Middletown, NY Homes

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  /28

  $489,999 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  20 Tammy Dr, Middletown, NY 10941

  LOCATION,LOCATION,LOCATION CLOSE TO WALMARTTHE METRO NORTH TRAIN STATION TO NYC, Abundance of Dining and Grocery options, The Galleria Mall, Garnet Medical Center, Major Highways Route 17M & Interstate I84, Home has 3 bedrooms and 2.5 bathrooms, Stainless Steel Appliances, Granite counter top with a breakfast nook., Hardwood Floor, En-suite bathroom in master bedroom, Large deck on upper level

  Sol Perry BHG Real Estate Green Team

  20 Tammy Dr, Middletown, NY 10941
• 

  

  

  /22

  $3,000 Per Month

  • 2 Beds
  • 4 Baths
  • 2,161 Sq Ft
  • Townhouse for Rent

  105 Woodlake Dr, Middletown, NY 10940

  Move-In Ready Townhome | Spring Hollow | Pool, Tennis & More Don't miss this stunning, well-maintained townhome in the sought-after Spring Hollow community!The bright living room features hardwood floors, large windows, a gas fireplace, and designer light fixtures. The open eat-in kitchen offers granite countertops, stainless steel appliances, a center island, breakfast nook, pantry, and

  Maxwell Zhong Panorama Realty

  105 Woodlake Dr, Middletown, NY 10940
• 

  $317,000 Sold Aug 08, 2025

  553 Route 17m, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 1,225 Sq Ft
  • Built 1920

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 98 Days On Market

  Current Estimated Value $291,505

  Last Listing Agent Derek Greene Greene Realty Group

  553 Route 17m, Middletown, NY 10940
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  Not Listed For Sale

  4 Beyers Rd, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,323 Sq Ft
  • Built 2024

  4 Beyers Rd, Middletown, NY 10941

  Last Sold Summary

  • $278/SF
  • 72 Days On Market

  • Last Sold Price $645,000
  • Feb 03, 2025

  Last Listing Agent Chris Ogden Realty Promotions Inc
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  /40

  $474,999 Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,055 Sq Ft

  12 Weather Vane Way, Middletown, NY 10940

  Nestled in the Rolling Meadows residential community in the Middletown School District, this 3-bedroom, 2.5-bathroom raised ranch bilevel home seamlessly blends absolute convenience with comfortable community living. The location is truly key, positioned just off East Main Street for incredibly quick access to major highways like Interstate 84 and Route 17, placing you less than 10 minutes from

  Ray Reyes Keller Williams Realty

  12 Weather Vane Way, Middletown, NY 10940
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  /7

  $2,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,142 Sq Ft
  • Apartment for Rent

  206 Golf Links Rd Unit 821, Middletown, NY 10940

  This new 2 bedroom 2 bath apartment features a modern and stylish design, with high quality finishes and attention to detail throughout. The living room is adorned with a large window that allows plenty of natural light to illuminate the space, creating an inviting and airy atmosphere. The kitchen is equipped with stainless steel appliances, sleek quartz countertops, ample cabinet storage, and a

  Victoria Fini Curasi Realty, Inc.

  206 Golf Links Rd Unit 821, Middletown, NY 10940
• 

  $455,000 Sold Apr 12, 2026

  145 Academy Ave, Middletown, NY 10940

  • 4 Beds
  • 2 Baths
  • 2,545 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $179/SF
  • 41 Days On Market

  Current Estimated Value $437,909

  Last Listing Agent Sandra Arnez Keller Williams Hudson Valley

  145 Academy Ave, Middletown, NY 10940
• 

  Est $294,938 Not Listed For Sale

  7-11 Crawford Place, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 1,188 Sq Ft
  • Built 1949

  7-11 Crawford Place, Middletown, NY 10940

  Last Sold Summary

  • 8% Above List Price
  • $231/SF
  • 93 Days On Market

  • Last Sold Price $274,000
  • Feb 07, 2025

  Last Listing Agent Pedro Garcia Curasi Realty, Inc.
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  /2

