Winchester Homes for Sale

/39
$795,000
- 4 Beds
- 2 Baths
- 1,373 Sq Ft
258 Perch Rock Trail, Winsted, CT 06098

Turn-key direct waterfront gem on Highland Lake! Perfectly positioned on the desirable east side of the lake, this beautifully maintained Cape offers abundant sunshine, gorgeous sunsets, & stunning water views. The updated kitchen features a breakfast bar, generous cabinet space, & opens to the dining room & inviting great room with hardwood floors & a gas fireplace. Enjoy lake views from the

Nancy Reardon Berkshire Hathaway NE Prop.

258 Perch Rock Trail, Winsted, CT 06098
Explore Winchester
/5
$200,000
- Land
- 15.9 Acres
- $12,579 per Acre
00 Chapel Rd, Winchester, CT 06098

Look no further for A Very Private location to build your Dream Home. A Wooded Hill top building site overlooking beautiful Winchester Center which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester. Convenient access agreement to the Rear lot is though 151 Chapel Rd. property.

Linda Ganem Borla & Associates Real Estate

00 Chapel Rd, Winchester, CT 06098
/40
$895,000
- 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
/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
/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
/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
/25
$285,000
- 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
/19
$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, mostly 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
/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
/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
/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
/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
/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 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
/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
/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
/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
$449,000
- 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
- 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
/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

Connecticut Litchfield County Winchester 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 $295,000. If you put a 20% down payment of $59,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $1,460 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $63K 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 57 days on the market compared to the national average of 57 days. The median sale price for homes in Winchester, CT over the last 12 months is $300,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$300,000

Median Single Family Sale Price

$320,000

Median Townhouse Sale Price

$160,000

Median 2 Bedroom Sale Price

$250,000

Median 1 Bedroom Sale Price

$127,900

Average Price Per Sq Ft

$246

Number of Homes for Sale

Last 12 months Home Sales

107

Months of Supply

1.00

Median List Price

$295,000

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

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage