Middletown Homes with Swimming Pool Amenities

Welcome to Middletown, Delaware, a charming town nestled in the heart of New Castle County. Known for its welcoming community and picturesque landscapes, Middletown offers a perfect blend of suburban tranquility and vibrant local culture. With its rich history and modern conveniences, this delightful town is an ideal place to call home.

Middletown boasts a variety of amenities, including parks, shopping centers, and top-rated schools, making it a family-friendly destination. The town's historical sites, such as the Olde Tyme Peach Festival and the annual Middletown Arts Festival, showcase its community spirit and commitment to preserving its heritage. For outdoor enthusiasts, the nearby parks and recreational areas provide ample opportunities for hiking, biking, and enjoying nature.

One of the standout features of homes in Middletown is the availability of properties with swimming pool amenities. Imagine coming home to your own private oasis, where you can unwind after a long day or host unforgettable gatherings with friends and family. Whether you prefer a luxurious in-ground pool or a charming above-ground option, there’s a variety of homes that cater to your desires for relaxation and entertainment.

With the warm summers that Delaware is known for, having a swimming pool at your residence is not just a luxury; it’s a lifestyle choice that enhances your living experience. Explore the beautiful homes in Middletown and discover the perfect property that combines comfort, style, and the joy of having your own backyard retreat. Welcome to your new home in Middletown, where every day feels like a vacation!

Newest Middletown Homes with Swimming Pool Amenities

$384,000

4 Beds ⋅ 4 Baths ⋅ DENC2110688 MLS

This Redford Interior townhome is one of the selected homes eligible for the Blenheim Cornerstone Initiative in compliance with the New Castle County MPDU program. Visit our website or NCC’s website for more details on qualifications and income requirements. ** This home is under construction. Delivery time frame should be discussed with a sales representative. Located in The Grove at Bayberry in Middletown, Delaware, The Redford blends contemporary comfort with everyday convenience in a way few homes can. Offering spacious rooms and open layouts with flexible living spaces, The Redford is thoughtfully crafted for all that want room to live, work, and unwind. From its inviting main level to its well-proportioned 4 bedrooms, every square foot is designed with livability in mind. Whether you’re hosting friends, setting up a home office, or simply enjoying a quiet evening in, this townhome adapts effortlessly to your lifestyle. What adds to The Redford's appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to life’s daily essentials like grocery store, pharmacy, dining, coffee, quick bites, and neighborhood services. The Grove is thoughtfully planned to support a connected and walkable way of living. Imagine grabbing dinner, running errands, or meeting friends without ever needing to get in the car, then returning to your dream home! Homeowners will also enjoy having their own clubhouse, pool, bocce and pickleball courts in The Grove in addition to being surrounded by miles of walking trails throughout Bayberry.

357 Edgar Degas Ln Unit #110, Middletown

$637,500

4 Beds ⋅ 4 Baths ⋅ DENC2110414 MLS

Welcome to 1023 Applecross Drive—where nearly new meets move-in ready in this sought after location of Middletown! Built in 2024 and offering 2,500 square feet of finished living space, this 4-bedroom, 3.5-bath home gives you plenty of room to spread out, gather together, entertain, and simply enjoy being home. Step inside and you'll immediately appreciate the fresh, modern feel. Luxury vinyl plank flooring, recessed lighting, and an easy-flowing layout create a space that feels comfortable and welcoming from the start. The open kitchen is a chef's dream, complete with quartz countertops, large island, and stainless-steel appliances. A convenient half bath and coat closet on the main level are small details that make everyday living just a little easier. Upstairs, the primary suite provides a comfortable place to retreat at the end of the day, complete with a private bath featuring a dual vanity and walk-in shower. Three additional bedrooms provide flexibility for guests, a home office, or hobby space. And with the laundry conveniently located on the second floor—and a washer and dryer already included—you can leave the laundry baskets upstairs where they belong! The finished basement area adds an entirely new level of living and entertaining space. Movie night may quickly become everyone's favorite night with a dedicated home theater and surround sound included. There's plenty of additional room to create the space that works for you, whether that's a game area, fitness space, home office, or a comfortable place for overnight guests. And when you're ready to get out of the house, there's plenty to enjoy without going far. Community amenities include a clubhouse, swimming pool, fitness center, and play area, while included lawn care means there's one less weekend chore competing for your time. Spend Saturday morning at the pool instead of behind the lawn mower—that sounds like a pretty good trade! At just two years young, 1023 Applecross Drive offers the appeal of newer construction without the wait. With generous living space, a finished basement, great entertaining areas, community amenities, and everyday conveniences already in place, all that's missing is someone ready to call it home. Come take a look, imagine yourself here, and see why 1023 Applecross Drive may be just the place you've been waiting for.

