20,156

Middletown, DE Homes

Section Image Section Image
  • 414 Goodwick Dr, Middletown, DE 19709
    414 Goodwick Dr, Middletown, DE 19709
    414 Goodwick Dr, Middletown, DE 19709
    /30

    $425,000 Sold Oct 24, 2025

    414 Goodwick Dr, Middletown, DE 19709

    • 3 Beds
    • 4 Baths
    • 2,024 Sq Ft
    • Built 2017

    Last Sold Summary

    • $210/SF
    • 9 Days On Market

    Current Estimated Value $421,906

    Last Listing Agent Marla Schechter Patterson-Schwartz-Middletown

    414 Goodwick Dr, Middletown, DE 19709
    • 101 Dawn Ct, Middletown, DE 19709
      101 Dawn Ct, Middletown, DE 19709
      101 Dawn Ct, Middletown, DE 19709
      /33

      Est $419,911 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,650 Sq Ft

      101 Dawn Ct, Middletown, DE 19709

      101 Dawn Ct, Middletown, DE 19709
  • 304 Daylilly Way, Middletown, DE 19709
    304 Daylilly Way, Middletown, DE 19709
    304 Daylilly Way, Middletown, DE 19709
    /20

    $420,000

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft

    304 Daylilly Way, Middletown, DE 19709

    Excellent opportunity to own in the desirable 55+ community of Springmill. Well maintained, first floor living with everything you need. 2 spacious bedrooms, 2 full baths, a beautiful kitchen and dining space, and a spacious 2-car garage. The back porch area is perfect for garden enthusiasts or a nice, relaxing area to entertain guests. This freshly painted home is completely move in ready. Just

    Justin Ashkenase Patterson-Schwartz-Hockessin

    304 Daylilly Way, Middletown, DE 19709
  • 102 Crystal Run Dr, Middletown, DE 19709
    102 Crystal Run Dr, Middletown, DE 19709
    102 Crystal Run Dr, Middletown, DE 19709
    /34

    $395,000 Sold Nov 17, 2025

    102 Crystal Run Dr, Middletown, DE 19709

    • 5 Beds
    • 3.5 Baths
    • 3,175 Sq Ft
    • Built 1988

    Last Sold Summary

    • $124/SF
    • 23 Days On Market

    Current Estimated Value $405,481

    Last Listing Agent Carol Quattrociocchi EXP Realty, LLC

    102 Crystal Run Dr, Middletown, DE 19709
    • 6 Springmill Dr, Middletown, DE 19709
      6 Springmill Dr, Middletown, DE 19709
      6 Springmill Dr, Middletown, DE 19709
      /50

      Est $465,846 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft

      6 Springmill Dr, Middletown, DE 19709

      6 Springmill Dr, Middletown, DE 19709
  • 241 Porky Oliver Dr, Middletown, DE 19709
    241 Porky Oliver Dr, Middletown, DE 19709
    241 Porky Oliver Dr, Middletown, DE 19709
    /54

    $572,000

    • 4 Beds
    • 2.5 Baths
    • 2,650 Sq Ft

    241 Porky Oliver Dr, Middletown, DE 19709

    Below market value & PRICED TO SELL!!!!! This meticulously maintained home reflects true pride of ownership, both inside and out. Thoughtfully priced and offering exceptional value, this home is ideally situated in the prestigious community of The Legends in Middletown, enjoying convenient access to shopping, dining, and everyday amenities while offering a peaceful, scenic setting overlooking the

    Theresa Russo Patterson-Schwartz-Middletown

    241 Porky Oliver Dr, Middletown, DE 19709
  • 2605 Alexander Calder Ct, Middletown, DE 19709
    2605 Alexander Calder Ct, Middletown, DE 19709
    2605 Alexander Calder Ct, Middletown, DE 19709
    /69

