20

Middletown Homes for Sale with Pool

Section Image Section Image
  • 51 Springmill Dr, Middletown, DE 19709
    51 Springmill Dr, Middletown, DE 19709
    51 Springmill Dr, Middletown, DE 19709
    /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
  • 3 W Kilts Ln, Middletown, DE 19709
    3 W Kilts Ln, Middletown, DE 19709
    3 W Kilts Ln, Middletown, DE 19709
    /57

    $695,000

    • 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
  • 253 Wickerberry Dr, Middletown, DE 19709
    253 Wickerberry Dr, Middletown, DE 19709
    253 Wickerberry Dr, 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
  • 56 Willow Grove Mill Dr, Middletown, DE 19709
    56 Willow Grove Mill Dr, Middletown, DE 19709
    56 Willow Grove Mill Dr, Middletown, DE 19709
    /62

    $689,000

    • 4 Beds
    • 3.5 Baths
    • 3,900 Sq Ft

    56 Willow Grove Mill Dr, Middletown, DE 19709

    Welcome to this inviting and beautifully maintained 4 bedroom, 3.5 bath home in the heart of the Town of Middletown, located in the award winning Appoquinimink School District. Lovingly cared for by its original owners, this home features an open floor plan with hardwood flooring throughout the first floor, a bright kitchen with a large island & pantry and an attached side-facing two-car garage.

    Christen McDade Thyme Real Estate Co LLC

    56 Willow Grove Mill Dr, Middletown, DE 19709
  • 152 Tywyn Dr, Middletown, DE 19709
    152 Tywyn Dr, Middletown, DE 19709
    152 Tywyn 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
  • 629 Spring Hollow Dr, Middletown, DE 19709
    629 Spring Hollow Dr, Middletown, DE 19709
    629 Spring Hollow Dr, Middletown, DE 19709
    /78

    $699,000

    • 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
  • 213 Casper Way, Middletown, DE 19709
    213 Casper Way, Middletown, DE 19709
    213 Casper Way, Middletown, DE 19709
    /80

    $649,900

    • 5 Beds
    • 3.5 Baths
    • 4,075 Sq Ft

    213 Casper Way, Middletown, DE 19709

    Welcome to 213 Casper Way, where your dream home is waiting with open arms. Located on the 4th hole of the golf course at Frog Hollow Golf Club, 213 Casper Way is abundant with upgrades inside and out, a truly move-in ready home with over 4,000 sqft for your family to enjoy. Upon arrival, this stunning corner lot with well maintained lawn and landscaping greets you, and the traditional front

    Megan Aitken Keller Williams Realty

    213 Casper Way, Middletown, DE 19709
  • 900 S Vernon St, Middletown, DE 19709
    900 S Vernon St, Middletown, DE 19709
    900 S Vernon St, 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
  • 66 Springmill Dr, Middletown, DE 19709
    66 Springmill Dr, Middletown, DE 19709
    66 Springmill Dr, Middletown, DE 19709
    /54

    $485,000

    • 2 Beds
    • 3 Baths
    • 2,350 Sq Ft

    66 Springmill Dr, Middletown, DE 19709

    Welcome to this beautifully maintained Dunbar model, located in the highly desirable active adult community of Springmill in Middletown, Delaware. This spacious home features 2 bedrooms, 3 full baths, a newer HVAC and a versatile loft, offering both comfort and functionality and all situated on a premium wooded lot. Enjoy low-maintenance living with lawn care, garden upkeep, and snow removal all

    Vicky Miller Patterson-Schwartz-Middletown

    66 Springmill Dr, Middletown, DE 19709
  • 417 Morning Glory Ln, Middletown, DE 19709
    417 Morning Glory Ln, Middletown, DE 19709
    417 Morning Glory Ln, Middletown, DE 19709
    /26

    $435,000

    • 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
  • 343 Daylilly Way, Middletown, DE 19709
    343 Daylilly Way, Middletown, DE 19709
    343 Daylilly Way, 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
  • 577 Whispering Trail, Middletown, DE 19709
    577 Whispering Trail, Middletown, DE 19709
    577 Whispering Trail, Middletown, DE 19709
    /53

    $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
  • 574 Whispering Trail, Middletown, DE 19709
    574 Whispering Trail, Middletown, DE 19709
    574 Whispering Trail, Middletown, DE 19709
    /61

    $475,000

    • 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
  • 340 Ellenwood Dr, Middletown, DE 19709
    340 Ellenwood Dr, Middletown, DE 19709
    340 Ellenwood Dr, 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
  • 439 Goodwick Dr, Middletown, DE 19709
    439 Goodwick Dr, Middletown, DE 19709
    439 Goodwick Dr, Middletown, DE 19709
    /20

    $420,000

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

    439 Goodwick Dr, Middletown, DE 19709

    **Back on the Market! This beautiful home in now available again due to no fault of the seller. Don't miss your change to own this wonderful home!** Welcome to this charming 3-bedroom, 3.5-bath townhouse with a one-car garage in the desirable Deep Creek community! The main level boasts a spacious living room that flows into the dining area, complete with a slider leading to the

    Christina Quinn Empower Real Estate, LLC

    439 Goodwick Dr, Middletown, DE 19709
  • 1032 Applecross Dr, Middletown, DE 19709
    1032 Applecross Dr, Middletown, DE 19709
    1032 Applecross 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
  • 277 Anglesey Dr, Middletown, DE 19709
    277 Anglesey Dr, Middletown, DE 19709
    277 Anglesey 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
  • 119 Tuscany Dr, Middletown, DE 19709
    119 Tuscany Dr, Middletown, DE 19709
    119 Tuscany 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
  • 830 Sweet Birch Dr, Middletown, DE 19709
    830 Sweet Birch Dr, Middletown, DE 19709
    830 Sweet Birch Dr, 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
  • 107 Gazebo Ln, Middletown, DE 19709
    107 Gazebo Ln, Middletown, DE 19709
    107 Gazebo Ln, Middletown, DE 19709
    /3

    $409,900 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,675 Sq Ft

    107 Gazebo Ln, Middletown, DE 19709

    Gary Bright Tesla Realty Group, LLC

    107 Gazebo Ln, Middletown, DE 19709
Delaware Middletown Middletown

Homes for Sale with Pool in Middletown, Middletown

Learn more about living in Middletown

Home Trends in Middletown, DE

On average, homes in Middletown, DE sell after 33 days on the market compared to the national average of 51 days. The median sale price for homes in Middletown, DE over the last 12 months is $420,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$420,000
Median Single Family Sale Price
$439,950
Median Townhouse Sale Price
$440,000
Median 2 Bedroom Sale Price
$267,500
Average Price Per Sq Ft
$193
Number of Homes for Sale
56
Last 12 months Home Sales
230
Months of Supply
2.90
Median List Price
$439,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home

In Middletown, there are currently 20 homes for sale with pool amenities, providing relaxation and recreation right at home. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer a refreshing retreat and a space for leisure. Alternatively, buyers can explore properties with access to community pools, providing a convenient and communal space for recreation and socializing. Whether you prefer a private pool or the convenience of a community pool, explore the selection of homes for sale with a pool in Middletown, Middletown and find your perfect slice of paradise.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group