1023 Applecross Dr, Middletown

$499,000

3 Beds ⋅ 2 Baths ⋅ DENC2110194 MLS

***OPEN HOUSE - SUNDAY 9/13 @ 12-2pm*** Welcome to 631 Red Maple Rd. This move-in-ready home in the sought-after community of Four Seasons at Silver Maple is priced to impress and ready to welcome its new owner! Situated on a one of the BEST lots in the neighborhood, which backs to open space and the community garden, this home offers a peaceful setting with added privacy and beautiful open views! This meticulously maintained home also features valuable upgrades including a whole-house generator, irrigation system, upgraded Trex deck, and screened in addition. Meticulously maintained, this home perfectly blends comfort, style, and low-maintenance living. Featuring 3 bedrooms, 2 full bathrooms, and a two-car garage, this spacious home offers gorgeous hardwood flooring that flows from the welcoming foyer throughout the main living areas. The bright, open-concept design seamlessly connects the living room with an abundance of natural light, to the gourmet kitchen featuring upgraded cabinetry, granite countertops, all appliances included, and a convenient island perfect for casual dining and entertaining. The spacious primary suite features a generous walk-in closet and private en-suite bathroom. Just beyond the living room, the inviting screened in addition provides a peaceful place to unwind year-round while enjoying the home's premium location overlooking the open community space and garden beyond. Step outside onto the upgraded Trex deck—the perfect setting for morning coffee, outdoor dining, or entertaining family and friends. With no homes immediately behind you and views of the community's open space and garden, the backyard setting is one of the features that truly sets this property apart. The full basement offers plenty of potential for future expansion, with endless possibilities for an at-home office, workshop, fitness room, hobby area, additional living space, or abundant storage. The active and carefree lifestyle you’ve been searching for is here! Residents enjoy exceptional amenities, including a heated swimming pool, paved walking trails, pickleball courts, a fitness area, billiards room, and a beautifully appointed clubhouse with endless opportunities to stay active, socialize, and connect. Best of all, the HOA fee includes lawn care and maintenance, snow removal, and trash service—giving you more time to enjoy your home and everything this incredible community has to offer. Conveniently located near local parks, shopping, Wawa, Walgreens, the Town of Middletown, and with easy access to Routes 1 and 9 and other major roadways. If you’re looking for space, functionality, low-maintenance living, and a premium lot with a peaceful open-space setting, 631 Red Maple Rd checks all the boxes. Opportunities like this don’t come along often—schedule your showing today and discover everything this wonderful home and community have to offer!

631 Red Maple Rd, Middletown

$483,900

3 Beds ⋅ 3 Baths ⋅ DENC2110214 MLS

BETTER THAN NEW! $60K+ IN UPGRADES! Welcome to 2318 Schubert Lane! This beautifully maintained 6-year-old residence has been enhanced with more than $60,000 in upgrades and truly shows like a professionally staged builder model home. From the moment you enter, you'll appreciate the home's wonderful flow, beautiful finishes, and attention to detail throughout. The generously sized first-floor primary suite offers exceptional convenience and features a private en-suite bathroom, creating a comfortable retreat away from the main living areas. The heart of the home is the impressive gourmet kitchen, offering abundant counter space, a beautiful backsplash, gas cooking, double oven, and stainless-steel appliances. Thoughtfully designed entertaining spaces continue throughout the home, including a dedicated coffee bar and wine/beverage bar that add both function and style. Freshly painted approximately one year ago, the home features updated lighting fixtures and window treatments throughout, giving the entire residence a fresh, polished, move-in-ready feel. Every room offers something special, with upgrades and finishing touches seemingly around every corner. Step outside and discover an inviting back patio entertaining space, perfect for relaxing, entertaining guests, or enjoying an evening around the gas fire pit. Even better, the outdoor furniture and fire pit are included with the sale. The entertainment package continues indoors, with four TVs and surround sound included, making this home truly ready for its next owner to move in and enjoy. With its combination of newer construction, extensive upgrades, stylish finishes, exceptional entertaining spaces, and thoughtful details throughout, this is a home that offers something today's buyers are looking for without the wait, expense, and uncertainty of building new. Conveniently located near restaurants, shopping, major highways, and everyday amenities, 2318 Schubert Lane delivers both comfort and convenience. Why build new when you can have better than new? Come see everything this exceptional home has to offer.