    $740,000 Sold Jun 18, 2025

    2605 Alexander Calder Ct, Middletown, DE 19709

    • 4 Beds
    • 5 Baths
    • 3,575 Sq Ft
    • Built 2018

    Last Sold Summary

    • $207/SF
    • 36 Days On Market

    Current Estimated Value $740,811

    Last Listing Agent Sean Ussery Century 21 Gold Key Realty

    2605 Alexander Calder Ct, Middletown, DE 19709
    • 12 Springmill Dr, Middletown, DE 19709
      12 Springmill Dr, Middletown, DE 19709
      12 Springmill Dr, Middletown, DE 19709
      /29

      Est $428,840 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,875 Sq Ft

      12 Springmill Dr, Middletown, DE 19709

      12 Springmill Dr, Middletown, DE 19709
  • Lot 157 Baldy, Middletown, DE 19709

    $639,999 New Construction

    • 2 Beds
    • 2 Baths
    • 2,053 Sq Ft

    Lot 157 Baldy, Middletown, DE 19709

    This stunning home offers exceptional style and comfort with thoughtfully designed upgrades throughout. Enjoy a bright and airy sunroom, a vaulted ceiling great room with a cozy fireplace, and a gourmet kitchen featuring granite countertops, stainless steel appliances, a gas cooktop, and beautiful dcor finishes. The home also includes a second-floor full bath and numerous flooring and design

    Benchmark Builders Builder
    Lot 157 Baldy, Middletown, DE 19709
  • 246 Anglesey Dr, Middletown, DE 19709
    246 Anglesey Dr, Middletown, DE 19709
    246 Anglesey Dr, Middletown, DE 19709
    /38

    $610,000 Sold Apr 29, 2025

    246 Anglesey Dr, Middletown, DE 19709

    • 3 Beds
    • 3 Baths
    • 3,275 Sq Ft
    • Built 2020

    Last Sold Summary

    • $186/SF
    • 2 Days On Market

    Current Estimated Value $618,565

    Last Listing Agent Zach Wolfe Long & Foster Real Estate, Inc.

    246 Anglesey Dr, Middletown, DE 19709
    • 11 Barnsdale Dr, Middletown, DE 19709
      11 Barnsdale Dr, Middletown, DE 19709
      11 Barnsdale Dr, Middletown, DE 19709
      /90

      Est $953,386 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 6,075 Sq Ft

      11 Barnsdale Dr, Middletown, DE 19709

      11 Barnsdale Dr, Middletown, DE 19709
  • 1222 Carrick Ct, Middletown, DE 19709
    1222 Carrick Ct, Middletown, DE 19709
    1222 Carrick Ct, Middletown, DE 19709
    /26

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,975 Sq Ft

    1222 Carrick Ct, Middletown, DE 19709

    Welcome to this well-maintained 3-bedroom townhome in the popular High Hook Farms community in Middletown. The beautiful eat-in kitchen features granite countertops, stainless steel appliances, and a dedicated pantry for added storage. Just off the dining area, a low-maintenance composite deck provides the perfect space for entertaining or relaxing outdoors. The kitchen opens to a spacious living

    William Sladek Redfin Corporation

    1222 Carrick Ct, Middletown, DE 19709
  • 2507 Saint Giles Dr, Middletown, DE 19709
    2507 Saint Giles Dr, Middletown, DE 19709
    2507 Saint Giles Dr, Middletown, DE 19709
    /27

    $306,900 Sold Mar 21, 2025

    2507 Saint Giles Dr, Middletown, DE 19709

    • 5 Beds
    • 3 Baths
    • 2,056 Sq Ft
    • Built 2025

    Last Sold Summary

    • $149/SF
    • 6 Days On Market

    Last Listing Agent David Vasso Atlantic Five Realty

    2507 Saint Giles Dr, Middletown, DE 19709
    • 147 Betsy Rawls Dr, Middletown, DE 19709
      147 Betsy Rawls Dr, Middletown, DE 19709
      147 Betsy Rawls Dr, Middletown, DE 19709
      /32

