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Explore Similar Apartments Within 2 Miles of Middlebury, CT

  • /36

    $385,000

    • 3 Beds
    • 3 Baths
    • 1,950 Sq Ft

    215 Scott St, Naugatuck, CT 06770

    Versatile 3-Family Property - 2 Buildings in Naugatuck, CT Great opportunity for investors or owner-occupants! This unique 3-family property features two separate buildings on one lot, offering excellent rental income potential in a convenient Naugatuck location. The first building is a two-family home, each unit offering 1 bedroom and 1 bathroom. Both units are currently ready for immediate

    Agent Photo

    Mike Albert

    RE/MAX RISE

    (203) 819-7236

    215 Scott St, Naugatuck, CT 06770
  • /39

    $385,000

    • 6 Beds
    • 3 Baths
    • 2,760 Sq Ft

    324 Congress Ave, Waterbury, CT 06708

    Multifamily Three-Family Property - Investor Special. Discover a rare opportunity to own fully unoccupied three-family home featuring a total of 6 bedrooms and 3 bathrooms (2/2/2). Perfectly suited for investors or owner-occupants, this property offers outstanding income potential, layout flexibility, and generous living space - ideal for multi-generational living or rental income. Whether you're

    Ahdehroh Lambert Mortimore Premier Properties of CT

    324 Congress Ave, Waterbury, CT 06708
  • /28

    $465,000

    • 9 Beds
    • 5 Baths
    • 3,600 Sq Ft

    278 Willow St, Waterbury, CT 06710

    Don't miss this spacious and updated 3-family property in the desirable Hillside area, with big unit mix, just minutes from Downtown Waterbury. Whether you're looking to live in one unit and rent the others, or start/add to your investment portfolio, this property checks all the boxes. The unit breakdown is as follows:1st floor is 3 bed/1 bath; 2nd floor is 2 bed/2 bath & 3rd floor is 4 bed/2

    Amanda Sheehan Oxford Realty

    278 Willow St, Waterbury, CT 06710
  • /32

    $489,900

    • 12 Beds
    • 3 Baths
    • 4,416 Sq Ft

    203 Cooke St, Waterbury, CT 06710

    Phenomenal investment or Owner-Occupant opportunity in Waterbury's North End! This turn-key multi-family property is a must see - updated, spacious and fully ready to owner occupy or offer a cash flow investment. Each of the three units features 4 bedrooms and 1 bathroom, and offers large, open floor plans filled with natural light. The 1st and 2nd floor units have been beautifully remodeled,

    Amanda Sheehan Oxford Realty

    203 Cooke St, Waterbury, CT 06710
  • /40

    $399,000

    • 8 Beds
    • 4 Baths
    • 3,834 Sq Ft

    98 Angel Dr, Waterbury, CT 06708

    Unique investment opportunity awaits! For sale is ONE building with 4 separate condo units: #A,#B,#C,#D- TO BE SOLD AS A PACKAGE. This is NOT a "multifamily" property, each unit has 2 bedrooms/1 bath with laundry hook ups. All 4 units are fully rented with long term tenants, monthly leases: $1,200 each - $232/month condo fee is PER UNIT includes water and sewer! Renters pay electricity and cable.

    Lauren Freedman Coldwell Banker Realty

    98 Angel Dr, Waterbury, CT 06708
  • /14

    $549,000

    • 6 Beds
    • 4 Baths
    • 2,865 Sq Ft

    105 John St, Naugatuck, CT 06770

    4-Unit Multi-Family Property at 105 John Street, Naugatuck, CT Discover this exceptional investment opportunity! This well-maintained multi-family residence boasts over 2,800 sq ft, featuring 6 spacious bedrooms and 4 bathrooms. All units are currently fully rented with established tenants, ensuring immediate cash flow for the new owner. The property is in good condition, providing a hassle-free

    Sandra Ramalhete Real Estate Two

    105 John St, Naugatuck, CT 06770
  • /22

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,448 Sq Ft

    137 Greenmount Terrace, Waterbury, CT 06708

    This fully renovated 2-family property features new kitchens and bathrooms, a newer roof, and a private in-law apartment-perfect for extended family or additional income. Enjoy abundant off-street parking, a spacious and well-maintained yard, and a stunning outdoor recreation room ideal for entertaining or relaxing. Nestled in a quiet, low-traffic neighborhood, this home offers comfort,

    Lynn LaForme Showcase Realty, Inc.

