5,089

Winchester, CT Homes

Section Image
  • 184 Newfield Rd, Winsted, CT 06098

    $325,000 Sold Oct 24, 2024

    • 1,598 Sq Ft
    • $203/SF
    • 97 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1995

    184 Newfield Rd, Winsted, CT 06098

    This country escape home is located in Litchfield County, just outside of quaint Winchester Center. If a quiet setting is what you're seeking, then this is the home for you. Situated on over 10 acres, you travel over a bridge and up a long driveway to find yourself immersed in complete privacy. Enjoy long warm summer nights and refreshing fall days in all that nature has to offer. This is a

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    184 Newfield Rd, Winsted, CT 06098
  • 29 Manchester Heights, Winsted, CT 06098

    $365,000 Sold Oct 17, 2024

    • 2,066 Sq Ft
    • $177/SF
    • 41 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1939

    29 Manchester Heights, Winsted, CT 06098

    Perched on a hill with stunning views, this beautifully maintained colonial in Winsted, CT provides the perfect blend of convenience and seclusion. Though close to town, the property feels like a private oasis. The spacious interior provides ample room for everyone, with the potential for additional living space in the walk-up attic. The main floor features beautifully refinished hardwood floors,

    Pascale Nejaime William Pitt Sotheby's Int'l

    29 Manchester Heights, Winsted, CT 06098
  • 164 Stillman Hill Rd, Colebrook, CT 06021

    $249,900 Sold Oct 16, 2024

    • 1,367 Sq Ft
    • $183/SF
    • 21 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    164 Stillman Hill Rd, Colebrook, CT 06021

    Great starter home in Colebrook! One level ranch, 2 bedrooms and 1 bath. Large family room with high ceilings, new gas stove(2023) and slider out the back. Home office, country kitchen with stainless steel appliances and gas stove open to the dining room, large master bedroom with walk-in closet and hardwood floors and slider to solarium out front. Wood deck out the back, patio area and fire pit

    LAURA BARTLETT Northwest CT Realty

    164 Stillman Hill Rd, Colebrook, CT 06021
  • 108 Highview Dr, Winsted, CT 06098

    $420,000 Sold Oct 11, 2024

    • 2,780 Sq Ft
    • $151/SF
    • 45 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1972

    108 Highview Dr, Winsted, CT 06098

    Nestled on just over 2 acres in a peaceful country cul-de-sac in Winchester Center, 108 Highview Dr offers over 2,300 sq ft of single-level living in a spacious ranch-style home. This 3-bedroom, 2.5-bath residence is designed with an open floor plan, providing ample space and a welcoming flow. The large kitchen seamlessly connects to the family room, where a cozy fireplace invites relaxation, and

    David Sartirana Northwest CT Realty

    108 Highview Dr, Winsted, CT 06098
  • 234 Smith Hill Rd, Winsted, CT 06098

    $287,500 Sold Oct 11, 2024

    • 1,461 Sq Ft
    • $197/SF
    • 59 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1958

    234 Smith Hill Rd, Winsted, CT 06098

    This charming 2-bedroom, 1-bathroom home, boasting over 1,400 square feet of living space, is ideally located near the Winchester/Colebrook town line. Outdoor enthusiasts will love the proximity to a variety of recreational activities, including fishing, hiking, and biking. Just 4 miles away, Norbrook Farm Brewery offers even more opportunities for leisure and adventure. This home has seen

    David Sartirana Northwest CT Realty

    234 Smith Hill Rd, Winsted, CT 06098
  • 268 Smith Hill Rd, Colebrook, CT 06021

    $324,900 Sold Oct 11, 2024

    • 1,635 Sq Ft
    • $199/SF
    • 122 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1955

    268 Smith Hill Rd, Colebrook, CT 06021

    Nestled in the charming town of Colebrook, this delightful 2-3 bedroom, 2 bath ranch home offers the perfect blend of comfort and convenience. The open floor plan welcomes you with a spacious family room featuring a cozy fireplace, seamlessly flowing into a combination dining room/living room adorned with a charming wood stove. The expansive eat-in kitchen is a culinary enthusiast's dream,

    David Sartirana Northwest CT Realty

    268 Smith Hill Rd, Colebrook, CT 06021
  • 24 Cottage St, Winsted, CT 06098

    $215,000 Sold Oct 07, 2024

    • 1,519 Sq Ft
    • $142/SF
    • 56 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1910

    24 Cottage St, Winsted, CT 06098

    Great opportunity to buy a solid house that needs a little work. There are four bedrooms on the second level and a fully finished attic with two more rooms. Huge backyard. Tall ceilings with lots of light.

