Homes in ZIP Code 06098

• 

  $862,500 Sold Jul 23, 2025

  • 2,113 Sq Ft
  • $408/SF
  • 61 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1955

  112 Shore Dr, Winsted, CT 06098

  Live like you're on vacation every day! This beautifully updated lakefront home sits directly on the water in Highland Lake's first Bay, offering a level backyard & a private dock just steps from your door. With 50+ feet of direct waterfront and a fenced, low-maintenance yard, this charming year-round home is the perfect blend of comfort, style, & lakefront living. The interior boasts an open

  Nancy Reardon Berkshire Hathaway NE Prop.

  112 Shore Dr, Winsted, CT 06098
• 

  Est $276,289 Not Listed For Sale

  • 3 Beds
  • 1,766 Sq Ft

  87 Wetmore Ave, Winsted, CT 06098

  87 Wetmore Ave, Winsted, CT 06098
• 

  

  

  /40

  $299,900 Under Contract

  • 4 Beds
  • 3 Baths
  • 1,874 Sq Ft

  106 Rockwell St, Winsted, CT 06098

  Looking to expand your investment portfolio-or live nearly rent-free while building one? This rare 3-family opportunity checks all the boxes! Hard to come by, this multi-family property features long-term, reliable tenants plus a vacant unit ready for an owner-occupant or a new rental. The lower level offers a comfortable 1-bedroom unit with walk-out patio. The main (2nd) level features 2

  Dawn Rousseau Showcase Realty, Inc.

  106 Rockwell St, Winsted, CT 06098
• 

  $1,200,000 Sold Jul 23, 2025

  • 2,407 Sq Ft
  • $499/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1948

  200 Perch Rock Trail, Winsted, CT 06098

  Exceptional Waterfront Living on Highland Lake - Your Dream Home Awaits! Seize this rare opportunity to own a stunning YEAR-ROUND WATERFRONT property on the highly sought-after EAST SIDE of Highland Lake! This turnkey gem is move-in ready and packed with modern features, offering the ultimate retreat for those seeking the serenity and excitement of lake life. Step into an open-concept kitchen and

  Annie Simard LPT Realty

  200 Perch Rock Trail, Winsted, CT 06098
• 

  Est $206,857 Not Listed For Sale

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

  111 Riverton Rd Unit 52, Winsted, CT 06098

  111 Riverton Rd Unit 52, Winsted, CT 06098
• 

  

  /6

  $12,500 Under Contract

  • Land
  • 0.23 Acre
  • $54,348 per Acre

  605 E Wakefield Blvd, Winchester, CT 06098

  Across from the lake. Lot does not meet the set backs & is unbuildable.

  Diane Gombieski Carl Guild & Associates

  605 E Wakefield Blvd, 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
• 

  Est $307,959 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 954 Sq Ft

  155 Alpha Ave, Winsted, CT 06098

  155 Alpha Ave, Winsted, CT 06098
• 

  

  /15

  $350,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 2,038 Sq Ft

  33 Shantry Rd, Colebrook, CT 06021

  One of the best properties in colebrook. The perfect piece of land. Level yard with a pond on the property. Oversized 2 car garage. Stone fireplace. 30X26 great room that's Great for entertaining. New roof installed 2024. Don't miss out on this one, won't last long.

  PATRICIA SHERWIN Dave Jones Realty, LLC

  33 Shantry Rd, Colebrook, CT 06021
• 

  $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
• 

  Est $309,782 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,114 Sq Ft

  136 Glendale Ave, Winsted, CT 06098

  136 Glendale Ave, Winsted, CT 06098
• 

  

  /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
• 

  $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
• 

  Est $596,703 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  732 W Wakefield Blvd, Winsted, CT 06098

  732 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /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
• 

  $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
• 

  Est $262,285 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  152 Pratt St, Winsted, CT 06098

  152 Pratt St, Winsted, CT 06098
• 

  

  /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
• 

  $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
• 

  Est $255,676 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,109 Sq Ft

  27 Benton St, Winsted, CT 06098

  27 Benton St, Winsted, CT 06098
• 

  

  /14

  $450,000 Under Contract

  • Land
  • 160 Acres
  • $2,812 per Acre

  430 Smith Hill Rd, Colebrook, CT 06021

  A rare opportunity to create your own private retreat in the peaceful foothills of Colebrook. Includes 18.7 acres of buildable land with the possibility to subdivide into two parcels, giving you options for your dream home or future investment. Tucked well off the beaten path, the setting is surrounded by natural beauty, offering unmatched privacy and a sense of seclusion. With selective

  Rodney Motta Berkshire Hathaway NE Prop.

