20,298

Middletown, DE Homes

Section Image Section Image
    • 107 Margaretta Dr, Middletown, DE 19709
      107 Margaretta Dr, Middletown, DE 19709
      107 Margaretta Dr, Middletown, DE 19709
      /47

      Est $491,032

      Not Listed For Sale

      107 Margaretta Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 2,925 Sq Ft
      • Built 2009
      107 Margaretta Dr, Middletown, DE 19709

      Last Sold Summary

      • 3 Days On Market

  • 1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
    1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
    1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
    /12

    $613,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,810 Sq Ft

    Kerr Plan at Four Seasons at Pennfield, Middletown, DE 19709

    Included Extra Suite, ideal for multi-generational living and long-term guests.Private home office off of foyer, to work from home with plenty of space.Spacious great room with slider to covered patio.Stylish kitchen with island and large pantry.Luxurious primary suite with triple windows.Relaxing primary bath with split vanities and walk-in closet.Convenient 3-car tandem

    K. Hovnanian Homes Builder
    1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
  • 189 Gillespie Ave, Middletown, DE 19709
    189 Gillespie Ave, Middletown, DE 19709
    189 Gillespie Ave, Middletown, DE 19709
    /68

    $325,000

    Sold Jan 27, 2026

    189 Gillespie Ave, Middletown, DE 19709

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2005

    Last Sold Summary

    • $176/SF
    • 72 Days On Market

    Current Estimated Value $338,747

    Last Listing Agent Peggy Sheehan Patterson-Schwartz-Middletown

    189 Gillespie Ave, Middletown, DE 19709
    • 448 Afton Dr, Middletown, DE 19709
      448 Afton Dr, Middletown, DE 19709
      448 Afton Dr, Middletown, DE 19709
      /37

      Est $451,764

      Not Listed For Sale

      448 Afton Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 2015
      448 Afton Dr, Middletown, DE 19709

      Last Sold Summary

      • 12 Days On Market

  • 137 Silver Maple Rd, Middletown, DE 19709
    137 Silver Maple Rd, Middletown, DE 19709
    137 Silver Maple Rd, Middletown, DE 19709
    /25

    $485,000

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,625 Sq Ft

    137 Silver Maple Rd, Middletown, DE 19709

    Beautiful 3BR, 2BA, 2-car garage home with gorgeous hardwood floors that flow from the foyer through the main living areas. The open-concept floor plan seamlessly connects the living room, featuring recessed lighting, to the gourmet kitchen with upgraded cabinetry, stainless steel appliances, granite countertops and nice breakfast bar area. The spacious primary suite includes a large walk-in

    Delcollo & Salva Team Patterson-Schwartz-Hockessin

    137 Silver Maple Rd, Middletown, DE 19709
  • 16 E Shakespeare Dr, Middletown, DE 19709
    16 E Shakespeare Dr, Middletown, DE 19709
    16 E Shakespeare Dr, Middletown, DE 19709
    /43

    $584,000

    Sold Dec 30, 2025

    16 E Shakespeare Dr, Middletown, DE 19709

    • 5 Beds
    • 3.5 Baths
    • 2,725 Sq Ft
    • Built 2004

    Last Sold Summary

    • $214/SF
    • 84 Days On Market

    Current Estimated Value $571,121

    Last Listing Agent Gary Stewart Century 21 Emerald

    16 E Shakespeare Dr, Middletown, DE 19709
    • 410 Afton Dr, Middletown, DE 19709
      410 Afton Dr, Middletown, DE 19709
      410 Afton Dr, Middletown, DE 19709
      /35

      Est $396,951

      Not Listed For Sale

      410 Afton Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 2,277 Sq Ft
      • Built 2010
      410 Afton Dr, Middletown, DE 19709

      Last Sold Summary

      • 4 Days On Market

  • 734 Wood Duck Ct, Middletown, DE 19709
    734 Wood Duck Ct, Middletown, DE 19709
    734 Wood Duck Ct, Middletown, DE 19709
    /35

    $639,900

    $5K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,025 Sq Ft

    734 Wood Duck Ct, Middletown, DE 19709

    Welcome to 734 Wood Duck Ct, an exceptional residence nestled in the heart of Middletown within the sought-after community of Dove Run. From the moment you arrive, you’ll be captivated by the home’s elegant curb appeal, highlighted by refined stone accents and meticulously maintained landscaping.Step inside to discover a grand two-story turned staircase and rich hardwood flooring that flows