    137 Greenmount Terrace, Waterbury, CT 06708
  • /22

    $369,000

    • 4 Beds
    • 2 Baths
    • 2,235 Sq Ft

    223 N Main St, Naugatuck, CT 06770

    This beautifully updated home is move-in ready and packed with modern upgrades! Enjoy peace of mind with a new furnace, new HVAC system, and updated electric & plumbing throughout. Freshly painted inside and out, the home features hardwood and waterproof flooring for both style and durability. Additional recent improvements include a new porch, new electric panels, new plywood & roof, and a

    Emmannuel Pina eXp Realty

    223 N Main St, Naugatuck, CT 06770
  • /24

    $399,900

    • 8 Beds
    • 3 Baths
    • 4,589 Sq Ft

    133 Willow St, Waterbury, CT 06710

    Welcome to 133 Willow Street in Waterbury-a spacious and versatile property offering both comfort and convenience. This well-maintained home features generous living space with bright natural light throughout, making it ideal for those seeking room to grow. The layout provides multiple possibilities, whether you're looking for a primary residence, rental opportunity, or investment property.

    Ben Weinberg Oxford Realty

    133 Willow St, Waterbury, CT 06710
  • /25

    $449,900

    • 8 Beds
    • 4 Baths
    • 3,444 Sq Ft

    27 Platt St, Waterbury, CT 06704

    CASH FLOWING & TURN KEY 3 family with bonus apartment + adjacent lot for sale in the North End of Waterbury. The unit mix consists of two 2 bed units w/LR & DR, 3 bed unit and one studio. The units are big w/approx. 1,150 SF each and various updates throughout all apartments including windows, flooring, fixtures, paint, kitchens, appliances and bath rooms. Utilities are separate & tenant paid.

    Amanda Sheehan Oxford Realty

    27 Platt St, Waterbury, CT 06704
  • /16

    $499,000

    • 6 Beds
    • 6 Baths
    • 3,294 Sq Ft

    93 Whitewood Rd, Waterbury, CT 06708

    Three townhouses. Located in Bunker Hill.

    Carolyn Butkevich Regency Real Estate, LLC

    93 Whitewood Rd, Waterbury, CT 06708
  • /40

    $475,000

    • 4 Beds
    • 2 Baths
    • 2,444 Sq Ft

    645 Wilson St, Waterbury, CT 06708

    Spoil yourself in this gorgeously remodeled 2-family home with all the bells and whistles for the main floor! Main floor is currently owner-occupied and has a remodeled kitchen with quartz countertops, stainless steel appliances, and breakfast bar island. Remodeled full bath with tile floor and tile surround shower. Living room and 2 bedrooms with hardwood floors. Paver patio, Gazebo and private

    John Donato Jr Showcase Realty, Inc.

    645 Wilson St, Waterbury, CT 06708
  • /18

    $325,000

    • 8 Beds
    • 3 Baths
    • 2,880 Sq Ft

    64 South St, Waterbury, CT 06706

    Waterbury three family with value add potential. Currently fully occupied with MTM tenants. Windows have been replaced in last five years. Separate, tenant paid utilities. First floor is oil and 2nd and 3rd floors are electric, but gas line is connected to property already for stoves, so conversion would be easy.

    Mike Sangapore KW Legacy Partners

    64 South St, Waterbury, CT 06706
  • /35

    $449,900

    • 6 Beds
    • 3 Baths
    • 3,582 Sq Ft

    230 Hill St, Waterbury, CT 06704

    Exceptional multi-family property, long term owner say its time to sell, this property offers versatility, and a prime location, convenient location close to shopping, dining, public transportation, major highways, whether you're an investor expanding your portfolio or looking to offset your mortgage with rental income, this property delivers flexibility and opportunity, a flexible front room in

    Donald Fitzgerald, Jr. Showcase Realty, Inc.

