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 06057 .

/6
$349,900 Coming Soon
- 3 Beds
- 1 Bath
- 1,282 Sq Ft
90 Colony Dr, Winsted, CT 06098

Turnkey Winsted gem completely renovated inside & out! Get ready to just move and and not worry. Here is a beautifully reimagined 3-bedroom, 1-bathroom property in Winsted, offering the perfect blend of modern luxury and ultimate peace of mind. Every detail has been thoughtfully updated to create a true turnkey experience. Step inside to a bright, inviting space where the wall between the

Michelle Grant Coldwell Banker Premier Real Estate

90 Colony Dr, Winsted, CT 06098
Explore Winchester
/38
$769,000 Coming Soon
- 4 Beds
- 3.5 Baths
- 2,265 Sq Ft
121 W Wakefield Blvd, Winsted, CT 06098

Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or

Elizabeth Stockwell Coldwell Banker Realty

121 W Wakefield Blvd, Winsted, CT 06098
/39
$499,000
- 3 Beds
- 2 Baths
- 1,654 Sq Ft
11 Old Creamery Rd, Colebrook, CT 06021

FULLY RENOVATED! In addition this home is fully insulated, energy-efficient, and enhanced with solar panels for low utility costs. The open floor plan and cozy fireplace create the perfect space for gatherings, while multiple decks, an above-ground pool, and serene natural surroundings provide a tranquil retreat-ideal for year-round living or a weekend getaway. Located perfectly on a beautiful

Rodrigo Aguiar William Raveis Real Estate

11 Old Creamery Rd, Colebrook, CT 06021
/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
/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
/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
/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
/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
/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
/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
/31
$162,500
- 2 Beds
- 1.5 Baths
- 992 Sq Ft
35 Riveredge Dr Unit 35, Winsted, CT 06098

Charming Riverview Townhouse with Patio Enjoy easy living in this well-located two-bedroom townhouse set on a slab and overlooking the river. The main level features a living room, dining room, and functional kitchen, perfect for everyday comfort and entertaining. Sliding glass doors lead to a private patio where you can relax and enjoy the peaceful water views. Upstairs offers two comfortable

Joanne Donne The Washington Agency

35 Riveredge Dr Unit 35, 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
/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
/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
/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
$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
/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
/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
/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
/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
/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 $347,425.

Are home prices dropping in Winchester?

Yes, home prices in Winchester are down 13% in the last 12 months.

How many homes have sold over the last 12 months in Winchester, CT?

4 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 06057.

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

The median home price in Winchester is $349,900. If you put a 20% down payment of $70,000 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $1,750 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $75K 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 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 Types of Homes for Sale

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