20,150

Middletown, DE Homes

Section Image Section Image
  • 24 W Shakespeare Dr, Middletown, DE 19709
    24 W Shakespeare Dr, Middletown, DE 19709
    24 W Shakespeare Dr, Middletown, DE 19709
    /87

    $610,000 Sold Jun 27, 2025

    24 W Shakespeare Dr, Middletown, DE 19709

    • 4 Beds
    • 4 Baths
    • 3,475 Sq Ft
    • Built 2004

    Last Sold Summary

    • $176/SF
    • 4 Days On Market

    Current Estimated Value $607,710

    Last Listing Agent Megan Aitken Keller Williams Realty

    24 W Shakespeare Dr, Middletown, DE 19709
    • 602 Cambria St, Middletown, DE 19709
      602 Cambria St, Middletown, DE 19709
      602 Cambria St, Middletown, DE 19709
      /35

      Est $550,042 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,061 Sq Ft

      602 Cambria St, Middletown, DE 19709

      602 Cambria St, Middletown, DE 19709
  • 460 Rederick Ln Unit MASSEY LOT 61, Middletown, DE 19709
    460 Rederick Ln Unit MASSEY LOT 61, Middletown, DE 19709
    460 Rederick Ln Unit MASSEY LOT 61, Middletown, DE 19709
    /12

    $384,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    460 Rederick Ln Unit MASSEY LOT 61, Middletown, DE 19709

    ** WORKFORCE HOUSING-BUYER MUST QUALIFY FOR THE NEW CASTLE COUNTY PROGRAM TOPURCHASE - MASSEY INTERIOR UNIT- 3 bedrooms, 2.5 baths, 1 car garage. Approx. 2001 SF! This home features a Finished den, 42" cabinets in kitchen, island, stainless range, dishwasher, microwave and recessed lighting in Kitchen. Tiled floor and Shower surround in master bath. 3 pc rough in walk out basement. Don't miss

    Lindsay Shaffer RE/MAX Elite

    460 Rederick Ln Unit MASSEY LOT 61, Middletown, DE 19709
  • 346 Goodwick Dr, Middletown, DE 19709
    346 Goodwick Dr, Middletown, DE 19709
    346 Goodwick Dr, Middletown, DE 19709
    /38

    $420,000 Sold Jul 31, 2025

    346 Goodwick Dr, Middletown, DE 19709

    • 3 Beds
    • 2.5 Baths
    • 2,550 Sq Ft
    • Built 2020

    Last Sold Summary

    • $165/SF
    • 10 Days On Market

    Current Estimated Value $433,626

    Last Listing Agent Alexis Laursen Long & Foster Real Estate, Inc.

    346 Goodwick Dr, Middletown, DE 19709
    • 373 Northhampton Way, Middletown, DE 19709
      373 Northhampton Way, Middletown, DE 19709
      373 Northhampton Way, Middletown, DE 19709
      /50

      Est $535,707 Not Listed For Sale

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

      373 Northhampton Way, Middletown, DE 19709

      373 Northhampton Way, Middletown, DE 19709
  • 845 Merlin Dr, Middletown, DE 19709
    845 Merlin Dr, Middletown, DE 19709
    845 Merlin Dr, Middletown, DE 19709
    /32

    $684,900 Pending

    • 5 Beds
    • 4 Baths
    • 2,797 Sq Ft

    845 Merlin Dr, Middletown, DE 19709

    The Knoxville home blends an open floorplan with timeless classic design, offering 5 bedrooms, 3 baths, and a 2-car garage — ideal for modern living with room to grow. Standout features include a finished basement for added living or entertainment space, a cozy fireplace, and laminate wood flooring that adds warmth and durability throughout the main level. The kitchen makes a statement with gray

    Barbara Heilman Delaware Homes Inc

    845 Merlin Dr, Middletown, DE 19709
  • 107 Avian Way, Middletown, DE 19709
    107 Avian Way, Middletown, DE 19709
    107 Avian Way, Middletown, DE 19709
    /26

    $412,000 Sold Apr 16, 2025

    107 Avian Way, Middletown, DE 19709

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1998

    Last Sold Summary

    • $294/SF
    • 5 Days On Market

    Current Estimated Value $392,290

    Last Listing Agent Brenda Murray BHHS Fox & Roach-Christiana

    107 Avian Way, Middletown, DE 19709
    • 367 Northhampton Way, Middletown, DE 19709
      367 Northhampton Way, Middletown, DE 19709
      367 Northhampton Way, Middletown, DE 19709
      /71

