20,298

Middletown, DE Homes

Section Image Section Image
    • 2804 Armoury Ln, Middletown, DE 19709
      2804 Armoury Ln, Middletown, DE 19709
      2804 Armoury Ln, Middletown, DE 19709
      /40

      Est $574,782

      Not Listed For Sale

      2804 Armoury Ln, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 2,389 Sq Ft
      • Built 2025
      2804 Armoury Ln, Middletown, DE 19709

      Last Sold Summary

      • 14 Days On Market

  • 460 Rederick Ln, Middletown, DE 19709
    460 Rederick Ln, Middletown, DE 19709
    /2

    $384,900

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

    460 Rederick Ln, Middletown, DE 19709

    Workforce Housing Unit Only. Follow link for more details:

    Benchmark Builders Builder
    460 Rederick Ln, Middletown, DE 19709
  • 3108 Pett Level Dr, Middletown, DE 19709
    3108 Pett Level Dr, Middletown, DE 19709
    3108 Pett Level Dr, Middletown, DE 19709
    /22

    $350,900

    Sold Feb 11, 2026

    3108 Pett Level Dr, Middletown, DE 19709

    • 5 Beds
    • 2 Baths
    • 2,669 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $131/SF
    • 102 Days On Market

    Current Estimated Value $521,070

    Lennar Venue at Winchelsea 55+ - Winchelsea Towns

    3108 Pett Level Dr, Middletown, DE 19709
    • 507 Maple Ave Unit 507, Middletown, DE 19709
      507 Maple Ave Unit 507, Middletown, DE 19709
      507 Maple Ave Unit 507, Middletown, DE 19709
      /13

      Not Listed For Sale

      507 Maple Ave Unit 507, Middletown, DE 19709

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 2003
      507 Maple Ave Unit 507, Middletown, DE 19709

      Last Sold Summary

      • 21 Days On Market

  • 206 Northern Oak St Unit 36495347, Middletown, DE 19709
    206 Northern Oak St Unit 36495347, Middletown, DE 19709
    206 Northern Oak St Unit 36495347, Middletown, DE 19709
    /22

    $499,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,780 Sq Ft

    Eastwood Plan at Four Seasons at Baymont Farms, Middletown, DE 19709

    Elegant foyer entry welcoming friends and family. Generous ceiling height for maximum natural light and openness. Open, single-story home design boasting dream kitchen with island. Spacious great room with optional fireplace creating relaxing atmosphere. Secluded owner's suite with oversized closet and private bath.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 36495347, Middletown, DE 19709
  • 222 E Crail Ct, Middletown, DE 19709
    222 E Crail Ct, Middletown, DE 19709
    222 E Crail Ct, Middletown, DE 19709
    /107

    $735,000

    Sold Dec 30, 2025

    222 E Crail Ct, Middletown, DE 19709

    • 4 Beds
    • 4.5 Baths
    • 4,700 Sq Ft
    • Built 2010

    Last Sold Summary

    • $156/SF
    • 11 Days On Market

    Current Estimated Value $756,044

    Last Listing Agent S Walton Simpson Walt Simpson Realty

    222 E Crail Ct, Middletown, DE 19709
    • 1702 Lord Tennyson Place, Middletown, DE 19709
      1702 Lord Tennyson Place, Middletown, DE 19709
      1702 Lord Tennyson Place, Middletown, DE 19709
      /43

      Est $614,700

      Not Listed For Sale

      1702 Lord Tennyson Place, Middletown, DE 19709

      • 4 Beds
      • 2.5 Baths
      • 2,504 Sq Ft
      • Built 2023
      1702 Lord Tennyson Place, Middletown, DE 19709

      Last Sold Summary

      • 8 Days On Market

  • 1621 Schwinn St, Middletown, DE 19709
    1621 Schwinn St, Middletown, DE 19709
    1621 Schwinn St, Middletown, DE 19709
    /14

    $649,340

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 2,730 Sq Ft

    1621 Schwinn St, Middletown, DE 19709

    Benchmark Builders Builder
    1621 Schwinn St, Middletown, DE 19709
  • 2216 Winchelsea Pkwy, Middletown, DE 19709
    2216 Winchelsea Pkwy, Middletown, DE 19709
    2216 Winchelsea Pkwy, Middletown, DE 19709
    /21

    $549,775

    Sold Mar 16, 2026

    2216 Winchelsea Pkwy, Middletown, DE 19709

    • 3 Beds
    • 2 Baths
    • 2,389 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $230/SF
    • 105 Days On Market

