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Middletown Houses for Sale

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  • /21

    $447,000

    • 2 Beds
    • 2 Baths
    • 1,875 Sq Ft

    51 Springmill Dr, Middletown, DE 19709

    Welcome to Springmill – where lifestyle meets value! This affordable and beautifully maintained home in Middletown’s premier 55+ community offers everything you need to start your next chapter. With a main-level primary suite, sun-filled family room, and a stylish kitchen featuring granite countertops, this home is designed for comfort and low-maintenance living. Enjoy your morning coffee in the

    Agent Photo

    Bob Teeven

    Long & Foster Real Estate, Inc.

    (302) 600-1290

    51 Springmill Dr, Middletown, DE 19709
  • /22

    $459,900 Open Sun 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    237 Trellis Ln, Middletown, DE 19709

    Welcome to this beautifully maintained single-family home nestled in the vibrant 55+ community of Spring Arbor. Featuring thoughtful updates throughout, this bright and inviting home offers comfort, convenience, and style all in one perfect package. Approach from the welcoming front porch and enter into a sun-drenched foyer with a large window that fills the space with natural light. The spacious

    Sherri Hill Redfin Corporation

    237 Trellis Ln, Middletown, DE 19709
  • /94

    $669,900

    • 4 Beds
    • 3.5 Baths
    • 3,425 Sq Ft

    20 W Kilts Ln, Middletown, DE 19709

    Showings begin 8/1/2025! Overnight Notice Required for ALL Showing Requests. Sellers Request a Settlement Date of 10/6/25 or later. Are you looking for a large/spacious home w/ a great open floor plan?! Look no further! This lovely home is ready for its new owner! Great curb appeal w/ mature trees & bushes & plenty of freshly mulched flower beds that you can customize every year if you want!

    Team Freebery EXP Realty, LLC

    20 W Kilts Ln, Middletown, DE 19709
  • /67

    $630,000 Open Sun 11AM - 1PM

    • 5 Beds
    • 4 Baths
    • 3,675 Sq Ft

    741 Wallasey Dr, Middletown, DE 19709

    BACK ON THE MARKET at no fault of the seller - your second chance at calling this stunning home yours won't last long! Welcome to the incredible community of Preserve at Deep Creek, where luxury and convenience meet to offer the location of your dreams. Just minutes from the heart of Middletown where there's an abundance of food, shopping, restaurants and award-winning Appoquinimink School

    Megan Aitken Keller Williams Realty

    741 Wallasey Dr, Middletown, DE 19709
  • /37

    $639,900

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

    540 Swansea Dr, Middletown, DE 19709

    Tucked away in the heart of the Preserve at Deep Creek, this beautifully upgraded 4/5-bedroom, 3.5-bath home offers nearly 4,000 sq ft of thoughtfully designed living space that’s both spacious and welcoming.Step inside and feel instantly at home. The open-concept main level features a gourmet kitchen with stainless steel appliances, granite countertops, a large island with seating, and a

    Deborah Cadwallader RE/MAX Horizons

    540 Swansea Dr, Middletown, DE 19709
  • /49

    $699,999

    • 5 Beds
    • 4 Baths
    • 4,700 Sq Ft

    50 Haggis Rd, Middletown, DE 19709

    Welcome to this beautiful 5 bedroom home located in the highly desirable Estates of St. Annes. This home has been impeccably maintained by its original owners. As you enter the home you have a formal dining area to your right, and a living room or office space to your right. Continuing down the hall you will enter the open kitchen and living room area with a gorgeous fireplace. There is also a

    Nigel Pokoy Compass

    50 Haggis Rd, Middletown, DE 19709
  • /57

    $695,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 4 Baths
    • 3,450 Sq Ft

    3 W Kilts Ln, Middletown, DE 19709

    Welcome to 3 West Kilts Lane, at The Estates at St Annes, where elegance meets modern convenience. Step inside to discover exquisite craftsmanship. The heart of this home is its gourmet kitchen, featuring granite countertops, a spacious pantry, stainless steel appliances, a double sink, recessed lighting, and beautiful hardwood floors. Adjacent, the morning room beckons with a vaulted ceiling, a

