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Middletown, DE Homes for Sale with Pool

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  • 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
  • 237 Trellis Ln, Middletown, DE 19709
    237 Trellis Ln, Middletown, DE 19709
    237 Trellis Ln, Middletown, DE 19709
    /32

    $459,900 Open House 8/17

    • 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
  • 206 Northern Oak St Unit 36495347, Middletown, DE 19709
    206 Northern Oak St Unit 36495347, Middletown, DE 19709
    206 Northern Oak St Unit 36495347, Middletown, DE 19709
    /22

    $499,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,780 Sq Ft

    Eastwood Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Elegant foyer entry welcoming friends and family. Generous ceiling height for maximum natural light and openness. Open, single-story home design boasting dream kitchen with island. Spacious great room with optional fireplace creating relaxing atmosphere. Secluded owner's suite with oversized closet and private bath.

    Builder Photo

    K. Hovnanian Homes

    Builder

    206 Northern Oak St Unit 36495347, Middletown, DE 19709
  • 206 Northern Oak St Unit 36451018, Middletown, DE 19709
    206 Northern Oak St Unit 36451018, Middletown, DE 19709
    206 Northern Oak St Unit 36451018, Middletown, DE 19709
    /19

    $548,900 New Construction

    • 2 Beds
    • 2 Baths
    • 2,080 Sq Ft

    Killarney I Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Cozy porch welcoming guests to your home. Inviting dining room, ideal for hosting dinner parties. Kitchen with large island and corner pantry. Great room with optional HovHub and wet bar. Owner's suite with private bath and oversized walk-in closet. Three-car tandem garage with additional storage. Opt. loft for additional living with bed and full bath.

    Builder Photo

    K. Hovnanian Homes

    Builder

    206 Northern Oak St Unit 36451018, Middletown, DE 19709
  • 206 Northern Oak St Unit 36472277, Middletown, DE 19709
    206 Northern Oak St Unit 36472277, Middletown, DE 19709
    206 Northern Oak St Unit 36472277, Middletown, DE 19709
    /19

    $574,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,462 Sq Ft

    Mont Blanc Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Spacious, inviting front entry porch. Kitchen with expansive island and dual pantries. Open great room and dining area ideal for entertaining. Convenient secondary bedrooms for guests. Owner's suite with private bath and walk-in closet. Direct access to laundry room keeping your home tidy. Three-car tandem garage with additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    206 Northern Oak St Unit 36472277, Middletown, DE 19709
  • 206 Northern Oak St Unit 36472485, Middletown, DE 19709
    206 Northern Oak St Unit 36472485, Middletown, DE 19709
    206 Northern Oak St Unit 36472485, Middletown, DE 19709
    /13

    $583,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,457 Sq Ft

    Lewes Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Open and airy kitchen with pantry and oversized island. Cozy dining area adjacent to kitchen for enjoying casual meals. Luxurious owner's suite with dual walk-in closets and large bath. Hall walk-in closet for additional storage. Direct access to laundry room from garage. Covered porch to enjoy evenings outdoors.

    Builder Photo

    K. Hovnanian Homes

    Builder

    206 Northern Oak St Unit 36472485, Middletown, DE 19709
  • 540 Swansea Dr, Middletown, DE 19709
    540 Swansea Dr, Middletown, DE 19709
    540 Swansea 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
  • 3028 Barber Ln, Middletown, DE 19709
    3028 Barber Ln, Middletown, DE 19709
    3028 Barber Ln, Middletown, DE 19709
    /39

    $580,000

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

    3028 Barber Ln, Middletown, DE 19709

    Luxury Ranch Home in Parks Edge at Bayberry South.Welcome to 3028 Barber Lane—a nearly new, upgraded ranch home on a premium corner lot in the premier 55+ community of Parks Edge. Enjoy a corner lot with open greenery space in the front and back along with true one-floor living offering everything, including laundry, on the main level.Luxury vinyl plank flooring runs through the open

    Daniel Fish Keller Williams Realty Wilmington

    3028 Barber Ln, Middletown, DE 19709
  • 445 Georgiana Dr, Middletown, DE 19709
    445 Georgiana Dr, Middletown, DE 19709
    445 Georgiana Dr, Middletown, DE 19709
    /60