  $475,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  153 Ridgewood Ave Unit 155, Middletown, NY 10940

  Welcome to 153 Ridgewood, a stunning 2022 built ranch style home that delivers the kind of single level living buyers dream about. From the moment you step inside, the vaulted ceilings, open concept layout, modern finishes, and natural flow of the home create an immediate “this is the one” feeling. With over 1,500 square feet of beautifully designed space, this home offers the rare combination of

  Isaiah Lopez Keller Williams Hudson Valley

  153 Ridgewood Ave Unit 155, Middletown, NY 10940
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  /16

  $2,350 Per Month

  • 3 Beds
  • 1 Bath
  • 1,158 Sq Ft
  • Apartment for Rent

  118 W Main St Unit 1, Middletown, NY 10940

  Gorgeous renovated first floor unit with 3 bedrooms and 1 bathroom in the heart of Middletown! Enjoy hardwood floors, washer and dryer in unit, dishwasher, and a private back porch. This bright and spacious apartment is move in ready and has everything you need! Tons of counter space and storage in the kitchen, newer appliances, and a newly redone bathroom. Close to public transportation, food,

  Victoria Wander Divine Realty NY, LLC

  118 W Main St Unit 1, Middletown, NY 10940
• 

  $335,000 Sold Sep 30, 2025

  317 Wawayanda Ave, Middletown, NY 10940

  • 4 Beds
  • 1 Bath
  • 1,124 Sq Ft
  • Built 1950

  Last Sold Summary

  • 3% Above List Price
  • $298/SF
  • 89 Days On Market

  Current Estimated Value $336,272

  Last Listing Agent Pete Wolven Hudson Valley Home Connection

  317 Wawayanda Ave, Middletown, NY 10940
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  Not Listed For Sale

  25 Fairways Dr Unit 2, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 2006

  25 Fairways Dr Unit 2, Middletown, NY 10940

  Last Sold Summary

  • $316/SF
  • 20 Days On Market

  • Last Sold Price $400,000
  • Oct 29, 2024

  Last Listing Agent Susanne Dermigny Howard Hanna Rand Realty
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  /41

  $449,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  239 Millsburg Rd, Middletown, NY 10940

  Set on a quiet country road in the Town of Greenville, 239 Millsburg Road offers a setting that feels removed from the noise of everyday life, yet remains highly practical for commuting and daily needs. This well-maintained log cabin is surrounded by natural beauty, and as the seasons change and the trees fill in, the property becomes a true private retreat. Mornings can begin on the rocking

  Frank Muccari Cronin & Company Real Estate

  239 Millsburg Rd, Middletown, NY 10940
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  /10

  $3,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,340 Sq Ft
  • House for Rent

  52 Horton Ave, Middletown, NY 10940

  This home is ideal for large or growing families seeking space, comfort, and convenience. The inviting layout features three generously sized bedrooms and two full bathrooms, along with a bright and open living area that creates a warm and comfortable atmosphere for everyday living. Designed with both functionality and flexibility in mind, the home easily accommodates a variety of family needs.

  Jin Pang Panorama Realty

  52 Horton Ave, Middletown, NY 10940
• 

  $407,500 Sold May 04, 2026

  29 Beacon St, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,886 Sq Ft
  • Built 1910

  Last Sold Summary

  • 4% Below List Price
  • $216/SF
  • 32 Days On Market

  Current Estimated Value $395,451

  Last Listing Agent Jessica Evans Keller Williams Hudson Valley

  29 Beacon St, Middletown, NY 10940
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  Est $508,544 Not Listed For Sale

  105 Jasmine Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft
  • Built 2010

  105 Jasmine Dr, Middletown, NY 10940

  Last Sold Summary

  • 6% Above List Price
  • $326/SF
  • 28 Days On Market

  • Last Sold Price $480,000
  • Aug 31, 2023

  Last Listing Agent Michelle Genatempo Howard Hanna Rand Realty
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  /35

