Winchester, CT Homes

/17
$249,900
- 3 Beds
- 1 Bath
- 1,422 Sq Ft
94 Holabird Ave, Winsted, CT 06098

Welcome to this charming New England Colonial that blends classic character with comfortable living. Step inside to an inviting, oversized living room featuring beautiful new vinyl flooring-perfect for relaxing, entertaining guests, or gathering with family. The main living level offers two convenient bedrooms and a laundry area, making everyday living easy and practical. Upstairs, you'll find

Rob Rosa

Berkshire Hathaway NE Prop.

(860) 492-6499

94 Holabird Ave, Winsted, CT 06098
Explore Winchester
/12
$2,400 total monthly price
- 3 Beds
- 1 Bath
- 1,860 Sq Ft
- House for Rent
101 Norfolk Rd, Winsted, CT 06098

Raised Ranch rental close to town on 1.33 wooded acres. The lower level features two large rooms with new vinyl plank flooring, fresh paint, and a spacious storage/utility room with laundry. The main floor includes a living room and an updated kitchen with quartz countertops and stainless steel appliances. Sliders lead to a large deck overlooking the private wooded yard. There is a large primary

Amanda Balaski

Northwest CT Realty

(860) 845-0664

101 Norfolk Rd, Winsted, CT 06098
$362,000 Sold Nov 18, 2025

147 Smith Hill Rd, Winsted, CT 06098
- 4 Beds
- 2 Baths
- 1,910 Sq Ft
- Built 1949
Last Sold Summary
- 6% Below List Price
- $190/SF
- 84 Days On Market
Current Estimated Value $367,196

Last Listing Agent SHARON GILSON Northwest CT Realty

147 Smith Hill Rd, Winsted, CT 06098

Est $264,762 Not Listed For Sale

14 Hamill Dr, Winsted, CT 06098
- 3 Beds
- 1.5 Baths
- 1,888 Sq Ft
- Built 1973
14 Hamill Dr, Winsted, CT 06098

Last Sold Summary
- 2% Above List Price
- $138/SF
- 27 Days On Market
Last Sold Price $260,000

Last Listing Agent Eva Casoria eXp Realty

/33
$399,000 Under Contract
- 3 Beds
- 2 Baths
- 2,196 Sq Ft
35 Glendale Ave, Winsted, CT 06098

Welcome to this spacious and well-maintained 2,196 sq. ft. one-owner home offering comfortable living in a convenient in-town location. This 3-bedroom, 2-bath residence features an open floor plan on the main living level, highlighted by a large formal living room with fireplace, dining room, expansive family room, and an updated kitchen-perfect for both everyday living and entertaining.

David Sartirana

Northwest CT Realty

(860) 864-5659

35 Glendale Ave, Winsted, CT 06098
/4
$165 total monthly price
- 200 Sq Ft
- House for Rent
113 Elm St Unit Left, Winsted, CT 06098

One of two available storage units. Each unit is 200 square feet and can be used as extra storage or as a garage.

Jeffrey Liskin

Northwest CT Realty

(860) 735-3947

113 Elm St Unit Left, Winsted, CT 06098
$920,000 Sold Nov 17, 2025

43 E Lake St, Winsted, CT 06098
- 4 Beds
- 3 Baths
- 2,131 Sq Ft
- Built 2002
Last Sold Summary
- 3% Below List Price
- $432/SF
- 56 Days On Market
Current Estimated Value $927,583

Last Listing Agent Keith Meyer Northwest CT Realty

43 E Lake St, Winsted, CT 06098

Est $207,823 Not Listed For Sale

111 Riverton Rd Unit 17, Winsted, CT 06098
- 2 Beds
- 1.5 Baths
- 1,204 Sq Ft
- Built 1987
111 Riverton Rd Unit 17, Winsted, CT 06098

Last Sold Summary
- 4% Above List Price
- $166/SF
- 87 Days On Market
Last Sold Price $199,900

Last Listing Agent Joanne Donne The Washington Agency

/25
$279,900 Under Contract
- 3 Beds
- 2 Baths
- 1,604 Sq Ft
44 Lewis St, Winsted, CT 06098

Enjoy years of maintenance-free living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated on a quiet side street just minutes from the beach at Highland Lake and the shops, restaurants, and conveniences of downtown Winsted. Completely remodeled in 2017, this home offers a long list of updates at that time including a new roof, updated baths, remodeled kitchen, all new

David Sartirana

Northwest CT Realty

(860) 318-9799

44 Lewis St, Winsted, CT 06098
/2
$165 total monthly price
- 200 Sq Ft
- House for Rent
113 Elm St Unit Right, Winsted, CT 06098

One of two available storage units. Each unit is 200 square feet and can be used as extra storage or as a garage.