      Est $640,794 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,975 Sq Ft

      147 Betsy Rawls Dr, Middletown, DE 19709

      147 Betsy Rawls Dr, Middletown, DE 19709
  • 2307 Winchelsea Pkwy, Middletown, DE 19709
    2307 Winchelsea Pkwy, Middletown, DE 19709
    2307 Winchelsea Pkwy, Middletown, DE 19709
    /22

    $489,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,443 Sq Ft

    2307 Winchelsea Pkwy, Middletown, DE 19709

    This new two-story townhome is designed to promote low-maintenance living with a sophisticated twist. On the first floor is everything you need day-to-day, featuring a private owner’s suite, a convenient study and an open-concept layout shared among the kitchen, dining room and spacious family room. The top floor presents a loft and two versatile bedrooms to customize as homeowners see fit.

    Lennar Builder
    2307 Winchelsea Pkwy, Middletown, DE 19709
  • 3110 Pett Level Dr, Middletown, DE 19709
    3110 Pett Level Dr, Middletown, DE 19709
    3110 Pett Level Dr, Middletown, DE 19709
    /22

    $457,000 Sold Dec 24, 2025

    3110 Pett Level Dr, Middletown, DE 19709

    • 3 Beds
    • 2 Baths
    • 2,443 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $187/SF
    • 53 Days On Market

    Lennar Venue at Winchelsea 55+ - Winchelsea Towns

    3110 Pett Level Dr, Middletown, DE 19709
    • 15 Palmer Dr, Middletown, DE 19709
      15 Palmer Dr, Middletown, DE 19709
      15 Palmer Dr, Middletown, DE 19709
      /56

      Est $698,612 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 4,425 Sq Ft

      15 Palmer Dr, Middletown, DE 19709

      15 Palmer Dr, Middletown, DE 19709
  • 1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709
    1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709
    1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709
    /19

    $416,000 Open Sun 11AM - 4:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709

    BASE PRICE LISTING - MODEL HOME IS NOT FOR SALE. Welcome to a stylish and spacious 3-storytownhome that offers 1 or 2 garages, square footage ranging from 2,001-2,333 & contemporary living at its finest. With 3 bedrooms, 2.5 baths, and a finished den on the first level with rough in plumbing for a future bathroom, this home is designed to provide both comfort and versatility. As you step

    Lindsay Shaffer RE/MAX Elite

    1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709
  • 512 Lilac Dr, Middletown, DE 19709
    512 Lilac Dr, Middletown, DE 19709
    512 Lilac Dr, Middletown, DE 19709
    /50

    $675,000 Sold May 29, 2025

    512 Lilac Dr, Middletown, DE 19709

    • 4 Beds
    • 4 Baths
    • 4,225 Sq Ft
    • Built 2000

    Last Sold Summary

    • $160/SF
    • 3 Days On Market

    Current Estimated Value $695,374

    Last Listing Agent Stephanie Marvel Keller Williams Real Estate - West Chester

    512 Lilac Dr, Middletown, DE 19709
    • 28 Palmer Dr, Middletown, DE 19709
      28 Palmer Dr, Middletown, DE 19709
      28 Palmer Dr, Middletown, DE 19709
      /41

      Est $623,079 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,650 Sq Ft

      28 Palmer Dr, Middletown, DE 19709

      28 Palmer Dr, Middletown, DE 19709
  • 114 Austrian Pine Ct, Middletown, DE 19709
    114 Austrian Pine Ct, Middletown, DE 19709
    114 Austrian Pine Ct, Middletown, DE 19709
    /20

    $720,000 Coming Soon

    • 4 Beds
    • 4 Baths
    • 2,595 Sq Ft

    114 Austrian Pine Ct, Middletown, DE 19709

    *** Coming Soon: More pics and info coming soon *** Looking for that perfect place to call home? Look no further! Not only is this gorgeous home on a quiet cul-de-sac in the peaceful yet conveniently located luxury 55+ active adult community of Four Seasons at Baymont Farms but it is also practically new at less than 2 years old. The home, itself, offers a true one level living and boasts an open