    Current Estimated Value $548,136

    Lennar Venue at Winchelsea 55+ - Winchelsea Singles

    2216 Winchelsea Pkwy, Middletown, DE 19709
    • 131 Goldleaf Dr W, Middletown, DE 19709
      131 Goldleaf Dr W, Middletown, DE 19709
      131 Goldleaf Dr W, Middletown, DE 19709
      /53

      Not Listed For Sale

      131 Goldleaf Dr W, Middletown, DE 19709

      • 4 Beds
      • 3.5 Baths
      • 3,651 Sq Ft
      • Built 2025
      131 Goldleaf Dr W, Middletown, DE 19709

      Last Sold Summary

      • 41 Days On Market

  • 1135 Majesty Ln, Middletown, DE 19709
    1135 Majesty Ln, Middletown, DE 19709
    1135 Majesty Ln, Middletown, DE 19709
    /45

    $789,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    1135 Majesty Ln, Middletown, DE 19709

    To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

    Andrea Harrington Compass

    1135 Majesty Ln, Middletown, DE 19709
  • 54 Meadow Dr, Middletown, DE 19709
    54 Meadow Dr, Middletown, DE 19709
    54 Meadow Dr, Middletown, DE 19709
    /60

    $590,000

    Sold Apr 29, 2026

    54 Meadow Dr, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 2,879 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $205/SF
    • 75 Days On Market

    Current Estimated Value $593,820

    Last Listing Agent Janie Trumbull Patterson-Schwartz-Middletown

    54 Meadow Dr, Middletown, DE 19709
    • 112 Goldleaf Dr W, Middletown, DE 19709
      112 Goldleaf Dr W, Middletown, DE 19709
      112 Goldleaf Dr W, Middletown, DE 19709
      /53

      Not Listed For Sale

      112 Goldleaf Dr W, Middletown, DE 19709

      • 4 Beds
      • 3.5 Baths
      • 3,651 Sq Ft
      • Built 2025
      112 Goldleaf Dr W, Middletown, DE 19709

      Last Sold Summary

      • 9 Days On Market

  • 206 Northern Oak St Unit 36451018, Middletown, DE 19709
    206 Northern Oak St Unit 36451018, Middletown, DE 19709
    206 Northern Oak St Unit 36451018, Middletown, DE 19709
    /19

    $550,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,080 Sq Ft

    Killarney I Plan at Four Seasons at Baymont Farms, Middletown, DE 19709

    Cozy porch welcoming guests to your home. Inviting dining room, ideal for hosting dinner parties. Kitchen with large island and corner pantry. Great room with optional HovHub and wet bar. Owner's suite with private bath and oversized walk-in closet. Three-car tandem garage with additional storage. Opt. loft for additional living with bed and full bath.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 36451018, Middletown, DE 19709
  • 203 Scotish Dr, Middletown, DE 19709
    203 Scotish Dr, Middletown, DE 19709
    203 Scotish Dr, Middletown, DE 19709
    /60

    $675,000

    Sold Dec 19, 2025

    203 Scotish Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 3,425 Sq Ft
    • Built 2005

    Last Sold Summary

    • $197/SF
    • 10 Days On Market

    Current Estimated Value $670,791

    Last Listing Agent Jonathan Unrath Keller Williams Real Estate - Media

    203 Scotish Dr, Middletown, DE 19709
    • 345 E Green St, Middletown, DE 19709
      345 E Green St, Middletown, DE 19709
      345 E Green St, Middletown, DE 19709
      /24

      Not Listed For Sale

      345 E Green St, Middletown, DE 19709

      • 4 Beds
      • 3.5 Baths
      • 2,123 Sq Ft
      • Built 2024
      345 E Green St, Middletown, DE 19709

      Last Sold Summary

      • 88 Days On Market

  • 1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    /26

    $541,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft

    Aberdeen II Plan at Four Seasons at Pennfield, Middletown, DE 19709

    Spacious kitchen with island and ample counterspace.Sunlit great room adjacent to kitchen and dining area.Relaxing primary suite with sitting room and luxurious bath.HovHub makes for a great home office or study space.Expansive covered patio, perfect for dining al fresco.HovHall with closet and access to 2-car garage.

    K. Hovnanian Homes Builder
    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
  • 124 Lakeside Dr, Middletown, DE 19709
    124 Lakeside Dr, Middletown, DE 19709
    124 Lakeside Dr, Middletown, DE 19709
    /40

    $524,900

    Sold Jan 23, 2026

    124 Lakeside Dr, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 1,925 Sq Ft
    • Built 2001

    Last Sold Summary

    • $273/SF
    • 39 Days On Market

    Current Estimated Value $534,773

    Last Listing Agent Amy Hurley Foraker Realty Co.

