Winchester, CT Homes

• 

  $8,000 Sold May 16, 2025

  • 980 Sq Ft
  • $8/SF
  • 44 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  104 Norfolk Rd, Winsted, CT 06098

  An opportunity for redevelopment! This bungalow-style home, situated on a 0.50-acre lot along State-maintained Route 44, is beyond salvageable and will require demolition. Offering 980 sq. ft. of living space with 5 rooms, including 2 bedrooms and 1 full bath, the property is in unsafe condition and there will be no access granted due to structural concerns. While located in a rural setting, it

  David Sartirana Northwest CT Realty

  104 Norfolk Rd, Winsted, CT 06098
• 

  Est $525,408 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  111 Mundry Rd, Torrington, CT 06790

  111 Mundry Rd, Torrington, CT 06790
• 

  

  

  /40

  $419,900

  • 3 Beds
  • 2 Baths
  • 2,105 Sq Ft

  17 Woodland Ave, Winsted, CT 06098

  Beautiful 3 bedroom updated colonial walking distance to Highland lake beach.Large eat in kitchen with granite counter tops,center island,bar area ,spacious sitting area with antique cooking stove that burns wood creates good heat.Living room with hardwood floors,fireplace and built ins.Nice patio off kitchen,yard is landscaped with fountains.2 car garage.This home is in great condition and wont

  Vincent DeVico Showcase Realty, Inc.

  17 Woodland Ave, Winsted, CT 06098
• 

  $190,000 Sold May 15, 2025

  • 1,848 Sq Ft
  • $103/SF
  • 20 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1905

  154 Wallens St, Winsted, CT 06098

  Investors & Owner Occupants, schedule your appointment NOW!!! Come view this 2-family home, price to sell!!! Located near all amenities! Seller is motivated, bring all offers!!!

  Adam Devine Dorrance Realty

  154 Wallens St, Winsted, CT 06098
• 

  Est $244,558 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft

  139 Boyd St, Winsted, CT 06098

  139 Boyd St, Winsted, CT 06098
• 

  

  /19

  $285,000

  • 6 Beds
  • 2 Baths
  • 2,225 Sq Ft

  126 Williams Ave, Winsted, CT 06098

  Excellent investment opportunity! This fully occupied two-family home generates a steady $3,300 in monthly rental income. The property has been completely overhauled in the past few years with almost everything updated. It is located in a great neighborhood in walking distance to all the schools in town. Close to playgrounds and the library. The recently painted exterior of this classic home

  Michelle Grant Coldwell Banker Premier Real Estate

  126 Williams Ave, Winsted, CT 06098
• 

  $379,000 Sold May 09, 2025

  • 1,531 Sq Ft
  • $248/SF
  • 90 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  244 Colebrook Rd, Winsted, CT 06098

  Welcome to 244 Colebrook Road, a beautifully renovated home that perfectly blends modern upgrades with timeless charm. Move-in ready, this home features thoughtful updates designed to suit all your lifestyle needs. Virtually staged. The first floor opens to a formal living room that seamlessly connects to a gourmet kitchen, outfitted with all-new appliances and a large quartz island seating

  Carol York For Sale By Owner Connecticut

  244 Colebrook Rd, Winsted, CT 06098
• 

  Est $259,507 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  174 Wallens St Unit D3, Winsted, CT 06098

  174 Wallens St Unit D3, Winsted, CT 06098
• 

  

  /24

  $375,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 2,160 Sq Ft

  181 Torringford St, Winsted, CT 06098

  Charming Colonial on Nearly an Acre! Discover the perfect blend of comfort and space in this 3-bedroom, 1.5-bathroom Colonial home. Situated on almost an acre of flat, usable land, the property features a brand new grand circular driveway and a detached two-car garage. The inviting exterior, with its covered front porch, welcomes you into a home ready for its next chapter. Complete with a

