Winchester, CT Homes for Sale under $500,000

/14
$299,000
- 4 Beds
- 2 Baths
- 2,270 Sq Ft
64 Wheeler St, Winsted, CT 06098

Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch,

David Sartirana

Northwest CT Realty

64 Wheeler St, Winsted, CT 06098
Explore Winchester
/37
$250,000
- Land
- 9 Acres
- $27,778 per Acre
321 Colebrook Rd, Winchester, CT 06098

321 Colebrook Road is a rare opportunity to own beautiful land with natural features and self-sustaining potential. A natural spring gently rolls through the property, surrounded by mature oak, ash, birch, black walnut, pine, and abundant sugar maple trees - perfect for producing your own maple syrup. The land is rich with native granite and sparkling quartz throughout, adding character and

Ariel Edery

mygoodagent

321 Colebrook Rd, Winchester, CT 06098
/35
$305,000

$35K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,442 Sq Ft
103 Cordano Rd, Winsted, CT 06098

Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary bedroom, and a full bath w/laundry, providing the convenience of

David Sartirana

Northwest CT Realty

103 Cordano Rd, Winsted, CT 06098
/37
$429,000

$121K PRICE DROP
- 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

55 Walnut St, Winsted, CT 06098
/28
$349,900

$20K PRICE DROP
- 4 Beds
- 1.5 Baths
- 2,722 Sq Ft
70 Walnut St, Winsted, CT 06098

Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, pocket doors, built-ins, decorative moldings, and stunning stained-glass accents that capture the craftsmanship of a

David Sartirana

Northwest CT Realty

70 Walnut St, Winsted, CT 06098
/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
/7
$499,900
- 6 Beds
- 5 Baths
- 2,864 Sq Ft
205 Old New Hartford Rd, Winchester, CT 06098

Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled on an expansive 1-acre lot, this multi-family property features 5 distinct living spaces, making it an ideal addition to your real estate portfolio. This property comprises 4 studio apartments and a spacious 2-bedroom apartment, catering to a variety of tenants and maximizing

TK Krumm Berkshire Hathaway NE Prop.

205 Old New Hartford 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
/6
$386,000
- Land
- 1.91 Acres
- $202,094 per Acre
00 Main St, Winsted, CT 06098

Exceptional 2+ Acre Development Opportunity - Route 44, Winsted, CT** Rare opportunity to acquire approximately 2+- acres with nearly 700 feet of frontage on Main Street (Route 44), one of Winsted's primary commercial corridors. Located within the Town Gateway Zone, this highly visible parcel offers outstanding flexibility for a variety of development opportunities, including commercial,

Dan Merrigan Merrigan & Lefebvre Realty

00 Main St, 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
/2
$299,899
- 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
/14
$395,000
- 3 Beds
- 2 Baths
- 1,909 Sq Ft
720 Main St, Winsted, CT 06098

Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Street with excellent exposure and constant pedestrian traffic, this property is an outstanding opportunity for entrepreneurs, investors, or anyone looking to combine business ownership with residential living. The street-level

Arlene Gonzalez The Gonzalez Property Group

720 Main St, Winsted, CT 06098
/29
$269,900

$30K PRICE DROP
- 2 Beds
- 1 Bath
- 702 Sq Ft
147 E Wakefield Blvd, Winsted, CT 06098

Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring

Mary Mary LeBlanc Realty

147 E Wakefield Blvd, Winsted, CT 06098
/17
$365,000

$35K PRICE DROP
- 3 Beds
- 2 Baths
- 1,820 Sq Ft
132 E Lake St, Winsted, CT 06098

Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for

Bryan Palladino Showcase Realty, Inc.

132 E Lake St, Winsted, CT 06098
/19
$469,900
- 3 Beds
- 2 Baths
- 1,768 Sq Ft
9 Loomis St, Winsted, CT 06098

Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Beautifully Remodeled from "TOP TO BOTTOM" for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwave, Refrigerator & Dishwasher.. 27' x 12' Living/Dining Combo with Bay/Bow Window that takes in Natural Light on

Marshall Cohen Cohen Agency

9 Loomis St, Winsted, CT 06098

Connecticut Litchfield County

Home Prices in Winchester, CT

The median home sale price in Winchester, CT is $345,000, down 10% year-over-year. Homes in Winchester sell in 50 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $345,000	Median Single Family Sale Price $345,000
Median 2 Bedroom Sale Price $370,000	Average Price Per Sq Ft $248
Number of Homes for Sale 0	Last 12 months Home Sales 4
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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