    Michelle Grant Coldwell Banker Premier Real Estate

    24 Cottage St, Winsted, CT 06098
  • 107 Indian Meadow Dr, Winsted, CT 06098

    $377,000 Sold Oct 04, 2024

    • 1,944 Sq Ft
    • $194/SF
    • 31 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1972

    107 Indian Meadow Dr, Winsted, CT 06098

    Spacious living and Scenic Views! Nestled on a sprawling 2.65-acre lot, this beautiful raised ranch offers the perfect blend of comfort and style. Thoughtfully designed layout, this home is perfect for both entertaining and everyday living. Step inside and you will be greeted by hardwood floors that run throughout the living room and bedrooms. The living room, bathed in natural light, offers a

    Kelly Sullivan Sullivan Real Estate Inc

    107 Indian Meadow Dr, Winsted, CT 06098
  • 141 Spencer St, Winsted, CT 06098

    $275,000 Sold Oct 02, 2024

    • 1,540 Sq Ft
    • $179/SF
    • 87 Days On Market
    • 4 Beds
    • 1 Bath
    • Built 1900

    141 Spencer St, Winsted, CT 06098

    Located in the charming little town of Winchester, this lovely four bedroom home has so much to offer. As soon as you drive up you'll notice the large wrap around covered porch which beckons you to sit outside, relax and enjoy the tranquil setting. In the rear of the home there is a patio for entertaining or simply to sit and enjoy the beautiful outcropping of stone with plantings of flowers

    Susanne Vasquez Coldwell Banker Realty

    141 Spencer St, Winsted, CT 06098
  • 67 Strong Terrace, Winsted, CT 06098

    $276,000 Sold Sep 30, 2024

    • 1,307 Sq Ft
    • $211/SF
    • 34 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1936

    67 Strong Terrace, Winsted, CT 06098

    Charming remodeled 3-bedroom, 1.5-bath Cape on a .35-acre lot in-town. Features include a 2-car detached garage, hardwood floors on the main level, and a living room with a fireplace, built-in cabinets, and shelving. The bright, updated kitchen boasts stainless steel appliances and granite countertops. Enjoy modern conveniences with updated mechanicals, natural gas heat, city water, and sewer.

    Becky Grieco Berkshire Hathaway NE Prop.

    67 Strong Terrace, Winsted, CT 06098
  • 138 Mountain Rd, Winsted, CT 06098

    $410,000 Sold Sep 30, 2024

    • 1,654 Sq Ft
    • $248/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1934

    138 Mountain Rd, Winsted, CT 06098

    Welcome to your own private sanctuary tucked within 1.46 acres of pristine woodlands. This charming Dutch Colonial home offers the perfect blend of modern amenities and natural serenity, for a true escape from the bustle of daily life. Boasting 3 bedrooms & 2.5 baths, there is ample space for relaxation and entertainment. Remodeled kitchen with elegant granite countertops and all new appliances.

    Yvette Owens William Raveis Real Estate

    138 Mountain Rd, Winsted, CT 06098
  • 265 Colebrook Rd, Winsted, CT 06098

    $380,000 Sold Sep 27, 2024

    • 1,232 Sq Ft
    • $308/SF
    • 19 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1977

    265 Colebrook Rd, Winsted, CT 06098

    Enjoy your private homestead situated on 4+ Acres!!! Distant views, adjacent to state forest property. Professionally landscaped with pavers, stone patio, water fountain, and two outbuildings. The home features an open floor plan, light filled rooms, dining and kitchen open to the living area with vaulted wood beamed ceilings, hardwood floors, loft, recessed and under counter lighting. Floor to

    James Kaniewski Town & Country Real Estate

    265 Colebrook Rd, Winsted, CT 06098
  • 425 Platt Hill Rd, Winsted, CT 06098

    $529,900 Sold Sep 27, 2024

    • 2,218 Sq Ft
    • $239/SF
    • 77 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1988

    425 Platt Hill Rd, Winsted, CT 06098

    Contemporary ranch home has great room with vaulted natural wood ceiling featuring kitchen with granite counters, Sub Zero six burner gas cook top, Meile double oven and a large center island. Dining area has large windows and french doors leading out to an extra-large deck with amazing views. The spacious living room has a brick fireplace/pellet stove insert. Primary bedroom suite has new wall

    Dawn Bucciarelli Joseph Bette REALTORS Inc

    425 Platt Hill Rd, Winsted, CT 06098
  • 134 Torringford St, Winchester, CT 06098

    $18,000 Sold Sep 25, 2024

    • Land
    • 1.27 Acres
    • $14,196 per Acre
    • 76 Days On Market

    134 Torringford St, Winchester, CT 06098

    Private Lot tucked into Hillside offers views, a natural setting, while still being close to amenities. Driveway has been roughed in. Map of Septic Plan Available. Easy access to Rte. 8. Priced to sell.

