20,150

Middletown, DE Homes

Section Image Section Image
    • 458 Brockton Dr, Middletown, DE 19709
      458 Brockton Dr, Middletown, DE 19709
      458 Brockton Dr, Middletown, DE 19709
      /35

      Est $340,878 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,675 Sq Ft

      458 Brockton Dr, Middletown, DE 19709

      458 Brockton Dr, Middletown, DE 19709
  • 2228 Winchelsea Pkwy, Middletown, DE 19709
    2228 Winchelsea Pkwy, Middletown, DE 19709
    2228 Winchelsea Pkwy, Middletown, DE 19709
    /21

    $509,900 New Construction

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

    2228 Winchelsea Pkwy, Middletown, DE 19709

    Welcome to the Carson—an elegant and versatile 3-bed, 2.5-bath home spanning 2,389 square feet, designed for modern living. The main level features a welcoming foyer that opens into a spacious great room with a gas fireplace, a bright breakfast nook, and a thoughtfully planned kitchen, creating the perfect hub for gatherings. Homeowners will appreciate the convenience of a first-floor owner’s

    Lennar Builder
    2228 Winchelsea Pkwy, Middletown, DE 19709
  • 367 Andrew Ct, Middletown, DE 19709
    367 Andrew Ct, Middletown, DE 19709
    367 Andrew Ct, Middletown, DE 19709
    /22

    $464,900 Sold Apr 17, 2025

    367 Andrew Ct, Middletown, DE 19709

    • 3 Beds
    • 4 Baths
    • 2,295 Sq Ft
    • Built 2024

    Last Sold Summary

    • $203/SF
    • 188 Days On Market

    Current Estimated Value $484,348

    Last Listing Agent Barbara Heilman Delaware Homes Inc

    367 Andrew Ct, Middletown, DE 19709
    • 913 Lansdowne Rd, Middletown, DE 19709
      913 Lansdowne Rd, Middletown, DE 19709
      913 Lansdowne Rd, Middletown, DE 19709
      /32

      Est $344,498 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,650 Sq Ft

      913 Lansdowne Rd, Middletown, DE 19709

      913 Lansdowne Rd, Middletown, DE 19709
  • 530 Wheelmen St Unit 36500725, Middletown, DE 19709
    530 Wheelmen St Unit 36500725, Middletown, DE 19709
    530 Wheelmen St Unit 36500725, Middletown, DE 19709
    /3

    $554,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft

    Middleton Reserve Plan at The Town of Whitehall - Mapleton Village, Middletown, DE 19709

    Open 5 days a week, 11 a.m. 5 p.m. Please call ahead or email lshaffer@benchmarkbuilders.com to check tour availability. Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    530 Wheelmen St Unit 36500725, Middletown, DE 19709
  • 2614 W Dali Dr, Middletown, DE 19709
    2614 W Dali Dr, Middletown, DE 19709
    2614 W Dali Dr, Middletown, DE 19709
    /54

    $550,000 Sold Apr 11, 2025

    2614 W Dali Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 2,175 Sq Ft
    • Built 2017

    Last Sold Summary

    • $253/SF
    • 85 Days On Market

    Current Estimated Value $550,331

    Last Listing Agent Jason Golden Coldwell Banker Realty

    2614 W Dali Dr, Middletown, DE 19709
    • 939 Lansdowne Rd, Middletown, DE 19709
      939 Lansdowne Rd, Middletown, DE 19709
      939 Lansdowne Rd, Middletown, DE 19709
      /45

      Est $377,252 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,075 Sq Ft

      939 Lansdowne Rd, Middletown, DE 19709

      939 Lansdowne Rd, Middletown, DE 19709
  • 1525 Lesterfield Way, Middletown, DE 19709
    1525 Lesterfield Way, Middletown, DE 19709
    1525 Lesterfield Way, Middletown, DE 19709
    /27

    $699,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    1525 Lesterfield Way, Middletown, DE 19709

    Polished kitchen with Slate Grey cabinetry & vast center island. Connected dining area & great room featuring vaulted ceiling. Cozy fireplace with shiplap adds warmth to main living areas. Lavish primary suite & bath featuring walk-in closet. Private home office, perfect for working remotely. Versatile screened deck for relaxing with friends. Finished basement for entertaining guests. Attached

    K. Hovnanian Homes Builder
    1525 Lesterfield Way, Middletown, DE 19709
  • 20 W Main St, Middletown, DE 19709
    20 W Main St, Middletown, DE 19709
    20 W Main St, Middletown, DE 19709
    /18

