Homes in ZIP Code 06098

• 

  

  

  /31

  $339,000

  • 6 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  157 Elm St, Winsted, CT 06098

  Bring your vision to this spacious 6-bedroom, 2.5-bath home full of character and potential. Featuring a newer roof and boiler, this property offers peace of mind while leaving room for your personal touch. Enjoy the classic Victorian details and generous layout, perfect for creating your dream home. Situated on a sidewalk-lined street just steps from downtown eateries, a local brewery, and

  

  Doreen Gagnon

  Coldwell Banker Realty

  (860) 590-8606

  157 Elm St, Winsted, CT 06098
• 

  

  /2

  $1,495 total monthly price

  • 2 Beds
  • 1 Bath
  • 667 Sq Ft
  • House for Rent

  80 Gay St Unit 1, Winsted, CT 06098

  Bright and sunny, first floor, two-bedroom apartment close to town. Large front porch, off-street parking and nice yard. Washer/dryer can be added for additional monthly charge. Pets considered. First month and two months security required.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 351-1472

  80 Gay St Unit 1, Winsted, CT 06098
• 

  $324,900 Sold Nov 21, 2025

  • 3,303 Sq Ft
  • $98/SF
  • 32 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  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
• 

  Est $395,638 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  51 Millbrook Rd, Colebrook, CT 06021

  51 Millbrook Rd, Colebrook, CT 06021
• 

  

  /2

  $29,000

  • Land
  • 1.88 Acres
  • $15,426 per Acre

  52 White St, Winsted, CT 06098

  Discover the possibilities with this 1.8-acre parcel located on a peaceful in-town street. The property offers a convenient location close to town amenities while maintaining a quiet, private setting. Public water and sewer are available in the street, though not currently connected to the property. While the land is developable, the seller will retain easements for drainage and access to

  

  David Sartirana

  Northwest CT Realty

  (860) 856-5386

  52 White St, Winsted, CT 06098
• 

  /2

  $1,295 total monthly price

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • House for Rent

  144 Wetmore Ave Unit 1, Winsted, CT 06098

  Adorable one bedroom, first floor apartment close to town and college. Pets considered. First month and two months security required. Credit and background check required.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 926-2306

  144 Wetmore Ave Unit 1, Winsted, CT 06098
• 

  $227,500 Sold Nov 20, 2025

  • 1,334 Sq Ft
  • $171/SF
  • 91 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 2007

  174 Wallens St Unit H1, Winsted, CT 06098

  Discover effortless living in this inviting home at the sought-after Clockmaker's Hill community. The thoughtfully designed open floor plan creates seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining room, perfect for hosting friends and family. The sun-drenched kitchen features a convenient breakfast bar for casual dining and morning coffee. The

  Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, Winsted, CT 06098
• 

  Est $473,763 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,933 Sq Ft

  125 Old Rd N, Winchester, CT 06098

  125 Old Rd N, Winchester, 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

  (860) 453-5624

  48 Bridge St, Winsted, CT 06098
• 

  

  /18

  $1,600 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,890 Sq Ft
  • Townhouse for Rent

  31 Benton St, Winchester, CT 06098

  Adorable Duplex, newly remodeled Kitchen and bath. Harwood floors throughout with a new gas furnace. Deck off kitchen. A must see!

  

  Victoria Stillings

  Coldwell Banker Realty

  (860) 743-1027

  31 Benton St, Winchester, CT 06098
• 

  $360,000 Sold Nov 19, 2025

  • 1,304 Sq Ft
  • $276/SF
  • 41 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1965

  52 Bricklemaier Rd, Colebrook, CT 06021

  Beautifully landscaped with flowering trees and established perennials, this three-bedroom home offers a peaceful country setting with minimal traffic. Set on 1.68 acres with an additional one-acre adjacent lot included in the sale, the property provides flexibility and room to grow. The home features hardwood floors throughout and two fireplaces, one of which is in the lower level. An additional

  Wendy Eichman Raynard & Peirce Realty,LLC

  52 Bricklemaier Rd, Colebrook, CT 06021
• 

  Est $380,157 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  126 Newfield Rd, Winchester, CT 06098

  126 Newfield Rd, Winchester, CT 06098
• 

  

  /34

  $299,900 Pending

  • 5 Beds
  • 2 Baths
  • 2,344 Sq Ft

  49 Walnut St, Winsted, CT 06098

  Well-maintained two-family home situated on a large, level lot in an area of well-cared-for properties. Conveniently located near downtown, schools, Northwestern Connecticut Community College, shopping, and restaurants. The first-floor unit features an eat-in kitchen, dining area, living room, two bedrooms, and a full bath. The second-floor unit offers a spacious kitchen/living area, 2-3