    $579,000

    • 5 Beds
    • 3.5 Baths
    • 2,900 Sq Ft

    445 Georgiana Dr, Middletown, DE 19709

    Welcome to your next chapter in comfort and convenience! This spacious five-bedroom, three-and-a-half-bath home offers a layout designed for both everyday living and entertaining. The open floor plan connects the kitchen, dining, and living areas, making gatherings easy and enjoyable—whether you’re hosting game night or just making pancakes on a Sunday morning.Downstairs, the finished

    Tiny Reamer RE/MAX 1st Choice - Middletown

    445 Georgiana 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
  • 4602 Bogart Ln, Middletown, DE 19709
    4602 Bogart Ln, Middletown, DE 19709
    4602 Bogart Ln, Middletown, DE 19709
    /31

    $582,000

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

    4602 Bogart Ln, Middletown, DE 19709

    Welcome to the Ponds at Bayberry, a 55+ community in Middletown Delaware. Offering a 2-1/2 year young Kelly Americana with 3 beds and 2 baths, this home has an open floor plan which features LVP throughout the main living areas, 9’ ceilings, a great room with a high-efficiency gas fireplace, dining area and a designer kitchen that boasts 42" cabinets, quartz countertops, combo in-wall microwave

    Helen Garton EXP Realty, LLC

    4602 Bogart Ln, Middletown, DE 19709
  • 1429 Whispering Woods Rd, Middletown, DE 19709
    1429 Whispering Woods Rd, Middletown, DE 19709
    1429 Whispering Woods Rd, Middletown, DE 19709
    /49

    $454,900

    • 2 Beds
    • 2 Baths
    • 2,025 Sq Ft

    1429 Whispering Woods Rd, Middletown, DE 19709

    Welcome to this warm and inviting interior carriage-style home with a quaint courtyard leading to your front door, located in a vibrant 55+ community in the desirable neighborhood of Whispering Woods. This home offers one floor living with 2 bedrooms & 2 full baths on the main level along with a versatile loft space highlighted by stylish ceiling molding that adds a truly custom touch. The

    Terra King RE/MAX 1st Choice - Middletown

    1429 Whispering Woods Rd, 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
  • 2510 Chopin Dr, Middletown, DE 19709
    2510 Chopin Dr, Middletown, DE 19709
    2510 Chopin Dr, Middletown, DE 19709
    /31

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    2510 Chopin Dr, Middletown, DE 19709

    Showcase 3-bedroom, 2.1-bathroom town home in Bayberry South, one of the most sought after Active Adult Communities in New Castle County. This stunning home boasts a first-floor primary bedroom with a en suite bath and walk-in with a Elfa organizer. The open floor plan is loaded with custom features, including a gourmet kitchen with quartz counters, stainless steel appliances, wall oven, custom

    George Manolakos Patterson-Schwartz-Brandywine

    2510 Chopin Dr, Middletown, DE 19709
  • 404 Paper Birch St, Middletown, DE 19709
    404 Paper Birch St, Middletown, DE 19709
    404 Paper Birch St, Middletown, DE 19709
    /35

    $570,000

    • 2 Beds
    • 2 Baths
    • 1,825 Sq Ft

    404 Paper Birch St, Middletown, DE 19709

    Why wait for new construction when you can have it all—right now? This impeccably maintained and neutral designed 2-bedroom, 2-bath home in the Baymont Farms 55+ community could be yours without the hassle of new construction. Skip the dust and delays and move right in! From the moment you arrive, the welcoming front porch sets the tone. The open-concept living space is anchored by a gourmet

    stephanie kelly Patterson-Schwartz - Greenville

    404 Paper Birch St, 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

    $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
  • 240 Armata Dr, Middletown, DE 19709
    240 Armata Dr, Middletown, DE 19709
    240 Armata Dr, Middletown, DE 19709
    /48

    $599,000

    • 5 Beds
    • 4.5 Baths
    • 3,600 Sq Ft

    240 Armata Dr, Middletown, DE 19709

    Enjoy nearly 3,600 sq ft of living space—an outstanding value at $599K in the 5-bedroom market—nestled near the end of a quiet cul-de-sac in the sought-after Appoquinimink School District, with key comparables ranging from $579K to $605K. A thoughtfully designed, 5 bed, 4.5 bath, 3,600 sq. ft modern home located near the end of a quiet cul-de-sac, where peace, privacy, and convenience

