Winchester Homes for Sale

/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
Explore Winchester
/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
/35
$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
/15
$499,000
- 4 Beds
- 2.5 Baths
- 3,556 Sq Ft
5 Stadler Heights, Winsted, CT 06098

Spacious and full of potential, this 10-room home offers 4 bedrooms and 2.5 baths with plenty of room for everyone. Priced below current market value, this property presents a fantastic opportunity for buyers willing to make some cosmetic updates and build instant equity. Set in a quiet country location within a private development known for its large lots and peaceful surroundings, the home

David Sartirana

Northwest CT Realty

(860) 467-0358

5 Stadler Heights, Winsted, CT 06098
/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
/21
$360,000
- 3 Beds
- 1.5 Baths
- 1,312 Sq Ft
262 Holabird Ave, Winsted, CT 06098

Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows

Mary Anne Casey D. Beckley Realty

262 Holabird Ave, Winsted, CT 06098
/37
$779,900
- 5 Beds
- 1.5 Baths
- 1,258 Sq Ft
156 Shore Dr, Winsted, CT 06098

Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor

Bryan Palladino Showcase Realty, Inc.

156 Shore Dr, 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
/15
$859,000
- Land
- 65.29 Acres
- $13,157 per Acre
257-259 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

257-259 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
/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
/36
$1,850,000
- 9 Beds
- 5.5 Baths
- 7,000 Sq Ft
431 W Wakefield Blvd, Winsted, CT 06098

Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

Lisa Ogren Berkshire Hathaway NE Prop.

431 W Wakefield Blvd, Winsted, CT 06098

Connecticut Litchfield County Winchester Winchester

Why Live in Winchester

First settled in 1732, the rural town of Winchester retains its historic look and feel. This forested expanse at the base of the Berkshire Mountains is speckled with Colonial Revivals and Craftsman-inspired homes that range from cozy cabins to ...

Learn more about living in Winchester

Frequently Asked Questions

Is Winchester a good place to live?

Winchester is a good place to live. Winchester is considered very car-dependent and somewhat bikeable with minimal transit options. Winchester is a rural neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Winchester has 6 parks for recreational activities. It has a median age of 46. The average household income is $92,461 which is below the national average. College graduates make up 26.1% of residents. A majority of residents in Winchester are home owners, with 39.2% of residents renting and 60.8% of residents owning their home. A local real estate agent serving Winchester can help you decide if this neighborhood is the right one for you. Learn more on our Winchester neighborhood guide.

Is Winchester, CT a safe neighborhood?

Winchester, CT is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.

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

The median home price in Winchester is $298,500. If you put a 20% down payment of $59,700 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $1,490 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $64K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $92K.

What are the best public schools in Winchester?

The best public schools that serve Winchester are:

Pearson School has a B Niche grade and a student teacher ratio of 12:1.

What are the best private schools in Winchester?

The best private schools that serve Winchester are:

The Gilbert School has an A- Niche grade, a student teacher ratio of 8:1 and an average review score of 4.0.

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

The most popular zip codes in Winchester, Winchester, CT include 06098, 06790, 06063, 06021 and 06057.

Home Trends in Winchester, CT

On average, homes in Winchester, CT sell after 58 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 $289,900, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$289,900

Median Single Family Sale Price

$320,000

Median Townhouse Sale Price

$160,000

Median 2 Bedroom Sale Price

$224,000

Median 1 Bedroom Sale Price

$127,900

Average Price Per Sq Ft

$241

Number of Homes for Sale

Last 12 months Home Sales

111

Months of Supply

0.80

Median List Price

$298,500

Median Change From 1st List Price

Median Home Sale Price YoY Change

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

Winchester Types of Homes for Sale

Winchester Land for Sale

More About Living in Winchester

Homes for Sale in Nearby Cities

Homes for Sale in Nearby Counties

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