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

Homes Under $500K in Middletown, DE

Homes Under $500K in Middletown, DE

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24 of 53 Listings
Map

Homes Under $500K in Middletown, DE

24 of 53 Listings

  1. 2213 Winchelsea Pkwy — photo67Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #RB-0020869

Call Thomas

$447,509

3 bd · 3 ba · 2,443 sqft

2213 Winchelsea Pkwy, Middletown, DE

David Vasso · Atlantic Five Realty

  • 353 Edgar Degas Lane Edgar Degas #108 — photo15Active

    $476,500

    3 bd · 3 ba · 2,358 sqft

    353 Edgar Degas Lane Edgar Degas #108, Middletown, DE

    Ashley Painter · Blenheim Marketing LLC

  • 3310 Rookery Ln — photo22Active

    $499,570

    3 bd · 3 ba · 3,015 sqft

    3310 Rookery Ln, Middletown, DE

    David Vasso · Atlantic Five Realty

  • 359 Edgar Degas Lane Edgar Degas #111 — photo15Active

    $476,500

    3 bd · 3 ba · 2,358 sqft

    359 Edgar Degas Lane Edgar Degas #111, Middletown, DE

    Ashley Painter · Blenheim Marketing LLC

  • 357 Edgar Degas Ln #110 — photo15Active

    $384,000

    4 bd · 4 ba · 2,040 sqft

    357 Edgar Degas Ln #110, Middletown, DE

    Ashley Painter · Blenheim Marketing LLC

  • 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

  • 161 Springfield Cir — photo58Active

    $420,000

    3 bd · 3 ba · 2,375 sqft

    161 Springfield Cir, Middletown, DE

    Audrey Ellen Wagamon · First Class Properties

  • 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

  • 2318 Schubert Ln — photo51Active

    $489,900

    3 bd · 3 ba · 2,350 sqft

    2318 Schubert Ln, Middletown, DE

    Derrik N Scarpinato · Coldwell Banker Realty

  • 6624 Harko Dr — photo27Active

    $471,485

    3 bd · 4 ba · 2,361 sqft

    6624 Harko Dr, Middletown, DE

    David Vasso · Atlantic Five Realty

  • 1026 Wickersham Way — photo28Active

    $379,990

    3 bd · 3 ba · 1,500 sqft

    1026 Wickersham Way, Middletown, DE

    Jordan Brown · Real Broker LLC

  • 122 Boxwood Rd — photo12Active

    $70,000

    3 bd · 2 ba · 980 sqft

    122 Boxwood Rd, Middletown, DE

    Terri Knauer · Samson Properties of DE, LLC

  • 17 Mount Pleasant Trailer Ct #B017 — photo1Active

    $84,000

    3 bd · 2 ba · 980 sqft

    17 Mount Pleasant Trailer Ct #B017, Middletown, DE

    Eugene Lestardo III · Coldwell Banker Realty

  • 307 S Cass St — photoPrice Reduced37Active

    $375,000

    3 bd · 3 ba · 1,706 sqft

    307 S Cass St, Middletown, DE

    Rebecca L. Conway · Crown Homes Real Estate

  • 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

  • 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

  • 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

  • 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

  • 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

  • 2638 Fairlight Dr — photoPrice Reduced32Active

    $460,000

    3 bd · 3 ba · 2,443 sqft

    2638 Fairlight Dr, Middletown, DE

    Katina Geralis · EXP Realty, LLC

  • 334 Hostetter Blvd #334 — photoPrice Reduced17Active

    $69,950

    3 bd · 2 ba · 980 sqft

    334 Hostetter Blvd #334, Middletown, DE

    Robyn D Roberts · BHHS Fox & Roach-Christiana

  • 209 Aspen Cir — photo8Active

    $124,900

    3 bd · 2 ba · 0 sqft

    209 Aspen Cir, Middletown, DE

    Daniel J. Demers · Sell Your Home Services

  • 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

  • 406 Wilmore Dr — photo24Active

    $368,000

    3 bd · 3 ba · 1,750 sqft

    406 Wilmore Dr, Middletown, DE

    MICHELE STEED · EXP Realty, LLC

  • 123

    Explore Middletown homes

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    • With a pool
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #RB-0020869

    Call Thomas

    Listing data & MLS disclosures

    Bright MLS
    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.
    Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-08 04:08:50 UTC

    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

    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 · 52 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 24, 2026

    Median sale price
    $524,895$363,750–$683,165 typical range
    Price per sq. ft.
    $224
    Sales
    86
    Paid in cash
    38.4%

    Homes on the market · MLS, as of Aug 30, 2026–Aug 31, 2026

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

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

    Year-over-year
    -13.2%

    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.