Winchester, CT Homes

• 

  Est $557,084 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  319 Taylor Brook Rd, Winsted, CT 06098

  319 Taylor Brook Rd, Winsted, CT 06098
• 

  

  

  /21

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  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
• 

  $290,000 Sold Apr 21, 2025

  • 2,338 Sq Ft
  • $124/SF
  • 6 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1886

  18 Upland Rd, Winsted, CT 06098

  A Great Investment opportunity in this classic charming multi two unit home. The location is convenient to many amenities including Dining, Community College, Highland Lake recreation and much more. Each unit has Washer & Dryer hookups. Up grades include New High Gas Efficiency Furnaces and Hot Water Heaters in 2020. New Thermal Windows & Blown In Insulation 2021 & 2022. Two Car Garage, Large

  Linda Ganem Borla & Associates Real Estate

  18 Upland Rd, Winsted, CT 06098
• 

  Est $261,051 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,654 Sq Ft

  220 Walnut St, Winsted, CT 06098

  220 Walnut St, Winsted, CT 06098
• 

  

  

  /3

  $225,000

  • Land
  • 0.23 Acre
  • $978,261 per Acre

  129 Shore Dr, Winsted, CT 06098

  A RARE OPPORTUNITY on HIGHLAND LAKE! This approved buildable lot is ready and waiting for you to build your dream! Lake life is a great life, make it yours!

  Annie Simard LPT Realty

  129 Shore Dr, Winsted, CT 06098
• 

  $275,000 Sold Apr 17, 2025

  • 1,287 Sq Ft
  • $214/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1948

  58 Cherry St, Winsted, CT 06098

  Charming Cape Cod retreat just a short stroll from the beautiful beaches of Highland Lake! This well-maintained 3-bedroom, 2-bath home has been a cherished getaway for years, offering the perfect blend of comfort and convenience. The main level features a sun-filled living room, a dining room ideal for gatherings, and a kitchen with a center island for easy meal prep. A cozy bedroom and a full

  David Sartirana Northwest CT Realty

  58 Cherry St, Winsted, CT 06098
• 

  Est $247,288 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  39 Rockwell St, Winsted, CT 06098

  39 Rockwell St, Winsted, CT 06098
• 

  

  /9

  $739,900

  • Land
  • 93 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
• 

  $275,000 Sold Apr 16, 2025

  • 1,277 Sq Ft
  • $215/SF
  • 114 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  493 N Main St, Winsted, CT 06098

  Highest and best by 3/10 at 6 PM. Back on the market! Enjoy living in your own home nestled in the scenic Litchfield Hills in this newly renovated three-bedroom house with many updates: Refrigerator, range, microwave, dishwasher, and first floor washer/dryer less than a year old. Hot water heater 2023. Updated electrical 2024. Furnace serviced and updated with new burner 2024. 3 new exterior

  Jessica Sperry Maverick Realty

  493 N Main St, Winsted, CT 06098
• 

  Est $837,601 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  206 E Wakefield Blvd, Winsted, CT 06098

  206 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /4

  $14,999

  • Land
  • 0.12 Acre
  • $124,992 per Acre

  320 White Oak Trail, Winchester, CT 06098

  Plot Of Land Valued at $32,060 Property ID #: 033 105C 044+45 Zoning: HL

  Dillon Cass eRealty Advisors, Inc.

  320 White Oak Trail, Winchester, CT 06098
• 

  $395,000 Sold Apr 08, 2025

  • 1,818 Sq Ft
  • $217/SF
  • 106 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1875

  47 Orchard St, Winsted, CT 06098

  Renovated to 4 Bedroom and 3 Full-bath home with 2028 SQFT, this stunning Colonial on Private Road a short walk to Highland Lake. This newly remodeled 1875 home seamlessly blends historic charm with modern amenities. Inside discover a spacious floor plan offering an abundance of natural light perfect for both entertaining and everyday living. The custom kitchen is a chef's dream featuring sleek

  Bryan Palladino Showcase Realty, Inc.