    $1,050,000 Sold Nov 25, 2025

    20 W Main St, Middletown, DE 19709

    • Studio
    • 6,384 Sq Ft
    • Built 1918

    Last Sold Summary

    • $164/SF
    • 45 Days On Market

    Last Listing Agent Paul Pantano Pantano Real Estate Inc

    20 W Main St, Middletown, DE 19709
    • 953 Lansdowne Rd, Middletown, DE 19709
      953 Lansdowne Rd, Middletown, DE 19709
      953 Lansdowne Rd, Middletown, DE 19709
      /35

      Est $372,184 Not Listed For Sale

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

      953 Lansdowne Rd, Middletown, DE 19709

      953 Lansdowne Rd, Middletown, DE 19709
  • 1220 N Olmsted Pkwy, Middletown, DE 19709
    1220 N Olmsted Pkwy, Middletown, DE 19709
    1220 N Olmsted Pkwy, Middletown, DE 19709
    /29

    $579,000 Open Sun 10AM - 12PM

    • 2 Beds
    • 2 Baths
    • 1,850 Sq Ft

    1220 N Olmsted Pkwy, Middletown, DE 19709

    Welcome home to 1218 N Olmsted Pkwy located in the sought-after Village of Bayberry North. Upon arrival, you’ll immediately notice the beautiful stone veneer exterior, offering timeless curb appeal and setting the tone for this well-maintained, 5-year-old ranch home. An inviting covered front porch welcomes you in, perfect for morning coffee, evening relaxation, or connecting with neighbors..

    Andrea Harrington Compass

    1220 N Olmsted Pkwy, Middletown, DE 19709
  • 3126 Pett Level Dr, Middletown, DE 19709
    3126 Pett Level Dr, Middletown, DE 19709
    3126 Pett Level Dr, Middletown, DE 19709
    /22

    $459,500 Sold Oct 29, 2025

    3126 Pett Level Dr, Middletown, DE 19709

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

    Move in Ready Sold Summary

    • $188/SF
    • 28 Days On Market

    Lennar Venue at Winchelsea 55+ - Winchelsea Towns

    3126 Pett Level Dr, Middletown, DE 19709
    • 1007 Sherbourne Rd, Middletown, DE 19709
      1007 Sherbourne Rd, Middletown, DE 19709
      1007 Sherbourne Rd, Middletown, DE 19709
      /3

      Est $375,716 Not Listed For Sale

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

      1007 Sherbourne Rd, Middletown, DE 19709

      1007 Sherbourne Rd, Middletown, DE 19709
  • 318 Northhampton Way, Middletown, DE 19709
    318 Northhampton Way, Middletown, DE 19709
    318 Northhampton Way, Middletown, DE 19709
    /57

    $515,000

    • 4 Beds
    • 2.5 Baths
    • 2,825 Sq Ft

    318 Northhampton Way, Middletown, DE 19709

    BACK ON THE MARKET at no fault of the seller, don't miss your second chance to call 318 Northhampton Way home! This meticulously maintained 4-bedroom, 2.5-bath home offering 2,825 square feet of comfortable living space in one of Middletown’s most sought-after neighborhoods. From the moment you arrive, pride of ownership is evident throughout every detail. The stunning curb appeal draws you in

    Megan Aitken Keller Williams Realty

    318 Northhampton Way, Middletown, DE 19709
  • 152 Tuscany Dr, Middletown, DE 19709
    152 Tuscany Dr, Middletown, DE 19709
    152 Tuscany Dr, Middletown, DE 19709
    /59

    $745,000 Sold Jun 17, 2025

    152 Tuscany Dr, Middletown, DE 19709

    • 6 Beds
    • 4.5 Baths
    • 5,400 Sq Ft
    • Built 2007

    Last Sold Summary

    • $138/SF
    • 154 Days On Market

    Current Estimated Value $762,440

    Last Listing Agent Kelly Clark Crown Homes Real Estate

    152 Tuscany Dr, Middletown, DE 19709
    • 1011 Sherbourne Rd, Middletown, DE 19709
      1011 Sherbourne Rd, Middletown, DE 19709
      1011 Sherbourne Rd, Middletown, DE 19709
      /39

      Est $364,395 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft

      1011 Sherbourne Rd, Middletown, DE 19709

      1011 Sherbourne Rd, Middletown, DE 19709
  • 3027 Ivyhouse Ln, Middletown, DE 19709
    3027 Ivyhouse Ln, Middletown, DE 19709
    3027 Ivyhouse Ln, Middletown, DE 19709
    /16

