Newest Homes for Sale in Winchester, CT

Q: What are the most popular zip codes in Winchester, CT?

The most popular zip codes in Winchester, CT include 06098 , 06790 , 06063 , 06021 and 06058 .

/23
$230,000
- 2 Beds
- 1.5 Baths
- 1,172 Sq Ft
9 John St, Winsted, CT 06098

Beautifully renovated 1870 Colonial offering 1,172 sq. ft. of updated and functional living space. The home features hardwood floors in the living room and both bedrooms, adding warmth and durability throughout. A convenient first-floor bedroom provides flexibility, while the spacious primary bedroom is located on the second level. The kitchen has been completely refreshed with new flooring,

Michael Grady William Raveis Real Estate

9 John St, Winsted, CT 06098
Explore Winchester
/31
$339,000
- 6 Beds
- 2.5 Baths
- 2,376 Sq Ft
157 Elm St, Winsted, CT 06098

Bring your vision to this spacious 6-bedroom, 2.5-bath home full of character and potential. Featuring a newer roof and boiler, this property offers peace of mind while leaving room for your personal touch. Enjoy the classic Victorian details and generous layout, perfect for creating your dream home. Situated on a sidewalk-lined street just steps from downtown eateries, a local brewery, and

Doreen Gagnon

Coldwell Banker Realty

(860) 590-8606

157 Elm St, Winsted, CT 06098
/31
$269,999
- 3 Beds
- 2 Baths
- 1,652 Sq Ft
118 Meadow St, Winsted, CT 06098

This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample

Ashley Henry The Washington Agency

118 Meadow St, Winsted, CT 06098
/38
$395,000
- 3 Beds
- 1.5 Baths
- 1,909 Sq Ft
720 Main St, Winsted, CT 06098

Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe,

Ryan Marconi The Washington Agency

720 Main St, Winsted, CT 06098
/40
$399,000 Open Sun 12AM - 3PM
- 4 Beds
- 1.5 Baths
- 2,365 Sq Ft
187 Torringford St, Winsted, CT 06098

Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm,

Jessica Washington William Raveis Real Estate

187 Torringford St, Winsted, CT 06098
/12
$750,000
- 4 Beds
- 2 Baths
- 5,389 Sq Ft
436 Main St, Winsted, CT 06098

One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year

Tony Goia The Washington Agency

436 Main St, Winsted, CT 06098
/21
$879,990
- Land
- 131.5 Acres
- $6,692 per Acre
000000 Norfolk Rd, Winchester, CT 06098

Rare Multi-Parcel Land Opportunity - 5 Parcels, Endless Possibilities Discover this exceptional assemblage of five contiguous parcels spanning the scenic towns of Winchester and Colebrook in Connecticut's pristine Litchfield County. This remarkable offering combines the best of both worlds with a captivating mixture of open fields and mature forest, creating a diverse landscape that's as

John Harney William Pitt Sotheby's Int'l

000000 Norfolk Rd, Winchester, CT 06098
/2
$299,900
- Land
- 63 Acres
- $4,760 per Acre
32 Norfolk Rd, Winchester, CT 06098

63-Acre Rural Retreat Abutting Algonquin State Forest - A Nature Lover's Dream! Discover the perfect blend of seclusion and accessibility with this 63-acre wooded paradise, directly abutting Algonquin State Forest. Located on a state highway and directly across from a scenic dry dam, this unique parcel provides endless possibilities-whether you're looking to build your dream home, start a

David D'Amore Northwest CT Realty

32 Norfolk Rd, Winchester, CT 06098
/8
$389,000
- Land
- 20.87 Acres
- $18,639 per Acre
7 Stadler Heights, Winsted, CT 06098

Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39

Hector Ortiz KW Legacy Partners

7 Stadler Heights, Winsted, CT 06098
/7
$259,000
- 3 Beds
- 1 Bath
- 1,488 Sq Ft
312 Colebrook River Rd, Colebrook, CT 06021

Charming Colonial on a 2-acre lot. Inside, you'll find an updated kitchen featuring granite countertops and newer appliances. The large, sunny family room on the first floor is filled with natural light, creating a warm and inviting atmosphere. A combined living and dining room with a cozy wood stove adds charm and functionality to the main level. Recent upgrades to the home include a new roof in

Amanda Balaski

Northwest CT Realty

(860) 891-2072

312 Colebrook River Rd, Colebrook, CT 06021
/27
$375,000
- 3 Beds
- 3,660 Sq Ft
57 Main St, Winsted, CT 06098

Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

Stacy LaQuerre Regall Realty, LLC

57 Main St, Winsted, CT 06098
/13
$649,900
- Land
- 41.23 Acres
- $15,763 per Acre
115 Old Robertsville Rd, Winsted, CT 06098

Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The home

Jared Tedesco Litchfield County Real Estate

115 Old Robertsville Rd, Winsted, CT 06098
/9
$850,000
- Land
- 116.5 Acres
- $7,296 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
/2
$69,000
- Land
- 2 Acres
- $34,500 per Acre
503 N Main St, Winsted, CT 06098

Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

Charles Albertario William Raveis Real Estate

503 N Main St, Winsted, CT 06098
/5
$300,000
- Land
- 15.9 Acres
- $18,868 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
/39
$920,000
- 4 Beds
- 2 Baths
- 3,088 Sq Ft
469 Platt Hill Rd, Winsted, CT 06098

HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

Marshall Cohen Cohen Agency

469 Platt Hill Rd, Winsted, CT 06098
/5
$1,350,000
- Land
- 124.92 Acres
- $10,807 per Acre
0 Winsted Norfolk Rd Unit 24089254, Colebrook, CT 06021

Intriguing Litchfield County / Colebrook CT Location: Great Opportunity to Own this Surveyed 124.92 Acre Site. Excellent Visible Corner Location. Lightly Wooded with Good Road Frontage. Potential as a Commercial / Residential Development, Private Estate Style Compound, Agricultural Use. Put your imagination to work here. Includes an existing Golf Driving Range at the Corner of Route 44

Marshall Cohen Cohen Agency

0 Winsted Norfolk Rd Unit 24089254, Colebrook, CT 06021
/34
$749,900
- 7 Beds
- 3 Baths
- 3,486 Sq Ft
39 S Main St, Winsted, CT 06098

THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

Ryan Horvay Smith & DeGroat Real Estate

39 S Main 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

(860) 891-6121

124 Rockwell 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

(860) 946-4468

99 Hubbard St, Winsted, CT 06098
/2
$23,900
- 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
/37
$499,999
- 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
/40
$2,199,000
- 9 Beds
- 5.5 Baths
- 7,000 Sq Ft
431 W Wakefield Blvd, Winsted, CT 06098

AMAZING!!!!!! IMAGINE LIVING THE RESORT LIFE YEAR ROUND!!!!! LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. 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

Lisa Ogren Berkshire Hathaway NE Prop.

431 W Wakefield Blvd, Winsted, CT 06098
/5
$158,000
- Land
- 1.18 Acres
- $133,898 per Acre
843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098

1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL

David D'Amore Northwest CT Realty

843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
/2
$299,900
- Land
- 30 Acres
- $9,997 per Acre
00 Ramsgate Ln, Barkhamsted, CT 06063

30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

00 Ramsgate Ln, Barkhamsted, CT 06063
/2
$59,900
- Land
- 0.41 Acre
- $146,098 per Acre
105,107 E Mountain Rd, Winchester, CT 06098

105 & 107 Mountain Road parcels are contiguous and located on a dirt road . . Deed indicates right of way to Highland lake water frontage within walking distance. See documents attached for Deed , Site plan, Peculation tests , Survey and Septic testing available . Possible city sewer access at buyers expense . Seller will consider financing with a minimum of 15% DOWN PAYMENT FOR A 2 YEAR BALLOON

David D'Amore Northwest CT Realty

105,107 E Mountain Rd, Winchester, CT 06098

Connecticut Litchfield County Winchester

Frequently Asked Questions

What is the average home price in Winchester, CT?

Homes for sale in Winchester, CT have an average home price of $344,950.

Are home prices dropping in Winchester?

Yes, home prices in Winchester are down 11% in the last 12 months.

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.

What are the most popular zip codes in Winchester, CT?

The most popular zip codes in Winchester, CT include 06098, 06790, 06063, 06021 and 06058.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $344,950. If you put a 20% down payment of $69,000 and had a 30-year fixed mortgage with an interest rate of 6.16%, your estimated principal and interest payment would be $1,680 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $72K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Winchester, CT?

Winchester, CT has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Colebrook Consolidated School, Lakeview High School and Northwestern Regional High School. Browse all the schools in Winchester, CT to learn more.

Home Trends in Winchester, CT

On average, homes in Winchester, CT sell after 45 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, CT over the last 12 months is $354,375, down 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$354,375

Median Single Family Sale Price

$354,375

Average Price Per Sq Ft

$270

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

0.00

Median List Price

$344,950

Median Change From 1st List Price

-3%

Median Home Sale Price YoY Change

-8%

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