      Est $538,505 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,330 Sq Ft

      367 Northhampton Way, Middletown, DE 19709

      367 Northhampton Way, Middletown, DE 19709
  • 15 Golden Raintree Ct, Middletown, DE 19709
    15 Golden Raintree Ct, Middletown, DE 19709
    15 Golden Raintree Ct, Middletown, DE 19709
    /25

    $569,900 Pending

    • 2 Beds
    • 2 Baths
    • 1,859 Sq Ft

    15 Golden Raintree Ct, Middletown, DE 19709

    Welcome to the Dorchester home design. An open, ranch style home slated for an October delivery. The popular model features first floor living with bright spaces. Its three bedrooms and 2 full baths are conveniently on one level. Plenty of storage with a 2-car garage and unfinished basement. A wide screen porch overlooking open space is perfect for outdoor dining. The home also features a large

    Barbara Heilman Delaware Homes Inc

    15 Golden Raintree Ct, Middletown, DE 19709
  • 2670 Fairlight Dr, Middletown, DE 19709
    2670 Fairlight Dr, Middletown, DE 19709
    2670 Fairlight Dr, Middletown, DE 19709
    /22

    $485,509 Sold Jul 23, 2025

    2670 Fairlight Dr, Middletown, DE 19709

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

    Move in Ready Sold Summary

    • $199/SF
    • 83 Days On Market

    Current Estimated Value $479,432

    Lennar Venue at Winchelsea 55+ - Winchelsea Towns

    2670 Fairlight Dr, Middletown, DE 19709
    • 354 Northhampton Way, Middletown, DE 19709
      354 Northhampton Way, Middletown, DE 19709
      354 Northhampton Way, Middletown, DE 19709
      /45

      Est $537,269 Not Listed For Sale

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

      354 Northhampton Way, Middletown, DE 19709

      354 Northhampton Way, Middletown, DE 19709
  • 435 Rederick Ln, Middletown, DE 19709
    435 Rederick Ln, Middletown, DE 19709
    /2

    $489,624 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,351 Sq Ft

    435 Rederick Ln, Middletown, DE 19709

    Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    435 Rederick Ln, Middletown, DE 19709
  • 1082 Marl Pit Rd, Middletown, DE 19709
    1082 Marl Pit Rd, Middletown, DE 19709
    1082 Marl Pit Rd, Middletown, DE 19709
    /28

    $435,000 Sold May 28, 2025

    1082 Marl Pit Rd, Middletown, DE 19709

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • Built 1985

    Last Sold Summary

    • $235/SF
    • 0 Days On Market

    Current Estimated Value $440,564

    Last Listing Agent Curtis Tyler RE/MAX Associates-Wilmington

    1082 Marl Pit Rd, Middletown, DE 19709
    • 531 Middlesex Dr, Middletown, DE 19709
      531 Middlesex Dr, Middletown, DE 19709
      531 Middlesex Dr, Middletown, DE 19709
      /34

      Est $530,287 Not Listed For Sale

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

      531 Middlesex Dr, Middletown, DE 19709

      531 Middlesex Dr, Middletown, DE 19709
  • 1 Hogan Cir, Middletown, DE 19709
    1 Hogan Cir, Middletown, DE 19709
    1 Hogan Cir, Middletown, DE 19709
    /54

    $599,900

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    1 Hogan Cir, Middletown, DE 19709

    Discover the charm of this stunning traditional home nestled in the desirable subdivision of The Legends. This beautifully maintained residence, built in 2001, boasts a generous 2,700 sq. ft. of finished living space, perfect for creating lasting memories. Situated on a spacious corner lot, this property offers both privacy and a welcoming atmosphere. Step inside to find a harmonious blend of

    Victor Koveleski Long & Foster Real Estate, Inc.

