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Newest Homes for Sale in Winsted, CT

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  • /40

    $319,900

    Open Sun 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft

    325 E Wakefield Blvd, Winsted, CT 06098

    Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features

    Anthony Gonsalves RE/MAX RISE

    325 E Wakefield Blvd, Winsted, CT 06098
  • /7

    $325,000

    • 4 Beds
    • 2.5 Baths
    • 2,257 Sq Ft

    48 Center St, Winsted, CT 06098

    Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    48 Center St, Winsted, CT 06098
  • /8

    $275,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    1 Division St, Winsted, CT 06098

    Well-maintained and move-in ready, this charming one-level ranch offers 912 square feet of comfortable living space with 2 bedrooms and 1 full bath. Features include a one-car garage and convenient main-level laundry. The functional layout offers easy one-level living. Conveniently located close to town and local amenities. A great opportunity for buyers looking for a manageable home in a

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    1 Division St, Winsted, CT 06098
  • /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    837 E Wakefield Blvd, Winsted, CT 06098
  • /11

    $309,900

    Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,346 Sq Ft

    94 Colony Dr, Winsted, CT 06098

    Welcome home to this beautifully maintained 2bedroom Cape offering the perfect blend of comfort, character, and modern updates. Set in a soughtafter neighborhood, this property delivers movein readiness with valuable improvements already completed. (New roof and electric panel). Step inside to find a bright, inviting living space featuring wood floors, updated kitchen, a cozy fireplace, and

    Debra Stewart Integrity Real Estate

    94 Colony Dr, Winsted, CT 06098
  • /23

    $339,900

    New Construction
    • 2 Beds
    • 1 Bath
    • 1,034 Sq Ft

    14 Bank St, Winsted, CT 06098

    New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitchen with Island and granite countertops. All stainless steel kitchen appliances. Separate laundry room on main level. Glass paneled door to covered deck off the living room area. Two spacious bedrooms with large closets. Entry foyer with large walkin closet Large heated garage

    David White OwnerEntry.com

    14 Bank St, Winsted, CT 06098
  • /40

    $600,000

    • 4 Beds
    • 2.5 Baths
    • 3,486 Sq Ft

    205 Wallens St, Winsted, CT 06098

    Welcome to this beautifully crafted 3,486 sq. ft. Colonial, offering exceptional quality, thoughtful design, and plenty of space both inside and out. Set privately on 2.03 acres at the end of a long driveway, this 10-room home was built in 2007 and has been meticulously maintained. The main level features gleaming hardwood floors, a spacious family room with fireplace, and an incredible gourmet

    Kelly Sullivan Sullivan Real Estate Inc

    205 Wallens St, Winsted, CT 06098
  • /37

    $799,900

    Open Sun 1:30PM - 3:30PM
    • 2 Beds
    • 1 Bath
    • 1,044 Sq Ft

    804 W Wakefield Blvd, Winsted, CT 06098

    Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residence, weekend escape, vacation home, or income-producing rental. Perfectly positioned on the widest part of Highland Lake's coveted Third Bay, enjoy breathtaking sunrises, panoramic water views, and bald eagles soaring overhead

    Agent Photo

    Pamela Dostilio

    Coldwell Banker Realty

    804 W Wakefield Blvd, 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
  • /16

    $399,900

    • 4 Beds
    • 1.5 Baths
    • 1,944 Sq Ft

    122 Standard Ave, Winsted, CT 06098

    Well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated eat-in kitchen with updated cabinetry, countertops, and finishes, perfect for everyday living and gathering. The comfortable layout includes a spacious living room and dining area, while four bedrooms offer flexibility for family, guests, or a home office. Enjoy the large yard,

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    122 Standard Ave, Winsted, CT 06098
  • /23

    $199,900

    • 4 Beds
    • 2 Baths
    • 1,376 Sq Ft

    46 Cherry St, Winsted, CT 06098

    A wonderful opportunity to own a spacious antique Colonial with endless potential! This 4-bedroom, 2-full-bath home features a living room, dining room, and an eat-in kitchen, providing a solid foundation for your vision. While the home would benefit from updates, it offers an excellent opportunity for buyers to add their personal style and transform it into a truly standout property. Ideally

    Debra Jablonski Berkshire Hathaway NE Prop.