    Veta McCarther VRA Realty

    240 Armata Dr, Middletown, DE 19709
  • 5924 Ravel Ln, Middletown, DE 19709
    5924 Ravel Ln, Middletown, DE 19709
    5924 Ravel Ln, Middletown, DE 19709
    /35

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,175 Sq Ft

    5924 Ravel Ln, Middletown, DE 19709

    Welcome to your new home in Bayberry! This 55+ retirement community offers lots of activities and amenities to its residents, including clubhouse, gym, and pool! The home was built in 2021 and has been well kept by its owner so you can essentially buy new construction without the wait! As you enter, you'll be greeted by an open living space with room for a seating area and dining table. The

    Megan Toll KW Empower

    5924 Ravel Ln, Middletown, DE 19709
  • 5910 Ravel Ln, Middletown, DE 19709
    5910 Ravel Ln, Middletown, DE 19709
    5910 Ravel Ln, Middletown, DE 19709
    /59

    $438,000

    • 2 Beds
    • 2.5 Baths
    • 2,025 Sq Ft

    5910 Ravel Ln, Middletown, DE 19709

    55+ Community. Enter a bright, open floor plan with gleaming hardwood floors. Entertain friends and family in your gourmet kitchen complete with stainless steel appliances, granite countertops, flat top range, double oven and oversized island. First floor laundry and master bedroom, with a full bathroom, offers much convenience. The main floor also has a powder room, storage closet and garage

    Margaret Poisson Century 21 Gold Key-Dover

    5910 Ravel Ln, Middletown, DE 19709
  • 216 Baldy Ln, Middletown, DE 19709
    216 Baldy Ln, Middletown, DE 19709
    216 Baldy Ln, Middletown, DE 19709
    /41

    $654,900

    • 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
  • 1512 Lesterfield Way, Middletown, DE 19709
    1512 Lesterfield Way, Middletown, DE 19709
    1512 Lesterfield Way, Middletown, DE 19709
    /33

    $594,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft

    1512 Lesterfield Way, Middletown, DE 19709

    Vaulted ceiling unites great room, kitchen & dining area.Winstead Quill cabinets, floating shelves & pendant lighting in kitchen.Fireplace adds cozy character to the spacious great room.Screened deck spans the width of the dining area & great room.Primary suite includes bonus space ideal for a sitting room.Dual sinks in primary bath offer everyday convenience.

    Builder Photo

    K. Hovnanian Homes

    Builder

    1512 Lesterfield Way, Middletown, DE 19709
  • 414 Highland St Unit 138, Middletown, DE 19709
    414 Highland St Unit 138, Middletown, DE 19709
    414 Highland St Unit 138, Middletown, DE 19709
    /21

    $449,500 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,794 Sq Ft

    414 Highland St Unit 138, Middletown, DE 19709

    IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Annandale Carriage Town Home. This interior first floor owner suite comes w/a 2nd bedroom, loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community offers trails, in ground pool w/lounge areas, open clubhouse featuring exercise room, billiards, gathering space, full

    Lindsay Shaffer RE/MAX Elite

    414 Highland St Unit 138, Middletown, DE 19709
  • 1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    /36

    $573,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft

    Aberdeen II Plan at K. Hovnanian’s® Four Seasons at Pennfield, Middletown, DE 19709

    Spacious kitchen with island and ample counterspace.Sunlit great room adjacent to kitchen and dining area.Relaxing primary suite with sitting room and luxurious bath.HovHub makes for a great home office or study space.Expansive covered patio, perfect for dining al fresco.HovHall with closet and access to 2-car garage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
  • 1415 Pennfield Dr Unit 36479735, Middletown, DE 19709
    1415 Pennfield Dr Unit 36479735, Middletown, DE 19709
    1415 Pennfield Dr Unit 36479735, Middletown, DE 19709
    /12

    $593,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,349 Sq Ft

    Morse Plan at K. Hovnanian’s® Four Seasons at Pennfield, Middletown, DE 19709

    Welcoming foyer leading to private home office.HovHall with convenient valet leading to laundry room.Spacious great room with vaulted ceiling and large windows.Kitchen with corner pantry and large island.Dining area with sliding door to covered patio.Secluded primary suite with large sitting room.Primary bath with large shower and walk-in closet.