    DALE SAVAGE Sullivan Real Estate Inc

    134 Torringford St, Winchester, CT 06098
  • 123 Highview Dr, Winsted, CT 06098

    $375,000 Sold Sep 20, 2024

    • 1,882 Sq Ft
    • $199/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    123 Highview Dr, Winsted, CT 06098

    Contemporary style Colonial located in Winchester Center sits far back from the road and offers privacy! Situated on 2 beautiful acres surrounded by nature and backs up to State Forest land. The kitchen features quartz counters, tiled flooring and a breakfast bar. Livingroom with a floor to ceiling stone fireplace, decorative accent wall and sliders to the deck. Formal dining room is great for

    Lindsay J. Warner Tier 1 Real Estate

    123 Highview Dr, Winsted, CT 06098
  • 624 Wynne Rd, Winsted, CT 06098

    $60,000 Sold Sep 20, 2024

    • 672 Sq Ft
    • $89/SF
    • 46 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1920

    624 Wynne Rd, Winsted, CT 06098

    Cozy cottage available at Highland Lake. Come take a look.

    Amy Rio Executive Real Estate Inc.

    624 Wynne Rd, Winsted, CT 06098
  • 265 W Lake St, Winsted, CT 06098

    $600,000 Sold Sep 18, 2024

    • 1,112 Sq Ft
    • $540/SF
    • 286 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1800

    265 W Lake St, Winsted, CT 06098

    This is a Fourth Generation home for so many reasons! It's now your turn … Be the next family to enjoy making cherished memories on water & land ... friends & family gatherings/celebrations, holidays,boating,kayaking,swimming,ice fishing & so much more - A lakeside gem offering year round magical views, activities & serenity! Relax on the private covered porch & enjoy your morning coffee, lunch

    Lisa Bredice William Raveis Real Estate

    265 W Lake St, Winsted, CT 06098
  • 39 Wetmore Ave, Winsted, CT 06098

    $309,000 Sold Sep 17, 2024

    • 2,918 Sq Ft
    • $106/SF
    • 43 Days On Market
    • 7 Beds
    • 1.5 Baths
    • Built 1887

    39 Wetmore Ave, Winsted, CT 06098

    Step back in time with this stunning Victorian home, built in 1887, offering a perfect blend of historic charm and modern convenience. Nestled on a spacious .53-acre lot, this 2,918 sq. ft. home is a true gem, featuring 7 bedrooms (not a misprint) 1.5 baths and a total of 12 beautifully appointed rooms. The property also includes a 1,000 sq. ft. barn, ideal for storage or creative projects. The

    Kelly Sullivan Sullivan Real Estate Inc

    39 Wetmore Ave, Winsted, CT 06098
  • 107 Ashley Rd, Winchester, CT 06098

    $450,000 Sold Sep 16, 2024

    • 1,956 Sq Ft
    • $230/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1969

    107 Ashley Rd, Winchester, CT 06098

    Situated beautifully on 3.9 acres along with an abutting .35 acre parcel on a private and picturesque location just minutes from Winchester Center. This 3 bedroom, 2 bath home is exceptionally maintained with pride of ownership evident throughout the home. The main level master bedroom lends itself to convenience and ease, with the kitchen and living room just steps away. Some of the homes

    John Mendela Coldwell Banker Realty

    107 Ashley Rd, Winchester, CT 06098
  • 103 Schueman Rd, Winchester, CT 06098

    $365,000 Sold Sep 13, 2024

    • 1,694 Sq Ft
    • $215/SF
    • 40 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1988

    103 Schueman Rd, Winchester, CT 06098

    Charming 3 Bedroom Cape nestled on a serene 2.4-acre lot, this delightful 3-bedroom Cape Cod-style home was lovingly built and cherished by the current owner for 34 years. Offering a tranquil retreat with ample privacy, this property presents a unique opportunity for those seeking a peaceful lifestyle. The home features: Welcoming hardwood floors throughout, adding warmth and character. A cozy

    Becky Grieco Berkshire Hathaway NE Prop.

    103 Schueman Rd, Winchester, CT 06098

Showing Results 201 - 240, Page 6 of 18

Connecticut Winchester

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group