    Andrea Harrington Compass

    734 Wood Duck Ct, Middletown, DE 19709
  • 870 Sweet Birch Dr, Middletown, DE 19709
    870 Sweet Birch Dr, Middletown, DE 19709
    870 Sweet Birch Dr, Middletown, DE 19709
    /58

    $775,000

    Sold May 18, 2026

    870 Sweet Birch Dr, Middletown, DE 19709

    • 5 Beds
    • 3.5 Baths
    • 5,100 Sq Ft
    • Built 2021

    Last Sold Summary

    • 3% Below List Price
    • $152/SF
    • 65 Days On Market

    Current Estimated Value $796,673

    Last Listing Agent Jackie Patrick Compass

    870 Sweet Birch Dr, Middletown, DE 19709
    • 123 Margaretta Dr, Middletown, DE 19709
      123 Margaretta Dr, Middletown, DE 19709
      123 Margaretta Dr, Middletown, DE 19709
      /39

      Est $464,592

      Not Listed For Sale

      123 Margaretta Dr, Middletown, DE 19709

      • 4 Beds
      • 3.5 Baths
      • 2,525 Sq Ft
      • Built 2012
      123 Margaretta Dr, Middletown, DE 19709

      Last Sold Summary

      • 32 Days On Market

  • 407 Northhampton Way, Middletown, DE 19709
    407 Northhampton Way, Middletown, DE 19709
    407 Northhampton Way, Middletown, DE 19709
    /77

    $550,000

    Sold Aug 28, 2025

    407 Northhampton Way, Middletown, DE 19709

    • 4 Beds
    • 3.5 Baths
    • 3,523 Sq Ft
    • Built 2008

    Last Sold Summary

    • $156/SF
    • 19 Days On Market

    Current Estimated Value $570,103

    Last Listing Agent Michelle Brown EXP Realty, LLC

    407 Northhampton Way, Middletown, DE 19709
    • 461 Toftrees Dr, Middletown, DE 19709
      461 Toftrees Dr, Middletown, DE 19709
      461 Toftrees Dr, Middletown, DE 19709
      /40

      Est $404,398

      Not Listed For Sale

      461 Toftrees Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2014
      461 Toftrees Dr, Middletown, DE 19709

      Last Sold Summary

      • 8 Days On Market

  • 204 Baldy Ln Unit 36490855, Middletown, DE 19709
    204 Baldy Ln Unit 36490855, Middletown, DE 19709
    204 Baldy Ln Unit 36490855, Middletown, DE 19709
    /46

    $587,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,004 Sq Ft

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

    Cayot Stylish Comfort with Plenty of Space The Cayot offers 2,004 sq. ft. of well-designed living, featuring 3 bedrooms and 2 baths, including a main-level owners suite for easy, one-floor living. The open-concept kitchen and great room make entertaining a breeze, while the two-car rear-entry garage adds convenience. This home combines functionality and style perfectly for active adults who want

    Benchmark Builders Builder
    204 Baldy Ln Unit 36490855, Middletown, DE 19709
  • 540 Swansea Dr, Middletown, DE 19709
    540 Swansea Dr, Middletown, DE 19709
    540 Swansea Dr, Middletown, DE 19709
    /37

    $629,900

    Sold Sep 03, 2025

    540 Swansea Dr, Middletown, DE 19709

    • 5 Beds
    • 3.5 Baths
    • 4,447 Sq Ft
    • Built 2018

    Last Sold Summary

    • $142/SF
    • 16 Days On Market

    Current Estimated Value $662,401

    Last Listing Agent Deborah Cadwallader RE/MAX Horizons

    540 Swansea Dr, Middletown, DE 19709
    • 100 Ridgemont Dr, Middletown, DE 19709
      100 Ridgemont Dr, Middletown, DE 19709
      100 Ridgemont Dr, Middletown, DE 19709
      /32

      Est $420,253

      Not Listed For Sale

      100 Ridgemont Dr, Middletown, DE 19709

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft
      • Built 2016
      100 Ridgemont Dr, Middletown, DE 19709

      Last Sold Summary

      • 3 Days On Market

  • 27 Browning Cir, Middletown, DE 19709
    27 Browning Cir, Middletown, DE 19709
    27 Browning Cir, Middletown, DE 19709
    /6