  Michelle Grant Coldwell Banker Premier Real Estate

  181 Torringford St, Winsted, CT 06098
• 

  $160,000 Sold May 07, 2025

  • 992 Sq Ft
  • $161/SF
  • 37 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  37 Riveredge Dr Unit 37, Winsted, CT 06098

  Enjoy the private and peaceful setting of Still River right from your bedroom window or private patio all the while being close to the many amenities offered in town. Inside this well-maintained condo you'll find an abundance of natural light flowing in every room, a bright slider opening up to your own patio, all new paint throughout, lots of storage and durable like-new flooring on the main and

  Erin Ruwet Century 21 AllPoints Realty

  37 Riveredge Dr Unit 37, Winsted, CT 06098
• 

  Est $238,522 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  174 Wallens St Unit D2, Winsted, CT 06098

  174 Wallens St Unit D2, Winsted, CT 06098
• 

  

  /9

  $999,000

  • Land
  • 116 Acres
  • $8,575 per Acre

  82 Riverton Rd, Colebrook, CT 06021

  Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

  Suzie Larson Turning Point Realty, LLC

  82 Riverton Rd, Colebrook, CT 06021
• 

  $269,000 Sold May 05, 2025

  • 1,175 Sq Ft
  • $229/SF
  • 35 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1880

  39 Finn St, Winsted, CT 06098

  Fabulous Opportunity to own in the Highland lake community. Walking distance to both beaches and boat launch. This adorable3-4 bedroom home has new hardwood floors thru out the first floor, has been freshly painted, new fridge and stove, roof only 2 yrs old, thermal paned windows. Large storage shed. Open concept with a living room/dining room combo. Large area for gardening and ready to move

  Christine Hunter Hunter Real Estate, LLC

  39 Finn St, Winsted, CT 06098
• 

  Est $240,771 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit D1, Winsted, CT 06098

  174 Wallens St Unit D1, Winsted, CT 06098
• 

  

  /27

  $388,000

  • 5 Beds
  • 2 Baths
  • 2,403 Sq Ft

  409 N Main St, Winsted, CT 06098

  This versatile 2-family home has space for the growing family. This would make a perfect owner occupant first floor unit with 3 bedrooms; with a 2 bedroom second floor apartment. Private entrances with separate utilities. Let your rental income help pay your mortgage. Each unit comes with formal living and dining rooms. Pellet stove in the main dining room. Refinished wide pine flooring. Large

  Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  $70,000 Sold May 01, 2025

  • 2,016 Sq Ft
  • $35/SF
  • 18 Days On Market

  • 5 Beds
  • Built 1800

  50-52 Cottage St, Winchester, CT 06098

  Investor Special! This four-level, two-family property at 50-52 Cottage St. was previously prepared for demolition but may still hold potential for the right investor. A complete rehab or possible teardown, this property is being sold as-is and will require vision, expertise, and cash-no financing will qualify. Whether you're looking for a full-scale renovation project or a lot for future

  David Sartirana Northwest CT Realty

  50-52 Cottage St, Winchester, CT 06098
• 

  Est $284,322 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  174 Wallens St Unit C3, Winsted, CT 06098

  174 Wallens St Unit C3, Winsted, CT 06098
• 

  

  /24

  $199,900

  • 5 Beds
  • 1.5 Baths
  • 2,310 Sq Ft

  30 Mountain Ave, Winsted, CT 06098

  Not afraid of some peeling paint or rotting wood? This is the house for you! 30 Mountain Ave with 5 beds, 1.5 baths is your opportunity to bring a vision to life. Located in a welcoming neighborhood, it offers a generous layout ready for customization and renovation. Whether you're a seasoned investor or a first-time buyer with a knack for design, this home has the bones to become something

  Derek Greene Derek Greene

  30 Mountain Ave, Winsted, CT 06098
• 

  $679,000 Sold Apr 30, 2025

  • 3,870 Sq Ft
  • $175/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  110 South Rd, Winsted, CT 06098