  430 Smith Hill Rd, Colebrook, CT 06021
• 

  $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
• 

  Est $608,368 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,032 Sq Ft

  233 Colebrook Rd, Winsted, CT 06098

  233 Colebrook Rd, Winsted, CT 06098
• 

  

  /13

  $189,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  14 Curtice St, Winsted, CT 06098

  Attention investors and buyers looking to build equity! Welcome to 14 Curtice Street, a home has incredible value and potential in the heart of Winsted. This 3-bedroom, 1-bath home features approximately 1,248 square feet of living space and is ideal for sweat-equity seekers or rehab-minded buyers. Exterior updates have already been completed, including a newer roof, siding, and windows, giving

  Michael Johnson Lock and Key Realty, Inc

  14 Curtice St, Winsted, CT 06098
• 

  $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
• 

  Est $221,244 Not Listed For Sale

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

  111 Riverton Rd Unit 10, Winsted, CT 06098

  111 Riverton Rd Unit 10, Winsted, CT 06098
• 

  $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
• 

  Est $287,228 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,006 Sq Ft

  98 Meadow St, Winsted, CT 06098

  98 Meadow St, Winsted, CT 06098
• 

  $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
• 

  Est $1,202,198 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,320 Sq Ft

  630 E Wakefield Blvd, Winsted, CT 06098

  630 E Wakefield Blvd, Winsted, CT 06098
• 

  $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
• 

  Est $266,691 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,054 Sq Ft

  185 N Main St, Winsted, CT 06098

  185 N Main St, Winsted, CT 06098
• 

  $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
• 

  Est $489,750 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  213 Spencer Hill Rd, Winsted, CT 06098

  213 Spencer Hill Rd, Winsted, CT 06098
• 

  $255,000 Sold Jun 24, 2025

  • 1,524 Sq Ft
  • $167/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  10 Meeting House Rd, Winsted, CT 06063

  3 Bedroom Split Level Ranch on 1.4 acres awaiting your creativity. Hardwood floors, newer siding and roof (6 Yrs) and large open Living room. To be sold "as is". Bring your ideas to this affordable property. Barkhamsted is home to great recreation including Barkhamsted Reservoir, Peoples state forest and the designated wild and scenic Farmington River.

  Scott Holmes William Pitt Sotheby's Int'l

  10 Meeting House Rd, Winsted, CT 06063
• 

  Est $276,991 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,430 Sq Ft

  107 Lake St, Winsted, CT 06098

  107 Lake St, Winsted, CT 06098
• 

  $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
• 

  Est $247,509 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  10 Hurlbut St, Winsted, CT 06098

  10 Hurlbut St, Winsted, CT 06098
• 

  $501,000 Sold Jun 24, 2025

  • 1,648 Sq Ft
  • $304/SF
  • 29 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1930

  351 Smith Hill Rd, Colebrook, CT 06021

  Introducing: Ella. Tucked into the gentle rise of the land, this 3-bedroom, 2-bathroom home feels like a natural extension of the Colebrook landscape-low-profile and perfectly at ease in its surroundings. Enter up natural stone steps, through the mudroom, and into the kitchen. Sunlight pours in, dancing off hardwood floors that run throughout the home. Countertops stretch the length of the space

  Elvia Gignoux William Pitt Sotheby's Int'l

  351 Smith Hill Rd, Colebrook, CT 06021
• 

  Est $283,527 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,796 Sq Ft

  25 Stanton Ave, Winsted, CT 06098

  25 Stanton Ave, Winsted, CT 06098

Showing Results 201 - 240, Page 6 of 18