    Catherine Ortner Compass

    3 W Kilts Ln, Middletown, DE 19709
  • /98

    $799,000

    • 5 Beds
    • 5 Baths
    • 5,100 Sq Ft

    253 Wickerberry Dr, Middletown, DE 19709

    Welcome to 253 Wickerberry Drive in the sought after community of PARKSIDE. This home from the moment you pull up has such wonderful curb appeal...The Stone Front, the front porch and the lovely landscaping. Come inside to this beautiful traditional home that has so much to offer, 5 bedrooms, 5 bathrooms large office, great kitchen with a large morning room, a finished basement and one of the

    Ann Marie Germano Patterson-Schwartz-Middletown

    253 Wickerberry Dr, Middletown, DE 19709
  • /68

    $635,000

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

    94 Willow Grove Mill Dr, Middletown, DE 19709

    Welcome to the home you’ve been waiting for! This beautifully maintained 4-bedroom, 2.5-bath home is ideally situated on a premium lot—backing to mature trees and nestled beside open space with a tranquil pond. Located in a desirable, established neighborhood, within the sought-after Appoquinimink School District, this home stands out the moment you arrive.The turned garage provides extra

    Rick Anibal RE/MAX 1st Choice - Middletown

    94 Willow Grove Mill Dr, Middletown, DE 19709
  • /28

    $675,000

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

    152 Tywyn Dr, Middletown, DE 19709

    JUST MOVE IN!! That is what this house offers you. It's all done for you. This beautiful home boasts 5 bedrooms, 3.5 baths with 3 levels of spacious living space for you and your family The first floor has a beautiful front entry, formal living room, dining room, spacious kitchen with upgraded cabinets, granite countertops, and large island with eating area, huge family room,

    Barbara Allsopp Patterson-Schwartz-Middletown

    152 Tywyn Dr, Middletown, DE 19709
  • /36

    $619,900

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

    124 Willow Grove Mill Dr, Middletown, DE 19709

    Welcome to this charming Colonial-style home located in the desirable Longmeadow in the Town of Middletown. The beautiful washed brick facade and covered front door welcomes you in. This spacious property boasts 4 bedrooms, 2.5 bathrooms, and is spread across 2 levels/stories, offering ample space for comfortable living. As you enter, you are greeted by a two story foyer with the formal living

    Ann Marie Deysher Patterson-Schwartz-Hockessin

    124 Willow Grove Mill Dr, Middletown, DE 19709
  • /56

    $600,000 Open Sat 1PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 4,175 Sq Ft

    25 Browning Cir, Middletown, DE 19709

    Nestled in the charming Middletown Crossing, this inviting expanded cape, offers a perfect blend of comfort and functionality. With 4 spacious bedrooms and 3.5 bathrooms, this residence boasts a generous 4,175 sq. ft. of finished living space, ideal for both relaxation and entertaining. Step inside to discover an open floor plan that seamlessly connects the kitchen, dining area, and family room,

    Victoria Lawson Long & Foster Real Estate, Inc.

    25 Browning Cir, Middletown, DE 19709
  • /50

    $999,000

    • 5 Beds
    • 5.5 Baths
    • 6,840 Sq Ft

    448 Spring Hollow Dr, Middletown, DE 19709

    Welcome to 448 Spring Hollow Drive. This well-maintained freshy painted colonial home sits on a lovely corner lot located in the desirable community of Parkside, with an additional 1/2 acre of non-buildable open space behind the property. Being a former model home, this 5 bedroom, 5 1/2 bath home features many well-executed upgrades, 4 fireplaces, stunning trim and lighting upgrades throughout.