    Sandra Lamprecht Coldwell Banker Realty

    114 Austrian Pine Ct, Middletown, DE 19709
  • 120 Emily Way, Middletown, DE 19709
    120 Emily Way, Middletown, DE 19709
    120 Emily Way, Middletown, DE 19709
    /22

    Sold Aug 15, 2025

    120 Emily Way, Middletown, DE 19709

    • 4 Beds
    • 3.5 Baths
    • 2,178 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • 4 Days On Market

    Current Estimated Value $369,500

    Ryan Homes Crossings at Silver Lake - Townhomes

    120 Emily Way, Middletown, DE 19709
    • 39 Watson Ln, Middletown, DE 19709
      39 Watson Ln, Middletown, DE 19709
      39 Watson Ln, Middletown, DE 19709
      /30

      Est $615,581 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,475 Sq Ft

      39 Watson Ln, Middletown, DE 19709

      39 Watson Ln, Middletown, DE 19709
  • 503 Tarbet Ct Unit PHIL GRAND LOT 31, Middletown, DE 19709
    503 Tarbet Ct Unit PHIL GRAND LOT 31, Middletown, DE 19709
    503 Tarbet Ct Unit PHIL GRAND LOT 31, Middletown, DE 19709
    /67

    $1,196,340 Pending

    • 4 Beds
    • 3.5 Baths
    • 4,400 Sq Ft

    503 Tarbet Ct Unit PHIL GRAND LOT 31, Middletown, DE 19709

    Welcome to Highlands at Back Creek- a small community of only 42 lots. All homesites are a minimum of 3/4 acre to a FULL ACRE. Are you tired of massive developments with no sense of community? This is the place for you. ;) Check out some of the standard features- 9' first and second-floor ceilings, crown molding in the living room, dining room, foyer, and second-floor hallway. Shaw hardwood

    Elizabeth Page-Kramer EXP Realty, LLC

    503 Tarbet Ct Unit PHIL GRAND LOT 31, Middletown, DE 19709
  • 1169 S Olmsted Pkwy, Middletown, DE 19709
    1169 S Olmsted Pkwy, Middletown, DE 19709
    1169 S Olmsted Pkwy, Middletown, DE 19709
    /76

    $570,000 Sold Jan 16, 2026

    1169 S Olmsted Pkwy, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 2,975 Sq Ft
    • Built 2019

    Last Sold Summary

    • $192/SF
    • 41 Days On Market

    Last Listing Agent Dustin Oldfather Compass

    1169 S Olmsted Pkwy, Middletown, DE 19709
    • 787 Idlewyld Dr, Middletown, DE 19709
      787 Idlewyld Dr, Middletown, DE 19709
      787 Idlewyld Dr, Middletown, DE 19709
      /65

      Est $671,875 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,900 Sq Ft

      787 Idlewyld Dr, Middletown, DE 19709

      787 Idlewyld Dr, Middletown, DE 19709
  • 204 Baldy Ln Unit BRISTOLE, Middletown, DE 19709
    204 Baldy Ln Unit BRISTOLE, Middletown, DE 19709
    204 Baldy Ln Unit BRISTOLE, Middletown, DE 19709
    /39

    $548,500 Open Sun 11AM - 5PM

    • 3 Beds
    • 2 Baths
    • 2,441 Sq Ft

    204 Baldy Ln Unit BRISTOLE, Middletown, DE 19709

    The Bristol Model is a thoughtfully designed 3-bedroom home that is TO BE BUILT in the highly sought-after 55+ community of Traditions at Whitehall. This home features an open floor plan with a spacious dining area, kitchen, great room, and perfect for modern living and entertaining. The large Owner’s Suite offers two walk-in closets, an en-suite bath with a double vanity, and a luxurious 5-foot