  Discover your private sanctuary in the heart of historic Winchester Center, where tranquility meets nature! This contemporary Cape-style home boasts spacious, light-filled rooms that have been thoughtfully updated throughout. Elegant details such as crown molding, beams, skylights & oversized windows invite the beauty of the outdoors in-all showcasing your private pond! The main floor is designed

  Matthew Egan Regency Real Estate, LLC

  110 South Rd, Winsted, CT 06098
• 

  Est $546,428 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,804 Sq Ft

  452 Platt Hill Rd, Winsted, CT 06098

  452 Platt Hill Rd, Winsted, CT 06098
• 

  

  /18

  $244,000

  • 2 Beds
  • 1 Bath
  • 674 Sq Ft

  343 W Wakefield Blvd, Winsted, CT 06098

  Your oasis awaits!!! Schedule your appointment today and come view this adorable Bungalow. There is so much potential to be made here. Bring your ideas and creativity as the seller is motivated, bring all offers!!!

  Patrick Precourt Dorrance Realty

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  $160,000 Sold Apr 29, 2025

  • 992 Sq Ft
  • $161/SF
  • 0 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  14 Riveredge Dr Unit 14, Winsted, CT 06098

  Come see this wonderful sought after condo in a great neighborhood that has been freshly painted and all new appliances in the kitchen as well as a newer water heater that is just a few years old. Close proximity to town and route 8 and just down the street from the Northwestern Connecticut Community College. This unit has a garage that is directly across from the condo and has an additional

  Maria Smith Turning Point Realty, LLC

  14 Riveredge Dr Unit 14, Winsted, CT 06098
• 

  Est $1,083,446 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,963 Sq Ft

  411 W Wakefield Blvd, Winsted, CT 06098

  411 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /40

  $1,595,000

  • 5 Beds
  • 2 Baths
  • 3,693 Sq Ft

  424 E Wakefield Blvd, Winsted, CT 06098

  Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

  KAREN NEWTON William Pitt Sotheby's Int'l

  424 E Wakefield Blvd, Winsted, CT 06098
• 

  $90,000 Sold Apr 25, 2025

  • 936 Sq Ft
  • $96/SF
  • 18 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1935

  109 Marshall St, Winsted, CT 06098

  Charming bungalow with great potential! This 936 sq. ft. home features 6 rooms, including 3 bedrooms and 1 full bath, situated on a spacious 0.80-acre lot. A detached one-car garage provides additional storage or parking. While this home is in poor condition and will require significant renovation, it presents an excellent opportunity for investors or buyers looking to restore and customize. Will

  David Sartirana Northwest CT Realty

  109 Marshall St, Winsted, CT 06098
• 

  Est $280,644 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, Winsted, CT 06098
• 

  

  /4

  $250,000

  • Land
  • 16 Acres
  • $15,723 per Acre

  00 Chapel Rd, Winchester, CT 06098

  Look no further for A Very Private location to build your Dream Home?? On this Lot there is the Hilltop which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester may be the place for you. The access to the Rear lot is though 151 Chapel Rd. property.

  Linda Ganem Borla & Associates Real Estate

  00 Chapel Rd, Winchester, CT 06098
• 

  $410,000 Sold Apr 24, 2025

  • 2,313 Sq Ft
  • $177/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1971

  52 Lakeview Rd, Winsted, CT 06098

  Welcome to 52 Lakeview Rd, a meticulously maintained Colonial home that has been lovingly cared for by the same family for over 50 years. This 2,300 sq. ft. residence is set on a spacious .47-acre lot in a peaceful, rural neighborhood, offering both privacy and convenience. The main level features a well-designed layout, including a formal living room and dining room, perfect for entertaining.