2318 Schubert Ln, Middletown

$384,000

4 Beds ⋅ 4 Baths ⋅ DENC2108908 MLS

334 Edgar Degas Ln Unit #100, Middletown

$759,900

4 Beds ⋅ 3 Baths ⋅ DENC2107988 MLS

To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back charm of Delaware living, Monarch delivers the perfect balance of comfort, style, and convenience—all just minutes from Middletown’s shopping, dining, and entertainment. The Bethany is a spacious, highly customizable single-family floor plan by Schell Brothers, offering 3,028 to 6,824 sq. ft. of heated space, 4 to 8 bedrooms, and 2.5 to 6.5 bathrooms. Notable features include a courtyard-style garage, vaulted great room ceilings, and an optional first-floor owner's suite. Options include additional bedrooms, baths, and outdoor living spaces. Monarch’s HOA fee includes grass cutting on your property, curbside garbage and recycling services, common area maintenance including walking paths, landscaping, streetlights, entrance monuments, and all community amenities.

1121 Majesty Ln, Middletown

$664,900

5 Beds ⋅ 4 Baths ⋅ DENC2108390 MLS ⋅ D.R. Horton BLDG.

Move-in ready and only 3 years old, this spacious D.R. Horton two-story home offers 5 bedrooms, 3.5 bathrooms, a finished basement, two-car garage, and oversized deck. The basement features a game room with wet bar, media room, workshop or exercise room, full bathroom, and plenty of storage. The welcoming foyer includes a coat closet, while the bright front room offers enough space for both living and dining areas. The spacious kitchen features birch cabinetry, granite countertops, stainless steel appliances, a pantry, and an island with seating, and opens to the breakfast area and family room with a cozy fireplace. A powder room and first-floor laundry are conveniently located on the main level. Upstairs, the owner’s suite features two walk-in closets and an oversized ensuite bathroom, along with four additional generously sized bedrooms and a hall bathroom. The attached storage shelving in the garage will be removed prior to the new owner taking possession. The home also includes a 10-year structural warranty offered by the builder.

1245 Pimpernell Path, Middletown

$469,900

2 Beds ⋅ 2 Baths ⋅ DENC2108110 MLS

Massive Price Improvement to $469,900! Welcome to easy, low-maintenance living in the sought-after Spring Arbor 55+ community in Middletown, Delaware! Built in 2017, this beautifully maintained 1,778-square-foot ranch home offers an inviting open-concept floor plan with hardwood flooring throughout most of the main living areas and brand new carpeting in the bedrooms. The spacious kitchen flows seamlessly into the living and dining spaces, while a stunning sunroom with a cathedral ceiling fills the home with natural light and provides the perfect place to relax. The primary suite features a tray ceiling, a private full bath, and generous closet space, while a second bedroom and full bath offer comfort for guests. High-end real wood plantation shutters, a nearly $9,000 upgrade, add timeless style and elegance throughout the home. Enjoy the welcoming front porch, entertain on the low-maintenance composite deck, and appreciate the peace of mind that comes with a new HVAC system installed in 2021. Complete with a two-car garage and situated on a .17-acre lot, this exceptional home combines quality upgrades, thoughtful design, and the active lifestyle that makes Spring Arbor one of Middletown's most desirable 55+ communities.

