5,104

Winchester, CT Homes

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  • 103 E Mountain Ave, Winsted, CT 06098

    $275,000 Sold Aug 01, 2024

    • 1,304 Sq Ft
    • $211/SF
    • 29 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1955

    103 E Mountain Ave, Winsted, CT 06098

    Welcome home to 103 E Mountain Ave, an adorable and well cared for ranch on a gorgeous lot which is fenced in from the street. Nice open floor plan with hardwood floors, three bedrooms, plus an office. Remodeled kitchen with a slider to the back deck, and the dishwasher, range, and microwave were replaced last year. Beautiful living room with built ins and a brick fireplace with gas insert for

    David Merrigan Merrigan & Lefebvre Realty

    103 E Mountain Ave, Winsted, CT 06098
  • Unlisted Address

    $450,000 Sold Jul 26, 2024

    • 2,464 Sq Ft
    • $183/SF
    • 51 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1991

    Unlisted Address

    Welcome to your absolutely amazing new home, a gorgeously maintained colonial nestled in a dream-like, wooded oasis, close to Highland Lake! Step into this magical 3-bedroom, 2.5-bathroom haven that sparkles with brand new flooring and walls painted in the freshest of hues.The exterior has undergone a fantastic transformation with new siding, giving it a modern and inviting look that's sure to

    Sandie Terenzi KW Legacy Partners

    Unlisted Address
  • 27 Benton St, Winsted, CT 06098

    $220,000 Sold Jul 26, 2024

    • 1,109 Sq Ft
    • $198/SF
    • 107 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1962

    27 Benton St, Winsted, CT 06098

    This property is eligible under the Freddie Mac First Look Initiative through 5/10/2024. 2 Bedrooms, 1.1 bath cape on .43 acres. Features a two car garage, deck off of the kitchen, wood flooring in some rooms, NEW OIL FURNACE. Close to shopping, amenities, and highways. Schedule a showing today!

    James Ray A-Gold Action Realty

    27 Benton St, Winsted, CT 06098
  • 44 Wetmore Ave, Winsted, CT 06098

    $250,600 Sold Jul 25, 2024

    • 1,945 Sq Ft
    • $129/SF
    • 52 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1900

    44 Wetmore Ave, Winsted, CT 06098

    Welcome to 44 Wetmore Ave; the only 3 Family home for sale in Winchester, CT! This Three Family home is conveniently located on a corner lot with two driveways- plenty of parking for everyone. Unit 44 features a one bedroom apartment with a large living room and eat in kitchen. The bedroom comes with a beautiful french slider out to the balcony and an on-suite full bathroom. Unit 46 is this

    Macey Mazzella RE/MAX RISE

    44 Wetmore Ave, Winsted, CT 06098
  • 17 Chestnut St, Winsted, CT 06098

    $243,000 Sold Jul 22, 2024

    • 1,932 Sq Ft
    • $126/SF
    • 84 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1900

    17 Chestnut St, Winsted, CT 06098

    Spacious and well-kept two family in a very convenient location, walkable to all of downtown Winsted. Large barn/ garage in the back which is currently rented for $250 a month. Three bedroom unit on the first floor and a two-bedroom unit on the second floor. The owner is a licensed Realtor in the state of Connecticut.

    Michelle Grant Coldwell Banker Premier Real Estate

    17 Chestnut St, Winsted, CT 06098
  • 404 Colebrook Rd, Colebrook, CT 06021

    $687,000 Sold Jul 19, 2024

    • 3,860 Sq Ft
    • $178/SF
    • 22 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1989

    404 Colebrook Rd, Colebrook, CT 06021

    Located on 7.87 acres in the peaceful woods of Litchfield County, CT, this charming, yet modern country estate awaits. As you drive down the long driveway you'll pass the pond & brook that traverse the property. The wrap around deck, patio & covered side porch are a perfect vantagepoint from which to watch & listen to the stream & wildlife. Discover the multiple waterfalls found on the property.

    Lori Meyerson Coldwell Banker Realty

    404 Colebrook Rd, Colebrook, CT 06021
  • 874 W Wakefield Blvd, Winsted, CT 06098

    $775,000 Sold Jul 18, 2024

    • 2,240 Sq Ft
    • $346/SF
    • 59 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1950

    874 W Wakefield Blvd, Winsted, CT 06098

    Direct Waterfront at Highland Lake, perfect for a year 'round or vacation home with it's own sandy beach and dock. Make a lifetime of lake life memories in this stunning mid century modern style 3 bedroom/2 bath home located on the sunny side of the lake. Enjoy the lake views from one of three composite decks in this tri-level home. Be wowed by the fabulous open floor plan with a European

    DONNA MEMBRINO William Pitt Sotheby's Int'l

    874 W Wakefield Blvd, Winsted, CT 06098
  • 42 Upland Rd, Winsted, CT 06098

    $209,000 Sold Jul 11, 2024

    • 1,236 Sq Ft
    • $169/SF
    • 71 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1891

    42 Upland Rd, Winsted, CT 06098

    This charming home includes updated kitchen and bathroom. include newer appliances cabinets and countertops. Oak hardwood floors adorn the dining room and living rooms. A sliding glass door provides access to the private large deck from the Dining room. The Bedrooms are located on the second floor along with an over sized bathroom and laundry room. The location is close to shopping, restaurants,

    Glenn Kohrs Coldwell Banker Realty

    42 Upland Rd, Winsted, CT 06098
  • 339 W Wakefield Blvd, Winsted, CT 06098

    $525,000 Sold Jul 10, 2024

    • 1,322 Sq Ft
    • $397/SF
    • 62 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1940

    339 W Wakefield Blvd, Winsted, CT 06098

    HIGHLAND LAKE 4 Season Home For Sale. 3 bedrooms,2 full bathrooms. Including 50 feet of private waterfront with private dock and solar powered covered boat lift. The home has lake views from every room . It boasts a huge primary ensuite bedroom with vaulted ceilings and exceptional water views. Ample storage is provided by a convenient 1.5 car garage and walk -up attic ensuring you have plenty

    Amy Pelletier Berkshire Hathaway NE Prop.