    $559,495 New Construction

    • 3 Beds
    • 3 Baths
    • 2,386 Sq Ft

    3027 Ivyhouse Ln, Middletown, DE 19709

    Welcome to 3027 Ivyhouse Ln — a beautifully upgraded Mendocino Luxe home offering 2,386 square feet of above ground living space, plus an unfinished basement for all your storage needs! This home features an open-concept main level anchored by a gourmet kitchen which flows seamlessly into the spacious family room, making it ideal for both everyday living and entertaining. Treat your guests to a

    Lennar Builder
    3027 Ivyhouse Ln, Middletown, DE 19709
  • 16 W Minglewood Dr, Middletown, DE 19709
    16 W Minglewood Dr, Middletown, DE 19709
    16 W Minglewood Dr, Middletown, DE 19709
    /63

    $548,000 Sold May 30, 2025

    16 W Minglewood Dr, Middletown, DE 19709

    • 4 Beds
    • 3.5 Baths
    • 3,828 Sq Ft
    • Built 2002

    Last Sold Summary

    • $143/SF
    • 5 Days On Market

    Current Estimated Value $560,807

    Last Listing Agent Yuliana Goldin-Dunn Patterson-Schwartz-Middletown

    16 W Minglewood Dr, Middletown, DE 19709
    • 1049 Sherbourne Rd, Middletown, DE 19709
      1049 Sherbourne Rd, Middletown, DE 19709
      1049 Sherbourne Rd, Middletown, DE 19709
      /19

      Est $358,705 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft

      1049 Sherbourne Rd, Middletown, DE 19709

      1049 Sherbourne Rd, Middletown, DE 19709
  • 692 Bayview Rd, Middletown, DE 19709
    692 Bayview Rd, Middletown, DE 19709
    692 Bayview Rd, Middletown, DE 19709
    /45

    $1,200,000

    • 7,026 Sq Ft

    692 Bayview Rd, Middletown, DE 19709

    A lovely brick federal style home with some Georgian characteristics. This home is placed on the national historic register. The property itself is 14.6 acres improved by mature trees, magnificent boxwoods, and lots of privacy. The home and numerous outbuildings were originally built during the local peach era, making Monterey one of Middletown's peach plantation homes. The outbuildings have just

    A. John Price Patterson-Schwartz Real Estate

    692 Bayview Rd, Middletown, DE 19709
  • 525 Wheelmen St, Middletown, DE 19709
    525 Wheelmen St, Middletown, DE 19709
    525 Wheelmen St, Middletown, DE 19709
    /44

    $565,000 Sold Jun 24, 2025

    525 Wheelmen St, Middletown, DE 19709

    • 4 Beds
    • 3.5 Baths
    • 2,425 Sq Ft
    • Built 2016

    Last Sold Summary

    • $233/SF
    • 58 Days On Market

    Current Estimated Value $563,730

    Last Listing Agent Rachel Burroughs Long & Foster Real Estate, Inc.

    525 Wheelmen St, Middletown, DE 19709
    • 395 Wilmore Dr, Middletown, DE 19709
      395 Wilmore Dr, Middletown, DE 19709
      395 Wilmore Dr, Middletown, DE 19709
      /25

      Est $362,582 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,650 Sq Ft

      395 Wilmore Dr, Middletown, DE 19709

      395 Wilmore Dr, Middletown, DE 19709
  • 204 Baldy Ln Unit 36491203, Middletown, DE 19709
    204 Baldy Ln Unit 36491203, Middletown, DE 19709
    204 Baldy Ln Unit 36491203, Middletown, DE 19709
    /4

    $515,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,059 Sq Ft

    Belville Plan at Traditions at Whitehall - 55+ Active Adult - Single Family, Middletown, DE 19709

    Belville Relaxed Living with Room to Spare Welcome to the Belville, a thoughtfully designed 2,059 sq. ft. ranch home that blends comfort and style for carefree 55+ living. Enjoy a spacious open layout with a large great room, chef-friendly kitchen, and a first-floor owners suite for ultimate convenience. A charming front porch, full basement, and two-car rear-entry garage add curb appeal and

    Benchmark Builders Builder
    204 Baldy Ln Unit 36491203, 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