  

  David Sartirana

  Northwest CT Realty

  (860) 374-7309

  49 Walnut St, Winsted, CT 06098
• 

  

  /9

  $1,695 total monthly price

  • 4 Beds
  • 1 Bath
  • 2,564 Sq Ft
  • House for Rent

  26 Case Ave Unit 2, Winsted, CT 06098

  Large second floor, four bedroom apartment, close to town. Washer/ dryer in unit. Pets considered, off street parking. First month rent and two months security required. Credit and background check done by listing office.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 750-9337

  26 Case Ave Unit 2, Winsted, CT 06098
• 

  $362,000 Sold Nov 18, 2025

  • 1,910 Sq Ft
  • $190/SF
  • 84 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1949

  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
• 

  Est $389,168 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,203 Sq Ft

  191 Danbury Quarter Rd, Winchester Center, CT 06098

  191 Danbury Quarter Rd, Winchester Center, CT 06098
• 

  

  /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

  (860) 650-5076

  0 Old Robertsville Rd, Winchester, CT 06098
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  /34

  $1,500 - $1,800 per month plus fees

  Mill at Still River

  1 - 2 Beds

  101 Whiting St, Winsted, CT 06098

  By far the best place to live in Winsted, Connecticut. Turn of the century construction, every unit overlooks the beautiful Still River, our 700-1000 square-foot one and two bedroom interiors are bright and charming and feature exposed wood beams, 10-foot ceilings, oversized industrial windows, and exposed brick walls. We deliver nature at your door. Our community amenities include same-floor

  101 Whiting St, Winsted, CT 06098
• 

  $920,000 Sold Nov 17, 2025

  • 2,131 Sq Ft
  • $432/SF
  • 56 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  43 E Lake St, Winsted, CT 06098

  Enjoy beautiful sunsets from the large composite deck of this year-round, westerly facing, 4 bedroom, 3 full bath, waterfront home. The peaceful location in Hurlbut cove in first bay allows for kayaking and swimming without the usual boat traffic on Highland Lake. A sandy wading area for little ones is next to the maintenance free aluminum boat dock. There are hardwood floors throughout the

  Keith Meyer Northwest CT Realty

  43 E Lake St, Winsted, CT 06098
• 

  Est $322,345 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,267 Sq Ft

  151 Newfield Rd, Winchester, CT 06098

  151 Newfield Rd, Winchester, CT 06098
• 

  

  /8

  $299,900 Pending

  • 6 Beds
  • 2 Baths
  • 2,699 Sq Ft

  77 Hubbard St, Winsted, CT 06098

  Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 452-3957

  77 Hubbard St, Winsted, CT 06098
• 

  

  /10

  $1,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,199 Sq Ft
  • House for Rent

  22 Upson Ave, Winsted, CT 06098

  Beautiful First-Floor Apartment with Classic Charm and Modern Updates! This spacious first-floor apartment features gleaming hardwood floors, fresh paint, and an updated kitchen. Enjoy the high ceilings and beautiful woodwork that add character and warmth throughout. Conveniently located close to downtown, offering easy access to shopping, dining, and commuting routes.

  Kelly Sullivan Sullivan Real Estate Inc

  22 Upson Ave, Winsted, CT 06098
• 

  $243,000 Sold Nov 17, 2025

  • 1,334 Sq Ft
  • $182/SF
  • 33 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  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
• 

  Est $353,370 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,606 Sq Ft

  283 Colebrook Rd, Winsted, CT 06098

  283 Colebrook Rd, Winsted, CT 06098
• 

  

  /23

  $229,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft

  32 Charles St, Winsted, CT 06098

  Charming Cape on a Quiet Dead-End Street Welcome to 32 Charles Street - a cute and cozy 1,044 sq. ft. Cape-style home located just moments from the downtown area. The first floor offers an inviting eat-in kitchen, a comfortable living room, two bedrooms, and a full bath. Upstairs, you'll find one additional bedroom and 1 room providing flexibility for guests, a home office, or hobby space. The

  

  David Sartirana

  Northwest CT Realty

  (860) 352-1991

  32 Charles St, Winsted, CT 06098
• 

  