    230 Hill St, Waterbury, CT 06704
  • /29

    $449,900

    • 5 Beds
    • 2 Baths
    • 2,526 Sq Ft

    23 Ward St, Naugatuck, CT 06770

    A Home with Room for Everyone - and Every Dream - For years, this warm and welcoming 2-family home has been lovingly cared for by its owner. Now, it's ready for a new chapter-yours. Step onto the inviting first floor, where three sun-filled bedrooms and a spacious eat-in kitchen set the stage for family breakfasts, holiday dinners, and late-night conversations. The remodeled bathroom sparkles,

    Rebecca Zandvliet Coldwell Banker Realty 2000

    23 Ward St, Naugatuck, CT 06770
  • /23

    $425,000

    • 5 Beds
    • 4 Baths
    • 3,156 Sq Ft

    460 Congress Ave, Waterbury, CT 06708

    Central air on the 2nd floor accents this huge owner-occupied 2-family with over 3,000 square feet of above-grade living space, hardwood floors! Amenities include gas heat, 2nd floor family room with cathedral ceiling and fireplace and in-unit laundry, full basement with full bath, rec room, summer kitchen and laundry area.

    Margaret Shea William Raveis Real Estate

    460 Congress Ave, Waterbury, CT 06708
  • /27

    $400,000

    • 6 Beds
    • 4 Baths
    • 3,705 Sq Ft

    17 Congress Ave, Waterbury, CT 06708

    Back on the market - previous buyer was unable to secure financing. Great Cash Flowing Potential!Versatile Mixed-Use Property with Residential & Commercial Income Potential. A rare investment opportunity! This well-maintained mixed-use building features two spacious residential units, 3 bedrooms eac,h and one flexible commercial space, ideal for a variety of business types, including a

    Sadiki Thames Weichert Realtors MRG

    17 Congress Ave, Waterbury, CT 06708
  • /20

    $540,000

    • 9 Beds
    • 3 Baths
    • 3,753 Sq Ft

    83 Vernon St, Waterbury, CT 06708

    Located in the highly desirable Town Plot neighborhood, this updated 3-family property is a prime investment opportunity. Each of the three spacious units offers 3 bedrooms, 1 full bathroom, and a well-appointed eat-in kitchen featuring hardwood floors that flow seamlessly into a cozy living area-perfect for comfortable everyday living. Updated in 2022, all units provide washer and dryer on

    Antoinette Fortuna Coldwell Banker Realty

    83 Vernon St, Waterbury, CT 06708
  • /29

    $2,750,000

    • 9 Beds
    • 3 Baths
    • 7,728 Sq Ft

    701 S Main St, Waterbury, CT 06706

    Truly TURN KEY portfolio opportunity with 8% CAP in the South End almost entirely renovated inside and out! The sale consists of 3 adjacent parcels with 6 buildings = 23 apartments and 2 commercial spaces for a total of 25 units. The unit mix is: (6) 4 bed units, (11) 3 bed units and (6) 2 bed units. 5 Bldgs feature separate, and tenant paid utilities - all electric H, HW & cooking. Bldg 701 has

    Amanda Sheehan Oxford Realty

    701 S Main St, Waterbury, CT 06706
  • /29

    $1,399,900

    • 1 Bed
    • 1 Bath
    • 10,276 Sq Ft

    365 Willow St, Waterbury, CT 06710

    SEMI-RENOVATION PROJECT AVAILABLE! Don't miss this opportunity to buy a 20 unit property with renovations underway. Located in upper Willow neighborhood. The unit mix consists of all studio/1 bed units. The roof is like new and vinyl siding is in good condition, plus there are replacement windows throughout. The building interior is halfway to completion. Many of the units have new cabinets,

    Amanda Sheehan Oxford Realty

    365 Willow St, Waterbury, CT 06710
  • /31

    $399,000

    • 5 Beds
    • 3 Baths
    • 3,705 Sq Ft

    21 Poplar St, Waterbury, CT 06708

    Investors Take Notice of this Income Producing Three Family Home in Waterbury that is Fully Rented. The First and Seconds Floor Units have Two Bedrooms with an Extra Room in Each Unit that can Possible be used as a Third Bedroom. Schedule Your Showing and Submit Your Offer ASAP Before This Multi-Family Property is Gone!!! Generating $4,100 in Rental Income Each Month!!!