    1 Hogan Cir, Middletown, DE 19709
  • 527 Swansea Dr, Middletown, DE 19709
    527 Swansea Dr, Middletown, DE 19709
    527 Swansea Dr, Middletown, DE 19709
    /53

    $452,500 Sold Feb 03, 2026

    527 Swansea Dr, Middletown, DE 19709

    • 3 Beds
    • 3.5 Baths
    • 2,550 Sq Ft
    • Built 2022

    Last Sold Summary

    • $177/SF
    • 63 Days On Market

    Last Listing Agent Ann Marie Germano Patterson-Schwartz-Middletown

    527 Swansea Dr, Middletown, DE 19709
    • 194 Gloucester Blvd, Middletown, DE 19709
      194 Gloucester Blvd, Middletown, DE 19709
      194 Gloucester Blvd, Middletown, DE 19709
      /44

      Est $606,845 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,025 Sq Ft

      194 Gloucester Blvd, Middletown, DE 19709

      194 Gloucester Blvd, Middletown, DE 19709
  • 1215 Bunker Hill Rd, Middletown, DE 19709
    1215 Bunker Hill Rd, Middletown, DE 19709
    1215 Bunker Hill Rd, Middletown, DE 19709
    /54

    $1,219,000

    • 4 Beds
    • 4.5 Baths
    • 4,300 Sq Ft

    1215 Bunker Hill Rd, Middletown, DE 19709

    Welcome home! Just 6 years young, this home has been meticulously maintained. A true blend of craftsman style and casual coastal charm, it offers endless possibilities with its thoughtful layout and multiple living spaces. Outside enjoy crisp fall evenings on the paved patio with fire-pit. Or take advantage of the 3 bay detached garage, perfect for extra vehicles, hobbies and all of your extra

    Jeanette Cantoran Crown Homes Real Estate

    1215 Bunker Hill Rd, Middletown, DE 19709
  • 108 Yorkshire Ct, Middletown, DE 19709
    108 Yorkshire Ct, Middletown, DE 19709
    108 Yorkshire Ct, Middletown, DE 19709
    /47

    $620,000 Sold Apr 04, 2025

    108 Yorkshire Ct, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • Built 1994

    Last Sold Summary

    • $253/SF
    • 40 Days On Market

    Current Estimated Value $614,620

    Last Listing Agent Brian Ferreira BHHS Fox & Roach-Greenville

    108 Yorkshire Ct, Middletown, DE 19709
    • 192 Gloucester Blvd, Middletown, DE 19709
      192 Gloucester Blvd, Middletown, DE 19709
      192 Gloucester Blvd, Middletown, DE 19709
      /36

      Est $609,685 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,825 Sq Ft

      192 Gloucester Blvd, Middletown, DE 19709

      192 Gloucester Blvd, Middletown, DE 19709
  • 3227 S Central Park Dr, Middletown, DE 19709
    3227 S Central Park Dr, Middletown, DE 19709
    3227 S Central Park Dr, Middletown, DE 19709
    /42

    $734,500 Pending

    • 3 Beds
    • 2 Baths
    • 2,757 Sq Ft

    3227 S Central Park Dr, Middletown, DE 19709

    Gorgeous Lot -Backs to open space! Great opportunity to buy at the new 55+ Parks Edge at Bayberry- The Tracy II Quick Delivery! Come experience the active adult lifestyle that home owners are raving about: a vibrant social scene, luxury amenities, stunning outdoor spaces and a place that will make you feel welcome and at home form the day you move in. Enjoy maintenance-free living with grass

    Brittany Stephens Blenheim Marketing LLC

    3227 S Central Park Dr, Middletown, DE 19709
  • 41 Millwood Dr, Middletown, DE 19709
    41 Millwood Dr, Middletown, DE 19709
    41 Millwood Dr, Middletown, DE 19709
    /34

    $575,000 Sold Apr 15, 2025

    41 Millwood Dr, Middletown, DE 19709

    • 4 Beds
    • 4 Baths
    • 2,550 Sq Ft
    • Built 2001

    Last Sold Summary

    • $225/SF
    • 104 Days On Market

    Current Estimated Value $600,146

    Last Listing Agent Elizabeth Page-Kramer EXP Realty, LLC

    41 Millwood Dr, Middletown, DE 19709
    • 184 Gloucester Blvd, Middletown, DE 19709
      184 Gloucester Blvd, Middletown, DE 19709
      184 Gloucester Blvd, Middletown, DE 19709
      /60

      Est $557,318 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,650 Sq Ft

      184 Gloucester Blvd, Middletown, DE 19709

      184 Gloucester Blvd, Middletown, DE 19709
  • 624 Nesting Ln, Middletown, DE 19709
    624 Nesting Ln, Middletown, DE 19709
    624 Nesting Ln, Middletown, DE 19709
    /50

    $770,000

    • 4 Beds
    • 4.5 Baths
    • 4,725 Sq Ft

    624 Nesting Ln, Middletown, DE 19709

    The search is over! You will be amazed from the moment you walk inside. A stunning 2 story 4725 sq foot colonial home PLUS finished basement with 4th full bathroom offers the new buyers a turnkey option on an amazing private lot backing to woods that has been professional landscaped with a low maintenance salt water inground pool! Enter into an open foyer with Cathedral ceilings, catwalk above