    Christopher Carr HomeZu

    448 Spring Hollow Dr, Middletown, DE 19709
  • /43

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,950 Sq Ft

    48 Springmill Dr, Middletown, DE 19709

    Welcome to 48 Springmill Drive in the wonderful 55+ community of Springmill. This home has a bright & open flow, spacious den/office, beautiful sunroom, inspiring natural light throughout, and a private patio with tree-lined view. A manicured landscape welcomes you to this home. Step inside and you will find the office/den and dining room on either side of the foyer. The office features custom

    Michael McKee Long & Foster Real Estate, Inc.

    48 Springmill Dr, Middletown, DE 19709
  • /28

    $399,000

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

    900 S Vernon St, Middletown, DE 19709

    Welcome to 900 S Vernon St, located in the heart of Middletown, DE, within the desirable Sharondale community. This charming brick rancher features three bedrooms, one full bathroom, a fully enclosed sunroom with heat and air conditioning, a partially finished basement with inside and outside access, and an in-ground pool with a new cover. Recent updates include new hardwood flooring in two

    Kelly Clark Crown Homes Real Estate

    900 S Vernon St, Middletown, DE 19709
  • /26

    $430,000

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    417 Morning Glory Ln, Middletown, DE 19709

    Welcome to your ideal low-maintenance lifestyle in this beautifully maintained 2-bedroom, 2-bath home featuring a spacious loft and inviting outdoor space. Nestled in a vibrant 55+ community of Springmill, this residence offers the perfect blend of comfort, convenience, and style. The beautiful landscaping welcomes you inside where you'll find an open-concept layout with a large kitchen with

    Ann Marie Deysher Patterson-Schwartz-Hockessin

    417 Morning Glory Ln, Middletown, DE 19709
  • /78

    $665,000

    • 4 Beds
    • 3.5 Baths
    • 3,950 Sq Ft

    629 Spring Hollow Dr, Middletown, DE 19709

    Welcome to 629 Spring Hollow Dr, where every inch is dripping with beauty and elegance. In one of Middletown's most sought after communities of Parkside, 629 Spring Hollow Dr is situated on a corner lot with beautiful views, endearing front porch, board and batten siding, stone skirting, and gorgeous landscaping - the curb appeal leaves nothing to be desired. Professionally designed from top to

    Megan Aitken Keller Williams Realty

    629 Spring Hollow Dr, Middletown, DE 19709
  • /52

    $465,000

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

    343 Daylilly Way, Middletown, DE 19709

    Welcome to 343 Daylilly Way, a beautifully maintained home in the sought-after 55+ community of Springmill in Middletown, DE. This 2-bedroom, 3-bath home features a smart layout with two bedrooms and a flex room on the main floor, plus a private loft with a third full bath—ideal for guests or hobbies. Hardwood floors flow throughout the main living areas, accented by crown molding and natural

    Lalisa Sweat Crown Homes Real Estate

    343 Daylilly Way, Middletown, DE 19709
  • /47

    $670,000

    • 4 Beds
    • 3 Baths
    • 3,025 Sq Ft

    734 Wood Duck Ct, Middletown, DE 19709

    Welcome to 734 Wood Duck Ct – A Stunning Blend of Comfort and Style in Middletown!Nestled on a quiet cul-de-sac in one of Middletown’s most desirable neighborhoods, this beautifully maintained 4-bedroom, 3-full-bath home is the perfect combination of space, function, and modern updates. Step inside to find an inviting layout featuring a dedicated home office, ideal for remote work or

    Cristina TLASECA Madison Real Estate Inc. DBA MRE Residential Inc.

    734 Wood Duck Ct, Middletown, DE 19709
  • /54

    $479,900

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

    577 Whispering Trail, Middletown, DE 19709

    Welcome home to this impeccably maintained Coleridge model, ideally situated within the sought-after Active Adult Community of Springmill in Middletown, Delaware. This residence has been meticulously cared for and offers recent upgrades, including a new roof, HVAC system, and electric water heater, ensuring peace of mind for years to come. Upon entering, you’ll be greeted by gleaming hardwood

    Vicky Miller Patterson-Schwartz-Middletown

    577 Whispering Trail, Middletown, DE 19709
  • /68

    $899,000 Open Sat 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 5,800 Sq Ft