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit BRISTOLE, Middletown, DE 19709
  • 1248 Lorewood Grove Rd, Middletown, DE 19709
    1248 Lorewood Grove Rd, Middletown, DE 19709
    1248 Lorewood Grove Rd, Middletown, DE 19709
    /40

    $400,000 Sold Mar 21, 2025

    1248 Lorewood Grove Rd, Middletown, DE 19709

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1970

    Last Sold Summary

    • $167/SF
    • 39 Days On Market

    Current Estimated Value $401,998

    Last Listing Agent Raymond Petkevis Real Broker LLC

    1248 Lorewood Grove Rd, Middletown, DE 19709
    • 805 Sweet Birch Dr, Middletown, DE 19709
      805 Sweet Birch Dr, Middletown, DE 19709
      805 Sweet Birch Dr, Middletown, DE 19709
      /57

      Est $941,457 Not Listed For Sale

      • 6 Beds
      • 5.5 Baths
      • 5,775 Sq Ft

      805 Sweet Birch Dr, Middletown, DE 19709

      805 Sweet Birch Dr, Middletown, DE 19709
  • 1487 Bunker Hill Rd, Middletown, DE 19709
    1487 Bunker Hill Rd, Middletown, DE 19709
    1487 Bunker Hill Rd, Middletown, DE 19709
    /33

    $705,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,498 Sq Ft

    1487 Bunker Hill Rd, Middletown, DE 19709

    Build Your Dream Home in Middletown with Schaeffer Homes! Home is to be built. Photos and virtual tours show the same base model with optional upgrades. Discover our most quintessential rancher with the Weatherby! This generously-sized home starts at 2,498 square feet of living space. The Weatherby includes 3 bedrooms, 2 1⁄2 bathrooms, 2-car garage, as well as a study! With one of our most

    Eddie Barksdale Barksdale & Affiliates Realty

    1487 Bunker Hill Rd, Middletown, DE 19709
  • 342 Wilmore Dr, Middletown, DE 19709
    342 Wilmore Dr, Middletown, DE 19709
    342 Wilmore Dr, Middletown, DE 19709
    /32

    $350,000 Sold Nov 21, 2025

    342 Wilmore Dr, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 1,750 Sq Ft
    • Built 2009

    Last Sold Summary

    • $200/SF
    • 7 Days On Market

    Last Listing Agent Kristina Rice Real Broker LLC

    342 Wilmore Dr, Middletown, DE 19709
    • 803 Sweet Birch Dr, Middletown, DE 19709
      803 Sweet Birch Dr, Middletown, DE 19709
      803 Sweet Birch Dr, Middletown, DE 19709
      /66

      Est $949,459 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 5,600 Sq Ft

      803 Sweet Birch Dr, Middletown, DE 19709

      803 Sweet Birch Dr, Middletown, DE 19709
  • 224 W Old Squaw Rd, Middletown, DE 19709
    224 W Old Squaw Rd, Middletown, DE 19709
    224 W Old Squaw Rd, Middletown, DE 19709
    /43

    $449,900

    • 4 Beds
    • 3.5 Baths
    • 3,075 Sq Ft

    224 W Old Squaw Rd, Middletown, DE 19709

    Welcome to 224 W. Old Squaw; this charming two-story colonial home sits proudly on a .56 acre lot, backing to scenic marshland and a tributary leading to the Appoquinimink River. Nestled in a quiet, low-traffic neighborhood with stunning aerial views of winding waterways and abundant wildlife, this home delivers the best of Delaware living: privacy, space, and proximity to Middletown's growing

    Travis L. Dorman RE/MAX Elite

    224 W Old Squaw Rd, Middletown, DE 19709
  • 314 Tranquility Way, Middletown, DE 19709
    314 Tranquility Way, Middletown, DE 19709
    314 Tranquility Way, Middletown, DE 19709
    /56