    46 Cherry St, Winsted, CT 06098
  • /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
  • /24

    $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
  • /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    70 Walnut St, Winsted, CT 06098
  • /38

    $1,600,000

    • 4 Beds
    • 2.5 Baths
    • 2,129 Sq Ft

    752 Lake Dr, Winsted, CT 06098

    Great for you, sad for him. Buyer terminated due to health issues. Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100' x 14' Brazilian hardwood deck, a 35' x 6' stationary Trex and steel dock, and a private cabana-perfect for relaxing, boating, swimming, and entertaining. Soak

    Agent Photo

    Pam Famiglietti

    William Raveis Real Estate

    752 Lake Dr, 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
  • /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
  • /2

    $45,000

    • Land
    • 17,859 Sq Ft
    • $109,756 per Acre

    32 Hubbard St, Winsted, CT 06098

    Rare opportunity to build in a convenient in-town location! This level 0.41-acre lot is ideally situated close to downtown amenities while offering easy access to Highland Lake's public beach and boat launch. Formerly improved with a three-story Colonial home, the property presents a unique opportunity to redevelop an established homesite. Public water, public sewer, and natural gas are available

    Agent Photo

    David Sartirana

    Northwest CT Realty

    32 Hubbard St, Winsted, CT 06098
  • /5

    $37,900

    $32K PRICE DROP
    • Land
    • 5,227 Sq Ft
    • $315,833 per Acre

    319 White Oak Trail, Winchester, CT 06098

    Wooded interior lot located at the end of a dead-end street, offering a private setting. The parcel is slightly sloped and accessed from the end of the road. Clients, do your homework , including but not limited to surveys, zoning, and building approvals. Convenient location with approximately a 15-minute walk to Resha Beach on Highland Lake for recreational enjoyment. Lake rights are granted to

    Matt Tearman Coldwell Banker Realty

    319 White Oak Trail, Winchester, CT 06098
  • /8

    $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
  • /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
  • /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
  • /19

    $549,000

    $30K PRICE DROP
    • 11 Beds
    • 5.5 Baths
    • 5,233 Sq Ft

    150 Oak St, Winsted, CT 06098

    *PRICE REDUCTION* 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 3-4 bedroom, 1 1/2 bath

    Pamela Silvestri Turning Point Realty, LLC

    150 Oak St, Winsted, CT 06098
  • /31

    $259,000

    $31K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,652 Sq Ft

    118 Meadow St, Winsted, CT 06098

    This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample

    Ashley Henry The Washington Agency

    118 Meadow St, 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
  • /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    55 Walnut 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

Frequently Asked Questions

What is the average home price in Winsted, CT?
Homes for sale in Winsted, CT have an average home price of $431,467.
How many homes have sold over the last 12 months in Winsted, CT?
108 homes have sold in Winsted, CT over the last 12 months.
What are the most popular zip codes in Winsted, CT?
The most popular zip codes in Winsted, CT include 06098, 06790, 06063, 06021 and 06057.
How much do you need to make to afford a house in Winsted?
The median home price in Winsted is $317,000. If you put a 20% down payment of $63,400 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $1,630 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $70K a year to afford the median home price in Winsted. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Winsted, CT?
Winsted, CT has highly rated public and private schools. Some of the best schools in Winsted based on Niche Grades are Northwestern Regional High School, Barkhamsted Elementary School and Northwestern Regional Middle School. Browse all the schools in Winsted, CT to learn more.

Home Price Trends

Median Sale Price
$312,500
Median Single Family Sale Price
$332,500
Median Townhouse Sale Price
$160,000
Median 2 Bedroom Sale Price
$265,000
Median 1 Bedroom Sale Price
$244,250
Average Price Per Sq Ft
$281
Number of Homes for Sale
18
Last 12 months Home Sales
108
Months of Supply
2.00
Median List Price
$317,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
8%
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