  107 Peck Rd, 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
• 

  $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
• 

  Est $293,121 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
• 

  

  /34

  $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
• 

  $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
• 

  Est $331,929 Not Listed For Sale

  • 5 Beds
  • 2,820 Sq Ft

  204 Gilbert Ave, Winsted, CT 06098

  204 Gilbert Ave, 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
• 

  $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
• 

  Est $283,763 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,294 Sq Ft

  28 Moore Ave, Winsted, CT 06098

  28 Moore Ave, 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
• 

  $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
• 

  Est $239,267 Not Listed For Sale

  • 6 Beds
  • 2,421 Sq Ft

  3 Brookside Ave, Winsted, CT 06098

  3 Brookside Ave, 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
• 

  $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 $204,632 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
• 

  /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
• 

  $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 $231,774 Not Listed For Sale

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

  45 Beach St, Winsted, CT 06098

  45 Beach St, 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
• 

  $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
• 

  Est $409,725 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
• 

  

  /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
• 

  $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
• 

  Est $358,670 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,379 Sq Ft

  160 Hinsdale Ave, Winsted, CT 06098

  160 Hinsdale Ave, Winsted, CT 06098
• 

  /2

  $69,000

  • Land
  • 2 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
• 

  $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
• 

  Est $257,742 Not Listed For Sale

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

  234 Oak St, Winsted, CT 06098

  234 Oak St, Winsted, CT 06098
• 

  /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
• 

  $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
• 

  Est $184,358 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
• 

  /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
• 

  $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
• 

  Est $281,495 Not Listed For Sale

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

  24 Union St, Winsted, CT 06098

  24 Union St, Winsted, CT 06098

Showing Results 81 - 120, Page 3 of 18