149

Recently Sold Winchester, CT Homes

Section Image
  • 126 Williams Ave, Winsted, CT 06098

    $292,000 Sold Jul 25, 2025

    • 2,225 Sq Ft
    • $131/SF
    • 42 Days On Market
    • 6 Beds
    • 2 Baths
    • Built 1890

    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
  • 200 Perch Rock Trail, 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
  • 112 Shore Dr, Winsted, CT 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
  • 203 Holabird Ave, Winchester Center, 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
  • 100 Norfolk Rd, Winsted, CT 06098

    $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
  • 39 Orchard St, Winsted, CT 06098

    $208,900 Sold Jul 18, 2025

    • 1,200 Sq Ft
    • $174/SF
    • 131 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1875

    39 Orchard St, Winsted, CT 06098

    Back on the market, buyer's financing fell through. Welcome to this beautifully updated 3-bedroom, 1.5-bath colonial in the heart of Winsted! This home seamlessly blends classic charm with modern conveniences, featuring a spacious layout, abundant natural light, and stylish updates throughout. The inviting living room offers a cozy atmosphere perfect for gatherings. The updated kitchen boasts

    Michael J Flaherty Jr Sullivan Real Estate Inc

    39 Orchard St, Winsted, CT 06098
  • 284 Gilbert Ave, 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
  • 88 Strong Terrace, 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
  • 11 Gibbs St Unit 7, 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
  • 150 Mathew Rd, 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
  • 39 Baker St, Winsted, CT 06098

    $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
  • 508 W Wakefield Blvd, 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
  • 355 W Lake 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
  • 19 Riveredge Dr Unit 19, 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
  • 115 Stanton Ave, 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
  • 399 Colebrook Rd, Colebrook, CT 06021

    $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
  • 11 Gibbs St Unit 9, Winsted, CT 06098

    $113,000 Sold Jun 23, 2025

    • 570 Sq Ft
    • $198/SF
    • 10 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1985

    11 Gibbs St Unit 9, Winsted, CT 06098

    Welcome to easy, one-level living in this rarely available first-floor end 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.

    David Sartirana Northwest CT Realty

    11 Gibbs St Unit 9, Winsted, CT 06098
  • 288 Torringford St, Winsted, CT 06098

    $460,000 Sold Jun 20, 2025

    • 3,021 Sq Ft
    • $152/SF
    • 128 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1875

    288 Torringford St, Winsted, CT 06098

    Welcome to this charming four-bedroom antique home that is beautifully renovated to blend timeless character with modern comforts. As you step inside you'll be greeted by the warmth of refinished hardwood floors and an inviting living room featuring a cozy fireplace and built-in bookcases perfect for relaxing or entertaining. The heart of the home is the brand-new kitchen boasting sleek granite

    Mark Porriello RE/MAX Right Choice

    288 Torringford St, Winsted, CT 06098
  • 174 Boyd St, Winsted, CT 06098

    $280,000 Sold Jun 16, 2025

    • 1,424 Sq Ft
    • $197/SF
    • 110 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1900

    174 Boyd St, Winsted, CT 06098

    A charming house located 2 blocks from highland lake. This 3 bedroom, 1 large full bath is move-in ready. The dining room has a beautiful built in, the 3 large windows allowing for natural light to brighten the room. Off of the dining room is a nice family room. The kitchen is large and spacious and off the kitchen in the back is a lovely sunroom with a fireplace (natural gas) that has sliders

    Margaret Alexson Elyse Harney Real Estate

    174 Boyd St, Winsted, CT 06098
  • 704 W Wakefield Blvd, Winsted, CT 06098

    $495,000 Sold Jun 09, 2025

    • 754 Sq Ft
    • $656/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1911

    704 W Wakefield Blvd, Winsted, CT 06098

    Quintessential New England Lake Cottage! Three season sweet lakefront retreat with charm and character on Highland Lake - one of CT's largest lakes. Waterfront dock, deck offering long views over the lake and plenty of seating for family bbq's. Recently remodeled kitchen, charming livingroom with stone fireplace, hardwood floors, beams, newer windows / sliding doors, half bath and shower lower

    KAREN NEWTON William Pitt Sotheby's Int'l

    704 W Wakefield Blvd, Winsted, CT 06098
  • 421 Unity Place, Winsted, CT 06098

    $286,000 Sold Jun 09, 2025

    • 1,440 Sq Ft
    • $199/SF
    • 25 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1927

    421 Unity Place, Winsted, CT 06098

    UPDATED | SERENE | CHARMING | 2 LOTS | This Highland Lake retreat is ideal for the 1st time homeowner, getaway retreat or investment opportunity. Nestled in New England's natural beauty, you are sure to enjoy your lush surroundings & stunning views, truly a nature lovers delight. 3+ generous bedrooms, 2 full bathrooms, dining room, fireplaced living room, updated kitchen with stainless

    Michelle Lorenzetti Premier Re Group LLC

    421 Unity Place, Winsted, CT 06098
  • 323 E Wakefield Blvd, Winsted, CT 06098

    $397,000 Sold Jun 04, 2025

    • 1,426 Sq Ft
    • $278/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1989

    323 E Wakefield Blvd, Winsted, CT 06098

    Charming 3-Bedroom Cape in Sought-After Lake Community. Welcome to this beautifully updated 3-bedroom, 2.5-bath Cape nestled in a vibrant lake community offering year-round fun! Enjoy boating, waterskiing, tubing, and all the perks of lake life just steps from your door, with serene water views to enjoy every day. The main level features a bright, inviting living room with hardwood floors and a