Jeffrey Liskin

Northwest CT Realty

(860) 809-5763

113 Elm St Unit Right, Winsted, CT 06098
$460,000 Sold Jun 20, 2025

288 Torringford St, Winsted, CT 06098
- 4 Beds
- 3 Baths
- 3,021 Sq Ft
- Built 1875
Last Sold Summary
- 14% Below List Price
- $152/SF
- 128 Days On Market
Current Estimated Value $473,102

Last Listing Agent Mark Porriello RE/MAX Right Choice

288 Torringford St, Winsted, CT 06098

Est $276,037 Not Listed For Sale

86 Maple St, Winsted, CT 06098
- 4 Beds
- 2 Baths
- 1,428 Sq Ft
- Built 1880
86 Maple St, Winsted, CT 06098

Last Sold Summary
- 3% Above List Price
- $188/SF
- 128 Days On Market
Last Sold Price $268,000

Last Listing Agent Chris LaCava Coldwell Banker Realty

/2
$24,900
- Land
- 0.44 Acre
- $56,591 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

(860) 891-6121

124 Rockwell St, Winsted, CT 06098
/8
$1,695 total monthly price
- 3 Beds
- 1 Bath
- 1,080 Sq Ft
- Townhouse for Rent
131-133 Willow St, Winchester, CT 06098

Bright and sunny 3-bedroom duplex, ideally located close to town. This spacious home features a large eat-in kitchen, a separate dining room, and a cozy living room. Enjoy the convenience of gas heat, with washer/dryer hook-up available in the basement, or can be provided for an extra $75 per month. Minimum credit score of 700. Pets considered, and a background and credit check are required.

Amanda Balaski

Northwest CT Realty

(860) 981-0563

131-133 Willow St, Winchester, CT 06098
$305,000 Sold Dec 22, 2025

49 Walnut St, Winsted, CT 06098
- 5 Beds
- 2 Baths
- 2,344 Sq Ft
- Built 1824
Last Sold Summary
- 2% Above List Price
- $130/SF
- 6 Days On Market
Current Estimated Value $311,269

Last Listing Agent David Sartirana Northwest CT Realty

49 Walnut St, Winsted, CT 06098

Est $386,534 Not Listed For Sale

126 Newfield Rd, Winchester, CT 06098
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 1952
126 Newfield Rd, Winchester, CT 06098

Last Sold Summary
- 7% Above List Price
- $257/SF
- 1 Day On Market
Last Sold Price $360,000

Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway Home Services

/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

(860) 946-4468

99 Hubbard St, Winsted, CT 06098
/2
$1,500 total monthly price
- 2 Beds
- 1 Bath
- 800 Sq Ft
- House for Rent
244 Walnut St, Winsted, CT 06098

Bright first-floor 2-bedroom, 1-bath apartment available at 244 Walnut St in Winsted, CT. This well-maintained unit features all new windows that provide plenty of natural light and improved energy efficiency, along with natural gas heat for affordable utilities. Conveniently located in a quiet residential area close to downtown Winsted, shopping, and local amenities. Comfortable first-floor

William Kallberg

Berkshire Hathaway NE Prop.

(860) 730-1457

244 Walnut St, Winsted, CT 06098
$370,000 Sold Mar 25, 2026

171 Wallens St, Winchester, CT 06098
- 2 Beds
- 2 Baths
- 1,274 Sq Ft
- Built 1957
Last Sold Summary
- 3% Above List Price
- $290/SF
- 23 Days On Market
Current Estimated Value $343,810

Last Listing Agent Meagan Albert Tier 1 Real Estate

171 Wallens St, Winchester, CT 06098

Est $288,880 Not Listed For Sale

151 Newfield Rd, Winchester, CT 06098
- 2 Beds
- 1 Bath
- 1,267 Sq Ft
- Built 1930
151 Newfield Rd, Winchester, CT 06098

Last Sold Summary
- 28% Above List Price
- $178/SF
- 25 Days On Market
Last Sold Price $225,000

Last Listing Agent Maya Brown Coldwell Banker Realty

/9
$739,900 Pending
- Land
- 93.38 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

(860) 650-5076

0 Old Robertsville Rd, Winchester, CT 06098
/8
$1,495 total monthly price
- 2 Beds
- 1 Bath
- 900 Sq Ft
- House for Rent
112 Rockwell St Unit 1, Winsted, CT 06098

Bright and sunny, first floor, 2 bedroom apartment. Washer/dryer in the unit. Large, private porch. Pets considered. Off street parking. Minimum credit score required. Credit and background check done by listing office. required. Two months security, if applicable.

