Homes in ZIP Code 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

  Better Homes and Gardens Real Estate Executive Real Estate

  (860) 452-3957

  77 Hubbard St, Winsted, CT 06098
• 

  

  

  /8

  $1,250 Per Month

  • 1 Bed
  • 1 Bath
  • 2,031 Sq Ft
  • House for Rent

  25 Lake St, Winsted, CT 06098

  Totally renovated one bedroom apartment with a new bathroom and new flooring throughout. Washer/dryer can be added for an additional $75 per month. Pets considered. Easy access to to shopping, restaurants, and college. First month and two months security and minimum credit score required.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 891-6046

  25 Lake St, Winsted, CT 06098
• 

  $350,000

  Sold May 22, 2026

  9 Colony Dr, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1966

  Last Sold Summary

  • 6% Above List Price
  • $221/SF
  • 27 Days On Market

  Current Estimated Value $328,189

  Last Listing Agent David Sartirana Northwest CT Realty

  9 Colony Dr, Winsted, CT 06098
• 

  Est $311,106

  Not Listed For Sale

  155 Mathew Rd, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,536 Sq Ft
  • Built 1979

  155 Mathew Rd, Winsted, CT 06098

  Last Sold Summary

  • 56 Days On Market
• 

  

  

  /35

  $339,900

  Pending

  • 2 Beds
  • 1 Bath
  • 975 Sq Ft

  621 Wynne Rd, Winsted, CT 06098

  Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of

  

  David Sartirana

  Northwest CT Realty

  (860) 385-6622

  621 Wynne Rd, Winsted, CT 06098
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  /34

  Starting at $1,500 Plus Fees

  • 1 Bed

  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

  Mill at Still River

  (860) 744-5205

  101 Whiting St, Winsted, CT 06098
• 

  $362,000

  Sold Nov 18, 2025

  147 Smith Hill Rd, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft
  • Built 1949

  Last Sold Summary

  • 6% Below List Price
  • $190/SF
  • 84 Days On Market

  Current Estimated Value $373,238

  Last Listing Agent SHARON GILSON Northwest CT Realty

  147 Smith Hill Rd, Winsted, CT 06098
• 

  Est $260,644

  Not Listed For Sale

  150 Meadow St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,094 Sq Ft
  • Built 1860

  150 Meadow St, Winsted, CT 06098

  Last Sold Summary

  • 80 Days On Market
• 

  

  /15

  $499,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,556 Sq Ft

  5 Stadler Heights, Winsted, CT 06098

  Spacious and full of potential, this 10-room home offers 4 bedrooms and 2.5 baths with plenty of room for everyone. Priced below current market value, this property presents a fantastic opportunity for buyers willing to make some cosmetic updates and build instant equity. Set in a quiet country location within a private development known for its large lots and peaceful surroundings, the home

  

  David Sartirana

  Northwest CT Realty

  (860) 467-0358

  5 Stadler Heights, Winsted, CT 06098
• 

  

  /20

  Starting at $1,150 Plus Fees

  • 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

  Gilbert Clock Apartments

  (959) 335-6388

  

  13 Wallens St, Winsted, CT 06098
• 

  $920,000

  Sold Nov 17, 2025

  43 E Lake St, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 2,131 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $432/SF
  • 56 Days On Market

  Current Estimated Value $930,148

  Last Listing Agent Keith Meyer Northwest CT Realty

  43 E Lake St, Winsted, CT 06098
• 

  Est $144,657

  Not Listed For Sale

  287 Colebrook Rd, Winsted, CT 06098

  287 Colebrook Rd, Winsted, CT 06098

  Last Sold Summary

  • 180 Days On Market
• 

  

  /26

  $998,000

  • 4 Beds
  • 3 Baths
  • 3,330 Sq Ft

  878 W Wakefield Blvd, Winsted, CT 06098

  WATERFRONT AND PRIVACY-WIN, WIN! PACK YOUR CLOTHES AND TOOTHBRUSH, THIS GEM IS TURN KEY AND WAITING FOR YOU! FULLY REMODELED INSIDE AND OUT! Nestled along the shores of HIGHLAND LAKE, this stunning waterfront retreat offers the perfect blend of year-round living and vacation-style comfort. Featuring 4 bedrooms and 3 bathrooms, this spacious home is designed to capture breathtaking lake views

  

  Annie Q Simard

  LPT Realty

  (860) 891-6304

  878 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /10

  Starting at $1,525 Plus Fees

  • 2 Beds

  15 Mountain View Terrace, Winsted, CT 06098

  Litchfield Heights Apartments is nestled quietly in the greenery of the Berkshires. We are situated close to the border of Massachusetts with easy access from Routes 8 & 44. We offer generously sized 1 bedroom flats, and 2 or 3 bedroom Townhouse. Enjoy the ease of maintenance free living when you make Litchfield Heights Apartments your home. Call Litchfield Heights Apartments today for further