  47 Orchard St, Winsted, CT 06098
• 

  Est $200,198 Not Listed For Sale

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

  111 Riverton Rd Unit 30, Winsted, CT 06098

  111 Riverton Rd Unit 30, Winsted, CT 06098
• 

  

  /36

  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
• 

  $305,000 Sold Apr 07, 2025

  • 1,826 Sq Ft
  • $167/SF
  • 62 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1900

  178 Boyd St, Winsted, CT 06098

  Rare Side-by-Side Duplex with Highland Lake Views Don't miss this unique side-by-side duplex offering stunning views of Highland Lake! This versatile property features an open-concept layout on the first floor in both units, creating a spacious and inviting atmosphere. One unit boasts a vaulted ceiling in the updated kitchen, while the other offers a finished attic that adds two additional

  David Sartirana Northwest CT Realty

  178 Boyd St, Winsted, CT 06098
• 

  Est $259,440 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  36 Charles St, Winsted, CT 06098

  36 Charles St, 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

  99 Hubbard St, Winsted, CT 06098
• 

  $206,000 Sold Apr 01, 2025

  • 1,204 Sq Ft
  • $171/SF
  • 22 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  111 Riverton Rd Unit 9, Winsted, CT 06098

  This 3-story condominium boasts two large bedrooms, and 1.5 bathrooms, as well as a 2-car garage with a private indoor entrance. The primary bedroom provides lofty ceilings, a walk-in closet, and its own entry way into the full bath. On the main level, the pellet stove is powerful enough to heat the entire living space whilst having its own thermostat to ensure a comfortable temperature

  Kathleen Miller CT Home Pro, LLC

  111 Riverton Rd Unit 9, Winsted, CT 06098
• 

  Est $418,305 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  43 Spencer St, Winsted, CT 06098

  43 Spencer St, 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

  124 Rockwell St, Winsted, CT 06098
• 

  $270,000 Sold Mar 31, 2025

  • 1,192 Sq Ft
  • $227/SF
  • 39 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1930

  325 E Wakefield Blvd, Winsted, CT 06098

  Enjoy water views from this charming Colonial located just across the street from Highland Lake. This cozy retreat blends historic charm with modern updates, offering a perfect escape for year-round living or a weekend getaway. Inside, refinished wide-plank hardwood floors add warmth and character, while the freshly painted interior enhances the bright and inviting atmosphere. The living room

  Brigitte Richter William Pitt Sotheby's Int'l

  325 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $200,146 Not Listed For Sale

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

  111 Riverton Rd Unit 88, Winsted, CT 06098

  111 Riverton Rd Unit 88, Winsted, CT 06098
• 

  

  /33

  $450,000

  • 4 Beds
  • 1.5 Baths
  • 2,239 Sq Ft

  51 Pratt St, Winsted, CT 06098

  Welcome to this beautifully renovated home, nicely tucked away in historic Winsted. This lovely property features over 2,200 square feet of gross interior living space. The large kitchen, dining, and living room areas provide a seamless flow, perfect for entertaining. The home boasts four spacious bedrooms and one and a half baths. The beautifully renovated attic adds even more charm and

  Lourdes Galvan-Dominguez Coldwell Banker Realty

  51 Pratt St, Winsted, CT 06098
• 

  $395,000 Sold Mar 28, 2025

  • 1,792 Sq Ft
  • $220/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  102 Sunny Ridge Dr, Winsted, CT 06098

  Charming One-Owner Split Level in a Private Rural Setting. Discover the perfect blend of privacy, space, and convenience in this beautifully maintained 1,800 sq. ft. split-level home, nestled on a serene 1-acre lot at the end of a cul-de-sac abutting the Barkhamsted town line. This home offers seven well-appointed rooms, including a spacious living room with a propane stove set in the fireplace,

  David Sartirana Northwest CT Realty

  102 Sunny Ridge Dr, Winsted, CT 06098
• 

  Est $349,807 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  155 West Rd, Winsted, CT 06098

  155 West Rd, Winsted, CT 06098
• 

  

  /39

  $950,000

  • 14 Beds
  • 7 Baths
  • 4,860 Sq Ft

  175 N Main St, Winsted, CT 06098

  Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail) in Winsted with anchor tenant Noli's Restaurant (Rent $2,266 w 3% increase/year) w over 20 years in business! Pride of Ownership is evident with Capital Improvements made by the current owners, including: new water heaters, heating zones, electrical

  Ryan Rea Berkshire Hathaway NE Prop.

  175 N Main St, Winsted, CT 06098
• 

  $85,000 Sold Mar 27, 2025

  • Land
  • 3.06 Acres
  • $27,742 per Acre

  • 5 Days On Market

  0 Platt Hill Rd Unit 24079213, Winsted, CT 06098

  Build on this 3+ acre lot that adjoins Winchester Land Trust. Old soil tests, would need to be re-tested.

