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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
  • /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
  • /38

    $335,000

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft

    117 Golden Hill St, Naugatuck, CT 06770

    Charming Two-Family Owner-Occupied Home with Spacious Yard and Prime Location! This well-maintained two-family residence features two comfortable bedrooms on each floor, perfect for owners and tenants alike. Each unit offers a full bathroom and many rooms showcase beautiful, well-preserved hardwood floors, adding warmth and character throughout. Enjoy a spacious yard with a previously established

    Elijah Boles Better Living Realty, LLC

    117 Golden Hill St, Naugatuck, CT 06770
  • /17

    $235,000

    • 3 Beds
    • 2.5 Baths
    • 2,104 Sq Ft

    Unlisted Address

    Welcome to this fantastic opportunity for a seasoned investors. Each unit offers 2 bedrooms, 1 full bath, an eat-in kitchen, and a bright living area. The property overlooks Fulton park lake. It needs extensive work

    Levi Judqin Brass Moon Realty

    Unlisted Address
  • /17

    $360,000

    • 8 Beds
    • 3 Baths
    • 3,175 Sq Ft

    70 Elmwood Ave, Waterbury, CT 06710

    Charming Two- Family Home- Airbnb- Ready. Welcome to this versatile and centrally located two- family property, perfect for both investment and personal use. The first floor unit has been successfully operated as an Airbnb comes fully furnished, offering a turnkey opportunity for short- term rental income. It features of welcoming layout, ideal for guest, seeking comfort and convenience. The

    Shari Jones Coldwell Banker Realty

    70 Elmwood Ave, Waterbury, CT 06710
  • /35

    $419,900

    • 7 Beds
    • 3 Baths
    • 2,496 Sq Ft

    383 Davis St, Oakville, CT 06779

    Spacious 3-Family in the Heart of Watertown! This large multi-family property features two generous 2-bedroom, 1-bath units on the first and second floors, with a 1-bedroom, 1-bath unit on the third floor with potential to add another bedroom. Perfect for both owner-occupants and savvy investors, the home sits on a sizable lot offering plenty of yard space for outdoor enjoyment. With solar panels

    Nicholas Burrus Santana Realty Group LLC

    383 Davis St, Oakville, CT 06779
  • /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

    $419,000

    • 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

    $379,000

    • 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 Open Sat 12PM - 3PM

    • 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

    $470,000

    • 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

    $285,000

    • 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

    $350,000

    • 7 Beds
    • 4 Baths
    • 3,958 Sq Ft

    61 Holmes Ave, Waterbury, CT 06710

    Don't miss this value add investment opportunity at 61 Holmes Avenue. This partially completed 4-unit office-to-residential conversion is ideally located near downtown, highways, and public transportation. The approved layout features two 1-bedroom units, one 2-bedroom, and one 3-bedroom-offering excellent rental income potential. Major upgrades are already well underway, including new HVAC,

    Richard Santana Santana Realty Group LLC

    61 Holmes Ave, Waterbury, CT 06710
  • /40

    $647,900

    • 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
  • /26

    $459,000

    • 8 Beds
    • 3 Baths
    • 2,822 Sq Ft

    69 W Liberty St, Waterbury, CT 06706

    3 Family with all New Pressure treated - Front and Rear Outside Staircases & Decks to all 3 Floors, 3/3/2 Bedrooms, All Floors Rented but on a Month to Month Basis, All Floors can be Higher

    Paul Roger Full Service Realty LLC

    69 W Liberty St, Waterbury, CT 06706
  • /33

    $389,000

    • 4 Beds
    • 2 Baths
    • 2,217 Sq Ft

    33 Aetna St, Naugatuck, CT 06770

    Fantastic Opportunity for Owner-Occupants or Investors! This well-maintained 2-family home has been owned by the same owner for over 35 years and offers both guaranteed income and long-term value. Each unit features two spacious bedrooms and one full bath, with oversized living and dining areas, gleaming hardwood floors, and fully equipped kitchens. Newer mechanicals, separate utilities, and

    Michael Bachmann Houlihan Lawrence WD

    33 Aetna 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
  • /19

    $350,000

    • 4 Beds
    • 2 Baths
    • 1,904 Sq Ft

    56 Vine St, Waterbury, CT 06704

    Welcome to 56 Vine Street, this thoughtfully updated two-family home. This well-maintained property features a total of four bedrooms and two full bathrooms, with each unit offering two spacious bedrooms and one recently renovated bathroom. Both units have been updated with modern kitchens, fresh paint, and new flooring, giving the home a clean, contemporary feel. Whether you're an investor

    Rob Squeglia Sky Realty Group

    56 Vine St, 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
  • /11

    $385,000

    • 5 Beds
    • 3 Baths
    • 2,010 Sq Ft

    54 Morningside Ave, Waterbury, CT 06708

    BUNKER HILL 2 FAMILY TOTALLY RENOVATED IN 2017- 1ST FLOOR APT HAS 4 ROOMS, 2 BEDROOMS, 1 BATH & A GAS HOT WATER BOILER FOR HEAT- 2ND & 3RD FLOOR APT HAS 6 ROOMS, 3 BEDROOMS, 2 FULL BATHS & ELECTRIC HEAT- NEW ROOF IN 2017- NEWER ELECTRIC SERVICE- 1 CAR DET GARAGE- PLENTY OF OFF STREET PARKING

    Michael Vitale Vitale Realty

    54 Morningside Ave, Waterbury, CT 06708
  • /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
  • /7

    $850,000

    • 15 Beds
    • 9 Baths
    • 7,440 Sq Ft

    915 S Main St, Waterbury, CT 06706

    Investors take note! Fantastic investment opportunity at 915 South Main St. in the heart of Waterbury! This multi-family property features 9 units with strong rental income potential. There are three 3 bedroom units, two 1 bedrooms, and 4 studio units. Unfinished basement. Plenty off-street parking is available at the rear of the property. Conveniently located near shopping, schools, public

    Levi Judqin Brass Moon Realty

    915 S Main St, Waterbury, CT 06706
  • /40

    $499,900

    • 3 Beds
    • 1 Bath
    • 2,704 Sq Ft

    151 Highland Ave, Waterbury, CT 06708

    OPPORTUNITY AWAITS YOU. Be your own boss in this owner occupied MIXED USE-RETAIL-APARTMENT building C/A ZONED! Home of an established Deli & Convenience store for approx. 22 years! Seller is asking an additional $150,000 for business and equipment. Many upgrades and improvements completed over the years. Business and Building MUST be sold as a PACKAGE ONLY! Beautiful 6 room, 3 bedroom apartment

    Judith Caputo Advantage Realty Group, Inc.

    151 Highland Ave, Waterbury, CT 06708
  • /19

    $299,900

    • 4 Beds
    • 2 Baths
    • 1,689 Sq Ft

    40 N Beacon St, Waterbury, CT 06704

    Overlook section! Updated two-family home features many updates incl. newer roof, vinyl siding, most windows, bathrooms and kitchens! Attached garage, gas heat, and hardwood floors.One 2 bedroom apartment on first floor and one, 1 bedroom or possibly two bedroom apartment on 2nd floor? Investor or owner occupied! Corner lot, patio, and 90 min from NYC! Won't last.

    James Kane Showcase Realty, Inc.

    40 N Beacon St, Waterbury, CT 06704
  • /28

    $449,000

    • 6 Beds
    • 3 Baths
    • 3,106 Sq Ft

    33 Lounsbury St, Naugatuck, CT 06770

    Investors and owner occupants take notice! This 3 family home sits on quiet section of Naugatuck with plenty of off-street/garage parking and close proximity to shopping, hospitals, and highways. Centrally located to RT34, RT8, Merritt Pky, and I-95, makes this perfect for the weekend or daily traveler. Located on a cul-de-sac, this 3-family home is a fantastic opportunity for all. The front

    Antonino Mogavero Carey & Guarrera Real Estate

    33 Lounsbury St, Naugatuck, CT 06770
  • /12

    $314,900

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    215 Lincoln St, Waterbury, CT 06710

    Great 2 family for sale. Separate utilities, 2 car garage. property is fully occupied with excellent tenants. 2nd floor expands into a partially finished 3rd floor.