    Joe Koontz eXp Realty

    21 Poplar St, Waterbury, CT 06708
  • /15

    $339,900

    • 4 Beds
    • 2 Baths
    • 1,448 Sq Ft

    400 Washington Ave, Waterbury, CT 06708

    Well-maintained two-family home with private parking! This property offers great flexibility with 2 bedrooms on each floor, and separate heating systems - natural gas on the 1st floor and electric on the 2nd. The basement has potential to be finished as in-law apartment, providing additional living space or rental income. Why rent when you can own and have a tenant help pay your mortgage? Enjoy

    Rosa Toledo Toledo Realty

    400 Washington Ave, Waterbury, CT 06708
  • /23

    $460,000

    • 6 Beds
    • 3 Baths
    • 4,187 Sq Ft

    51 Crown St, Waterbury, CT 06704

    Multi-family 3 unit house for sale in the inner city of Waterbury. First floor includes 2 bedroom with a additional room, full bathroom. Second floor and third floor include 2 bedrooms, one full bathroom. Full unfinished basement includes washer dryer hook up and two additional rooms. No leases, tenants are month to month. Property sold as is.

    Joanna Escobar Century 21 Scala Group

    51 Crown St, Waterbury, CT 06704
  • /21

    $295,000

    • 4 Beds
    • 2 Baths
    • 2,184 Sq Ft

    71 Fleming St, Waterbury, CT 06710

    Welcome to 71 Fleming Street, Waterbury - This property presents a fantastic opportunity for investors seeking value-add potential or buyers looking to live in one unit while renovating and renting the other. While the home needs cosmetic and mechanical updates throughout, the solid structure and recent roofing work provide a strong foundation for your investment. Perfect for contractors, handy

    Levi Judqin Brass Moon Realty

    71 Fleming St, Waterbury, CT 06710
  • /26

    $460,000

    • 6 Beds
    • 3 Baths
    • 3,393 Sq Ft

    163 Draher St, Waterbury, CT 06708

    3 family home offers 5 rooms 2brs each floor .. open front and rear porches.. walkup attic.. above ground basement.. off street parking with fenced yard in rear.. Fully Rented. Also great additional storage space with walk up attic & basement. (Both potential for additional units) Come & take a look at the opportunity that awaits those who are seeking tap into a fully rented 3 family home!

    James Jordan Berkshire Hathaway NE Prop.

    163 Draher St, Waterbury, CT 06708
  • /16

    $269,900

    • 4 Beds
    • 2 Baths
    • 1,264 Sq Ft

    Unlisted Address

    Discover this two-family property offering a great opportunity for owner-occupants or investors. Each unit occupies its own floor, with both featuring two bedrooms, hardwood floors, ceiling fans, and abundant natural light throughout. The second-floor unit includes access to a finished attic, providing extra space for a home office, playroom, or additional storage. Conveniently located near I-84

    Jessica Chavez Turning Point Realty, LLC

    Unlisted Address
  • /40

    $449,900

    • 6 Beds
    • 3.5 Baths
    • 3,510 Sq Ft

    124 Geddes Terrace, Waterbury, CT 06708

    Back On Market!!! Location, Location, Location! Attention all investors nows yours chance to own this one of a kind Town Plot Trophy Piece! Nestled in the heart of Town Plot on a dead end road, this oversized fully renovated two-family home is the investment property opportunity or multi-generational living solution you've been waiting for! Perfectly situated on a very private corner lot, this

    Patrick Capobianco Dave Jones Realty, LLC

    124 Geddes Terrace, Waterbury, CT 06708
  • /40

    $647,100

    • 7 Beds
    • 2 Baths
    • 3,030 Sq Ft

    122 Oak St, Naugatuck, CT 06770

    Highly unusual and desirable! A real compound consisting of a single family home and a separate 2 family home. Big bonus is large detached 3 car garage and huge amount of off street parking for other vehicles or storage! Both buildings have been thoroughly remodeled and are move in ready. Location at the end of a cul de sac means privacy! Each unit has beautiful flooring and new bathrooms and

    Mayer Behrend Mary Helen Levine Real Estate LLC

    122 Oak St, Naugatuck, CT 06770
  • /13

    $340,000

    • 6 Beds
    • 3 Baths
    • 2,985 Sq Ft

    578 Columbia Boulevard Extension, Waterbury, CT 06704

    Investor opportunity! Don't miss this spacious multi-family property ideally situated on a large corner lot, offering an abundance of yard space perfect for outdoor enjoyment and family gatherings. Conveniently located just minutes from Route 8, this home is a commuter's dream with easy access to major roadways. Residents will also enjoy proximity to a variety of plazas featuring diverse dining

