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Winchester, CT Homes for Sale

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  • /36

    $199,000

    • 2 Beds
    • 2 Baths
    • 1,154 Sq Ft

    192 Ledge Dr Unit 192, Torrington, CT 06790

    Bright and spacious 2 bedroom, 2 full bathroom townhouse. This Hideaway model in the highly desirable Lakeridge complex features a main level with a bedroom, a full bathroom with custom tile shower and glass doors, a laundry area, living/dining room and a fully-equipped kitchen. The large living room with vaulted ceiling and floor to ceiling accent wall surrounding the fireplace create a

    Agent Photo

    Alexa Skalandunas

    William Raveis Real Estate

    192 Ledge Dr Unit 192, Torrington, CT 06790
  • /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
  • /40

    $959,900

    • 2 Beds
    • 1.5 Baths
    • 1,472 Sq Ft

    204 E Wakefield Blvd, Winsted, CT 06098

    Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with

    Agent Photo

    David Sartirana

    Northwest CT Realty

    204 E Wakefield Blvd, Winsted, CT 06098
  • /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,

    Agent Photo

    David Sartirana

    Northwest CT Realty

    64 Wheeler St, Winsted, CT 06098
  • /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

    Agent Photo

    Ariel Edery

    mygoodagent

    321 Colebrook Rd, Winchester, CT 06098
  • /2

    $49,000

    • Land
    • 2 Acres
    • $24,500 per Acre

    18 Pine Rd, Colebrook, CT 06021

    Discover the perfect setting for your dream home on this private 2.0-acre parcel in the scenic hills of Colebrook. Featuring 236 feet of road frontage on quiet Pine Road, this property offers a beautiful building site situated on a gently elevated plateau with desirable southern and western exposures, providing excellent sunlight and the potential for stunning sunset views. Surrounded by nature

    Agent Photo

    David Sartirana

    Northwest CT Realty

    18 Pine Rd, Colebrook, CT 06021
  • /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

    Agent Photo

    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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    55 Walnut 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

    $49,999

    $20K PRICE DROP
    • Land
    • 5,227 Sq Ft
    • $416,658 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
  • /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
  • /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
  • /5

    $158,000

    $3K PRICE INCREASE
    • 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
  • /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

    $795,000

    • Land
    • 10,018 Sq Ft
    • $3,456,522 per Acre

    535,538 W Wakefield Blvd, Winchester, CT 06098

    This waterfront property is ideal for contractors or individuals who want to build a year-round home on Highland Lake's West side. The property is being sold as a package (3 lots have been approved for construction, parking, and a well ). The lots consist of .10 acres across the street from the water and .023 acres on the water.

    chris marino Cohen Agency

    535,538 W Wakefield Blvd, Winchester, CT 06098
  • /26

    $1,080,000

    $120K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,307 Sq Ft

    77 Deer Hill Rd, Colebrook, CT 06021

    Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at

    MICHAEL CONLOGUE William Pitt Sotheby's Int'l

    77 Deer Hill Rd, Colebrook, CT 06021
  • /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

    $9K PRICE DROP
    • 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
  • /3

    $79,900

    • Land
    • 1.32 Acres
    • $60,530 per Acre

    -00 Colebrook Rd, Colebrook, CT 06021

    Set in the quiet beauty of Colebrook, this 1.32-acre approved building lot offers an excellent opportunity to bring your new home plans to life. Much of the early groundwork has already been completed, including a perc test, survey, driveway plan, septic design, and approvals for up to a 4-bedroom home, helping streamline the path from concept to construction. The lot has been cleared, offering a

    Steve Howey Coldwell Banker Realty

    -00 Colebrook Rd, Colebrook, CT 06021
  • /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
  • /19

    $150,000

    • Land
    • 6.18 Acres
    • $24,272 per Acre

    0 Ashley Rd Unit Lot 6, Winchester, CT

    Build Your Dream Retreat in Litchfield County! Escape the noise and pace of the city and discover 6.18 private wooded acres nestled in the scenic hills of Winchester, Connecticut. This approved 4-bedroom building lot offers the perfect opportunity to create a custom home or weekend retreat surrounded by nature, all within an easy drive of New York City and The Berkshires. Located just 200 yards

    Pascale Nejaime William Pitt Sotheby's Int'l

    0 Ashley Rd Unit Lot 6, Winchester, CT
  • /40

    $735,000

    • 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
  • /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
  • /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
  • /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

    $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
  • /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
  • /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
  • /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

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.

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 is the average household income in Winchester, CT?
The average household income in Winchester, CT is $87K.
What are the most popular zip codes in Winchester, CT?
The most popular zip codes in Winchester, CT include 06098, 06790, 06021, 06058 and 06063.
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 6.66%, your estimated principal and interest payment would be $1,800 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $77K 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 $87K.
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 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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