    $515,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,050 Sq Ft

    27 Browning Cir, Middletown, DE 19709

    You'll want to see this well cared for, lovingly maintained home in Middletown Crossing. Tastefully decorated & ready for its new owners, 27 Browning is calling your name. This colonial style home's curb appeal is enhanced by mature trees, and clean, easy to maintain landscaping. The 2 car garage will be appreciated in the rain and colder months, with inside access. Head inside to the vaulted

    Dorothy Donovan Keller Williams Realty Wilmington

    27 Browning Cir, Middletown, DE 19709
  • 47 Spring Arbor Dr, Middletown, DE 19709
    47 Spring Arbor Dr, Middletown, DE 19709
    47 Spring Arbor Dr, Middletown, DE 19709
    /41

    $475,000

    Sold Dec 01, 2025

    47 Spring Arbor Dr, Middletown, DE 19709

    • 2 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 20 Days On Market

    Current Estimated Value $484,649

    Last Listing Agent Rick Anibal RE/MAX Advantage Realty

    47 Spring Arbor Dr, Middletown, DE 19709
    • 438 Toftrees Dr, Middletown, DE 19709
      438 Toftrees Dr, Middletown, DE 19709
      438 Toftrees Dr, Middletown, DE 19709
      /43

      Est $417,896

      Not Listed For Sale

      438 Toftrees Dr, Middletown, DE 19709

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft
      • Built 2010
      438 Toftrees Dr, Middletown, DE 19709

      Last Sold Summary

      • 2 Days On Market

  • 2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    /19

    $462,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,443 Sq Ft

    Taylor Plan at Venue at Winchelsea 55+ - Winchelsea Towns, 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
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
  • 878 Sweet Birch Dr, Middletown, DE 19709
    878 Sweet Birch Dr, Middletown, DE 19709
    878 Sweet Birch Dr, Middletown, DE 19709
    /97

    $960,000

    Sold Jul 28, 2025

    878 Sweet Birch Dr, Middletown, DE 19709

    • 6 Beds
    • 5 Baths
    • 5,250 Sq Ft
    • Built 2020

    Last Sold Summary

    • $183/SF
    • 9 Days On Market

    Current Estimated Value $993,364

    Last Listing Agent Ann Marie Germano Patterson-Schwartz-Middletown

    878 Sweet Birch Dr, Middletown, DE 19709
    • 100 Merrimac Ave, Middletown, DE 19709
      100 Merrimac Ave, Middletown, DE 19709
      100 Merrimac Ave, Middletown, DE 19709
      /29

      Est $420,404

      Not Listed For Sale

      100 Merrimac Ave, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 1,975 Sq Ft
      • Built 2019
      100 Merrimac Ave, Middletown, DE 19709

      Last Sold Summary

      • 2 Days On Market

  • 400 Rederick Ln Unit 36457195, Middletown, DE 19709
    400 Rederick Ln Unit 36457195, Middletown, DE 19709
    400 Rederick Ln Unit 36457195, Middletown, DE 19709
    /3

    $582,500

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,589 Sq Ft

    Oxford Plan at Ponds of Odessa - Single Family Homes, Middletown, DE 19709

    Large open-concept floor plan, 4 bedrooms, 2.5 baths, airy 2 stories. Tours by appointment onlyplease call 302-865-0759 to schedule. Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    400 Rederick Ln Unit 36457195, Middletown, DE 19709
  • 932 Lissicasey Loop, Middletown, DE 19709
    932 Lissicasey Loop, Middletown, DE 19709
    932 Lissicasey Loop, Middletown, DE 19709
    /40

    $412,000

    Sold Jan 23, 2026

    932 Lissicasey Loop, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Built 2018

    Last Sold Summary

    • $196/SF
    • 28 Days On Market

    Current Estimated Value $416,668

    Last Listing Agent Emma Stricker First Class Properties

    932 Lissicasey Loop, Middletown, DE 19709
    • 433 Toftrees Dr, Middletown, DE 19709
      433 Toftrees Dr, Middletown, DE 19709
      433 Toftrees Dr, Middletown, DE 19709
      /29

      Est $390,316

      Not Listed For Sale

      433 Toftrees Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2009
      433 Toftrees Dr, Middletown, DE 19709

      Last Sold Summary

      • 2 Days On Market

  • 1102 Highland St, Middletown, DE 19709
    1102 Highland St, Middletown, DE 19709
    1102 Highland St, Middletown, DE 19709
    /14

    $504,900

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,715 Sq Ft

    1102 Highland St, Middletown, DE 19709

    Photos shown are of a previously built Oxford model and are for illustrative purposes only. Features, finishes, and layout may vary in the actual home.