Amanda Balaski

Northwest CT Realty

(860) 609-3853

112 Rockwell St Unit 1, Winsted, CT 06098
$208,900 Sold Jul 18, 2025

39 Orchard St, Winsted, CT 06098
- 3 Beds
- 1.5 Baths
- 1,200 Sq Ft
- Built 1875
Last Sold Summary
- 9% Below List Price
- $174/SF
- 131 Days On Market
Current Estimated Value $283,131

Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc

39 Orchard St, Winsted, CT 06098

Est $54,402 Not Listed For Sale

287 Colebrook Rd, Winsted, CT 06098
287 Colebrook Rd, Winsted, CT 06098

Last Sold Summary
- 9% Above List Price
- $1/SF
- 180 Days On Market
Last Sold Price $50,000

Last Listing Agent Adam Towers Berkshire Hathaway Home Services

/37
$469,000
- 5 Beds
- 4 Baths
- 5,016 Sq Ft
55 Walnut St, Winsted, CT 06098

Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

David Sartirana

Northwest CT Realty

(860) 390-5071

55 Walnut St, Winsted, CT 06098
/10
$1,450 total monthly price
- 2 Beds
- 1 Bath
- 800 Sq Ft
- House for Rent
79 Chestnut St, Winsted, CT 06098

Located at 79 Chestnut Street, this third-floor apartment offers 2 bedrooms and 1 full bathroom with approximately 750 sq ft of living space in a multi-family building built in 1915. The unit features a comfortable layout with a living room, kitchen, and two bedrooms, along with thermopane windows and natural gas baseboard heating. A washer/dryer hookup is conveniently located inside the unit,

William Kallberg

Berkshire Hathaway NE Prop.

(860) 981-0377

79 Chestnut St, Winsted, CT 06098
$225,000 Sold Dec 10, 2025

32 Charles St, Winsted, CT 06098
- 3 Beds
- 1 Bath
- 1,044 Sq Ft
- Built 1953
Last Sold Summary
- 2% Below List Price
- $216/SF
- 41 Days On Market
Current Estimated Value $230,049

Last Listing Agent David Sartirana Northwest CT Realty

32 Charles St, Winsted, CT 06098

Est $46,759 Not Listed For Sale

90 Reaching Hill Rd, Winsted, CT 06098
90 Reaching Hill Rd, Winsted, CT 06098

Last Sold Summary
- 23% Above List Price
- 184 Days On Market
Last Sold Price $38,000

Last Listing Agent Christopher Gueniat Northwest CT Realty

/2
$23,900 Pending
- Land
- 0.15 Acre
- $159,333 per Acre
48 Bridge St, Winsted, CT 06098

Nestled just steps from downtown, this .15-acre lot offers a fantastic opportunity in a highly convenient location. The property is fairly level and provides easy access to shopping, restaurants, The Gilson Theater, and Little Red Barn Brewery. With city water and sewer available, this lot is ready for your vision. Whether you're looking to build or invest, this prime spot puts you right in the

David Sartirana

Northwest CT Realty

(860) 453-5624

48 Bridge St, Winsted, CT 06098
/7
$1,195 total monthly price
- 1 Bed
- 1 Bath
- 1,400 Sq Ft
- House for Rent
112 Rockwell St Unit LL, Winsted, CT 06098

Private 1bedroom apartment with its own porch and yard, plus in-unit washer/dryer. Pets considered. Conveniently located near the center of town and Highland Lake. First month's rent plus two months' security deposit required. Credit and background check performed by the listing office.