    Jonathan Gineo Silver and Oak Realty

    578 Columbia Boulevard Extension, Waterbury, CT 06704
  • /37

    $920,000

    • 1 Bed
    • 1 Bath
    • 10,401 Sq Ft

    63 Cherry St, Waterbury, CT 06702

    Investors take notice of this package offering 2 adjacent properties with cash flow and big unit mix with a 9% CAP! TOTAL OF 9 UNITS = 8 apartments + 1 large commercial space. 57 Cherry St is a 2-family with two 2 bed/1 bath units - fully occupied. The property has separate & tenant paid utilities. 63 Cherry is a large mixed-use building with six 3 bed/1 bath apartments + 1 large commercial space

    Amanda Sheehan Oxford Realty

    63 Cherry St, Waterbury, CT 06702
  • /36

    $554,900

    • 9 Beds
    • 4 Baths
    • 3,440 Sq Ft

    48 & 50 Anderson St, Naugatuck, CT 06770

    ATTENTION INVESTORS why own only 1 when you can own 2...Yes that's right 2 homes on 1 lot - 48 Anderson is a single-family 7 rms, 3 BR's, 1 full bath. Basement garage, side patio accessible from 1st floor and full walkup attic. 50 Anderson is a 3-family with separate electric including owners service, gas hot water heaters and gas-fired heating. Properties well maintained with multiple

    Hank Witkoski Witkoski Associates, LLC.

    48 & 50 Anderson St, Naugatuck, CT 06770
  • /37

    $470,000

    • 7 Beds
    • 3 Baths
    • 2,650 Sq Ft

    50 Beacon St, Waterbury, CT 06704

    Behold anyone looking for a multi family for investment purposes or owner occupied. The space in the units are more than accommodating 1st floor three bedrooms loyal long term tenant features large eat in kitchen & pantry, large living room with jack & Jill bathroom, 1st floor rent is below market value. Second floor unit at fair market value two bedrooms, spacious eat in kitchen, dining room,

    Angel Torres Century 21 Scala Group

    50 Beacon St, Waterbury, CT 06704
  • /3

    $352,000

    • 6 Beds
    • 2 Baths
    • 1,714 Sq Ft

    238 Bishop St, Waterbury, CT 06704

    Investors take notice. Three units fully occupied. Two units are 3 bedroom apartments. There are open and enclosed porches. One car garage under. All tenants are month to month.

    Sharon Sirois Showcase Realty, Inc.

    238 Bishop St, Waterbury, CT 06704
  • /2

    $352,000

    • 4 Beds
    • 2 Baths
    • 1,815 Sq Ft

    32 Ridge St, Waterbury, CT 06706

    Investment potential Some electrical updates 2018. Some window and door replacements in 2017. Roof 2012. Remodel 2010.

    Sharon Sirois Showcase Realty, Inc.

    32 Ridge St, Waterbury, CT 06706
  • /8

    $849,000

    • 10 Beds
    • 5 Baths
    • 4,800 Sq Ft

    227 Hillside Ave, Waterbury, CT 06710

    Prime 6-Family Investment Property - 227 Hillside Ave, Waterbury, CT A fantastic opportunity for investors! This fully renovated 6-family property features all 2-bedroom units, each updated for modern living and designed for long-term tenant retention. Located in a convenient and accessible area of Waterbury, this turn-key asset offers strong rental potential and minimal maintenance demands.

    Alban Dedvukaj Lakeshore Realty

    227 Hillside Ave, Waterbury, CT 06710
  • /8

    $499,000

    • 6 Beds
    • 4 Baths
    • 2,418 Sq Ft

    34 Katie Ln, Waterbury, CT 06708

    Great Duplex Style Home featuring 5 room, 3 bedroom, 1.5 bath units, Eat-In Kitchen, Living Room on each side with 1 Car Garage, Raised Panes thoughout and both Units are nicely kept. Close to Schools, Parks, Restaurants with easy commute to 8 & 84.

