4,836

Winsted, CT Homes

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  • 88 Strong Terrace, Winsted, CT 06098
    88 Strong Terrace, Winsted, CT 06098
    88 Strong Terrace, Winsted, CT 06098
    /24

    $289,900 Pending

    • 5 Beds
    • 1.5 Baths
    • 2,470 Sq Ft

    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
  • 234 E Wakefield Blvd, Winsted, CT 06098

    $135,000 Sold Feb 28, 2025

    • 816 Sq Ft
    • $165/SF
    • 3 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1939

    234 E Wakefield Blvd, Winsted, CT 06098

    Abundant opportunity awaits for you to live in the highly-desired Highland Lake area. With some vision and determination, you can transform this property into your home. The property features newer roofing, new siding, and new replacement windows. There is a level lot for your enjoyment and a two-car garage with loft storage above. This property could also be a great investment opportunity. Cash

    Jeffrey Liskin Northwest CT Realty

    234 E Wakefield Blvd, Winsted, CT 06098
  • 19 Riveredge Dr Unit 19, Winsted, CT 06098
    19 Riveredge Dr Unit 19, Winsted, CT 06098
    19 Riveredge Dr Unit 19, Winsted, CT 06098
    /13

    $159,999 Pending

    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft

    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 Turning Point Realty, LLC

    19 Riveredge Dr Unit 19, Winsted, CT 06098
  • 220 Gilbert Ave, Winsted, CT 06098

    $375,000 Sold Feb 19, 2025

    • 2,176 Sq Ft
    • $172/SF
    • 77 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1900

    220 Gilbert Ave, Winsted, CT 06098

    WOW - Welcome to 220 Gilbert Ave! Stop by for a visit and view the amazing transformation of this FABULOUS 2 family dwelling. Home has been completely remodeled inside and out. Relax and enjoy the level, private back yard or the sprawling, open front porch. The open floor plan boasts, spacious rooms, space for everyone and storage galore! The list of amenities is endless in this beautiful home!

    Linda Muraski Century 21 Classic Homes

    220 Gilbert Ave, Winsted, CT 06098
  • 11 Gibbs St Unit 7, Winsted, CT 06098
    11 Gibbs St Unit 7, Winsted, CT 06098
    11 Gibbs St Unit 7, Winsted, CT 06098
    /16

    $109,900 Pending

    • 1 Bed
    • 1 Bath
    • 570 Sq Ft

    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
  • 113 Preston Rd, Winsted, CT 06098

    $343,000 Sold Feb 14, 2025

    • 1,566 Sq Ft
    • $219/SF
    • 53 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1993

    113 Preston Rd, Winsted, CT 06098

    This 1,566 sq. ft. cape log home sits on a mostly wooded 6.04 acre lot. The home consists of 2 bedroom, 2 bath, an open living/kitchen concept, primary suite, great closet space, laundry on the main level as well as a bonus room. Kitchen appliances included along with laundry set. Full basement with workshop area and a two car detached garage.

    Roberta LeJeune Marrin Santore Realty LLC

    113 Preston Rd, Winsted, CT 06098
  • 29 Walnut St, Winsted, CT 06098
    29 Walnut St, Winsted, CT 06098
    29 Walnut St, Winsted, CT 06098
    /39

    $310,000 Pending

    • 3 Beds
    • 5 Baths
    • 2,623 Sq Ft

    29 Walnut St, Winsted, CT 06098

    Introducing 29 Walnut: a grand Victorian home with a front porch view complimented by perennial rose gardens, a terrace fit for garden parties, and a large back yard. Upon entry, look upward to high ceilings, a spacious entryway and a grand, swirling staircase. Note precise finish work and period correct trim as you move into the open living, kitchen, and dining area with a chic half bath. Make

    Rosemary Scanlon Coldwell Banker Realty

    29 Walnut St, Winsted, CT 06098
  • 86 Strong Terrace, Winsted, CT 06098

    $288,000 Sold Feb 14, 2025

    • 1,646 Sq Ft
    • $175/SF
    • 69 Days On Market
    • 5 Beds
    • 1.5 Baths
    • Built 1880

    86 Strong Terrace, Winsted, CT 06098

    Lovely 4-5 bedroom Colonial in the quaint town of Winchester is updated throughout and move in ready! This home offers a unique blend of classic charm and modern amenities. Fantastic yard is great for entertaining with a patio, garden areas, fire pit, a detached Carriage house style barn and a fenced in area great for pets. Welcoming covered front porch entry way. Gorgeous newly built rear

    Lindsay J. Warner Tier 1 Real Estate

    86 Strong Terrace, Winsted, CT 06098
  • 11 Gibbs St Unit 9, Winsted, CT 06098
    11 Gibbs St Unit 9, Winsted, CT 06098
    11 Gibbs St Unit 9, Winsted, CT 06098
    /22

    $109,900 Pending

    • 1 Bed
    • 1 Bath
    • 570 Sq Ft

    11 Gibbs St Unit 9, Winsted, CT 06098

    Welcome to easy, one-level living in this rarely available first-floor end 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.