    124 Lakeside Dr, Middletown, DE 19709
    • 122 Goldleaf Dr E, Middletown, DE 19709
      122 Goldleaf Dr E, Middletown, DE 19709
      122 Goldleaf Dr E, Middletown, DE 19709
      /33

      Not Listed For Sale

      122 Goldleaf Dr E, Middletown, DE 19709

      • 4 Beds
      • 5 Baths
      • 5,032 Sq Ft
      • Built 2025
      122 Goldleaf Dr E, Middletown, DE 19709

      Last Sold Summary

      • 18 Days On Market

  • 903 Johnson Dr, Middletown, DE 19709
    903 Johnson Dr, Middletown, DE 19709
    903 Johnson Dr, Middletown, DE 19709
    /61

    $615,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,388 Sq Ft

    903 Johnson Dr, Middletown, DE 19709

    Welcome to 903 Johnson Drive, a beautifully maintained Colonial-style home located in the highly sought-after Village of Bayberry North. Built in 2016 and offering approximately 3,300 square feet of living space, this 4-bedroom, 2.5-bath home combines spacious living, modern finishes, and an exceptional community lifestyle. A charming covered front porch welcomes you inside, where you'll find a

    Kyle Lounsbury EXP Realty, LLC

    903 Johnson Dr, Middletown, DE 19709
  • 1850 Congressional Village Dr Unit 5302, Middletown, DE 19709
    1850 Congressional Village Dr Unit 5302, Middletown, DE 19709
    1850 Congressional Village Dr Unit 5302, Middletown, DE 19709
    /36

    $265,000

    Sold Apr 10, 2026

    1850 Congressional Village Dr Unit 5302, Middletown, DE 19709

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Built 2006

    Last Sold Summary

    • $262/SF
    • 133 Days On Market

    Last Listing Agent Julie Spagnolo Northrop Realty

    1850 Congressional Village Dr Unit 5302, Middletown, DE 19709
    • 2640 Fairlight Dr, Middletown, DE 19709
      2640 Fairlight Dr, Middletown, DE 19709
      2640 Fairlight Dr, Middletown, DE 19709
      /32

      Est $453,564

      Not Listed For Sale

      2640 Fairlight Dr, Middletown, DE 19709

      • 3 Beds
      • 2 Baths
      • 2,443 Sq Ft
      2640 Fairlight Dr, Middletown, DE 19709

      Last Sold Summary

      • 11 Days On Market

  • 126 Green Forest Dr Unit 36481949, Middletown, DE 19709
    126 Green Forest Dr Unit 36481949, Middletown, DE 19709
    126 Green Forest Dr Unit 36481949, Middletown, DE 19709
    /4

    $669,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,105 Sq Ft

    Jamison Plan at Rothwell Estates, Middletown, DE 19709

    Tours by appointment onlyplease call 302-274-0712 to schedule. Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    126 Green Forest Dr Unit 36481949, Middletown, DE 19709
  • 340 Ellenwood Dr, Middletown, DE 19709
    340 Ellenwood Dr, Middletown, DE 19709
    340 Ellenwood Dr, Middletown, DE 19709
    /41

    $725,000

    Sold Oct 03, 2025

    340 Ellenwood Dr, Middletown, DE 19709

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft
    • Built 2023

    Last Sold Summary

    • $213/SF
    • 110 Days On Market

    Current Estimated Value $749,606

    Last Listing Agent Eric Buck Long & Foster Real Estate, Inc.

    340 Ellenwood Dr, Middletown, DE 19709
    • 2604 Fairlight Dr, Middletown, DE 19709
      2604 Fairlight Dr, Middletown, DE 19709
      2604 Fairlight Dr, Middletown, DE 19709
      /34

      Est $460,757

      Not Listed For Sale

      2604 Fairlight Dr, Middletown, DE 19709

      • 3 Beds
      • 3 Baths
      • 2,142 Sq Ft
      • Built 2025
      2604 Fairlight Dr, Middletown, DE 19709

      Last Sold Summary

      • 46 Days On Market

  • 27 Springmill Dr, Middletown, DE 19709
    27 Springmill Dr, Middletown, DE 19709
    27 Springmill Dr, Middletown, DE 19709
    /24

    $400,000

    $35K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 2,275 Sq Ft

    27 Springmill Dr, Middletown, DE 19709

    Enjoy easy main-level living in this beautifully designed home featuring 2 bedrooms, 2 bathrooms, and a 2-car garage in the sought-after Springmill 55+ resort-style community. The inviting layout offers a living room with a gas fireplace, plus a sitting room and dining room at the front of the home for added flexibility and charm. The spacious kitchen is well-equipped with a center island,

    Michael McKee Long & Foster Real Estate, Inc.