    Builder Photo

    K. Hovnanian Homes

    Builder

    1415 Pennfield Dr Unit 36479735, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041416, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041416, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041416, Middletown, DE 19709
    /13

    $440,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,968 Sq Ft

    Beacon II Plan at Venue at Winchelsea 55+ - Winchelsea Carriages, Middletown, DE 19709

    This two-story home showcases a luxurious and comfortable design, hosting an open-concept floorplan for easy entertaining and two bedrooms on the first level. The expansive owner’s suite is nestled into a back corner for optimal privacy, featuring an en-suite bathroom and walk-in closet. Upstairs, a versatile loft area provides shared living on the second floor, next to a spacious storage room.

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041416, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041415, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041415, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041415, Middletown, DE 19709
    /19

    $441,190 New Construction

    • 2 Beds
    • 2 Baths
    • 1,965 Sq Ft

    Astor II Plan at Venue at Winchelsea 55+ - Winchelsea Carriages, Middletown, DE 19709

    This two-story home is designed to offer optimal comfort and luxury. A secondary bedroom and full-sized bathroom can be found off the foyer, leading to an open-concept floorplan combining the kitchen with the dining and living areas. A luxurious owner’s suite at the back of the home features an en-suite bathroom and generous walk-in closet. Upstairs is a multifunctional loft, perfect for

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041415, Middletown, DE 19709
  • 204 Baldy Ln Unit CAYOT, Middletown, DE 19709
    204 Baldy Ln Unit CAYOT, Middletown, DE 19709
    204 Baldy Ln Unit CAYOT, Middletown, DE 19709
    /40

    $579,000 Open Sat 11AM - 5PM

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

    204 Baldy Ln Unit CAYOT, Middletown, DE 19709

    Welcome to the Cayot Model, in the desirable 55+ community of Traditions at Whitehall. This charming 3-bedroom home has a great open concept floor plan which offers all one floor living and a welcoming dining room and great room upon entry. At the rear of the home, you will find the luxurious owner's suite complete with walk-in closet and an en-suite bath, including a 5-foot tile shower. With a

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit CAYOT, Middletown, DE 19709
  • 204 Baldy Ln Unit CHELSEA, Middletown, DE 19709
    204 Baldy Ln Unit CHELSEA, Middletown, DE 19709
    204 Baldy Ln Unit CHELSEA, Middletown, DE 19709
    /11

    $599,000 Open Sat 11AM - 5PM

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft

    204 Baldy Ln Unit CHELSEA, Middletown, DE 19709

    Introducing the CHELSEA Model, to be built in the highly desirable 55+ community of Traditions at Whitehall. This thoughtfully designed 3-bedroom, 2-bath home features an open-concept floor plan, with a spacious foyer, formal dining area, and a large great room that flows into the kitchen perfect for entertaining. The Owner’s Suite includes a walk-in closet and an en-suite bath with a double

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit CHELSEA, Middletown, DE 19709
  • 420 Highland St Unit 141 ALRICH CARRIAGE, Middletown, DE 19709
    420 Highland St Unit 141 ALRICH CARRIAGE, Middletown, DE 19709
    420 Highland St Unit 141 ALRICH CARRIAGE, Middletown, DE 19709
    /3

    $455,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,794 Sq Ft

    420 Highland St Unit 141 ALRICH CARRIAGE, Middletown, DE 19709

    IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - ALRICH Carriage Town Home. First floor master comes w/a 2nd bedroom & loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community also offers trails, in ground pool w/lounge areas, open clubhouse featuring exercise room, billiards, gathering space, full kitchen and a

    Lindsay Shaffer RE/MAX Elite

    420 Highland St Unit 141 ALRICH CARRIAGE, Middletown, DE 19709
  • 830 Sweet Birch Dr, Middletown, DE 19709
    830 Sweet Birch Dr, Middletown, DE 19709
    830 Sweet Birch Dr, Middletown, DE 19709
    /89

