Winchester, CT Homes

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  /9

  $739,900 Pending

  • Land
  • 93.38 Acres
  • $7,924 per Acre

  0 Old Robertsville Rd, Winchester, CT 06098

  Nestled along a peaceful country road near the Colebrook and Barkhamsted town lines, this breathtaking 93.38-acre parcel embodies the timeless charm of rural New England. Once part of a cherished family farm, the land offers a harmonious blend of rolling meadows, majestic forests, and the gentle, winding presence of the Still River, which meanders through a substantial portion of the property.

  David Sartirana Northwest CT Realty

  0 Old Robertsville Rd, Winchester, 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
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  Est $354,111 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,249 Sq Ft

  143 Mountain Rd, Winsted, CT 06098

  143 Mountain Rd, Winsted, CT 06098
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  /18

  $399,900 Pending

  • 8 Beds
  • 5 Baths
  • 7,372 Sq Ft

  27 Thibault Ave, Winsted, CT 06098

  Here is your perfect chance to build your investment portfolio! 2 houses and a vacant lot create the perfect investment opportunity! Comprised of a 4 unit apartment building and a single unit house with a 4 car garage under and an adjacent vacant lot. The vacant lot is perfect for additional parking and or play area! All tenants have been there long term and pay regularly. Buyer and buyer agent

  Cathy Macias Northwest CT Realty

  27 Thibault Ave, Winsted, CT 06098
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  $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
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  Est $217,137 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft

  11 Orchard St, Winsted, CT 06098

  11 Orchard St, Winsted, CT 06098
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  /20

  $239,900 Pending

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  22 Curtice St, Winsted, CT 06098

  Step into timeless elegance with this beautifully updated colonial-style home, where classic charm meets modern convenience. Gleaming hardwood floors flow seamlessly throughout the main living areas, creating a warm and inviting atmosphere. The fully renovated kitchen is a chef's dream, featuring premium finishes, sleek countertops, and top-of-the-line appliances. Upstairs, you'll find spacious

  Terence Dominick Complete Real Estate

  22 Curtice St, Winsted, CT 06098
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  $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
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  Est $264,839 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,652 Sq Ft

  118 Meadow St, Winsted, CT 06098

  118 Meadow St, Winsted, CT 06098
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  /22

  $179,900 Pending

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

  111 Riverton Rd Unit 90, Winsted, CT 06098

  Discover the ease of condo living with the charm of a riverside retreat at Riverwalk Condos. This beautifully cared-for 2-bedroom, 1.5-bath home offers an inviting layout designed for comfort and relaxation. The spacious living room with its warm fireplace opens to a private deck overlooking the Still River-an ideal spot to unwind at the end of the day or entertain with a view. The kitchen also

  David Sartirana Northwest CT Realty

  111 Riverton Rd Unit 90, Winsted, CT 06098
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  $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
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  Est $255,057 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft

  151 Hinsdale Ave, Winsted, CT 06098

  151 Hinsdale Ave, Winsted, CT 06098
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  /28

  $225,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,299 Sq Ft

  30 Rock St, Winsted, CT 06098

  Charming 2-family home offering 2,299 sq ft of living space in Litchfield County. Featuring a total of 4 bedrooms and 2 full bathrooms, this property sits on a manageable 0.18-acre lot within the Winchester School District. Great opportunity for owner-occupants or investors alike with spacious layouts and income potential.

  Patrick Precourt Dorrance Realty

  30 Rock St, Winsted, CT 06098
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  $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
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  Est $540,263 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,364 Sq Ft

  16 Alexandria Dr, Winsted, CT 06063

  16 Alexandria Dr, Winsted, CT 06063
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  /16

  $280,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,323 Sq Ft

  331 Colebrook Rd, Winsted, CT 06098

  Nestled in the scenic Litchfield Hills, this charming 2-bedroom, 1.5-bath Cape has been lovingly restored over the past 11 years and thoughtfully updated with room to expand. Combining modern convenience with timeless character, improvements & remodeling include electrical upgrades, replacement of the majority of the windows in the house, insulation, newer appliances, a new back door, refinished

  Alison Malkin Essentia Realty

  331 Colebrook Rd, Winsted, CT 06098
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  $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
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  Est $351,498 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,664 Sq Ft

  5 Hillside Ave, Winsted, CT 06098

  5 Hillside Ave, Winsted, CT 06098
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  /26

  $350,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft

  147 Smith Hill Rd, Winsted, CT 06098

  HUGE PRICE REDUCTION!! Make this beautiful Cape your home! Features 4 spacious bedrooms and a full bathroom on each floor. Enjoy watching the birds & other wildlife on the huge rear deck or enjoy the peaceful setting on the enclosed porch. The grounds have been lovingly maintained.

  SHARON GILSON Northwest CT Realty

  147 Smith Hill Rd, Winsted, CT 06098
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  $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
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  Est $233,954 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,380 Sq Ft

  36 S Main St, Winsted, CT 06098

  36 S Main St, Winsted, CT 06098
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  /36

  $299,000 Pending

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  152 E Lake St, Winsted, CT 06098

  Well-maintained and move-in ready, this charming one-level ranch offers 900 square feet of comfortable living just steps from Highland Lake. Featuring 2 bedrooms and 2 full bathrooms, this home is perfect as a full-time residence, weekend retreat, or summer getaway. Enjoy lake living without the high taxes, with public water and sewer already in place. The property includes a private backyard

  Bryan Palladino Showcase Realty, Inc.