    Crystal Graham Patterson-Schwartz-Middletown

    624 Nesting Ln, Middletown, DE 19709
  • 204 Sloop Ln, Middletown, DE 19709
    204 Sloop Ln, Middletown, DE 19709
    204 Sloop Ln, Middletown, DE 19709
    /50

    $660,000 Sold Apr 15, 2025

    204 Sloop Ln, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • 2,825 Sq Ft
    • Built 1995

    Last Sold Summary

    • $234/SF
    • 120 Days On Market

    Current Estimated Value $672,545

    Last Listing Agent Theresa Craw RE/MAX Advantage Realty

    204 Sloop Ln, Middletown, DE 19709
    • 304 Northhampton Way, Middletown, DE 19709
      304 Northhampton Way, Middletown, DE 19709
      304 Northhampton Way, Middletown, DE 19709
      /74

      Est $658,905 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,225 Sq Ft

      304 Northhampton Way, Middletown, DE 19709

      304 Northhampton Way, Middletown, DE 19709
  • 129 Ayshire Dr Unit PHILADELPHIAN GRAND, Middletown, DE 19709
    129 Ayshire Dr Unit PHILADELPHIAN GRAND, Middletown, DE 19709
    129 Ayshire Dr Unit PHILADELPHIAN GRAND, Middletown, DE 19709
    /67

    $844,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 4,400 Sq Ft

    129 Ayshire Dr Unit PHILADELPHIAN GRAND, Middletown, DE 19709

    Welcome to Highlands at Back Creek- a small community of only 42 lots. All homesites are a minimum of 3/4 acre to a FULL ACRE. Are you tired of massive developments with no sense of community? This is the place for you. ;) Check out some of the standard features- 9' first and second-floor ceilings, crown molding in the living room, dining room, foyer, and second-floor hallway. Shaw hardwood

    Elizabeth Page-Kramer EXP Realty, LLC

    129 Ayshire Dr Unit PHILADELPHIAN GRAND, Middletown, DE 19709
  • 1201 Chesapeake View Dr, Middletown, DE 19709
    1201 Chesapeake View Dr, Middletown, DE 19709
    1201 Chesapeake View Dr, Middletown, DE 19709
    /29

    $675,000 Sold Oct 23, 2025

    1201 Chesapeake View Dr, Middletown, DE 19709

    • 4 Beds
    • 2.5 Baths
    • Built 2025

    Last Sold Summary

    • 82 Days On Market

    Last Listing Agent Brenda Mendenhall Monument Sotheby's International Realty

    1201 Chesapeake View Dr, Middletown, DE 19709
    • 114 Plymouth Place, Middletown, DE 19709
      114 Plymouth Place, Middletown, DE 19709
      114 Plymouth Place, Middletown, DE 19709
      /46

      Est $636,182 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,025 Sq Ft

      114 Plymouth Place, Middletown, DE 19709

      114 Plymouth Place, Middletown, DE 19709
  • 530 Wheelmen St Unit 36455671, Middletown, DE 19709
    530 Wheelmen St Unit 36455671, Middletown, DE 19709
    /2

    $540,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft

    Middleton Elite 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 36455671, Middletown, DE 19709
  • 722 Marian Dr, Middletown, DE 19709
    722 Marian Dr, Middletown, DE 19709
    722 Marian Dr, Middletown, DE 19709
    /26

    $308,000 Sold Dec 16, 2025

    722 Marian Dr, Middletown, DE 19709

    • 3 Beds
    • 4 Baths
    • 1,835 Sq Ft
    • Built 2002

    Last Sold Summary

    • $168/SF
    • 2 Days On Market

    Last Listing Agent Melissa Spencer Patterson-Schwartz-Newark

    722 Marian Dr, Middletown, DE 19709
    • 242 Wilgus Ct, Middletown, DE 19709
      242 Wilgus Ct, Middletown, DE 19709
      242 Wilgus Ct, Middletown, DE 19709
      /101

      Est $632,289 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,525 Sq Ft

      242 Wilgus Ct, Middletown, DE 19709

      242 Wilgus Ct, Middletown, DE 19709
  • 8 Redding Cir, Middletown, DE 19709
    8 Redding Cir, Middletown, DE 19709
    8 Redding Cir, Middletown, DE 19709
    /16

    $386,900

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

    8 Redding Cir, Middletown, DE 19709

    If you’ve been searching for a move-in ready home that blends style, comfort, and convenience — this is the one. Located in the highly desirable Appoquinimink School District, this beautiful ranch-style home has been designed with today’s lifestyle in mind. Step inside and you’ll immediately notice the open layout, natural light, and thoughtful details throughout. The kitchen is truly the heart

    Clifton Skinner Long & Foster Real Estate, Inc.