    David Sartirana Northwest CT Realty

    11 Gibbs St Unit 9, Winsted, CT 06098
  • 35 Riveredge Dr Unit 35, Winsted, CT 06098

    $146,000 Sold Feb 10, 2025

    • 992 Sq Ft
    • $147/SF
    • 3 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1986

    35 Riveredge Dr Unit 35, Winsted, CT 06098

    Come see this wonderful sought after condo on a cul-de-sac. Freshly painted and new carpet on stairs and upper level. This unit overlooks the river from the back patio. Great surrounding neighborhoods. Close proximity to town and route 8. Parking space is directly in front of the condo!

    Maria Smith Turning Point Realty, LLC

    35 Riveredge Dr Unit 35, Winsted, CT 06098
  • 203 Holabird Ave, Winchester Center, CT 06098
    203 Holabird Ave, Winchester Center, CT 06098
    203 Holabird Ave, Winchester Center, CT 06098
    /34

    $369,900 Pending

    • 5 Beds
    • 4 Baths
    • 3,690 Sq Ft

    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
  • 111 Riverton Rd Unit 7, Winsted, CT 06098

    $180,000 Sold Feb 10, 2025

    • 1,204 Sq Ft
    • $150/SF
    • 68 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1987

    111 Riverton Rd Unit 7, Winsted, CT 06098

    Welcome to 111 Riverton Road, Unit 7. Discover the charm and convenience of this well-maintained Riverwalk townhouse, ideally situated in a peaceful section of the complex with no through traffic, expansive green spaces, and a serene wooded backdrop. This 2-bedroom, 1.5-bath home offers an inviting blend of comfort and style, featuring newer flooring on the main level. The bright, airy kitchen is

    David Sartirana Northwest CT Realty

    111 Riverton Rd Unit 7, Winsted, CT 06098
  • 508 W Wakefield Blvd, Winsted, CT 06098
    508 W Wakefield Blvd, Winsted, CT 06098
    508 W Wakefield Blvd, Winsted, CT 06098
    /20

    $1,650,000 Pending

    • 7 Beds
    • 4 Baths
    • 2,687 Sq Ft

    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
  • 63 Meadow St, Winsted, CT 06098

    $330,000 Sold Jan 31, 2025

    • 2,602 Sq Ft
    • $127/SF
    • 31 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1900

    63 Meadow St, Winsted, CT 06098

    Welcome to 63 Meadow, an updated, well maintained and income producing property, making it a match made in investing heaven for both the landlord and tenant. This property boasts three spacious units, shared outdoor space, a two-car attached garage, and 5 parking spaces. The prime location is minutes from route 8 ramps, local university, shopping and every convenience, not to mention a 3 minute

    Lauren Hill Mark Tavares Realty, LLC

    63 Meadow St, Winsted, CT 06098
  • 174 Boyd St, Winsted, CT 06098
    174 Boyd St, Winsted, CT 06098
    174 Boyd St, Winsted, CT 06098
    /18

    $289,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,424 Sq Ft

    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
  • 19 Cottage St, Winsted, CT 06098

    $375,000 Sold Jan 31, 2025

    • 2,674 Sq Ft
    • $140/SF
    • 100 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1890

    19 Cottage St, Winsted, CT 06098

    Welcome to 19 Cottage Street, a stunning turnkey Colonial in the heart of Winsted that beautifully blends modern functionality with classic charm. As you enter, a spacious foyer with new tile flooring leads into a bright living room featuring gleaming hardwood floors, create a warm, inviting atmosphere. A dedicated office space presents an ideal setting for productivity, while the heart of the

    Michael Bianca Showcase Realty, Inc.

    19 Cottage St, Winsted, CT 06098
  • 97 Taylor Rd, Winsted, CT 06063
    97 Taylor Rd, Winsted, CT 06063
    97 Taylor Rd, Winsted, CT 06063
    /34

    $599,900 Open Sun 12PM - 3PM

    • 4 Beds
    • 3 Baths
    • 3,100 Sq Ft

    97 Taylor Rd, Winsted, CT 06063

    Welcome to this beautifully updated country retreat home, nestled in a peaceful setting, just minutes from everyday amenities. Enjoy serene summer evenings on the inviting covered front porch, where the sounds of nature & a nearby river within walking distance create the perfect ambiance. Ideal for entertaining, the outdoor space features a spacious deck, bluestone patio & hot tub. Inside, the

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    97 Taylor Rd, Winsted, CT 06063
  • 20 Riveredge Dr Unit 20, Winsted, CT 06098

    $155,000 Sold Jan 09, 2025

    • 992 Sq Ft
    • $156/SF
    • 1 Day On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1986

    20 Riveredge Dr Unit 20, Winsted, CT 06098

    Come see this renovated condo! New Carpeting on stairs and in bedrooms; fresh coat of paint throughout and flooring on lower level still looks brand new. Slider in living room opens to a private little patio area. Great surrounding neighborhoods. Close proximity to town.