  152 E Lake St, Winsted, CT 06098
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  $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
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  Est $210,623 Not Listed For Sale

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

  111 Riverton Rd Unit 55, Winsted, CT 06098

  111 Riverton Rd Unit 55, Winsted, CT 06098
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  /13

  $179,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  14 Pratt St, Winsted, CT 06098

  Don't let the outside fool you! Perfect alternative to condominium living! No HOA and plenty of off street parking at this in-town location. Nice size living room; large kitchen/dining combination with access to the deck and the 1/2 bath laundry room make up the first floor of this cute home. Upstairs you will find 2 modest size bedrooms along with the large primary and the full bath which has a

  Amy Sartirana Northwest CT Realty

  14 Pratt St, Winsted, CT 06098
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  $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
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  Est $216,055 Not Listed For Sale

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

  111 Riverton Rd Unit 45, Winsted, CT 06098

  111 Riverton Rd Unit 45, Winsted, CT 06098
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  /4

  $39,000 Pending

  • Land
  • 0.41 Acre
  • $95,122 per Acre

  130 Alpha Ave, Winsted, CT 06098

  Discover the Perfect Canvas for Your Dream Home in Winchester, Connecticut! This exceptional .41-acre parcel (owner reports closer to .5 ac) combines eight contiguous lots to create a prime opportunity for building your ideal residence. Nestled in the serene surroundings of the Highland Lake neighborhood, the property is lightly wooded with mature, straight-standing hardwoods and features a

  Suzie Larson Turning Point Realty, LLC

  130 Alpha Ave, Winsted, CT 06098
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  $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
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  Est $238,246 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,310 Sq Ft

  20 Gay St, Winsted, CT 06098

  20 Gay St, Winsted, CT 06098
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  /27

  $349,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 3,303 Sq Ft

  135 Elm St Unit 137, Winsted, CT 06098

  Welcome to 135-137 Elm Street! This well-maintained two-family home offers an excellent opportunity for owner-occupants or investors alike. The main level unit features 5 rooms, including 2 bedrooms and 1 full bath, and is in excellent condition. It's equipped with a natural gas warm-air furnace that also provides central air for year-round comfort. The second-floor unit mirrors the first-floor

  David Sartirana Northwest CT Realty

  135 Elm St Unit 137, Winsted, CT 06098
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  $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
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  Est $259,120 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft

  9 Fruit St, Winsted, CT 06098

  9 Fruit St, Winsted, CT 06098
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  /17

  $319,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,754 Sq Ft

  25 Center St, Winsted, CT 06098

  Don't miss this unique opportunity to own a multi family residential property and an office space! (Owner currently has permission from the town to create a 2nd residential unit on the first floor) - will have 2.5 baths when completed. Great central location close to all amenities that Winsted has to offer including restaurants, parks, college, public transportation and shopping. First floor

  Tony Goia The Washington Agency

  25 Center St, Winsted, CT 06098
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  $860,000 Sold Jun 24, 2025

  • 3,016 Sq Ft
  • $285/SF
  • 90 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1956

  399 Colebrook Rd, Colebrook, CT 06021

  HILLTOP COMFORT IN COLEBROOK - Welcome home and put those cares aside in this meticulously maintained Country Colonial, a home transformed in the 1990's with a seamless conversion from a single level house to a spacious two level home. The 10.15 acres includes two additional building lots, a spring fed pond, apple trees, stone walls, gardens that delight in any season, and a wonderful patio that

  David Taylor Elyse Harney Real Estate

  399 Colebrook Rd, Colebrook, CT 06021
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  Est $342,967 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  202 Old New Hartford Rd, Winsted, CT 06098

  202 Old New Hartford Rd, Winsted, CT 06098
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  /17

  $269,000 Under Contract

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

  38 Upland Rd, Winsted, CT 06098

  TO SETTLE ESTATE: Available for Immediate Occupancy is this Immaculate 3 to 4 Bedroom Colonial tucked away on a quiet street. Features Hardwood Floors throughout the house, 24' x 14' Family Room with Propane Gas Stove, Country Kitchen. Primary Bedroom with it's own office area. Oversized Full Bath. 3-Season 21' x 8' Enclosed Porch. 26' x 10' Concrete Patio. Detached One Car Garage. Attractive

  Marshall Cohen Cohen Agency

  38 Upland Rd, Winsted, CT 06098
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  $113,000 Sold Jun 23, 2025

  • 570 Sq Ft
  • $198/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1985

  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
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  Est $458,112 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,184 Sq Ft

  123 Skinner Rd, Winsted, CT 06098

  123 Skinner Rd, Winsted, CT 06098
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  /37

  $194,900 Under Contract

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

  111 Riverton Rd Unit 61, Winsted, CT 06098

  Beautifully Maintained Townhouse Condo Located in Small, Quiet Complex in Charming Winchester, CT! Unit Comes with Newer Floors, Updated Full Bath Offering Walk-in Shower with Seemless Glass Door and New Vanity. 2 Newer LG Smart Inverter Heat Pump Mini Split (Heat and AC). Sun Infused Living Room Offers Sliding Glass Doors to Private Upper Level Deck and Fireplace. Newer Stainless Steel

  Bethany Lydem Stone Crest Realty LLC

  111 Riverton Rd Unit 61, Winsted, CT 06098

Showing Results 161 - 200, Page 5 of 18