    $649,695 Sold Feb 20, 2025

    110 Goldleaf Dr W, Middletown, DE 19709

    • 4 Beds
    • 3.5 Baths
    • 3,983 Sq Ft
    • Built 2024

    Last Sold Summary

    • $163/SF
    • 51 Days On Market

    Last Listing Agent David Vasso Atlantic Five Realty

    110 Goldleaf Dr W, Middletown, DE 19709
    • 946 Lansdowne Rd, Middletown, DE 19709
      946 Lansdowne Rd, Middletown, DE 19709
      946 Lansdowne Rd, Middletown, DE 19709
      /32

      Est $402,027 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,075 Sq Ft

      946 Lansdowne Rd, Middletown, DE 19709

      946 Lansdowne Rd, Middletown, DE 19709
  • 29 W Reybold Dr, Middletown, DE 19709
    29 W Reybold Dr, Middletown, DE 19709
    29 W Reybold Dr, Middletown, DE 19709
    /11

    $60,000

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    29 W Reybold Dr, Middletown, DE 19709

    Welcome to 29 W Reybold Dr, a cozy and affordable 2-bedroom, 1-bath residence located in the well-established Villagebrook Trailer Park community in Middletown, DE. Perfect for first-time buyers or anyone seeking low-maintenance living, this home presents a wonderful opportunity to own in a friendly and conveniently located neighborhood.Enter to discover a comfortable, functional layout with

    Scott Kompa EXP Realty, LLC

    29 W Reybold Dr, Middletown, DE 19709
  • 1 Meadow Dr, Middletown, DE 19709
    1 Meadow Dr, Middletown, DE 19709
    1 Meadow Dr, Middletown, DE 19709
    /78

    $700,000 Sold Aug 26, 2025

    1 Meadow Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 4,325 Sq Ft
    • Built 1999

    Last Sold Summary

    • $162/SF
    • 4 Days On Market

    Current Estimated Value $698,841

    Last Listing Agent Dennis Snavely RE/MAX Elite

    1 Meadow Dr, Middletown, DE 19709
    • 966 Lansdowne Rd, Middletown, DE 19709
      966 Lansdowne Rd, Middletown, DE 19709
      966 Lansdowne Rd, Middletown, DE 19709
      /33

      Est $399,585 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,200 Sq Ft

      966 Lansdowne Rd, Middletown, DE 19709

      966 Lansdowne Rd, Middletown, DE 19709
  • 1430 Pennfield Dr, Middletown, DE 19709
    1430 Pennfield Dr, Middletown, DE 19709
    1430 Pennfield Dr, Middletown, DE 19709
    /11

    $704,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    1430 Pennfield Dr, Middletown, DE 19709

    Brand New 55+ Community in Middletown, DE The Carver DE showcases a thoughtfully designed open-concept layout that pairs classic design elements with modern comfort. Featuring 3 bedrooms (including one in the finished basement), 3.5 baths, and a 2.5-car garage, this home offers both style and flexibility for everyday living and entertaining. Standout features include a fireplace with shiplap

    Barbara Heilman Delaware Homes Inc

    1430 Pennfield Dr, Middletown, DE 19709
  • 841 Merlin Dr, Middletown, DE 19709
    841 Merlin Dr, Middletown, DE 19709
    841 Merlin Dr, Middletown, DE 19709
    /16

    $709,900 Sold Aug 01, 2025

    841 Merlin Dr, Middletown, DE 19709

    • 5 Beds
    • 4 Baths
    • 2,877 Sq Ft
    • Built 2024

    Last Sold Summary

    • $247/SF
    • 41 Days On Market

    Current Estimated Value $714,886

    Last Listing Agent Barbara Heilman Delaware Homes Inc

    841 Merlin Dr, Middletown, DE 19709
    • 972 Lansdowne Rd, Middletown, DE 19709
      972 Lansdowne Rd, Middletown, DE 19709
      972 Lansdowne Rd, Middletown, DE 19709
      /47

      Est $397,771 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,200 Sq Ft

      972 Lansdowne Rd, Middletown, DE 19709

      972 Lansdowne Rd, Middletown, DE 19709
  • 1481 Bunker Hill Rd, Middletown, DE 19709
    1481 Bunker Hill Rd, Middletown, DE 19709
    1481 Bunker Hill Rd, Middletown, DE 19709
    /25

    $750,000

    • Land
    • 3.85 Acres
    • $194,805 per Acre

    1481 Bunker Hill Rd, Middletown, DE 19709

    Last of the remaining lots!!!!! Unique and promising opportunity close to the Maryland Horse Farms, perfect for those seeking a picturesque and serene waterfront property to call home Lots #12 and #13 Great Bohemia Manor. Build your dream home today! No Builder Tie In. Lakefront property cleared flat land awaiting the perfect buyer, a total of 5 acres for both lots combined but lots can be