    339 W Wakefield Blvd, Winsted, CT 06098
  • 23 Curtice St, Winsted, CT 06098

    $289,000 Sold Jul 03, 2024

    • 1,380 Sq Ft
    • $209/SF
    • 32 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1900

    23 Curtice St, Winsted, CT 06098

    This home sounds like a fantastic find! With four bedrooms, including one on the main level, and 1.5 bathrooms, it offers both space and convenience. The updated kitchen with ample cabinet and counter space is a definite plus, and the hardwood flooring throughout most of the house adds warmth and charm. A large private backyard and a welcoming front porch provide great outdoor spaces for

    Amanda Balaski Northwest CT Realty

    23 Curtice St, Winsted, CT 06098
  • 152 Mountain Rd, Winsted, CT 06098

    $335,000 Sold Jul 01, 2024

    • 2,148 Sq Ft
    • $156/SF
    • 42 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1988

    152 Mountain Rd, Winsted, CT 06098

    Welcome to this charming 3-bedroom, 2-bath Raised Ranch, nestled on a serene 1.63-acre lot, offering the tranquility of rural living while being conveniently close to Highland Lake. The main level boasts a spacious living room with a cozy fireplace and elegant arched built-in bookcases. The large eat-in kitchen features a dining area and a sliding door leading to a private deck, perfect for

    David Sartirana Northwest CT Realty

    152 Mountain Rd, Winsted, CT 06098
  • 21 Greenwoods Ave, Winsted, CT 06098

    $275,000 Sold Jun 28, 2024

    • 2,918 Sq Ft
    • $94/SF
    • 2 Days On Market
    • 8 Beds
    • 4 Baths
    • Built 1900

    21 Greenwoods Ave, Winsted, CT 06098

    Investors take note! This 4 family property with 3 units rented is the perfect addition to your investment portfolio! Recording devices may be present on the property. Listing agent has limited information regarding the property, buyer to do due diligence. Seller desires an as is, where is sale.

    Carolyn Meehan Naples Realty Group, LLC

    21 Greenwoods Ave, Winsted, CT 06098
  • 80 John St, Winsted, CT 06098

    $345,000 Sold Jun 27, 2024

    • 1,514 Sq Ft
    • $228/SF
    • 81 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1875

    80 John St, Winsted, CT 06098

    16.88 ACRES! Unique and perfect for the outdoor enthusiast or someone looking for a private retreat. Located at the end of a cul-de-sac and the rear is in close proximity to Mad River Dam. This treed lot has easy access up a cleared road. Pole barn built with lumber harvested from the property could be used for animals, ATV storage or a secluded cabin in the woods. The home is ready for your

    Katie Breitkreutz Dave Jones Realty, LLC

    80 John St, Winsted, CT 06098
  • 302 Norcross Rd, Winsted, CT 06098

    $99,000 Sold Jun 25, 2024

    • 600 Sq Ft
    • $165/SF
    • 15 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1947

    302 Norcross Rd, Winsted, CT 06098

    Privately situated cottage in the Highland Lake District on 1 acre! This cottage has been gutted. It has a large living room area with fireplace. There is a well and septic. 200 amp service. Private beach rights with Town paid permit to Highland Lake. Not gps friendly. Property includes 300 and 302 Norcross Rd, 304 and 306 Norwood Rd Ext, 341, 343, and 345 Tiffany Rd

    Nadia Corvo Northwest CT Realty

    302 Norcross Rd, Winsted, CT 06098
  • 269 Walnut St, Winsted, CT 06098

    $45,000 Sold May 09, 2025

    • Land
    • 0.50 Acre
    • $90,000 per Acre
    • 72 Days On Market

    269 Walnut St, Winsted, CT 06098

    Prime Building Lot Near Downtown & Tatro's Pond!-Discover the perfect setting for your dream home on this level and open .50-acre lot at 269 Walnut St. Nestled on a lightly traveled street, this property offers a peaceful atmosphere while maintaining easy access to downtown amenities. The lot is flat and fully cleared, providing a generous building envelope to accommodate your vision. A

    David Sartirana Northwest CT Realty

    269 Walnut St, Winsted, CT 06098
  • Unlisted Address

    $270,000 Sold Oct 09, 2024

    • 2,669 Sq Ft
    • $101/SF
    • 25 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1910

    Unlisted Address

    Beautiful duplex walking distance to downtown Winsted!

    Austin Brochu Sullivan Real Estate Inc

    Unlisted Address
  • 106 Highview Dr, Winchester, CT 06098

    $54,900 Sold Jul 18, 2024

    • Land
    • 2.22 Acres
    • $24,730 per Acre
    • 263 Days On Market

    106 Highview Dr, Winchester, CT 06098

    RARE opportunity to own your own 2.22 acres in a neighborhood that is rural but just minutes to town and some of the state's biggest attractions. Less than 15 minutes to Highland Lake and Burr Pond State Park. Highview is off of the main road and a dead end street. Whether you are looking to build your dream home or you are looking for your next investment, now is your chance.

    Darren Sweeney Dan Combs Real Estate

    106 Highview Dr, Winchester, CT 06098

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