  Litchfield Heights

  (860) 909-8188

  

  15 Mountain View Terrace, Winsted, CT 06098
• 

  $365,000

  Sold May 15, 2026

  262 Holabird Ave, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,312 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $278/SF
  • 11 Days On Market

  Current Estimated Value $358,535

  Last Listing Agent Mary Anne Casey D. Beckley Realty

  262 Holabird Ave, Winsted, CT 06098
• 

  Est $44,958

  Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 184 Days On Market
• 

  /2

  $29,900

  • Land
  • 5,662 Sq Ft
  • $230,000 per Acre

  17 Birdsall St, Winsted, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.13-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

  

  David Sartirana

  Northwest CT Realty

  (860) 295-4250

  17 Birdsall St, Winsted, CT 06098
• 

  

  /9

  $2,200

  Total Monthly Price

  • 4 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  15 Upson Ave Unit Upson ave, Winsted, CT 06098

  Property is completely vacant and ready for move in. Serious inquiries only

  15 Upson Ave Unit Upson ave, Winsted, CT 06098
• 

  $460,000

  Sold Jun 20, 2025

  288 Torringford St, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft
  • Built 1875

  Last Sold Summary

  • 14% Below List Price
  • $152/SF
  • 128 Days On Market

  Current Estimated Value $466,278

  Last Listing Agent Mark Porriello RE/MAX Right Choice

  288 Torringford St, Winsted, CT 06098
• 

  Est $371,955

  Not Listed For Sale

  24 Simons Pond Rd, Colebrook, CT 06021

  • 2 Beds
  • 2.5 Baths
  • 1,934 Sq Ft
  • Built 1980

  24 Simons Pond Rd, Colebrook, CT 06021

  Last Sold Summary

  • 25 Days On Market
• 

  

  /25

  $349,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft

  102 Wallens St, Winsted, CT 06098

  This move-in-ready Colonial-style home blends classic charm with modern updates. Featuring a remodeled kitchen with a large center island, cherry cabinets, granite countertops, stainless steel appliances, and a wine fridge. The main level also offers a dining room with refinished hardwood floors, a living room, and a flexible family room. Upstairs includes three bedrooms and a full bath, with a

  

  Amanda Balaski

  Northwest CT Realty

  (860) 544-5816

  102 Wallens St, Winsted, CT 06098
• 

  

  /5

  $1,000 Per Month

  • 2 Beds
  • 1 Bath
  • 4,668 Sq Ft
  • Apartment for Rent

  440 Main St Unit B, Winchester, CT 06098

  Second Floor two Bedroom room apartment set in town. Convenient to stores, restaurants and medical facility.

  Linda Ganem Borla & Associates Real Estate

  440 Main St Unit B, Winchester, CT 06098
• 

  $305,000

  Sold Dec 22, 2025

  49 Walnut St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 2,344 Sq Ft
  • Built 1824

  Last Sold Summary

  • 2% Above List Price
  • $130/SF
  • 6 Days On Market

  Current Estimated Value $302,384

  Last Listing Agent David Sartirana Northwest CT Realty

  49 Walnut St, Winsted, CT 06098
• 

  Est $701,389

  Not Listed For Sale

  404 Colebrook Rd, Colebrook, CT 06021

  • 3 Beds
  • 2.5 Baths
  • 3,860 Sq Ft
  • Built 1989

  404 Colebrook Rd, Colebrook, CT 06021

  Last Sold Summary

  • 22 Days On Market
• 

  /2

  $29,000

  • Land
  • 5,227 Sq Ft
  • $241,667 per Acre

  82-84 Rockwell St, Winchester, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.12-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

  

  David Sartirana

  Northwest CT Realty

  (860) 419-2496

  82-84 Rockwell St, Winchester, CT 06098
• 

  

  /6

  $1,475

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,045 Sq Ft
  • 2 Bedroom Townhouse Apartment

  I 9 Nanni Dr Unit F-09, Winchester, CT 06098

  Nestled in the Hills of Litchfield County, our Large Town Homes Offer:• Updated eat in kitchen with dishwasher and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Kitchen and Bathroom.• Private Entrances with Slider to backyard • Over 1000 square feet of living space with heat and hot water included.Please come see why at

  I 9 Nanni Dr Unit F-09, Winchester, CT 06098
• 

  $370,000

  Sold Mar 25, 2026

  171 Wallens St, Winchester, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Above List Price
  • $290/SF
  • 23 Days On Market

  Current Estimated Value $349,443

  Last Listing Agent Meagan Albert Tier 1 Real Estate

  171 Wallens St, Winchester, CT 06098
• 

  Est $382,582

  Not Listed For Sale

  98 Pinney St, Colebrook, CT 06021

  • 3 Beds
  • 1 Bath
  • 1,294 Sq Ft
  • Built 1940

  98 Pinney St, Colebrook, CT 06021

  Last Sold Summary

  • 39 Days On Market
• 

  

