20

Winchester, CT Homes for Sale

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  • /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 390-5071

    55 Walnut St, Winsted, CT 06098
  • /2

    $249,900 Coming Soon

    • 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

    Agent Photo

    Rob Rosa

    Berkshire Hathaway NE Prop.

    (860) 492-6499

    94 Holabird Ave, 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

    Agent Photo

    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,

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 946-4468

    99 Hubbard St, Winsted, CT 06098
  • /12

    $314,000

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    230 E Wakefield Blvd, Winsted, CT 06098

    This Highland Lake house is in great condition, remodeled 4 years ago. Lower level has a separate entrance and was revamped with large living room and full bathroom. Walk to the Association beach in 5 mins.

    Peter D'Addeo Commercial Services Realty

    230 E Wakefield Blvd, Winsted, 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 minutes

    Hector Ortiz KW Legacy Partners

    7 Stadler Heights, Winsted, CT 06098
  • /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
  • /15

    $859,000

    • Land
    • 65.29 Acres
    • $13,157 per Acre

    257 Torringford St, Winchester, CT 06098

    Uncover this hidden gem - 65 pristine acres of raw land, with natural beauty and endless potential. This picturesque parcel features serene ponds and mature trees. Distant views can be enjoyed from the property. Much site work has been done to date. A driveway with a binder coarse is already in place offering easy access into and throughout the property. Many acres are cleared, stumps have been

    Lisa Toczko Home Valley Realty, LLC

    257 Torringford St, Winchester, 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 CONSIDER

    David D'Amore Northwest CT Realty

    843-845 (lots - 10A, E Wakefield Blvd, Winchester, 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
  • /5

    $240,000

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft

    107 Birdsall St, Winsted, CT 06098

    Spacious colonial with 4 bedrooms, 2 full baths, generous size living room, dining room, sitting room, sunroom. Looking for space, this home definitely has it. Harwood floors thorough, granite countertops, marble backsplash, Island in kitchen. Short walk to highland Lake With a little TLC this home will be a GEM! Home being sold AS-IS.

    Jesica Beaulieu Dave Jones Realty, LLC

    107 Birdsall 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

    $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
  • /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
  • /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
  • /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
  • /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 hunting

    David D'Amore Northwest CT Realty

    32 Norfolk Rd, Winchester, CT 06098
  • /2

    $299,900

    • Land
    • 34 Acres
    • $8,821 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
  • /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
  • /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

Why Live in Winchester

Winchester is a leafy town in the Litchfield Hills, a rural region whose rolling hills stretch across Connecticut’s northwestern corner. Known as the Gateway to the Berkshire Mountains, it offers a scenic foothill location with access to outdoor ...

Frequently Asked Questions

What is the average home price in Winchester, CT?
Homes for sale in Winchester, CT have an average home price of $343,266.
Are home prices dropping in Winchester?
Yes, home prices in Winchester are down 14% in the last 12 months.
How many homes have sold over the last 12 months in Winchester, CT?
3 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, 06063, 06790, 06021 and 06057.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $339,900. If you put a 20% down payment of $68,000 and had a 30-year fixed mortgage with an interest rate of 6.11%, your estimated principal and interest payment would be $1,650 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $71K 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

Housing Trends

Median Sale Price
$320,000
Median Single Family Sale Price
$320,000
Average Price Per Sq Ft
$233
Number of Homes for Sale
0
Last 12 months Home Sales
3
Months of Supply
0.00
Median List Price
$339,900
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
-17%
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