    102 W Crail Ct, Middletown, DE 19709

    Discover refined elegance in this stunning 5-bedroom, 3.5-bath mansion located in one of Middletown’s most sought-after neighborhoods. This expansive home features breathtaking marble flooring, soaring ceilings, and designer finishes throughout.The grand entry opens to beautifully appointed living and dining spaces, leading to a gourmet kitchen with high-end appliances, custom cabinetry,

    Grace Casella Crown Homes Real Estate

    102 W Crail Ct, Middletown, DE 19709
  • /61

    $465,000

    • 3 Beds
    • 2 Baths
    • 2,150 Sq Ft

    574 Whispering Trail, Middletown, DE 19709

    55 Community living at it's finest. 2-Bed + Loft in Active 55+ Community . Excellent Condition & Full of Charm!Welcome to this beautifully cared-for 2-bedroom, 2-bath home in a vibrant and friendly 55+ neighborhood! This home is in excellent condition and it shows, from the sparkling clean interiors to the thoughtful updates throughout. You’ll immediately notice the pride of ownership, with

    Kim Simpson Thyme Real Estate Co LLC

    574 Whispering Trail, Middletown, DE 19709
  • /41

    $769,900

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    340 Ellenwood Dr, Middletown, DE 19709

    Welcome to 340 Ellenwood Drive, located in one of Middletown’s most desirable communities within the Appoquinimink School District. This prime location offers close proximity to parks, shopping, dining, and commuter routes, all while providing a strong sense of community and everyday convenience. This home features a covered front porch, perfect for enjoying the peaceful neighborhood setting.

    Eric Buck Long & Foster Real Estate, Inc.

    340 Ellenwood Dr, Middletown, DE 19709
  • /46

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,875 Sq Ft

    522 Lilac Dr, Middletown, DE 19709

    Welcome to 522 Lilac Drive, Middletown, DE — where comfort meets convenience in this beautifully maintained single-family home! Located in the desirable Longmeadow neighborhood, this spacious 4-bedroom, 2.5-bathroom detached home offers nearly 3000 square feet of thoughtfully designed living space, perfect for both everyday living and entertaining. Step inside to find a bright and airy

    David Vetri Red Brick Realty, LLC

    522 Lilac Dr, Middletown, DE 19709
  • /68

    $750,000

    • 6 Beds
    • 5 Baths
    • 4,500 Sq Ft

    1032 Applecross Dr, Middletown, DE 19709

    Welcome to 1032 Applecross Drive in the Preserve at Deep Creek. This expansive & well-appointed home is the largest in its community and offers all the high-end features and amenities you could possibly want, and a blank canvas to make your very own! Spanning over 4,500 square feet amongst three levels of living spaces, the highlights include a bright & open floorplan with 9-foot ceilings, a

    Michael McKee Long & Foster Real Estate, Inc.

    1032 Applecross Dr, Middletown, DE 19709
  • /28

    $499,900

    • 3 Beds
    • 3 Baths
    • 2,325 Sq Ft

    277 Anglesey Dr, Middletown, DE 19709

    Welcome to the highly sought-after 55+ Preserve at Deep Creek Community. This stunning home, just three years old, offers the benefits of like-new construction without the wait or disruption. The exterior is truly impressive, featuring a stone water table front, an inground irrigation system, and an extra-wide garage door leading to a spacious two-car garage. As you step inside the front door,

    Vicky Miller Patterson-Schwartz-Middletown

    277 Anglesey Dr, Middletown, DE 19709
  • /79

    $699,900

    • 5 Beds
    • 3.5 Baths
    • 3,125 Sq Ft

    119 Tuscany Dr, Middletown, DE 19709

    PARKSIDE - Welcome to 119 Tuscany Drive, an elegant and inviting residence located in the heart of Middletown and within the APPOQUINIMINK SCHOOL DISTRICT. This exquisite 5-bedroom, 3.5-bathroom home offers a harmonious blend of sophistication and comfort. Newly built in 2015 by Lifestyle Builders, this home has been lovingly maintained by its original owners. Enter the foyer to find gleaming

