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
• 

  

  

  /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
• 

  $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
• 

  

  

  /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

  $1,495 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
• 

  $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
• 

  

  /30

  $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
• 

  /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
• 

  $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
• 

  

  /36

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,167 Sq Ft

  197 Spencer Hill Rd, Winsted, CT 06098

  Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a desirable rural neighborhood. Offering over 3,000 square feet of living space, this well-maintained home provides a flexible layout ideal for today's lifestyle. The main level features a formal living room, dining room, updated kitchen, den, sunroom with fireplace and hot tub, full bath, and convenient

  

  David Sartirana

  Northwest CT Realty

  (860) 419-0914

  197 Spencer Hill Rd, Winsted, CT 06098
• 

  

  /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
• 

  $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
• 

  

  /22

  $179,900

  • 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

  (860) 615-2545

  111 Riverton Rd Unit 90, 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
• 

  $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
• 

  

  /27

  $394,900

  • 2 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  212 Spencer Hill Rd, Winsted, CT 06098

  Welcome to your peaceful retreat in the heart of Winchester - a quiet, scenic town surrounded by natural beauty. Tucked away on a private lot, this thoughtfully maintained home offers a perfect blend of rustic charm and modern comfort, with every detail designed to enhance your connection to the outdoors. Step inside to discover gleaming original hardwood floors that stretch across the sun-filled

  

  Tammy Powling

  Showcase Realty, Inc.

  (860) 743-1453

  212 Spencer Hill Rd, 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
• 

  $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
• 

  

  /7

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft

  312 Colebrook River Rd, Colebrook, CT 06021

  Charming Colonial on a 2-acre lot. Inside, you'll find an updated kitchen featuring granite countertops and newer appliances. The large, sunny family room on the first floor is filled with natural light, creating a warm and inviting atmosphere. A combined living and dining room with a cozy wood stove adds charm and functionality to the main level. Recent upgrades to the home include a new roof in

  

  Amanda Balaski

  Northwest CT Realty

  (860) 891-2072

  312 Colebrook River Rd, Colebrook, CT 06021
• 

  

  /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
• 

  $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
• 

  /2

  $29,000

  • Land
  • 0.44 Acre
  • $65,909 per Acre

  124 Rockwell St, Winsted, CT 06098

  124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless

  

  David Sartirana

  Northwest CT Realty

  (860) 891-6121

  124 Rockwell St, 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
• 

  $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
• 

  /2

  $49,000

  • Land
  • 0.37 Acre
  • $132,432 per Acre

  99 Hubbard St, Winsted, CT 06098

  99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

  

  David Sartirana

  Northwest CT Realty

  (860) 946-4468

  99 Hubbard St, 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
• 

  $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
• 

  

  /37

  $499,999

  • 5 Beds
  • 4 Baths
  • 5,016 Sq Ft

  55 Walnut St, Winsted, CT 06098

  Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

  

  David Sartirana

  Northwest CT Realty

  (860) 390-5071

  55 Walnut St, Winsted, CT 06098
• 

  

  /29

  $4,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • House for Rent

  121 W Wakefield Blvd, Winsted, CT 06098

  Discover lakeside living at its finest with this renovated 5-bedroom, 4-bath family estate set privately on a full acre overlooking picturesque Highland Lake. Located just 0.7 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of a private dock and waterfront deck located directly across the

  Elizabeth Stockwell Coldwell Banker Realty

  121 W Wakefield Blvd, Winsted, 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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