  $499,900

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft

  19 Sunflower St, Middletown, NY 10940

  Welcome to easy, carefree living in the highly sought-after 55+ community of Wildflower at Wallkill. This beautifully maintained two-bedroom ranch offers the perfect blend of comfort, style, and convenience, all set within a vibrant, amenity-rich neighborhood. This home has been meticulously cared for, including fresh paint and new carpeting, ensuring a move-in-ready experience. Step inside to

  Patricia Sassi RE/MAX Benchmark Realty Group

  19 Sunflower St, Middletown, NY 10940
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  /15

  $2,300 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,241 Sq Ft
  • Townhouse for Rent

  25 Kensington Way, Middletown, NY 10940

  Beautiful lakefront condo with assigned parking and a stunning water-view backyard. This bright and spacious home features 2 bedrooms and 2.5 bathrooms, soaring cathedral ceilings, and a large eat-in kitchen. The sun-filled living room offers abundant natural light through sliding glass doors that lead to a private backyard patio — the perfect place to relax and enjoy the peaceful lake views.

  Yosseline Genao Keller Williams Hudson Valley

  25 Kensington Way, Middletown, NY 10940
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  $550,000 Sold Apr 18, 2026

  34 Feiertag Rd, Middletown, NY 10941

  • 3 Beds
  • 3 Baths
  • 3,021 Sq Ft
  • Built 2000

  Last Sold Summary

  • 15% Below List Price
  • $182/SF
  • 210 Days On Market

  Current Estimated Value $621,167

  Last Listing Agent Julianna Cotthaus 1st Independent Realty Grp

  34 Feiertag Rd, Middletown, NY 10941
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  Est $485,516 Not Listed For Sale

  107 Jasmine Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft
  • Built 2010

  107 Jasmine Dr, Middletown, NY 10940

  Last Sold Summary

  • 4% Above List Price
  • $316/SF
  • 197 Days On Market

  • Last Sold Price $465,000
  • Apr 16, 2024

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group
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  /24

  $499,900

  • 1 Bed
  • 1.5 Baths
  • 1,428 Sq Ft

  6 Bart Bull Rd, Middletown, NY 10941

  Step into a rare piece of local history with this stunning former schoolhouse, beautifully set in the Town of Wallkill. Rich in character and architectural charm, this one-of-a-kind property offers an abundance of natural light that highlights the craftsmanship of a bygone era. The open interior provides exceptional flexibility - perfect for a unique residence, artist's retreat, studio space, or

  Rebecca Matta-Candela Keller Williams Realty

  6 Bart Bull Rd, Middletown, NY 10941
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  /38

  $4,000 Per Month

  • 5 Beds
  • 2.5 Baths
  • 2,188 Sq Ft
  • House for Rent

  20 Scott Dr, Middletown, NY 10941

  Spacious 5-Bedroom Home for Rent Welcome to 20 Scott Dr, a rare rental opportunity in the heart of Middletown! This spacious 5-bedroom, 2 1/2-baths whole house rental offers a versatile layout perfect for those needing extra space. Inside, you’ll find: An open concept kitchens – ideal for large gatherings for added convenience. 5 generously sized bedrooms providing plenty of room for everyone. 2

  Kevin Grier Keller Williams Hudson Valley

  20 Scott Dr, Middletown, NY 10941
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  $371,000 Sold Aug 19, 2025

  16 Robertson Dr, Middletown, NY 10940

  • 2 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • Built 1955

  Last Sold Summary

  • 24% Above List Price
  • $264/SF
  • 19 Days On Market

  Current Estimated Value $374,449

  Last Listing Agent Virginia Corbett eXp Realty

  16 Robertson Dr, Middletown, NY 10940
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  Est $830,884 Not Listed For Sale