  /39

  $369,000

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

  212 Spencer Hill Rd, Winsted, CT 06098

  Nestled on a private lot in scenic Winchester, this beautifully maintained home offers a wonderful blend of comfort, character, and natural surroundings. Hardwood floors welcome you into the bright and inviting interior, where the custom kitchen serves as the heart of the home with hickory cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. The second floor features

  

  David Sartirana

  Northwest CT Realty

  (860) 452-3419

  212 Spencer Hill Rd, Winsted, CT 06098
• 

  

  /13

  $1,365 Per Month

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

  20-22 Allen St Unit 2nd flr rs, Winchester, CT 06098

  Efficient Pet Friendly 1 bedroom (second floor) rental available. Clean and bright. Private rear covered porch, gas range stainless refrigerator stackable washer and dryer provided for convenience. Trash and recycling included, only one off street parking space. Hardwood floors. Close to NWCC, shopping, restaurants, Highland Lake etc. Clean bright quiet and secure building. Gas and heat and hot

  Suzie Larson Turning Point Realty, LLC

  20-22 Allen St Unit 2nd flr rs, Winchester, CT 06098
• 

  $208,900

  Sold Jul 18, 2025

  39 Orchard St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1875

  Last Sold Summary

  • 9% Below List Price
  • $174/SF
  • 131 Days On Market

  Current Estimated Value $284,748

  Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc

  39 Orchard St, Winsted, CT 06098
• 

  Est $158,000

  Not Listed For Sale

  14 Pine Rd, Colebrook, CT 06021

  • 4 Beds
  • Built 1998

  14 Pine Rd, Colebrook, CT 06021

  Last Sold Summary

  • 43 Days On Market
• 

  /2

  $24,900

  $4K PRICE DROP Pending

  • Land
  • 19,166 Sq Ft
  • $56,591 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
• 

  

  /9

  $1,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Property for Rent

  936 Main St Unit 14, Winchester, CT 06098

  Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance to the property is being worked on now with 3 new homes to be put in front. The property will look much nicer when completed. This is the final phase. Beautiful free standing ranch style homes, 2 bedroom, 2 baths with attached closed porch available. There are 2 houses available

  Michael Block Building Blocks LLC

  936 Main St Unit 14, Winchester, CT 06098
• 

  $691,000

  Sold May 21, 2026

  156 Shore Dr, Winsted, CT 06098

  • 5 Beds
  • 1.5 Baths
  • 1,258 Sq Ft
  • Built 1930

  Last Sold Summary

  • 12% Below List Price
  • $549/SF
  • 31 Days On Market

  Current Estimated Value $779,019

  Last Listing Agent Bryan Palladino Showcase Realty, Inc.

  156 Shore Dr, Winsted, CT 06098
• 

  Est $331,180

  Not Listed For Sale

  268 Smith Hill Rd, Colebrook, CT 06021

  • 2 Beds
  • 2 Baths
  • 1,635 Sq Ft
  • Built 1955

  268 Smith Hill Rd, Colebrook, CT 06021

  Last Sold Summary

  • 122 Days On Market
• 

  /2

  $45,000

  • Land
  • 1.07 Acres
  • $42,056 per Acre

  132 Florence St, Winsted, CT 06098

  Rare opportunity to build your dream home on this 1.07-acre vacant lot conveniently located close to downtown shopping, dining, and everyday amenities. Situated in an established neighborhood, this property offers season-long westerly views and spectacular sunset vistas, creating the perfect backdrop for your future home. Public water and public sewer are available in the street (buyer to verify

  

  David Sartirana

  Northwest CT Realty

  (860) 217-5758

  132 Florence St, Winsted, CT 06098
• 

  

  /14

  $900 Per Month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Apartment for Rent

  277 N Main St Unit 3, Winsted, CT 06098

  Second-floor apartment available in a convenient Winsted location, close to local shops, dining, and everyday amenities. This freshly painted unit offers a bright, open living space with an efficient layout, along with an in-wall A/C unit for added comfort. The kitchen provides ample cabinet storage, and the unit is complemented by a clean, well-maintained bath. Enjoy the convenience of on-site

  Ryan Marconi The Washington Agency

  277 N Main St Unit 3, Winsted, CT 06098
• 

  $225,000

  Sold Dec 10, 2025

  32 Charles St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Below List Price
  • $216/SF
  • 41 Days On Market

  Current Estimated Value $233,674

  Last Listing Agent David Sartirana Northwest CT Realty

  32 Charles St, Winsted, CT 06098
• 

  Est $114,802

  Not Listed For Sale

  11 Gibbs St Unit 6, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1985

  11 Gibbs St Unit 6, Winsted, CT 06098

  Last Sold Summary

  • 62 Days On Market

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