    Benchmark Builders Builder
    1102 Highland St, Middletown, DE 19709
  • 859 Bullen Dr, Middletown, DE 19709
    859 Bullen Dr, Middletown, DE 19709
    859 Bullen Dr, Middletown, DE 19709
    /87

    $610,000

    Sold Jul 18, 2025

    859 Bullen Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 2,350 Sq Ft
    • Built 2000

    Last Sold Summary

    • $260/SF
    • 8 Days On Market

    Current Estimated Value $582,014

    Last Listing Agent Agent Donna007 Bond BHHS Fox & Roach-Greenville

    859 Bullen Dr, Middletown, DE 19709
    • 319 S Parkway Dr, Middletown, DE 19709
      319 S Parkway Dr, Middletown, DE 19709
      319 S Parkway Dr, Middletown, DE 19709
      /45

      Est $409,960

      Not Listed For Sale

      319 S Parkway Dr, Middletown, DE 19709

      • 4 Beds
      • 3.5 Baths
      • 2,225 Sq Ft
      • Built 2010
      319 S Parkway Dr, Middletown, DE 19709

      Last Sold Summary

      • 14 Days On Market

  • 216 Baldy Ln, Middletown, DE 19709
    216 Baldy Ln, Middletown, DE 19709
    216 Baldy Ln, Middletown, DE 19709
    /55

    $685,000

    • 3 Beds
    • 2 Baths
    • 2,925 Sq Ft

    216 Baldy Ln, Middletown, DE 19709

    Welcome to 216 Baldy Lane– A Stunning Ranch-Style Home in the Premier 55+ Community of Traditions at Whitehall. Step into luxury and comfort in this beautifully upgraded 3-bedroom, 2-bath ranch-style home that truly shows like a model. Thoughtfully designed and impeccably maintained, this residence offers exceptional one-level living with high-end finishes throughout. Start your day on the

    Jack Sanderson Patterson-Schwartz-Hockessin

    216 Baldy Ln, Middletown, DE 19709
  • 926 Cadman Dr, Middletown, DE 19709
    926 Cadman Dr, Middletown, DE 19709
    926 Cadman Dr, Middletown, DE 19709
    /48

    $695,000

    Sold Oct 06, 2025

    926 Cadman Dr, Middletown, DE 19709

    • 5 Beds
    • 5 Baths
    • 4,450 Sq Ft
    • Built 2021

    Last Sold Summary

    • $156/SF
    • 7 Days On Market

    Current Estimated Value $727,931

    Last Listing Agent Traci Madison Madison Real Estate Inc. DBA MRE Residential Inc.

    926 Cadman Dr, Middletown, DE 19709
    • 325 S Parkway Dr, Middletown, DE 19709
      325 S Parkway Dr, Middletown, DE 19709
      325 S Parkway Dr, Middletown, DE 19709
      /46

      Est $399,900

      Not Listed For Sale

      325 S Parkway Dr, Middletown, DE 19709

      • 3 Beds
      • 3.5 Baths
      • 1,975 Sq Ft
      • Built 2010
      325 S Parkway Dr, Middletown, DE 19709

      Last Sold Summary

      • 2 Days On Market

  • 3032 Ivyhouse Ln, Middletown, DE 19709
    3032 Ivyhouse Ln, Middletown, DE 19709
    3032 Ivyhouse Ln, Middletown, DE 19709
    /16

    $645,272

    New Construction
    • 3 Beds
    • 4 Baths
    • 2,386 Sq Ft

    3032 Ivyhouse Ln, Middletown, DE 19709

    Welcome to 3032 Ivyhouse Lane—a beautifully upgraded Mendocino Luxe home offering over 2,386 square feet of above ground living space, plus a partially finished basement with its own full bathroom! This home features an open-concept main level anchored by a gourmet kitchen with included and stainless-steel appliances. The kitchen flows seamlessly into the breakfast nook and spacious family room,