    Samuel Barksdale Barksdale & Affiliates Realty

    1481 Bunker Hill Rd, Middletown, DE 19709
  • 364 Norwalk Way, Middletown, DE 19709
    364 Norwalk Way, Middletown, DE 19709
    364 Norwalk Way, Middletown, DE 19709
    /39

    $599,000 Sold Dec 31, 2025

    364 Norwalk Way, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • Built 2005

    Last Sold Summary

    • $200/SF
    • 61 Days On Market

    Last Listing Agent Bill Coalson EXP Realty, LLC

    364 Norwalk Way, Middletown, DE 19709
    • 963 Lansdowne Rd, Middletown, DE 19709
      963 Lansdowne Rd, Middletown, DE 19709
      963 Lansdowne Rd, Middletown, DE 19709
      /21

      Est $358,120 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft

      963 Lansdowne Rd, Middletown, DE 19709

      963 Lansdowne Rd, Middletown, DE 19709
  • 29 W Kilts Ln, Middletown, DE 19709
    29 W Kilts Ln, Middletown, DE 19709
    29 W Kilts Ln, Middletown, DE 19709
    /123

    $735,000

    • 4 Beds
    • 4.5 Baths
    • 5,950 Sq Ft

    29 W Kilts Ln, Middletown, DE 19709

    Welcome to 29 W. Kilts Ln, an exceptional residence offering 5,950 square feet of finished living space designed for both everyday comfort and elevated entertaining. This stunning home features two staircases, 4 spacious bedrooms, and 4.5 bathrooms, with hardwood flooring throughout the main level and upstairs hallway. The heart of the home is the dramatic sunken family room with soaring 10’

    Megan Aitken Keller Williams Realty

    29 W Kilts Ln, Middletown, DE 19709
  • 141 Gillespie Ave, Middletown, DE 19709
    141 Gillespie Ave, Middletown, DE 19709
    141 Gillespie Ave, Middletown, DE 19709
    /41

    $357,000 Sold Oct 31, 2025

    141 Gillespie Ave, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 2,225 Sq Ft
    • Built 2005

    Last Sold Summary

    • $160/SF
    • 47 Days On Market

    Current Estimated Value $343,406

    Last Listing Agent Jackie Patrick Compass

    141 Gillespie Ave, Middletown, DE 19709
    • 337 Wilmore Dr, Middletown, DE 19709
      337 Wilmore Dr, Middletown, DE 19709
      337 Wilmore Dr, Middletown, DE 19709
      /43

      Est $359,416 Not Listed For Sale

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

      337 Wilmore Dr, Middletown, DE 19709

      337 Wilmore Dr, Middletown, DE 19709
  • 129 Patterson Ct Unit 36452296, Middletown, DE 19709
    129 Patterson Ct Unit 36452296, Middletown, DE 19709
    129 Patterson Ct Unit 36452296, Middletown, DE 19709
    /12

    $600,990 New Construction

    • 3 Beds
    • 3 Baths
    • 2,307 Sq Ft

    Fayetteville Plan at Pleasanton, Middletown, DE 19709

    Private home office off foyer, to work from home in comfort . Striking modern kitchen with Looks interior options available . Spacious great room with plenty of windows for natural light . Luxurious primary suite with walk-in closet . Relaxing primary bath with dual sinks . Versatile loft on second floor, great for a gameroom, play room, home theater, and more .

    K. Hovnanian Homes Builder
    129 Patterson Ct Unit 36452296, Middletown, DE 19709
  • 345 Jessica Dr, Middletown, DE 19709
    345 Jessica Dr, Middletown, DE 19709
    345 Jessica Dr, Middletown, DE 19709
    /45

    $625,000 Sold Aug 15, 2025

    345 Jessica Dr, Middletown, DE 19709

    • 5 Beds
    • 2.5 Baths
    • 3,400 Sq Ft
    • Built 1997

    Last Sold Summary

    • $184/SF
    • 63 Days On Market

    Current Estimated Value $631,776

    Last Listing Agent Katina Geralis EXP Realty, LLC

    345 Jessica Dr, Middletown, DE 19709
    • 336 Daylilly Way, Middletown, DE 19709
      336 Daylilly Way, Middletown, DE 19709
      336 Daylilly Way, Middletown, DE 19709
      /28

      Est $468,059 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,850 Sq Ft

      336 Daylilly Way, Middletown, DE 19709

      336 Daylilly Way, Middletown, DE 19709

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