    Maria Smith Turning Point Realty, LLC

    20 Riveredge Dr Unit 20, Winsted, CT 06098
  • 38 Upland Rd, Winsted, CT 06098
    38 Upland Rd, Winsted, CT 06098
    38 Upland Rd, Winsted, CT 06098
    /3

    $299,000 Open House 6/28

    • 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
  • 111 Riverton Rd Unit 50, Winsted, CT 06098

    $195,000 Sold Jan 08, 2025

    • 1,204 Sq Ft
    • $162/SF
    • 0 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1987

    111 Riverton Rd Unit 50, Winsted, CT 06098

    Fantastic opportunity to own this wonderful unit at the sought after Riverwalk complex!! Rarely available townhouse with so much space and a 2 CAR ATTACHED GARAGE!!!! Meticulously maintained unit with 2 bedrooms and 1.5 baths... sliders from the fireplaced living room out to a private deck! New windows in 2019...new garage doors, A/C units, garbage disposal and hot water in 2022...newer Samsung

    Tammy Varney William Raveis Real Estate

    111 Riverton Rd Unit 50, Winsted, CT 06098
  • 181 Torringford St, Winsted, CT 06098
    181 Torringford St, Winsted, CT 06098
    /2

    $375,000 Open Sun 1PM - 3PM

    • 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
  • 174 Wallens St Unit A3, Winsted, CT 06098

    $255,000 Sold Jan 08, 2025

    • 1,946 Sq Ft
    • $131/SF
    • 7 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2005

    174 Wallens St Unit A3, Winsted, CT 06098

    Welcome to Clockmakers Hill, a highly sought-after, active 55+ community. You will love this gorgeously maintained condo unit that boasts granite counter tops, 9ft ceilings, and a primary suite with full bath and walk in closet. There are two ground floor entrances as well as a finished lower level family room. With almost 2,000 square feet you must see this unit!

    Juli McGraw RE/MAX Heritage

    174 Wallens St Unit A3, Winsted, CT 06098
  • 141 Maloney Ct, Winsted, CT 06098
    141 Maloney Ct, Winsted, CT 06098
    141 Maloney Ct, Winsted, CT 06098
    /26

    $270,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 1,752 Sq Ft

    141 Maloney Ct, Winsted, CT 06098

    A charming ranch-style home, located in a desirable area, offers the convenience of single-level living. It features 4 bedrooms and 3 bathrooms, making it perfect for families or anyone in need of extra space. Upon entering the main floor, you'll find a spacious living room filled with natural light, which creates a warm and inviting atmosphere. The kitchen provides ample counter space and opens

    Marcy D'Angelo Coldwell Banker Realty

    141 Maloney Ct, Winsted, CT 06098
  • 124 Standard Ave, Winsted, CT 06098

    $265,000 Sold Jan 07, 2025

    • 1,152 Sq Ft
    • $230/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    124 Standard Ave, Winsted, CT 06098

    This wonderful Ranch is just waiting for you to call it home! With it's traditional layout 3 beds, 2baths, hardwoods partially finished lower level, and wonderful oversized deck overlooking a great yard. This home is just waiting for you to bring your style and make it yours! Enjoy time with your friends and guests and making tons of memories. Why wait? Being sold as-is. Highest & Best for Sunday

    Derek Greene Derek Greene

    124 Standard Ave, Winsted, CT 06098
  • 115 Stanton Ave, Winsted, CT 06098
    115 Stanton Ave, Winsted, CT 06098
    115 Stanton Ave, Winsted, CT 06098
    /24

    $269,900 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,424 Sq Ft

    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
  • 111 Riverton Rd Unit 53, Winsted, CT 06098

    $199,000 Sold Dec 31, 2024

    • 1,204 Sq Ft
    • $165/SF
    • 12 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1987

    111 Riverton Rd Unit 53, Winsted, CT 06098

    Welcome to 111 Riverton Road, Unit 53-your perfect home just in time for the holidays! This well-maintained Riverwalk end-unit townhouse is nestled in the last building of the complex, offering privacy without through traffic, large open green space, and serene water views of the Still River. This immaculate home features 2 bedrooms, 1.5 baths, and brand-new carpeting installed on November 15th.

    Samantha Behm William Pitt Sotheby's Int'l

    111 Riverton Rd Unit 53, Winsted, CT 06098
  • 355 W Lake St, Winsted, CT 06098
    355 W Lake St, Winsted, CT 06098
    355 W Lake St, Winsted, CT 06098
    /40

    $979,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,216 Sq Ft

    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

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