  172 Stony Ford Rd, Middletown, NY 10941

  • 4 Beds
  • 4 Baths
  • 4,538 Sq Ft
  • Built 1903

  172 Stony Ford Rd, Middletown, NY 10941

  Last Sold Summary

  • 57% Above List Price
  • $117/SF
  • 95 Days On Market

  • Last Sold Price $530,000
  • May 31, 2024

  Last Listing Agent Frank Cafarchio Keller Williams Realty
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  /47

  $465,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft

  122 Rolling Meadows Rd, Middletown, NY 10940

  Welcome to your dream home in the heart of Middletown, NY! This beautifully maintained 4 bedroom, 2 bathroom home with a bonus room/home office offers the perfect blend of comfort, convenience, and lifestyle. Nestled in a quiet neighborhood, this spacious property is ideal for today’s modern living with flexible space for working from home, entertaining guests, or simply relaxing in style. The

  Kristine Many Keller Williams Realty

  122 Rolling Meadows Rd, Middletown, NY 10940
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  /9

  $1,650 Per Month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  2 E Main St Unit 4, Middletown, NY 10940

  This beautiful third-level apartment offers a perfect blend of modern updates and classic charm. Located on the third and fourth levels of a downtown building, this one-bedroom, one-bath unit is sure to impress. Enjoy the warmth and elegance of hardwood floors throughout the living room and bedroom. Large windows flood the space with natural light, creating a bright and welcoming atmosphere. The

  Nancy LaBarbera Keller Williams Hudson Valley

  2 E Main St Unit 4, Middletown, NY 10940
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  $318,000 Sold Dec 12, 2025

  22 Bonnell St, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 1,374 Sq Ft
  • Built 1890

  Last Sold Summary

  • 14% Above List Price
  • $231/SF
  • 65 Days On Market

  Current Estimated Value $319,541

  Last Listing Agent Emmett McDowell Keller Williams Rlty Integrity

  22 Bonnell St, Middletown, NY 10940
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  Est $414,147 Not Listed For Sale

  14 W Jackson Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,818 Sq Ft
  • Built 1930

  14 W Jackson Ave, Middletown, NY 10940

  Last Sold Summary

  • 12% Above List Price
  • $204/SF
  • 17 Days On Market

  • Last Sold Price $370,000
  • Dec 20, 2023

  Last Listing Agent Thomas Smith Cronin & Company Real Estate
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  /41

  $440,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,848 Sq Ft

  4 Thistle Ln, Middletown, NY 10940

  Spacious & Versatile Raised Ranch in Prime Middletown Location! Not your average bi-level! This move-in-ready, raised-ranch-style home in Middletown, within the Minisink Valley School District, offers the perfect blend of convenience and comfort. Located near Garnet Medical Center, Crystal Run, shopping centers, supermarkets, and with easy access to Metro-North and major highways, it’s an ideal

  Soleil Jackman Howard Hanna Rand Realty

  4 Thistle Ln, Middletown, NY 10940
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  /28

  $1,900 Per Month

  • 1 Bed
  • 1 Bath
  • 770 Sq Ft
  • Apartment for Rent

  23 W Main St Unit 1, Middletown, NY 10940

  Beautifully renovated one bedroom unit in historic building in downtown City of Middletown. Extra high ceilings and large windows make this spacious unit feel even larger. Trendy loft feel with some original elements are a total vibe. The open floor plan is welcoming and will be an oasis at the end of a long day. Not sure if your furniture will fit? Check out the included floor plan! Municipal

  Hilary Ryan Goldman Howard Hanna Rand Realty

  23 W Main St Unit 1, Middletown, NY 10940
• 

  $463,750 Sold Jun 06, 2025

  42 Prince St, Middletown, NY 10940

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $266/SF
  • 163 Days On Market

  Current Estimated Value $460,625

  Last Listing Agent Jean DiMatteo DiMatteo Realty LLC

  42 Prince St, Middletown, NY 10940
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  Not Listed For Sale

  540 County Route 49, Middletown, NY 10940

  • 12 Beds
  • 3 Baths
  • 4,924 Sq Ft
  • Built 1986

  540 County Route 49, Middletown, NY 10940

  Last Sold Summary

  • $157/SF
  • 89 Days On Market

  • Last Sold Price $775,000
  • May 15, 2024

  Last Listing Agent John McCarey John I McCarey
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  /29