    Maria Vilar Weichert REALTORS Briotti Group

    34 Katie Ln, Waterbury, CT 06708
  • /7

    $449,000

    • 5 Beds
    • 2 Baths
    • 1,828 Sq Ft

    198 Maple St, Naugatuck, CT 06770

    A Perfect Owner-Occupant Opportunity! Welcome to this well-maintained two-family home, ideal for both investors and owner-occupants. The current owner resides on the first floor, while the second-floor unit is already rented-providing immediate rental income. Whether you're looking to offset your mortgage or expand your investment portfolio, this property is a smart choice. Enjoy the comfort of

    Ramazan Trepca Century 21 Scala Group

    198 Maple St, Naugatuck, CT 06770
  • /3

    $399,900

    • 9 Beds
    • 3 Baths
    • 3,496 Sq Ft

    33 Mitchell Ave, Waterbury, CT 06710

    Welcome to 33 Mitchell Avenue, a well-maintained multi-family property located in the heart of Waterbury. This charming residence offers the perfect blend of classic New England architecture and modern upgrades, making it an exceptional opportunity for both investors and owner-occupants. This spacious multi-family home features 3 units, each offering 2 bedrooms and 1 baths per unit, and generous

    George Noujaim Dave Jones Realty, LLC

    33 Mitchell Ave, Waterbury, CT 06710
  • /4

    $549,000

    • 12 Beds
    • 6 Baths
    • 4,860 Sq Ft

    861 Baldwin St, Waterbury, CT 06706

    Explore this fully occupied 6 family opportunity for under $600,000! Lease-up to achieve a return on investment of 35%. Featuring all two bedroom units and separate utilities, this apartment building is a great addition to your portfolio. Inquire today!

    Connor Wenchell VC Property Group, LLC

    861 Baldwin St, Waterbury, CT 06706
  • /14

    $730,000

    • 10 Beds
    • 5 Baths
    • 5,244 Sq Ft

    49 Hill St, Waterbury, CT 06704

    Prime Investment Opportunity--Fully Renovated Multi-Family + Commercial Unit. Unlock the potential of this turnkey mixed-use property, perfect for investors or owner-occupants looking for strong rental income. Situated on a spacious lot, this unique offering features two fully renovated buildings, maximizing both residential and commercial revenues streams. Property Highlights: * Multi-Family +

    Angel Mora eXp Realty

    49 Hill St, Waterbury, CT 06704

Why Live in Middlebury

Middlebury, Connecticut, is a picturesque New England town located in New Haven County, known for its scenic beauty and tight-knit community. With a population of 7,500, Middlebury offers a blend of rural charm and urban accessibility, being a short drive from New Haven. The town is surrounded by lush forests, state parks, rolling hills, and lakes, with nearly 2,000 acres of conserved land, making it a haven for outdoor activities. Residents enjoy local attractions such as Meadowview Park, Quassapaug Lake, and the Middlebury Greenway, as well as nearby state forests like Naugatuck, Mattatuck, and Paugussett, which offer extensive trails and recreational opportunities. Middlebury's educational system is highly regarded, with Pomperaug Regional School District No. 15 and Westover School providing top-notch education. The town's largest employers include Timex Group, Quassy Amusement Park, Waterbury Hospital, and Danbury Hospital. Middlebury maintains a low crime rate compared to the national average, contributing to its appeal for families and retirees. The housing market features classic New England homes, historic colonials, Cape Cods, and lakeside retreats, with properties often including antique barns and garden areas. Local businesses thrive in Middlebury, with popular spots like Willie’s Wood Smoked BBQ, The Local Gourmet, Vyne Restaurant, and Pies & Pub. The town's biggest entertainment draw is Quassy Amusement Park, one of the nation's oldest amusement parks. Middlebury is well-connected via Interstates 8 and 84, State Routes 63 and 64, and is close to Tweed New Haven Airport and Windsor Locks International Airport. Despite recent development proposals, the community remains committed to preserving its small-town charm.

Home Trends in Middlebury, CT

Housing Trends

Median Sale Price
$555,000
Median Single Family Sale Price
$555,000
Median Townhouse Sale Price
$556,230
Median 2 Bedroom Sale Price
$629,250
Average Price Per Sq Ft
$270
Number of Homes for Sale
25
Last 12 months Home Sales
119
Months of Supply
2.50
Median List Price
$599,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
1%
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