    27 Springmill Dr, Middletown, DE 19709
  • 776 Lorewood Grove Rd, Middletown, DE 19709
    776 Lorewood Grove Rd, Middletown, DE 19709
    776 Lorewood Grove Rd, Middletown, DE 19709
    /17

    $270,000

    Sold Oct 24, 2025

    776 Lorewood Grove Rd, Middletown, DE 19709

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft
    • Built 1960

    Last Sold Summary

    • $193/SF
    • 47 Days On Market

    Current Estimated Value $309,415

    Last Listing Agent Ray Dudkewitz Patterson-Schwartz-Newark

    776 Lorewood Grove Rd, Middletown, DE 19709
    • 2644 Fairlight Dr, Middletown, DE 19709
      2644 Fairlight Dr, Middletown, DE 19709
      2644 Fairlight Dr, Middletown, DE 19709
      /39

      Est $469,339

      Not Listed For Sale

      2644 Fairlight Dr, Middletown, DE 19709

      • 3 Beds
      • 2 Baths
      • 2,443 Sq Ft
      • Built 2025
      2644 Fairlight Dr, Middletown, DE 19709

      Last Sold Summary

      • 8 Days On Market

  • 27 E Minglewood Dr, Middletown, DE 19709
    27 E Minglewood Dr, Middletown, DE 19709
    27 E Minglewood Dr, Middletown, DE 19709
    /58

    $524,900

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 2,300 Sq Ft

    27 E Minglewood Dr, Middletown, DE 19709

    This traditional 4-bedroom, 3.5-bath home in Middletown offers the perfect blend of space, comfort, and convenience. Spacious bedrooms, multiple living areas, and a functional layout make this home ideal for everyday living. Step outside to enjoy the inviting paver patio—perfect for outdoor dining, gatherings, or quiet evenings—and a convenient storage shed for all your tools and seasonal items.

    Kate DiCesare Iron Valley Real Estate at The Beach

    27 E Minglewood Dr, Middletown, DE 19709
  • 462 Rederick Ln Unit MASSEY LOT 60, Middletown, DE 19709
    462 Rederick Ln Unit MASSEY LOT 60, Middletown, DE 19709
    /2

    $424,647

    Sold Jul 15, 2025

    462 Rederick Ln Unit MASSEY LOT 60, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 2,275 Sq Ft
    • Built 2025

    Last Sold Summary

    • $187/SF

    Last Listing Agent Lindsay Shaffer RE/MAX Elite

    462 Rederick Ln Unit MASSEY LOT 60, Middletown, DE 19709
    • 105 Goldleaf Dr W, Middletown, DE 19709
      105 Goldleaf Dr W, Middletown, DE 19709
      105 Goldleaf Dr W, Middletown, DE 19709
      /15

      Not Listed For Sale

      105 Goldleaf Dr W, Middletown, DE 19709

      • 4 Beds
      • 4.5 Baths
      • 3,718 Sq Ft
      • Built 2024
      105 Goldleaf Dr W, Middletown, DE 19709

      Last Sold Summary

      • 39 Days On Market

  • 147 Crystal Run Dr, Middletown, DE 19709
    147 Crystal Run Dr, Middletown, DE 19709
    147 Crystal Run Dr, Middletown, DE 19709
    /97

    $525,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,325 Sq Ft

    147 Crystal Run Dr, Middletown, DE 19709

    Welcome to this beautifully updated 4-bedroom, 3-full-bath home situated on a private 1.14-acre lot in a wonderful Middletown community within the sought-after Appoquinimink School District. Offering a rare combination of space, updates, privacy, and location, this home is truly one of a kind. The interior has been thoughtfully refreshed with brand-new carpet, all-new paint, new light fixtures,

    Megan Aitken Keller Williams Realty

    147 Crystal Run Dr, Middletown, DE 19709
  • 836 Merlin Dr, Middletown, DE 19709
    836 Merlin Dr, Middletown, DE 19709
    836 Merlin Dr, Middletown, DE 19709
    /11