    3032 Ivyhouse Ln, Middletown, DE 19709
  • 810 Ashby Dr, Middletown, DE 19709
    810 Ashby Dr, Middletown, DE 19709
    810 Ashby Dr, Middletown, DE 19709
    /79

    $885,000

    Sold Jun 12, 2026

    810 Ashby Dr, Middletown, DE 19709

    • 5 Beds
    • 4.5 Baths
    • 5,225 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Below List Price
    • $169/SF
    • 19 Days On Market

    Current Estimated Value $891,778

    Last Listing Agent Khalilah Ling Crown Homes Real Estate

    810 Ashby Dr, Middletown, DE 19709
    • 318 Gaither Dr, Middletown, DE 19709
      318 Gaither Dr, Middletown, DE 19709
      318 Gaither Dr, Middletown, DE 19709
      /32

      Est $406,738

      Not Listed For Sale

      318 Gaither Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 2,200 Sq Ft
      • Built 2015
      318 Gaither Dr, Middletown, DE 19709

      Last Sold Summary

      • 8 Days On Market

  • 2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    /22

    $530,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,936 Sq Ft

    Mendocino Plan at Venue at Winchelsea 55+ - Winchelsea Singles, Middletown, DE 19709

    This single-story home is designed to offer comfort and luxury at the same time. Off the foyer is a flex space for versatile uses and a formal dining room, followed by an open concept main living area with backyard access. In addition to the expansive owner’s suite with a private full-sized bathroom, there is a secondary bedroom that can be used for overnight guests or personal needs. A two-car

    Lennar Builder
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
  • 541 Diamond Dr, Middletown, DE 19709
    541 Diamond Dr, Middletown, DE 19709
    541 Diamond Dr, Middletown, DE 19709
    /19

    $550,000

    Sold Oct 31, 2025

    541 Diamond Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Built 2000

    Last Sold Summary

    • $262/SF
    • 13 Days On Market

    Current Estimated Value $584,219

    Last Listing Agent Derek Eisenberg Continental Real Estate Group

    541 Diamond Dr, Middletown, DE 19709
    • 302 N Parkway Dr, Middletown, DE 19709
      302 N Parkway Dr, Middletown, DE 19709
      302 N Parkway Dr, Middletown, DE 19709
      /49

      Est $441,614

      Not Listed For Sale

      302 N Parkway Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 2,200 Sq Ft
      • Built 2014
      302 N Parkway Dr, Middletown, DE 19709

      Last Sold Summary

      • 4 Days On Market

  • 251 Dillon Cir, Middletown, DE 19709
    251 Dillon Cir, Middletown, DE 19709
    251 Dillon Cir, Middletown, DE 19709
    /56

    $1,028,900

    $20K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 4,725 Sq Ft

    251 Dillon Cir, Middletown, DE 19709

    Presenting a distinguished 4-bedroom, 4 full-bathroom, Colorado II model in Summit Pointe, a newly built boutique community, crafted by K. Hovnanian Homes. This property, only 31⁄2 years old, offers 4,725 square feet of living space with an expanded floor plan (please refer to the attached floor plans, noting the upgraded, extended areas marked in blue), with a primarily brick front elevation.

    Sally Bittel Thomas Compass

    251 Dillon Cir, Middletown, DE 19709
  • 3006 Barber Ln, Middletown, DE 19709
    3006 Barber Ln, Middletown, DE 19709
    /2

    $568,500

    Sold Dec 22, 2025

    3006 Barber Ln, Middletown, DE 19709

    • 2 Beds
    • 2 Baths
    • 2,016 Sq Ft

    Last Sold Summary

    • $282/SF
    • 101 Days On Market

    Current Estimated Value $570,526

    Last Listing Agent Brittany Stephens Blenheim Marketing LLC

    3006 Barber Ln, Middletown, DE 19709
    • 335 S Parkway Dr, Middletown, DE 19709
      335 S Parkway Dr, Middletown, DE 19709
      335 S Parkway Dr, Middletown, DE 19709
      /65

      Est $407,024

      Not Listed For Sale

      335 S Parkway Dr, Middletown, DE 19709

      • 3 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2020
      335 S Parkway Dr, Middletown, DE 19709

      Last Sold Summary

      • 5 Days On Market

Showing Results 321 - 360, Page 9 of 18

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