    $500,000 Sold Aug 08, 2025

    314 Tranquility Way, Middletown, DE 19709

    • 3 Beds
    • 3 Baths
    • 2,175 Sq Ft
    • Built 2021

    Last Sold Summary

    • $230/SF
    • 14 Days On Market

    Current Estimated Value $506,773

    Last Listing Agent Jeff Hecker Monument Sotheby's International Realty

    314 Tranquility Way, Middletown, DE 19709
    • 518 Spring Hollow Dr, Middletown, DE 19709
      518 Spring Hollow Dr, Middletown, DE 19709
      518 Spring Hollow Dr, Middletown, DE 19709
      /74

      Est $805,362 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,500 Sq Ft

      518 Spring Hollow Dr, Middletown, DE 19709

      518 Spring Hollow Dr, Middletown, DE 19709
  • 377 Northhampton Way, Middletown, DE 19709
    377 Northhampton Way, Middletown, DE 19709
    377 Northhampton Way, Middletown, DE 19709
    /80

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 3,175 Sq Ft

    377 Northhampton Way, Middletown, DE 19709

    Welcome to 377 Northampton Drive—a beautifully renovated, move-in-ready home in Willow Grove Mill, perfectly positioned in the heart of Middletown where everyday convenience truly shines. Enjoy being minutes from shopping, grocery stores, restaurants, schools, and major commuter routes—close to everything, yet tucked into an established neighborhood setting. From the moment you step inside, the

    Megan Aitken Keller Williams Realty

    377 Northhampton Way, Middletown, DE 19709
  • 604 Hamilton Place Unit A604, Middletown, DE 19709
    604 Hamilton Place Unit A604, Middletown, DE 19709
    604 Hamilton Place Unit A604, Middletown, DE 19709
    /43

    $55,000 Sold Oct 31, 2025

    604 Hamilton Place Unit A604, Middletown, DE 19709

    • 3 Beds
    • 2 Baths
    • Built 2008

    Last Sold Summary

    • 10 Days On Market

    Last Listing Agent Jennifer Lindell Century 21 Gold Key Realty

    604 Hamilton Place Unit A604, Middletown, DE 19709
    • 538 Spring Hollow Dr, Middletown, DE 19709
      538 Spring Hollow Dr, Middletown, DE 19709
      538 Spring Hollow Dr, Middletown, DE 19709
      /55

      Est $678,321 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,400 Sq Ft

      538 Spring Hollow Dr, Middletown, DE 19709

      538 Spring Hollow Dr, Middletown, DE 19709
  • 303 Braemar St, Middletown, DE 19709
    303 Braemar St, Middletown, DE 19709
    303 Braemar St, Middletown, DE 19709
    /71

    $689,900 Open Sun 1PM - 3PM

    • 6 Beds
    • 3.5 Baths
    • 3,716 Sq Ft

    303 Braemar St, Middletown, DE 19709

    Beautiful 6 bedroom, 3 1/2 bathroom colonial offering a covered front porch, 2 car garage, partially finished basement and a backyard paradise. The main floor offers a guest/in-law suite with full bathroom, formal living room/office, dining room, family room with gas fireplace featuring exquisite word working including ship lap and coffered ceiling, Kitchen with center island, granite counter

    David Watlington Patterson-Schwartz-Middletown

    303 Braemar St, Middletown, DE 19709
  • 46 N New Rd, Middletown, DE 19709
    46 N New Rd, Middletown, DE 19709
    46 N New Rd, Middletown, DE 19709
    /14

    $232,500 Sold Aug 28, 2025

    46 N New Rd, Middletown, DE 19709

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1900

    Last Sold Summary

    • $232/SF
    • 200 Days On Market

    Current Estimated Value $216,683

    Last Listing Agent Kevin Hensley RE/MAX Eagle Realty

    46 N New Rd, Middletown, DE 19709

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