    $989,000

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

    830 Sweet Birch Dr, Middletown, DE 19709

    Welcome Home to 830 Sweet Birch Drive, located in the desirable PARKSIDE community in Middletown DE. This stunning home is a KINGFISHER Schell Brothers model has upgrades galore. This home is located on a wooded lot with one of the largest yard that is fully fenced in. A true walkout with a full apartment to welcome the extended family to live with you. Lets go back to the front of this home

    Ann Marie Germano Patterson-Schwartz-Middletown

    830 Sweet Birch Dr, Middletown, DE 19709
  • 810 Ashby Dr, Middletown, DE 19709
    810 Ashby Dr, Middletown, DE 19709
    810 Ashby Dr, Middletown, DE 19709
    /65

    $949,900

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

    810 Ashby Dr, Middletown, DE 19709

    Welcome to 810 Ashby Drive, an exquisite estate in the prestigious Ashby’s Place community. This expansive 5-bedroom, 5.5-bathroom Aspen II model by K. Hovnanian offers over 5,000 sq ft of living space, thoughtfully designed for comfort, entertaining, and modern family living.From the moment you step inside, you’re greeted by a dramatic two-story foyer, sweeping hardwood staircase, and rich

    Nakisha Powell-Jones EXP Realty, LLC

    810 Ashby Dr, Middletown, DE 19709
  • 448 Spring Hollow Dr, Middletown, DE 19709
    448 Spring Hollow Dr, Middletown, DE 19709
    448 Spring Hollow Dr, 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
  • 48 Springmill Dr, Middletown, DE 19709
    48 Springmill Dr, Middletown, DE 19709
    48 Springmill 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
  • 525 Contemplation Way, Middletown, DE 19709
    525 Contemplation Way, Middletown, DE 19709
    525 Contemplation Way, Middletown, DE 19709
    /27

    $482,900

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

    525 Contemplation Way, Middletown, DE 19709

    Welcome to 525 Contemplation Way, nestled in the highly sought-after 55+ community of Whispering Woods in Middletown, Delaware! This beautiful 3 bedroom, 2 full bathroom maintained home offers low-maintenance living with all the benefits of an active, resort-style lifestyle. Whether you're looking to downsize or embrace a vibrant new chapter, this home and community check every box. Located just

    Eric Buck Long & Foster Real Estate, Inc.

    525 Contemplation Way, Middletown, DE 19709
  • 1381 Pole Bridge Rd, Middletown, DE 19709
    1381 Pole Bridge Rd, Middletown, DE 19709
    1381 Pole Bridge Rd, Middletown, DE 19709
    /44

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,169 Sq Ft

    1381 Pole Bridge Rd, Middletown, DE 19709

    Motivated Seller! Here it is, your own piece of ground with a whole lot of extras. 1381 Pole Bridge Road offers nearly 8 acres with a pole building, in-ground heated pool, and 3,619 square foot home in Appo School District. This property offers privacy and serenity rarely found New Castle County. The home features and open concept layout with kitchen, dining, and family room flowing together on

    Travis L. Dorman RE/MAX Elite

    1381 Pole Bridge Rd, 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
  • 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
  • 417 Morning Glory Ln, Middletown, DE 19709
    417 Morning Glory Ln, Middletown, DE 19709
    417 Morning Glory Ln, 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
  • 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
    /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

Showing Results 1 - 40, Page 1 of 3

Delaware New Castle County Middletown

Homes for Sale with Pool in Middletown, DE

Home Trends in Middletown, DE

On average, homes in Middletown, DE sell after 67 days on the market compared to the national average of 70 days. The median sale price for homes in Middletown, DE over the last 12 months is $510,000, down 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$510,000
Median Single Family Sale Price
$649,947
Median Townhouse Sale Price
$454,900
Median 2 Bedroom Sale Price
$275,000
Average Price Per Sq Ft
$218
Number of Homes for Sale
31
Last 12 months Home Sales
385
Months of Supply
1.00
Median List Price
$519,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-6%
How to Buy a Home How to Finance a Home How to Sell a Home

In Middletown, there are currently 85 homes for sale with a pool, providing a refreshing retreat and a space for leisure. 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 recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Middletown, DE and discover your ideal residence.

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