Winchester, CT Homes for Sale under $900,000

/40
$749,900

Open Sat 11AM - 1PM
- 3 Beds
- 2 Baths
- 1,131 Sq Ft
180 Shore Dr, Winsted, CT 06098

Highest and best offer by noon on Monday 21st. Welcome to 180 Shore Dr - your own beautifully renovated waterfront retreat on highly desirable Lake! This exceptional year-round home offers the perfect combination of modern comfort, stunning water views, and the lake lifestyle you've been dreaming about. Featuring 3 bedrooms and 2 full bathrooms, the home has been extensively remodeled with

Jacek Mikolajczyk

Berkshire Hathaway NE Prop.

180 Shore Dr, Winsted, CT 06098
Explore Winchester
/40
$629,900
- 3 Beds
- 1.5 Baths
- 1,168 Sq Ft
837 E Wakefield Blvd, Winsted, CT 06098

Enjoy the best of Highland Lake living with this unique property offering a spacious home directly across the street from the lake along with your own separate waterfront parcel! The main house features 7 rooms, 3-4 bedrooms and 2 full baths, providing plenty of space for year-round living or a relaxing lake retreat. A deck overlooking the waterfront offers the perfect spot to enjoy the lake

David Sartirana

Northwest CT Realty

837 E Wakefield Blvd, Winsted, CT 06098
/28
$629,000
- 8 Beds
- 4.5 Baths
- 4,800 Sq Ft
143 Holabird Ave, Winsted, CT 06098

One of the finest grand classic Colonial homes where timeless charm and beautiful details can still be found throughout. Features include elegant crown molding, rich wood paneling, wide baseboard molding, gleaming hardwood floors, and a sweeping grand staircase-all adding to the warmth and character of this truly special home. This home features formal dining room, sitting room with fireplace,

Linda Ganem Borla & Associates Real Estate

143 Holabird Ave, Winsted, CT 06098
/38
$649,900
- 2 Beds
- 1 Bath
- 1,361 Sq Ft
600 E Wakefield Blvd, Winsted, CT 06098

Nestled along the coveted east shore of Highland Lake, 600 East Wakefield Boulevard presents a rare opportunity to own a piece of one of Connecticut's most sought-after waterfront communities. Filled with charm and character, this lakeside property offers the perfect canvas to create a custom retreat that reflects your vision and lifestyle. Spend your days swimming, boating, kayaking, and

Stacy Anselmo Coldwell Banker Realty

600 E Wakefield Blvd, Winsted, CT 06098
/15
$799,000

$60K PRICE DROP
- Land
- 65.29 Acres
- $12,238 per Acre
257-259 Torringford St, Winchester, CT 06098

Uncover this hidden gem - 65.29 pristine acres of raw land, with natural beauty and endless potential. This picturesque parcel features serene ponds and mature trees. Distant views and incredible sunsets can be enjoyed from the property. Much site work has been done to date. A driveway with a binder course is already in place offering easy access into and throughout the property. Many acres have

Lisa Toczko Home Valley Realty, LLC

257-259 Torringford St, Winchester, 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
/13
$850,000
- Land
- 39,204 Sq Ft
- $944,444 per Acre
414 E Wakefield Blvd, Winsted, CT 06098

An exceptional opportunity to create your dream home on the shores of highly sought-after Highland Lake. This waterfront property at 414 E Wakefield Boulevard offers the perfect setting to bring your vision of lakefront living to life. Existing plans for an impressive approximately 4,000-square-foot waterfront home are available, giving you the option to move forward with an already thoughtfully

Annie Q Simard LPT Realty

414 E Wakefield Blvd, Winsted, 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
/40
$715,000

$20K PRICE DROP
- 4 Beds
- 2.5 Baths
- 3,158 Sq Ft
44 Pine Rd, Colebrook, CT 06021

Enjoy exceptional privacy and peaceful country living in this spacious 4 bedroom, 2.5 bath contemporary Cape set atop a long winding driveway surrounded by natural beauty. The open floor plan on the main level offers comfortable living and entertaining spaces, including an updated eat in kitchen with stainless steel appliances, a dining room with a cozy wood burning fireplace, a generous living

Mike Gregor Cohen Agency SiM, LLC

44 Pine Rd, Colebrook, CT 06021
/35
$849,900
- 4 Beds
- 2 Baths
- 1,781 Sq Ft
119 W Wakefield Blvd, Winsted, CT 06098

Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

Mela Veltri Case KW Legacy Partners

119 W Wakefield Blvd, Winsted, CT 06098
/9
$850,000

$149K PRICE DROP
- 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

Connecticut Litchfield County

Home Prices in Winchester, CT

The median home sale price in Winchester, CT is $370,000, up 5% year-over-year. Homes in Winchester sell in 58 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $370,000	Median Single Family Sale Price $370,000
Median 2 Bedroom Sale Price $370,000	Average Price Per Sq Ft $232
Number of Homes for Sale 11	Last 12 months Home Sales 3
Months of Supply 0.00	Median List Price $359,900
Median Change From 1st List Price -3%	Median Home Sale Price YoY Change 5%

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