  $499,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft

  599 Guymard Turnpike, Middletown, NY 10940

  TIMELESS ELEGANCE - MODERN COMFORT - EFFORTLESS LIVINGNestled within the highly regarded Minisink Valley Central School District, this exquisitely updated vintage residence masterfully blends historic charm with refined contemporary living. THOUGHTFULLY RENOVATED, this home offers warmth, sophistication, and effortless functionality. The heart of the home is the stunning kitchen, featuring

  Mary Ann Mitchell eXp Realty

  599 Guymard Turnpike, Middletown, NY 10940
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  /15

  $2,200 Per Month

  • 3 Beds
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  126 W Main St Unit 2, Middletown, NY 10940

  MIDDLETOWN now offers this BEAUTIFUL 3 bedroom/1 bath apartment to rent! This newly remodeled unit is completely updated and ready to be called home. Enter into a living room followed by an eat-in kitchen with brand new stainless steel appliances, granite counters, & backsplash. 3 bedrooms and a gorgeous new tiled full bath with a tub, new lighting and accessories. For your convenience, laundry

  Sandra Arnez Keller Williams Hudson Valley

  126 W Main St Unit 2, Middletown, NY 10940
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  $319,000 Sold Nov 26, 2025

  82 Houston Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,124 Sq Ft
  • Built 1929

  Last Sold Summary

  • $284/SF
  • 26 Days On Market

  Current Estimated Value $320,160

  Last Listing Agent Wendy Beck Krumpfer Realty Group, LLC

  82 Houston Ave, Middletown, NY 10940
• 

  Est $555,056 Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 2,091 Sq Ft
  • Built 2009

  Unlisted Address

  Last Sold Summary

  • 4% Above List Price
  • $256/SF
  • 68 Days On Market

  • Last Sold Price $535,000
  • Dec 16, 2024

  Last Listing Agent Marilyn D'Andrea Integrity Real Estate, Inc.
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  /39

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  133 Blumel Rd, Middletown, NY 10941

  A Lot of House for the $$! This well maintained 3 BR, 2 Bath home is set back on lovely 1acre grounds with private back yard! Open floor plan! HW floors! C/A. 1 Car attached garage and detached 1 car garage with electric! Gutters have leaf guards! There's a whole house fan and power attic fan! Convenient to shopping and train station!

  Linda Clark Hudson Valley Griffith

  133 Blumel Rd, Middletown, NY 10941
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  /26

  $2,800 Per Month

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • House for Rent

  202 Midland Lake Rd, Middletown, NY 10941

  This Middletown home is close to everything but will feel like a private oasis. Included in this listing is the main house with large renovated eat-in-kitchen, full bathroom on the 1st floor, dining and living rooms, 1st floor bedroom, and bright sun porch. Large rooms with lots of windows for maximum natural light. Upstairs has additional bedrooms and bathroom. Full walk-up attic is great

  Hilary Ryan Goldman Howard Hanna Rand Realty

  202 Midland Lake Rd, Middletown, NY 10941
• 

  $345,000 Sold Jan 09, 2026

  1 Chancery Mews, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,604 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $215/SF
  • 64 Days On Market

  Current Estimated Value $343,757

  Last Listing Agent Sean Walker Keller Williams Realty

  1 Chancery Mews, Middletown, NY 10940
• 

  Est $497,963 Not Listed For Sale

  338 van Duzer Rd, Middletown, NY 10940

  • 4 Beds
  • 3.5 Baths
  • 2,758 Sq Ft
  • Built 1801

  338 van Duzer Rd, Middletown, NY 10940

  Last Sold Summary

  • 53% Above List Price
  • $118/SF
  • 62 Days On Market

  • Last Sold Price $325,000
  • Dec 04, 2023

  Last Listing Agent Nicholas Cuomo Keller Williams Realty

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