  Nadia Corvo Northwest CT Realty

  0 Platt Hill Rd Unit 24079213, Winsted, CT 06098
• 

  Est $352,791 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  133 E Wakefield Blvd, Winsted, CT 06098

  133 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /26

  $1,200,000

  • 5 Beds
  • 2.5 Baths
  • 3,307 Sq Ft

  77 Deer Hill Rd, Colebrook, CT 06021

  Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at

  MICHAEL CONLOGUE William Pitt Sotheby's Int'l

  77 Deer Hill Rd, Colebrook, CT 06021
• 

  $135,000 Sold Mar 27, 2025

  • 643 Sq Ft
  • $210/SF
  • 72 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1986

  13 Riveredge Dr Unit 13, Winsted, CT 06098

  This is your chance to experience turnkey condo-style living with modern upgrades and unbeatable comfort. The remodeled kitchen boasts newer appliances, sleek granite countertops, and stylish flooring, perfect for everyday living and entertaining. Enjoy peace of mind with a five-year-old water heater with a 10-year warranty. Imagine waking up to the serene, calming sounds of the river through

  James Bradshaw Berkshire Hathaway NE Prop.

  13 Riveredge Dr Unit 13, Winsted, CT 06098
• 

  Est $276,951 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  132 E Lake St, Winsted, CT 06098

  132 E Lake St, Winsted, CT 06098
• 

  

  /40

  $1,699,500

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft

  538 Wheelers Point, Winsted, CT 06098

  Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360' direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunning kitchen for folks who cook, charming diningroom with bar and window seat overlooking the waterfront, and spacious

  KAREN NEWTON William Pitt Sotheby's Int'l

  538 Wheelers Point, Winsted, CT 06098
• 

  $268,000 Sold Mar 18, 2025

  • 1,428 Sq Ft
  • $188/SF
  • 128 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1880

  86 Maple St, Winsted, CT 06098

  Completely renovated. Brand new appliances. Roof and furnace approx. 10 years old. Nice open yard. New gravel driveway. Walk up attic with plenty of storage. New floors and windows. Large eat-in kitchen with marble counters and stainless steel appliances. Main floor laundry. Two full baths; one upstairs and one on main level. One main level bedroom. 86 Maple St is waiting for you to make it your

  Chris LaCava Coldwell Banker Realty

  86 Maple St, Winsted, CT 06098
• 

  Est $277,374 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  107 Peck Rd, Winsted, CT 06098

  107 Peck Rd, Winsted, CT 06098
• 

  

  /40

  $1,400,000 Open House 7/06

  • 8 Beds
  • 4.5 Baths
  • 5,231 Sq Ft

  435 W Wakefield Blvd, Winsted, CT 06098

  Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.3 acres of level land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ high ceilings, offering an open, airy feel throughout. The kitchen has been updated w/ hardwood cabinets, featuring

  Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  435 W Wakefield Blvd, Winsted, CT 06098
• 

  $105,000 Sold Mar 14, 2025

  • 720 Sq Ft
  • $146/SF
  • 33 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  350 Walnut St, Winsted, CT 06098

  Attention investors! This 2-bedroom, 1-bathroom single ranch style home is a prime opportunity for a complete rehab. The property was involved in a fire and requires a full rehab with a 1-car garage and is being sold as-is. Subject to probate approval.

  Vincent Miller Hudson Home Services LLC

  350 Walnut St, Winsted, CT 06098
• 

  Est $188,244 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,156 Sq Ft

  78 Gay St, Winsted, CT 06098

  78 Gay St, Winsted, CT 06098
• 

  

  /40

  $2,600,000

  • 9 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  431 W Wakefield Blvd, Winsted, CT 06098

  This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
• 

  $199,900 Sold Mar 12, 2025

  • 1,204 Sq Ft
  • $166/SF
  • 87 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  111 Riverton Rd Unit 17, Winsted, CT 06098

  Two bedroom, 1 & 1/2 bath end unit Townhouse with wood floors throughout, living room with fireplace and sliders to deck, primary bedroom with walk in closet, deck has just been painted, Spacious 2 car garage. Unit has lower-level laundry room with entry into garage. Great space and ready for New Owner.

  Joanne Donne The Washington Agency

  111 Riverton Rd Unit 17, Winsted, CT 06098
• 

  Est $270,055 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,490 Sq Ft

  257 Walnut St, Winsted, CT 06098

  257 Walnut St, Winsted, CT 06098

Showing Results 81 - 120, Page 3 of 18