    8 Redding Cir, Middletown, DE 19709
  • 318 E Harvest Ln, Middletown, DE 19709
    318 E Harvest Ln, Middletown, DE 19709
    318 E Harvest Ln, Middletown, DE 19709
    /35

    $408,000 Sold Apr 25, 2025

    318 E Harvest Ln, Middletown, DE 19709

    • 3 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1999

    Last Sold Summary

    • $308/SF
    • 58 Days On Market

    Current Estimated Value $382,198

    Last Listing Agent Shane Pezick RE/MAX Associates-Wilmington

    318 E Harvest Ln, Middletown, DE 19709
    • 188 Gillespie Ave, Middletown, DE 19709
      188 Gillespie Ave, Middletown, DE 19709
      188 Gillespie Ave, Middletown, DE 19709
      /45

      Est $430,461 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,625 Sq Ft

      188 Gillespie Ave, Middletown, DE 19709

      188 Gillespie Ave, Middletown, DE 19709
  • 908 S Cass St, Middletown, DE 19709
    908 S Cass St, Middletown, DE 19709
    908 S Cass St, Middletown, DE 19709
    /28

    $430,000

    • 4 Beds
    • 1.5 Baths
    • 2,200 Sq Ft

    908 S Cass St, Middletown, DE 19709

    Rare opportunity to own a double lot in town at an affordable price. This spacious home offers a ton of possibilities. The current owner has done a lot of upgrades over the last few years by updating the kitchen, the flooring, vanities, interior doors and paint. The metal roof was installed in 2021 and the A/C is only 3 years old. The double lot adds to this property in many ways, build a pole

    Brooks Noll Iron Valley Real Estate Premier

    908 S Cass St, Middletown, DE 19709
  • 2664 Fairlight Dr, Middletown, DE 19709
    2664 Fairlight Dr, Middletown, DE 19709
    2664 Fairlight Dr, Middletown, DE 19709
    /22

    $480,105 Sold Jul 23, 2025

    2664 Fairlight Dr, Middletown, DE 19709

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

    Move in Ready Sold Summary

    • $197/SF
    • 113 Days On Market

    Current Estimated Value $483,041

    Lennar Venue at Winchelsea 55+ - Winchelsea Towns

    2664 Fairlight Dr, Middletown, DE 19709
    • 342 Norwalk Way, Middletown, DE 19709
      342 Norwalk Way, Middletown, DE 19709
      /2

      Est $412,807 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,375 Sq Ft

      342 Norwalk Way, Middletown, DE 19709

      342 Norwalk Way, Middletown, DE 19709
  • 795 Idlewyld Dr, Middletown, DE 19709
    795 Idlewyld Dr, Middletown, DE 19709
    795 Idlewyld Dr, Middletown, DE 19709
    /64

    $799,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 4,075 Sq Ft

    795 Idlewyld Dr, Middletown, DE 19709

    Welcome Home, to this stunning home in Parkside!!!! This is the one....A Stunning 6 year old Life style home. Curb appeal .... Location, next to pocket park...fenced in yard....New sunroom with a fireplace .....New finished basement....Updated Primary bathroom. So, Come on in....Look at this study, with custom arch doors...Formal dining room for those Holidays...Now the Extra large Family room

    Ann Marie Germano Patterson-Schwartz-Middletown

    795 Idlewyld Dr, Middletown, DE 19709
  • 38 N New Rd, Middletown, DE 19709
    38 N New Rd, Middletown, DE 19709
    38 N New Rd, Middletown, DE 19709
    /36

    $325,000 Sold Oct 16, 2025

    38 N New Rd, Middletown, DE 19709

    • 4 Beds
    • 1.5 Baths
    • 1,375 Sq Ft
    • Built 1920

    Last Sold Summary

    • $236/SF
    • 160 Days On Market

    Current Estimated Value $323,730

    Last Listing Agent Brandon Murray Long & Foster Real Estate, Inc.

    38 N New Rd, Middletown, DE 19709

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