Amanda Balaski

Northwest CT Realty

(860) 321-4592

112 Rockwell St Unit LL, Winsted, CT 06098
$280,000 Sold Jun 16, 2025

174 Boyd St, Winsted, CT 06098
- 3 Beds
- 1 Bath
- 1,424 Sq Ft
- Built 1900
Last Sold Summary
- 8% Below List Price
- $197/SF
- 110 Days On Market
Current Estimated Value $285,713

Last Listing Agent Margaret Alexson Elyse Harney Real Estate

174 Boyd St, Winsted, CT 06098

Est $739,641 Not Listed For Sale

404 Colebrook Rd, Colebrook, CT 06021
- 3 Beds
- 2.5 Baths
- 3,860 Sq Ft
- Built 1989
404 Colebrook Rd, Colebrook, CT 06021

Last Sold Summary
- 8% Above List Price
- $178/SF
- 22 Days On Market
Last Sold Price $687,000

Last Listing Agent Lori Meyerson Coldwell Banker Realty

/8
$299,900 Pending
- 6 Beds
- 2 Baths
- 2,699 Sq Ft
77 Hubbard St, Winsted, CT 06098

Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the

Amy Rio

Executive Real Estate Inc.

(860) 452-3957

77 Hubbard St, Winsted, CT 06098
/34

$1,500 - $1,800 per month plus fees

Mill at Still River

1 - 2 Beds

101 Whiting St, Winsted, CT 06098

By far the best place to live in Winsted, Connecticut. Turn of the century construction, every unit overlooks the beautiful Still River, our 700-1000 square-foot one and two bedroom interiors are bright and charming and feature exposed wood beams, 10-foot ceilings, oversized industrial windows, and exposed brick walls. We deliver nature at your door. Our community amenities include same-floor

101 Whiting St, Winsted, CT 06098
$300,000 Sold Nov 07, 2025

331 Colebrook Rd, Winsted, CT 06098
- 2 Beds
- 1.5 Baths
- 1,323 Sq Ft
- Built 1940
Last Sold Summary
- 7% Above List Price
- $227/SF
- 25 Days On Market
Current Estimated Value $296,089

Last Listing Agent Alison Malkin Essentia Realty

331 Colebrook Rd, Winsted, CT 06098

Est $214,528 Not Listed For Sale

14 Pine Rd, Colebrook, CT 06021
- 4 Beds
- Built 1998
14 Pine Rd, Colebrook, CT 06021

Last Sold Summary
- 13% Above List Price
- $54/SF
- 43 Days On Market
Last Sold Price $190,000

Last Listing Agent LAURA BARTLETT Northwest CT Realty

/33
$339,900 Coming Soon
- 2 Beds
- 1 Bath
- 975 Sq Ft
621 Wynne Rd, Winsted, CT 06098

Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of

David Sartirana

Northwest CT Realty

(860) 385-6622

621 Wynne Rd, Winsted, CT 06098
/3
$800 total monthly price
- 1 Bath
- 4,668 Sq Ft
- House for Rent
440 Main St Unit C, Winchester, CT 06098

Two room Studio apartment set in town. Convenient to stores, restaurants and medical facility.

Linda Ganem Borla & Associates Real Estate

440 Main St Unit C, Winchester, CT 06098
$160,000 Sold May 07, 2025

37 Riveredge Dr Unit 37, Winsted, CT 06098
- 2 Beds
- 1.5 Baths
- 992 Sq Ft
- Built 1986
Last Sold Summary
- $161/SF
- 37 Days On Market
Current Estimated Value $164,532

Last Listing Agent Erin Ruwet Century 21 AllPoints Realty

37 Riveredge Dr Unit 37, Winsted, CT 06098

Est $343,176 Not Listed For Sale

268 Smith Hill Rd, Colebrook, CT 06021
- 2 Beds
- 2 Baths
- 1,635 Sq Ft
- Built 1955
268 Smith Hill Rd, Colebrook, CT 06021

Last Sold Summary
- 6% Above List Price
- $199/SF
- 122 Days On Market
Last Sold Price $324,900

Last Listing Agent David Sartirana Northwest CT Realty

Showing Results 1 - 40, Page 1 of 18

Connecticut Litchfield County Winchester

Home Trends in Winchester, CT

On average, homes in Winchester, CT sell after 50 days on the market compared to the national average of 55 days. The median sale price for homes in Winchester, CT over the last 12 months is $345,000, down 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$345,000

Median Single Family Sale Price

$345,000

Average Price Per Sq Ft

$248

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

0.00

Median List Price

$349,900

Median Change From 1st List Price

-2%

Median Home Sale Price YoY Change

-10%

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Winchester, CT Homes

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Home Trends in Winchester, CT

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