  David Sartirana Northwest CT Realty

  52 Lakeview Rd, Winsted, CT 06098
• 

  Est $603,537 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,318 Sq Ft

  715 W Wakefield Blvd, Winsted, CT 06098

  715 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /26

  $1,200,000

  • Land
  • 65 Acres
  • $18,380 per Acre

  257 Torringford St, Winchester, CT 06098

  65+ Acre Property with infrastructure and natural features. Spanning over 65 acres, this private property is accessed via a 5,000 foot driveway and features a mix of open space and wooded terrain. The land is bordered by historic stone walls on both sides, adding character and clear boundary lines. Bonus: 14x40 horse barn, ready for livestock or storage. 24x32 building on a concrete slab,

  Sabrina Janco Century 21 Bay-Mar Realty

  257 Torringford St, Winchester, CT 06098
• 

  $220,000 Sold Apr 24, 2025

  • 3,115 Sq Ft
  • $71/SF
  • 14 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1900

  830 Main St, Winsted, CT 06098

  Large side by side duplex with 1 and half baths on each side and a finished attic on each side. Lots of potential here but freeze damage as well. As is sale or repairs possible.

  Michelle Grant Coldwell Banker Premier Real Estate

  830 Main St, Winsted, CT 06098
• 

  Est $258,856 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
• 

  

  /4

  $44,000

  • Land
  • 0.41 Acre
  • $107,317 per Acre

  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
• 

  $275,000 Sold Apr 23, 2025

  • 2,191 Sq Ft
  • $126/SF
  • 41 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1880

  151 Elm St, Winsted, CT 06098

  Step into the warmth and character of this beautiful 5-bedroom single-family home, ideally located in the heart of Winsted. With a wrap-around front porch and a screened rear porch, this home offers the perfect blend of classic charm and modern convenience. Inside, you'll find hardwood floors throughout most of the house, a full bay window in the living room that fills the space with natural

  Jeffrey Liskin Northwest CT Realty

  151 Elm St, Winsted, CT 06098
• 

  Est $158,958 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  17 Front St, Winsted, CT 06098

  17 Front St, Winsted, CT 06098
• 

  /2

  $39,900

  • Land
  • 0.92 Acre
  • $43,370 per Acre

  256 Colebrook Rd, Winchester Center, CT 06098

  Just under an acre of land and over 100 feet of road frontage available on Colebrook Road!

  Austin Brochu Sullivan Real Estate Inc

  256 Colebrook Rd, Winchester Center, CT 06098
• 

  $400,000 Sold Apr 21, 2025

  • 1,294 Sq Ft
  • $309/SF
  • 39 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  98 Pinney St, Colebrook, CT 06021

  Charming property nestled on 6+ acres in Colebrook. The house is set back on the property, drive by a lovely pond and garden areas as you drive up to a detached oversized 2-bay garage. A covered porch welcomes you to the front entry. A lovely respite in the warmer months. Enter into a vaulted living room with wood burning stove for those chilly nights. This space is well laid out and includes the

  Tracy Macgowan Elyse Harney Real Estate

  98 Pinney St, Colebrook, CT 06021
• 

  Est $233,984 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,010 Sq Ft

  22 Stanton Ave, Winsted, CT 06098

  22 Stanton Ave, Winsted, CT 06098
• 

  

  /35

  $499,000

  • 3 Beds
  • 3 Baths
  • 2,747 Sq Ft

  117 South Rd, Winsted, CT 06098

  Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

  Christina Niziolek William Raveis Real Estate

  117 South Rd, Winsted, CT 06098
• 

  $289,900 Sold Apr 21, 2025

  • 988 Sq Ft
  • $293/SF
  • 61 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1980

  315 E Wakefield Blvd, Winsted, CT 06098

  Charming ranch style home with year round water views! This beautifully updated 3-bedroom, 1-bath ranch home in the sought-after Highland Lake community in Winsted is a true gem. The home has been meticulously cared for, blending modern updates with classic charm. Inside, you'll find a cozy, well-maintained living space that feels inviting and comfortable. The property boasts a spacious, full

  Heather Crabtree Coldwell Banker Realty

  315 E Wakefield Blvd, Winsted, CT 06098

Showing Results 41 - 80, Page 2 of 18