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Homes Under $500K in Middletown, DE
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50 listings
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3 bedsNew constructionWith a pool

Homes Under $500K in Middletown, DE

Homes Under $500K in Middletown, DE

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24 of 50 Listings
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Homes Under $500K in Middletown, DE

24 of 50 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #RB-0020869

Call Thomas
  1. 1322 Carrick Ct — photoNew30Active

    $398,500

    3 bd · 3 ba · 2,600 sqft

    1322 Carrick Ct, Middletown, DE

    Carmen E Marra · EXP Realty, LLC

  2. 2213 Winchelsea Pkwy — photoNew67Active

    $447,509

    3 bd · 3 ba · 2,443 sqft

    2213 Winchelsea Pkwy, Middletown, DE

    David Vasso · Atlantic Five Realty

  3. 3310 Rookery Ln — photoNew22Active

    $499,570

    3 bd · 3 ba · 3,015 sqft

    3310 Rookery Ln, Middletown, DE

    David Vasso · Atlantic Five Realty

  4. 631 Red Maple Rd — photo69Active

    $499,000

    3 bd · 2 ba · 1,450 sqft

    631 Red Maple Rd, Middletown, DE

    Ashley Simmons · Crown Homes Real Estate

  5. 161 Springfield Cir — photo58Active

    $420,000

    3 bd · 3 ba · 2,375 sqft

    161 Springfield Cir, Middletown, DE

    Audrey Ellen Wagamon · First Class Properties

  6. 40 S Cummings Dr — photo55Active

    $409,000

    3 bd · 4 ba · 2,200 sqft

    40 S Cummings Dr, Middletown, DE

    Ashley Falkowski · Real Broker LLC

  7. 2318 Schubert Ln — photo51Active

    $489,900

    3 bd · 3 ba · 2,350 sqft

    2318 Schubert Ln, Middletown, DE

    Derrik N Scarpinato · Coldwell Banker Realty

  8. 54 Springmill Dr — photo47Active

    $465,000

    2 bd · 2 ba · 1,800 sqft

    54 Springmill Dr, Middletown, DE

    Peggy Centrella · Patterson-Schwartz-Hockessin

  9. 6624 Harko Dr — photo27Active

    $471,485

    3 bd · 4 ba · 2,361 sqft

    6624 Harko Dr, Middletown, DE

    David Vasso · Atlantic Five Realty

  10. 307 S Cass St — photo37Active

    $385,000

    3 bd · 3 ba · 1,706 sqft

    307 S Cass St, Middletown, DE

    Rebecca L. Conway · Crown Homes Real Estate

  11. 129 E Main St — photo33Active

    $228,000

    2 bd · 1 ba · 1,350 sqft

    129 E Main St, Middletown, DE

    Robert Buckingham · Crown Homes Real Estate

  12. 1803 N Pollock Way — photo40Active

    $470,000

    3 bd · 4 ba · 2,425 sqft

    1803 N Pollock Way, Middletown, DE

    Michael G Womer · Coldwell Banker Realty

  13. 104 E Main St — photo27Active

    $229,900

    2 bd · 2 ba · 1,575 sqft

    104 E Main St, Middletown, DE

    Robert Hoesterey · Crown Homes Real Estate

  14. 334 Edgar Degas Ln #100 — photo1Active

    $384,000

    4 bd · 4 ba · 2,040 sqft

    334 Edgar Degas Ln #100, Middletown, DE

    Ashley Painter · Blenheim Marketing LLC

  15. 1840 Congressional Village Dr #4302 — photo46Active

    $265,000

    2 bd · 2 ba · 1,050 sqft

    1840 Congressional Village Dr #4302, Middletown, DE

    Lynne R Holt · Patterson-Schwartz-Middletown

  16. 1034 Sherbourne Rd — photoPrice Reduced28Active

    $399,999

    3 bd · 3 ba · 2,075 sqft

    1034 Sherbourne Rd, Middletown, DE

    Lisa Marie · RE/MAX Advantage Realty

  17. 3164 Pett Level Dr — photoPrice Reduced61Active

    $445,559

    3 bd · 3 ba · 2,443 sqft

    3164 Pett Level Dr, Middletown, DE

    David Vasso · Atlantic Five Realty

  18. 2638 Fairlight Dr — photoPrice Reduced32Active

    $460,000

    3 bd · 3 ba · 2,443 sqft

    2638 Fairlight Dr, Middletown, DE

    Katina Geralis · EXP Realty, LLC

  19. 334 Hostetter Blvd #334 — photoPrice Reduced17Active

    $72,500

    3 bd · 2 ba · 980 sqft

    334 Hostetter Blvd #334, Middletown, DE

    Robyn D Roberts · BHHS Fox & Roach-Christiana

  20. 209 Aspen Cir — photo8Active

    $124,900

    3 bd · 2 ba · 0 sqft

    209 Aspen Cir, Middletown, DE

    Daniel J. Demers · Sell Your Home Services

  21. 623 Garden Gate Dr — photoPrice Reduced53Active

    $469,900

    2 bd · 2 ba · 1,775 sqft

    623 Garden Gate Dr, Middletown, DE

    Jason P Golden · Coldwell Banker Realty

  22. 406 Wilmore Dr — photo24Active

    $368,000

    3 bd · 3 ba · 1,750 sqft

    406 Wilmore Dr, Middletown, DE

    MICHELE STEED · EXP Realty, LLC

  23. 341 Tiger Lily Dr — photoPrice Reduced25Active

    $479,900

    4 bd · 3 ba · 2,925 sqft

    341 Tiger Lily Dr, Middletown, DE

    Isha A Shandilya · Realty Mark Associates

  24. 669 Old Summit Bridge Rd — photo8Active

    $475,000

    6 bd · 1 ba · 2,922 sqft

    669 Old Summit Bridge Rd, Middletown, DE

    Mark J. Levering · Patterson-Schwartz-Dover

123

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
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Middletown, DE community profile

Population
24,208
Median income
$100,643
Housing units
8,538
People per sq. mi.
288.5
Area
83.9 sq. mi.

Source: HJN community data

  • By feature

    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #RB-0020869

    Call Thomas

    Middletown housing market

    August 2026

    Middletown 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 44 sales · as of Aug 28, 2026

    Homes that sold · County records, as of Aug 13, 2026

    Median sale price
    $640,000$456,250–$977,060 typical range
    Price per sq. ft.
    $211
    Sales
    44
    Paid in cash
    38.6%

    Homes on the market · MLS, as of Aug 28, 2026–Aug 30, 2026

    Median list price
    $597,227
    Homes for sale
    202
    Median days on market
    20 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -1.8%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    2,285 sq. ft.