    Heather Crabtree Coldwell Banker Realty

    323 E Wakefield Blvd, Winsted, CT 06098
  • 155 Mathew Rd, Winsted, CT 06098

    $314,000 Sold May 30, 2025

    • 1,536 Sq Ft
    • $204/SF
    • 56 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1979

    155 Mathew Rd, Winsted, CT 06098

    Situated on a private road with views of Highland Lake, this beautifully updated home offers a perfect blend of modern comfort and quiet surroundings. Boasting a brand-new roof, siding, windows, as well as new front and back porches this home is ready to go for anyone looking for a great home. Step inside to discover an inviting, light-filled interior with contemporary finishes throughout. The

    Austin Brochu Sullivan Real Estate Inc

    155 Mathew Rd, Winsted, CT 06098
  • 150 Meadow St, Winsted, CT 06098

    $250,000 Sold May 30, 2025

    • 2,094 Sq Ft
    • $119/SF
    • 80 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1860

    150 Meadow St, Winsted, CT 06098

    Steeped in history and charm, this 1860-built home offers a blend of classic character and modern updates. With 8 rooms, 4 bedrooms, and 2 baths, this spacious home provides versatile living options. The main level features a kitchen with recent updates, a dining room, a cozy living room, a primary bedroom with an en-suite bath, and a home office. Upstairs, you'll find three bedrooms, a study

    David Sartirana Northwest CT Realty

    150 Meadow St, Winsted, CT 06098
  • 9 Loomis St, Winsted, CT 06098

    $144,000 Sold May 29, 2025

    • 1,768 Sq Ft
    • $81/SF
    • 18 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1910

    9 Loomis St, Winsted, CT 06098

    ZONING IS TG Regulations are tailored to promote desired development patterns that promote an appropriate transition from rural to town uses. Certain uses are permitted, while others require a Special Permit. Nestled just minutes from Highland Lake and downtown Winchester, 9 Loomis Street presents an excellent opportunity for those seeking a fixer-upper with great potential. This colonial-style

    Kristen Duchene Litchfield County Real Estate

    9 Loomis St, Winsted, CT 06098
  • 173 Torringford St, Winsted, CT 06098

    $355,000 Sold May 29, 2025

    • 2,239 Sq Ft
    • $159/SF
    • 46 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1955

    173 Torringford St, Winsted, CT 06098

    Welcome to this beautiful Cape Cod home, offering 2239 square feet of living space. Nestled on a serene 1.79 acre lot, this inviting property provides a perfect blend of comfort and style. Step inside to a generous entry that flows seamlessly into the open living and dining areas, creating an ideal space for both everyday living and entertaining. The huge family room is a true highlight,

    Sandy Fehrs Lamacchia Realty

    173 Torringford St, Winsted, CT 06098
  • 56 Lakeview Rd, Winsted, CT 06098

    $279,000 Sold May 19, 2025

    • 1,101 Sq Ft
    • $253/SF
    • 6 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    56 Lakeview Rd, Winsted, CT 06098

    Don't miss this 3 bedroom Ranch with a 2 car attached garage and an amazing view of Highland Lake - very close proximity to state boat launch and public beach. Some TLC will be well worth the effort here! Roof (2019), heating system (November 2017), and central air!

    Tony Goia The Washington Agency

    56 Lakeview Rd, Winsted, CT 06098
  • 47 Moore Ave, Winsted, CT 06098

    $320,000 Sold May 16, 2025

    • 1,509 Sq Ft
    • $212/SF
    • 29 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1964

    47 Moore Ave, Winsted, CT 06098

    Nestled in the charming town of Winchester, Connecticut, this beautifully remodeled ranch home offers the perfect blend of modern elegance and cozy comfort. Boasting four spacious bedrooms and seven total rooms, this residence features hardwood floors throughout and a thoughtfully updated galley kitchen that will inspire your inner chef. Gorgeous granite counters and new appliances, with a quaint

    Suzie Larson Turning Point Realty, LLC

    47 Moore Ave, Winsted, CT 06098
  • 104 Norfolk Rd, Winsted, CT 06098

    $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
  • 154 Wallens St, 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
  • 244 Colebrook Rd, 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
  • 37 Riveredge Dr Unit 37, 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
  • 39 Finn St, Winsted, CT 06098

    $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
  • 50-52 Cottage St, Winchester, 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
  • 110 South Rd, 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
  • 14 Riveredge Dr Unit 14, 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 KW Legacy Partners

    14 Riveredge Dr Unit 14, Winsted, CT 06098
  • 109 Marshall St, 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
  • 52 Lakeview Rd, Winsted, 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
  • 830 Main St, Winsted, 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
  • 151 Elm St, 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

Showing Results 1 - 40, Page 1 of 4

Connecticut Winchester

Recently Sold Real Estate & Homes in Winchester, CT

Frequently Asked Questions

What is the average home price in Winchester, CT?
Homes for sale in Winchester, CT have an average home price of $325,000.
What is the average time to sell a house in Winchester, CT?
The houses for sale in Winchester, CT spend an average of 40 days on the market.
What is the number of active homes for sale in Winchester, CT?
There are 0 active homes for sale in Winchester, CT.
How many homes have sold over the last 12 months in Winchester, CT?
2 homes have sold in Winchester, CT over the last 12 months.

Home Trends in Winchester, CT

On average, homes in Winchester, CT sell after 40 days on the market compared to the national average of 70 days. The median sale price for homes in Winchester, CT over the last 12 months is $365,000, up 54% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$365,000
Median Single Family Sale Price
$365,000
Average Price Per Sq Ft
$215
Number of Homes for Sale
0
Last 12 months Home Sales
2
Months of Supply
0.00
Median List Price
$325,000
Median Change From 1st List Price
-12%
Median Home Sale Price YoY Change
54%
How to Buy a Home How to Sell a Home How to Rent a Home

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