    $679,900

    Sold Jul 31, 2025

    836 Merlin Dr, Middletown, DE 19709

    • 4 Beds
    • 3.5 Baths
    • 2,737 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $248/SF
    • 11 Days On Market

    Current Estimated Value $715,841

    K. Hovnanian Homes Pleasanton

    836 Merlin Dr, Middletown, DE 19709
    • 110 Goldleaf Dr W, Middletown, DE 19709
      110 Goldleaf Dr W, Middletown, DE 19709
      110 Goldleaf Dr W, Middletown, DE 19709
      /13

      Not Listed For Sale

      110 Goldleaf Dr W, Middletown, DE 19709

      • 4 Beds
      • 3.5 Baths
      • 3,983 Sq Ft
      • Built 2024
      110 Goldleaf Dr W, Middletown, DE 19709

      Last Sold Summary

      • 51 Days On Market

  • 3 Espalier Ln, Middletown, DE 19709
    3 Espalier Ln, Middletown, DE 19709
    3 Espalier Ln, Middletown, DE 19709
    /38

    $497,000

    • 3 Beds
    • 2 Baths
    • 2,025 Sq Ft

    3 Espalier Ln, Middletown, DE 19709

    Fantastic opportunity in one of the best 55+ communities in the area. Spring Arbor is in the heart of Middletown where you can walk to the movies! This 2025 sf Brooks model is an incredible value and one of only 6 of that model that were built in the community. THREE bedrooms, and two full baths, spacious entry with extra wide hallways, tall ceilings and a tray ceiling in the primary suite.

    Kathleen Pigliacampi Patterson-Schwartz-Hockessin

    3 Espalier Ln, Middletown, DE 19709
  • 1517 Lesterfield Way, Middletown, DE 19709
    1517 Lesterfield Way, Middletown, DE 19709
    1517 Lesterfield Way, Middletown, DE 19709
    /10

    $654,900

    Sold Aug 21, 2025

    1517 Lesterfield Way, Middletown, DE 19709

    • 2 Beds
    • 2.5 Baths
    • 2,349 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $279/SF
    • 9,364 Days On Market

    Current Estimated Value $651,385

    K. Hovnanian Homes Four Seasons at Pennfield

    1517 Lesterfield Way, Middletown, DE 19709
    • 2636 Fairlight Dr, Middletown, DE 19709
      2636 Fairlight Dr, Middletown, DE 19709
      2636 Fairlight Dr, Middletown, DE 19709
      /39

      Est $466,462

      Not Listed For Sale

      2636 Fairlight Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 2,443 Sq Ft
      • Built 2025
      2636 Fairlight Dr, Middletown, DE 19709

      Last Sold Summary

      • 0 Days On Market

  • 1218 Pimpernell Path, Middletown, DE 19709
    1218 Pimpernell Path, Middletown, DE 19709
    1218 Pimpernell Path, Middletown, DE 19709
    /107

    $660,000

    $15K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,470 Sq Ft

    1218 Pimpernell Path, Middletown, DE 19709

    Welcome to 1218 Pimpernell Path, an exceptional residence in the highly sought-after and prestigious Shannon Cove community of Middletown. Priced at $675,000, this beautifully appointed home offers the perfect blend of elegance, comfort, functionality, and lifestyle, all within a community known for its spacious homesites, tree-lined streets, community pool, clubhouse, basketball courts, and tot

    Megan Aitken Keller Williams Realty

    1218 Pimpernell Path, Middletown, DE 19709
  • 269 Bucktail Dr, Middletown, DE 19709
    269 Bucktail Dr, Middletown, DE 19709
    269 Bucktail Dr, Middletown, DE 19709
    /51

    $660,000

    Sold Aug 08, 2025

    269 Bucktail Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 3,700 Sq Ft
    • Built 2004

    Last Sold Summary

    • $178/SF
    • 19 Days On Market

    Current Estimated Value $679,814

    Last Listing Agent Monica Peterson Innovate Real Estate

    269 Bucktail Dr, Middletown, DE 19709
    • 510 Ironleaf Dr, Middletown, DE 19709
      510 Ironleaf Dr, Middletown, DE 19709
      510 Ironleaf Dr, Middletown, DE 19709
      /33

      Est $742,430

      Not Listed For Sale

      510 Ironleaf Dr, Middletown, DE 19709

      • 4 Beds
      • 3.5 Baths
      • 3,651 Sq Ft
      • Built 2024
      510 Ironleaf Dr, Middletown, DE 19709

      Last Sold Summary

      • 12 Days On Market

Showing Results 201 - 240, Page 6 of 18

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