623 Garden Gate Dr, Middletown

$423,000

2 Beds ⋅ 2 Baths ⋅ DENC2106260 MLS

Nestled among the trees in the desirable 55+ Whispering Woods community of Middletown, Delaware, this charming coastal-style villa offers the ease of single-level living with a thoughtfully designed layout and quality finishes throughout. Featuring two bedrooms and two full bathrooms, the home combines comfort and style with luxury vinyl plank, plush carpet, and tile flooring. The open floor plan creates a bright and welcoming living space, enhanced by recessed lighting in the entry, living room, and kitchen. The spacious kitchen is designed for both everyday living and entertaining, complete with a gas stove, center island, and seamless flow into the main living and dining areas. The inviting primary suite showcases an elegant tray ceiling, abundant closet space, and a private ensuite bathroom featuring a step-in shower with built-in bench and safety grab bar and a spacious vanity. A second bedroom and full bath provide comfortable accommodations for guests or a home office. An energy efficient, on-demand hot water system not only helps reduce utility costs but also provides nearly instant hot water throughout the home for added comfort and convenience. The front garden and manicured lawn add to the curb appeal of this immaculately maintained residence. Enjoy low-maintenance living while taking advantage of exceptional community amenities, including a clubhouse with a fitness center, outdoor pool, and pickleball courts. Conveniently located, this home offers the perfect blend of peaceful, tree-lined surroundings and easy access to shopping, dining, healthcare and major roadways. This is a rare opportunity to experience low-maintenance living in an attractive neighborhood designed for comfort, convenience and an active lifestyle.

1428 Whispering Woods Rd, Middletown

$565,000

2 Beds ⋅ 3 Baths ⋅ DENC2104738 MLS

****SELLER IS MOTIVATED! REASONABLE OFFERS WILL BE CONSIDERED!!**** BEAUTY & BELONGING...This is your chance to steal a home & lifestyle! Welcome home! 130 Burlina Boulevard, where exceptional living extends far beyond your front door! Thoughtfully designed for comfort and convenience, this beautifully maintained home offers an outstanding floor plan, bright and inviting living spaces, low-maintenance flooring, and three full baths to accommodate family and guests alike. The custom built private deck and fenced yard create the perfect setting for morning coffee, evening gatherings, or simply unwinding at the end of the day. What truly sets this home apart is the lifestyle that comes with it. Spend your days enjoying pickle-ball, bocce, shuffleboard, an Olympic-size pool, a well-appointed clubhouse, fitness center, scenic walking trails, and beautifully maintained grounds. Whether you’re seeking an active social calendar or peaceful moments surrounded by friends and neighbors, you’ll find it here. Level up your lifestyle in every way—at home, in the community, and in the life you’ve worked hard to create. This isn't just a move - it's a lifestyle promotion!

130 Burlina Blvd, Middletown

$649,900

4 Beds ⋅ 3 Baths ⋅ DENC2102208 MLS

Welcome to 871 Sweet Birch, a great home in the sought-after community of Parkside.... Middletown, DE. As you walk inside this home take in the beautiful hardwood floors that span into the open concept living area. The main floor open living area creates a warm and comfortable setting for all your family and entertaining needs. The kitchen area has newer appliances, granite counter tops and is open to a very large family room and eating area with a gas fireplace an abundance of windows. fireplace. The second level property boasts 4 generously sized bedrooms and 2 full bathrooms while the finished basement adds to the charm and living space of this home. You'll love the convenience of the tankless water heater providing ample hot water on demand. EXTRA features.....Water softener for the entire home, RO for drinking water (Culigan ). Beautiful white fence with Arbors on both sides installed in( 2023), basement floors upgraded with all weather vinyl floor (2023), Dishwasher upgraded to a kitchen Aid (2023) washing machine upgraded to LG (2024) beautiful installed ceiling fans ((2022) The Parkside community features a newly expanded and upgrade pool area, fitness room, tot lot, tennis court/pickle ball, and plenty of pocket parks for your enjoyment. Take a tour of this spectacular home and the beauty of Parkside!!!

871 Sweet Birch Dr, Middletown

$689,900

3 Beds ⋅ 2 Baths ⋅ DENC2093526 MLS

To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back charm of Delaware living, Monarch delivers the perfect balance of comfort, style, and convenience—all just minutes from Middletown’s shopping, dining, and entertainment. The Mayberry is a ranch home starting at 2,254 sq. ft., with 3 bedrooms, 2 baths, and a flex space. Split-bedroom design offers privacy; open kitchen with walk-in pantry flows to great room and dining. Options available for extra bedrooms, baths, and outdoor spaces. Monarch’s HOA fee includes grass cutting on your property, curbside garbage and recycling services, common area maintenance including walking paths, landscaping, streetlights, entrance monuments, and all community amenities.

2206 Early Ct, Middletown

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