Winchester, CT Homes for Sale

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 .

/2
$24,900
- Land
- 19,166 Sq Ft
- $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
Explore Winchester
/2
$49,000
- Land
- 16,117 Sq Ft
- $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
/35
$339,900
- 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
/39
$499,000 Under Contract
- 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
/38
$749,000
- 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
/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
/30
$159,500
- 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
/29
$349,900
- 3 Beds
- 1.5 Baths
- 1,600 Sq Ft
1 Hamill Dr, Winsted, CT 06098

Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less

Paul Duh Realty ONE Group Connect

1 Hamill Dr, 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
/31
$990,000
- 3 Beds
- 3 Baths
- 2,097 Sq Ft
674 E Wakefield Blvd, Winsted, CT 06098

Experience the best of year-round waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home with stunning panoramic views and direct water access. Ideally located in the sought-after 3rd Bay, this property features a private dock-perfect for boating, swimming, kayaking, and enjoying everything lake life has to offer. Inside, an open and inviting layout connects the

Patrick Smith Smith & DeGroat Real Estate

674 E Wakefield Blvd, 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 Contiguous Parcels | Colebrook & Winchester, CT Discover an exceptional land offering spanning five contiguous parcels across two of Litchfield County's most desirable rural towns. This unique property features a strong presence in highly sought-after Colebrook, known for its scenic beauty, low-density living, and unspoiled New England charm-paired with the

John Harney William Pitt Sotheby's Int'l

000000 Norfolk Rd, Winchester, CT 06098
/2
$59,900
- Land
- 17,859 Sq Ft
- $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
/40
$1,595,000
- 5 Beds
- 2 Baths
- 3,693 Sq Ft
424 E Wakefield Blvd, Winsted, CT 06098

Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

KAREN NEWTON William Pitt Sotheby's Int'l

424 E Wakefield Blvd, Winsted, CT 06098
/40
$475,000 Open Sun 11AM - 3PM
- 7 Beds
- 5 Baths
- 3,538 Sq Ft
51 Hinsdale Ave, Winsted, CT 06098

Owner Occupants take notice: Rare three family home with market rents (one three-bedroom unit vacant) building is in exceptional condition!! A new roof will be installed in May before closing. One unit, a three-bedroom with a kitchen, living room, dining room, and two full bathrooms, this unit is rented @ $2136. per month ($2221.00 for the June 30, 2026-May 31, 2027 lease).) A one-year lease for

Suzie Larson Turning Point Realty, LLC

51 Hinsdale Ave, Winsted, CT 06098
/5
$295,000
- Land
- 51 Acres
- $5,784 per Acre
393 Winchester Rd, Winsted, CT 06098

WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

Tom McGowan Elyse Harney Real Estate

393 Winchester Rd, Winsted, CT 06098
/25
$279,999
- 2 Beds
- 1 Bath
- 720 Sq Ft
350 Walnut St, Winsted, CT 06098

Fully remodeled from top to bottom, 350 Walnut St offers the perfect blend of modern updates, efficient living, and outdoor space. This move-in-ready 2-bedroom, 1-bath ranch has been beautifully reimagined with a fresh, stylish feel and all the major improvements already done for you. Inside, you will find a brand-new kitchen with quartz countertops and stainless-steel appliances, a fully updated

Vincent Miller Hudson Home Services LLC

350 Walnut St, Winsted, CT 06098
/38
$274,900
- 2 Beds
- 1 Bath
- 993 Sq Ft
149 E Mountain Ave, Winsted, CT 06098

Welcome to this beautifully updated single-level home offering the ease of one-floor living. This charming property features two spacious bedrooms and an updated full bathroom, along with a generously sized living room perfect for relaxing or entertaining. The renovated kitchen boasts modern finishes and stainless steel appliances, providing both style and functionality. A heated sunroom adds

Kevin Eagan Berkshire Hathaway NE Prop.

149 E Mountain Ave, Winsted, 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
/26
$239,000
- 7 Beds
- 3 Baths
- 2,400 Sq Ft
Unlisted Address

Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space.

Frank J. Berg Broker/Owner Town & Country Real Estate

Unlisted Address
/34
$399,000
- 5 Beds
- 4 Baths
- 2,779 Sq Ft
217 Walnut St, Winsted, CT 06098

In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a

David D'Amore Northwest CT Realty

217 Walnut St, Winsted, CT 06098
/8
$579,000
- 11 Beds
- 5.5 Baths
- 5,233 Sq Ft
150 Oak St, Winsted, CT 06098

150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, some hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric

Pamela Silvestri Turning Point Realty, LLC

150 Oak St, 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
$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

Connecticut Litchfield County Winchester

Why Live in Winchester

Winchester, located in the Litchfield Hills of Connecticut, is known for its rural charm and scenic mountain views. This town, often referred to as the Gateway to the Berkshire Mountains, offers a variety of outdoor recreational activities. Highland Lake, a popular attraction, features two public beaches, a boat launch, and a marina with boat rentals and seasonal slips. Winchester Lake and Park Pond provide quieter spots for boating and freshwater fishing. Platt Hill State Park offers unmarked nature trails for hikers and birdwatchers, while nearby Burr Pond, Sunnybrook, and Stillwater Pond State Parks are within 5 miles. The Sue Grossmann Still River Greenway provides a paved path for walking, running, and biking. Green Woods Country Club boasts one of the only three 10-hole golf courses in the United States. Winsted, the downtown area of Winchester, has a walkable Main Street with shops, eateries, and creative spaces like Whiting Mills and the American Mural Project. The Gilbert School, a private secondary school functioning as the public middle and high school, is highly rated and offers various sports programs. Housing options in Winchester range from historic New England-style farmhouses and saltbox homes to Cape Cod and raised ranch-style homes in Winsted, with lakefront properties being more expensive. Winchester is car-dependent, with limited public transportation, but U.S. Route 44 and state Route 8 provide access to Torrington, Hartford, and Bradley International Airport, which is 29 miles away.

Learn more about living in 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 6.3%, your estimated principal and interest payment would be $1,730 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $74K 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 56 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

More About Living in Winchester

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