    Ronny Modiano Amity Realty Group, LLC

    215 Lincoln St, Waterbury, CT 06710
  • /30

    $420,000

    • 7 Beds
    • 3 Baths
    • 3,485 Sq Ft

    50 Chestnut Ave, Waterbury, CT 06710

    Spacious 3-Family Home with Expansion Potential!. Beautiful and well-kept multi-family home featuring three apartments, private parking, and a great patio. The large basemant offer future potential for added living space. Perfect for investors or owner-occupants--this property offers strong rental income and excellent appreciation potential.

    Angel Mora eXp Realty

    50 Chestnut Ave, Waterbury, CT 06710
  • /14

    $369,000

    • 4 Beds
    • 4 Baths
    • 2,288 Sq Ft

    48 High St, Naugatuck, CT 06770

    Fantastic income-producing opportunity! This 4-unit multifamily property features a large parking lot with ample space for all tenants, a rare and valuable amenity. Three of the units are currently rented at below-market rents, offering immediate upside potential for investors. The fourth unit is a gutted studio apartment, ready for renovation - a perfect chance to add value and boost rental

    Albano Costa Keller Williams Realty

    48 High St, Naugatuck, CT 06770
  • /39

    $675,000

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    671 Rubber Ave, Naugatuck, CT 06770

    Wonderful opportunity to own this multipurpose property in the heart of Naugatuck's business district. A well established gift and garden center with 3 income producing residential rental units. Business includes four greenhouses which have been a lovely oasis for flowers, garden supplies and gifts, plus an income generating propane pumping station. Apartments include one 2 bedroom and two studio

    Joseph Conforti BHGRE Gaetano Marra Homes

    671 Rubber Ave, Naugatuck, CT 06770
  • /33

    $451,900

    • 4 Beds
    • 2 Baths
    • 2,116 Sq Ft

    468 Perkins Ave, Waterbury, CT 06704

    Impressive two family on more than a half acre, perched at the end of a private paved driveway! Completely redone with upscale stainless appliances, granite counters, beautiful flooring, luxury bathrooms, walk in closets. Fresh and new throughout! A bonus is a full floored attic which could be convenient for a studio or storage. Additionally, the newer roof and just painted exterior complete the

    Mayer Behrend Mary Helen Levine Real Estate LLC

    468 Perkins Ave, Waterbury, CT 06704

Why Live in Middlebury

Middlebury, a small town in New Haven County, Connecticut, offers a blend of rural charm and urban accessibility. With a population of 7,500, it is known for its scenic beauty, high-ranking Pomperaug Regional School District No. 15, and the prestigious Westover School. The town is surrounded by lush forests, state parks, and lakes, with nearly 2,000 acres of conserved land, making it a haven for outdoor enthusiasts. Middlebury's most popular outdoor spots include Quassapaug Lake, Meadowview Park, and the Middlebury Greenway, a 7-mile paved trail. Nearby state forests such as Naugatuck, Mattatuck, and Paugussett offer extensive opportunities for hiking, fishing, and camping. The town maintains a tight-knit community with locally owned businesses and hosts events like "Celebrate Middlebury" at Shepardson Community Center. Dining options include Willie’s Wood Smoked BBQ, The Local Gourmet, and Vyne Restaurant. Middlebury's largest employers are Timex Group, Quassy Amusement Park, Waterbury Hospital, and Danbury Hospital. The town is safer than the national average, with low violent crime rates. Middlebury is accessible via Interstates 8 and 84, with Tweed New Haven Airport 30 miles away. The housing market features classic New England homes, historic colonials, and lakeside retreats. Middlebury Green, the historic center, is home to antique colonials, churches, and community amenities. Despite its small size, Middlebury offers a rich blend of attractions and a strong sense of community, making it an appealing place for families and retirees alike.

Home Trends in Middlebury, CT

Housing Trends

Median Sale Price
$477,014
Median Single Family Sale Price
$469,900
Median Townhouse Sale Price
$446,895
Median 2 Bedroom Sale Price
$524,950
Median 1 Bedroom Sale Price
$235,000
Average Price Per Sq Ft
$246
Number of Homes for Sale
4
Last 12 months Home Sales
54
Months of Supply
0.90
Median List Price
$469,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
19%
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