Winchester, CT Homes

• 

  $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
• 

  Est $550,233 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  319 Taylor Brook Rd, Winsted, CT 06098

  319 Taylor Brook Rd, Winsted, CT 06098
• 

  

  

  /5

  $158,000

  • Land
  • 1.18 Acres
  • $133,898 per Acre

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098

  1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL

  David D'Amore Northwest CT Realty

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, 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
• 

  Est $334,664 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  148 Mountain Rd, Winsted, CT 06098

  148 Mountain Rd, 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 100 feet of road frontage available on Colebrook rd!

  Austin Brochu Sullivan Real Estate Inc

  256 Colebrook Rd, Winchester Center, 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
• 

  Est $258,217 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,654 Sq Ft

  220 Walnut St, Winsted, CT 06098

  220 Walnut St, 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
• 

  $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
• 

  Est $258,969 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
• 

  /2

  $295,000

  • Land
  • 104 Acres
  • $2,830 per Acre

  00 Pinney St, Colebrook, CT 06098

  Ideal rural parcel for hunting and outdoor recreation. Land rises to the west away from Pinney Street. Wetlands mapping necessary to determine development potential.

  David Taylor Elyse Harney Real Estate

  00 Pinney St, Colebrook, 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
• 

  Est $795,067 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  206 E Wakefield Blvd, Winsted, CT 06098

  206 E Wakefield Blvd, Winsted, CT 06098
• 

  /2

  $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
• 

  $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
• 

  Est $314,544 Not Listed For Sale

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

  144 Meadow St, Winsted, CT 06098

  144 Meadow 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
• 

  $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
• 

  Est $202,844 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
• 

  /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
• 

  $500,000 Sold Jan 31, 2025

  • 2,532 Sq Ft
  • $197/SF
  • 11 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1830

  368 Sandy Brook Rd, Colebrook, CT 06021

  This charming and beautifully maintained Colonial is the perfect blend of nostalgia and modern living! With your own babbling brook across the street and a peaceful backyard nestled up against the Algonquin State Forest. The current owners took care in making updates, including a remodel of the full bath, improving the primary bedroom with its own private deck and entrance, a walk-in closet, and

  Nick Palazzo Century 21 Clemens Group

  368 Sandy Brook Rd, Colebrook, CT 06021
• 

  Est $257,964 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  36 Charles St, Winsted, CT 06098

  36 Charles St, Winsted, CT 06098
• 

  /2

  $299,900

  • Land
  • 63 Acres
  • $4,760 per Acre

  32 Norfolk Rd, Winchester, CT 06098

  63-Acre Rural Retreat Abutting Algonquin State Forest - A Nature Lover's Dream! Discover the perfect blend of seclusion and accessibility with this 63-acre wooded paradise, directly abutting Algonquin State Forest. Located on a state highway and directly across from a scenic dry dam, this unique parcel provides endless possibilities-whether you're looking to build your dream home, start a

  David D'Amore Northwest CT Realty

  32 Norfolk Rd, Winchester, 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
• 

  Est $409,470 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

  $299,900

  • Land
  • 30 Acres
  • $9,997 per Acre

  00 Ramsgate Ln, Barkhamsted, CT 06063

  30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

  Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  00 Ramsgate Ln, Barkhamsted, CT 06063
• 

  $175,000 Sold Jan 15, 2025

  • Land
  • 9 Acres
  • $19,663 per Acre

  • 1844 Days On Market

  0 Newfield Rd Unit 170255405, Torrington, CT 06790

  TOTAL OF 10.78 ACRES. 8.90 +/- ACRES IS ZONED R6 AND 1.88 +/- ACRE IS ZONED LOCAL BUSINESS. DEVELOPMENT POTENTIAL FOR APARTMENTS, CONDOS OR OTHER ALLOWED USES PER R6 ZONING OR BY SPECIAL EXCEPTION. CITY UTILITIES AVAILABLE. SURVEY MAPS ON THE ATTACHMENTS. CURRENT TOTAL ANNUAL REAL ESTATE TAXES ARE FOR THE COMBINED PROPERTIES IS $2,674.00

  Marshall Cohen Cohen Agency

  0 Newfield Rd Unit 170255405, Torrington, CT 06790
• 

  Est $201,262 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
• 

  /2

  $59,900

  • Land
  • 0.41 Acre
  • $146,098 per Acre

  105,107 E Mountain Rd, Winchester, CT 06098

  105 & 107 Mountain Road parcels are contiguous and located on a dirt road . . Deed indicates right of way to Highland lake water frontage within walking distance. See documents attached for Deed , Site plan, Peculation tests , Survey and Septic testing available . Possible city sewer access at buyers expense . Seller will consider financing with a minimum of 15% DOWN PAYMENT FOR A 2 YEAR BALLOON

  David D'Amore Northwest CT Realty

  105,107 E Mountain Rd, Winchester, 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
• 

  Est $370,249 Not Listed For Sale

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

  155 West Rd, Winsted, CT 06098

  155 West Rd, Winsted, CT 06098
• 

  

  /24

  $1,500,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,664 Sq Ft

  711 W Wakefield Blvd, Winchester Center, CT 06098

  Build your DREAM home! Largest lot available on the lake with great views and parking! Will build to suite. Don't miss this wonderful opportunity! WELL IS LOT CORNER at Forest Ave FRONTAGES ARE MARKED IN RED. +-a2 map and topo in documents.

  Peter Kores The Washington Agency

  711 W Wakefield Blvd, Winchester Center, 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
• 

  Est $342,369 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
• 

  

  /34

  $295,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,509 Sq Ft

  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
• 

  $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
• 

  Est $280,791 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
• 

  

  /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
• 

  $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

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