    Andrea Harrington Compass

    119 Tuscany Dr, Middletown, DE 19709
  • /46

    $540,000

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

    373 Northhampton Way, Middletown, DE 19709

    Say hello to this lovely home located in the tree-lined, quiet community of Willow Grove Mills, easily accessible to prestigious schools, shopping, dining, healthcare, and routes leading to the beach. The home features an open-concept living and dining room with lots of natural light and a fireplace for those cozy nights. The kitchen features an eat-in option with tall cabinets and granite

    Christian Webb Sky Realty

    373 Northhampton Way, Middletown, DE 19709
  • /27

    $989,000 Coming Soon

    • 5 Beds
    • 4.5 Baths
    • 4,600 Sq Ft

    830 Sweet Birch Dr, Middletown, DE 19709

    Coming Soon!!!!! walk out full apartment..backs to woods...Main floor primary suite.....Schell Brothers Kingfisher.....5 bedroom, 5 baths....description and pictures coming

    Ann Marie Germano Patterson-Schwartz-Middletown

    830 Sweet Birch Dr, Middletown, DE 19709
  • /26

    $439,900

    • 4 Beds
    • 2.5 Baths
    • 2,425 Sq Ft

    40 Browning Cir, Middletown, DE 19709

    Welcome to MIDDLETOWN CROSSING! The property is ready for its chance to shine again. The large footprint offering a bright and sunny breakfast nook off kitchen and the family room. Home also has both a separate formal dining and living rooms. The roomy lower level with over 1000 sq ft for any extra space needed! Home is close to plenty of shopping and dining choices.

    Dana Byrd First Coast Realty LLC

    40 Browning Cir, Middletown, DE 19709

Why Live in Middletown

Middletown, Delaware, established in 1861, offers a harmonious blend of suburban tranquility and urban conveniences. Located 60 miles south of Philadelphia, this New Castle County town is home to 25,000 residents and is celebrated for its small-town charm and welcoming community. The neighborhood features a variety of architectural styles, including Cape Cod, Victorian, and Foursquare homes, set on modest lots with simple landscaping. The grid-style streets are lined with sidewalks and leafy trees, providing ample street parking and wide roads. Families benefit from the highly rated Appoquinimink School District, which includes Silver Lake Elementary, Redding Middle School, and Middletown High School, all known for their excellent academic programs. Outdoor enthusiasts can explore the 100-acre Charles E. Memorial Park, which offers a modern playground, a dog park, paved walking trails, and a scenic lake. Silver Lake Park provides additional recreational facilities, including athletic fields, courts, and a playground. Golfers can enjoy Frog Hollow Golf Club & Restaurant. For dining, Downtown Middletown’s Main Street features Sully’s Irish Pub, La Banca for Italian cuisine, and Sweet Melissa Bakery. First State Brewing Company offers local craft beers and American fare. Shopping needs are met at Giant on Dove Run Centre Drive and the Dutch Country Farmers Market on Greenlawn Boulevard. Dove Run Shopping Center and other large retailers like Walmart, Kohl’s, and Home Depot are also nearby. Entertainment options include Westown Movies and Putters Paradise mini golf. The Appoquinimink Library on Catherine Street serves as a local resource for book lovers. While most residents rely on cars, the DART bus system provides public transportation, and Routes 1 and 71 offer easy access to nearby areas, Delaware beaches, and Philadelphia.

Home Trends in Middletown, DE

Housing Trends

Median Sale Price
$434,950
Median Single Family Sale Price
$439,900
Median Townhouse Sale Price
$430,000
Median 2 Bedroom Sale Price
$165,000
Median 1 Bedroom Sale Price
$335,000
Average Price Per Sq Ft
$238
Number of Homes for Sale
16
Last 12 months Home Sales
151
Months of Supply
1.30
Median List Price
$430,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-16%
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