  /23

  $1,150 - $1,550 per month plus fees

  Gilbert Clock Apartments

  Studio - 2 Beds

  13 Wallens St, Winsted, CT 06098

  At Gilbert Clock Apartments , our designer-inspired amenities set us apart from the competition. We pride ourselves on providing top-quality apartments outfitted with the everyday amenities you expect as well as luxury amenities to delight your senses and enhance your modern life. Indulge your culinary instincts in your state-of-the-art kitchen, furnished with Beautiful and energy-efficient

  13 Wallens St, Winsted, CT 06098
• 

  $370,000 Sold Nov 14, 2025

  • 2,024 Sq Ft
  • $183/SF
  • 77 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1898

  166 Torringford St, Winsted, CT 06098

  Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area

  Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
• 

  Est $55,108 Not Listed For Sale

  287 Colebrook Rd, Winsted, CT 06098

  287 Colebrook Rd, Winsted, CT 06098
• 

  

  /38

  $439,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,892 Sq Ft

  819 E Wakefield Blvd, Winsted, CT 06098

  Perched directly across the street from Highland Lake's 3rd Bay, this charming 1,900 sq. ft. Cape offers sweeping lake views and the enjoyment of a permanent right-of-way to access the water. The home features 7 rooms, including 3 bedrooms and 1.5 baths, and has been thoughtfully maintained with important updates: new propane heating and hot water systems (2022), a new roof on both the house and

  

  David Sartirana

  Northwest CT Realty

  (860) 497-9746

  819 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /37

  $4,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  880 W Wakefield Blvd, Winsted, CT 06098

  Discover lakeside living at its finest with this fully renovated, fully furnished 3 bedroom, sleeps 10, 2 full-baths, family estate set on a half acre of professionally landscaped grounds overlooking picturesque Highland Lake. Located just 0.6 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of

  Matt Crossen Coldwell Banker Realty

  880 W Wakefield Blvd, Winsted, CT 06098
• 

  $167,900 Sold Nov 14, 2025

  • 1,340 Sq Ft
  • $125/SF
  • 24 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  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
• 

  Est $46,941 Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098
• 

  

  /39

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,969 Sq Ft

  208 Spencer Hill Rd, Winsted, CT 06098

  Discover this beautifully maintained 3-bedroom, 1.5-bath Colonial set on a level one-acre lot less than two miles from town. This home has been thoughtfully updated over the years and is truly move-in ready. Enjoy a spacious living room and family room, each featuring a cozy fireplace-perfect for New England seasons. The updated kitchen offers modern appliances and a bright, comfortable

  

  David Sartirana

  Northwest CT Realty

  (860) 431-6356

  208 Spencer Hill Rd, Winsted, CT 06098
• 

  /2

  $1,050 per month plus fees

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  12 Beach St Unit 7, Winsted, CT 06098

  Property Id: 1615805Total 8 - 1 BED ROOM UNITS in the building CLOSE to Route 8 & WINSTED Mainstreet, on-site parking, coin operated laundry, REAR BALCONY.

  12 Beach St Unit 7, Winsted, CT 06098
• 

  $29,000 Sold Nov 11, 2025

  • Land
  • 0.41 Acre
  • $70,732 per Acre

  • 119 Days On Market

  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
• 

  Est $401,495 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,934 Sq Ft

  24 Simons Pond Rd, Colebrook, CT 06021

  24 Simons Pond Rd, Colebrook, CT 06021
• 

  

  /33

  $339,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  107 Peck Rd, Winsted, CT 06098

  Turnkey 3 Bedroom, 1 bathroom home on almost an acre in Winchester. The home is sited up a long driveway in a quiet, wooded setting across from state land. Completely renovated by current owner, top to bottom. Updated kitchen & bath, new roof, new hot water heater, new Trex deck, new pellet stove, new ductless mini splits in living area and primary bedroom and much more! Attached one car garage

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (860) 855-0150

  107 Peck Rd, Winsted, CT 06098
• 

  

  /8

  $2,200 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • House for Rent

  26 Elm St, Winchester, CT 06098

  Be the first to live in this completely renovated 3-bedroom, 1-bath apartment located just half a block from Main Street - walkable to all your favorite shops and restaurants! This bright and spacious home features a wide open floor plan with brand-new floors, all new appliances, modern cabinets, and granite countertops. Every detail has been thoughtfully upgraded, including new blinds and a

  Annie Simard LPT Realty

  26 Elm St, Winchester, CT 06098
• 

  $300,000 Sold Nov 07, 2025

  • 1,323 Sq Ft
  • $227/SF
  • 25 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1940

  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
• 

  Est $773,342 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,860 Sq Ft

  404 Colebrook Rd, Colebrook, CT 06021

  404 Colebrook Rd, Colebrook, CT 06021

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