Middletown Homes with Pool

Middletown Homes with Pool

Welcome to Middletown, a charming gem nestled in the heart of the United States. Known for its welcoming community and vibrant atmosphere, Middletown seamlessly blends small-town charm with modern conveniences. With a rich history and a variety of recreational activities, it’s no wonder that families and individuals alike are drawn to this delightful city.

Middletown boasts a diverse array of neighborhoods, each offering its own unique character and charm. From tree-lined streets to quaint parks, the city provides an ideal backdrop for a peaceful lifestyle. The local schools are highly regarded, making it a perfect place for families to settle down and grow. With a variety of shopping, dining, and entertainment options, residents enjoy a balanced lifestyle that caters to both relaxation and excitement.

One of the standout features of Middletown’s real estate market is the availability of stunning homes with pools. Imagine basking in the sun by your own private oasis, hosting summer barbecues, or enjoying a refreshing swim on a warm day. These homes not only provide a luxurious retreat but also enhance the overall quality of life for families and individuals seeking leisure and enjoyment right in their backyard.

Whether you’re looking for a cozy family home or a stylish retreat, Middletown has something to offer everyone. Discover the joy of living in a community that values connection, comfort, and the simple pleasures of life. Come explore Middletown, where your dream home with a pool awaits!

Newest Middletown Homes with Pool

$658,139
3 Beds ⋅ 2 Baths ⋅ DENC2111176 MLS
Discover an exceptional opportunity to embrace a luxurious lifestyle in this stunning new construction home, nestled within the exclusive Parks Edge at Bayberry, MIDDLETOWN 55+community. Set to be completed in 2026, this exquisite detached ranch-style home features three spacious bedrooms and two full bathrooms, providing ample space for relaxation and entertaining. The architectural design reflects a modern aesthetic, while the high-end construction materials promise durability and sophistication. With an expansive lot size of 0.29 acres, you'll enjoy a sense of privacy and tranquility in your own personal oasis. Step inside to discover a thoughtfully designed layout that maximizes both space and natural light. The unfinished basement presents a blank canvas, allowing you to customize it to your liking-whether it be a cozy den, a home gym, or additional storage. The attached two-car garage, complete with a garage door opener, offers convenience and security for your vehicles. As a resident of this vibrant community, you'll have access to a range of exclusive amenities, including a community clubhouse and pool that invites you to unwind and socialize with neighbors. The surrounding area is perfect for leisurely strolls, fostering a sense of camaraderie among residents who appreciate an active and engaging lifestyle. This property is not just a house; it's a place to call home, where luxury meets comfort in a welcoming environment. The meticulous attention to detail in the design and construction ensures that every corner of this residence exudes quality and style. Imagine hosting gatherings in your spacious living areas or enjoying quiet evenings on your patio, surrounded by the beauty of your new community. Don't miss the chance to be part of this extraordinary living experience. With its prime location, luxurious features, and a focus on an exclusive lifestyle, this home is poised to become a cherished retreat for those seeking the best in life. Embrace the opportunity to create lasting memories in a place that truly feels like home.

2901 Mailly Davis Ct Unit #164, Middletown
$539,000
3 Beds ⋅ 3 Baths ⋅ DENC2110072 MLS
Welcome to this well-maintained 3BR/3BA home in the desirable 55+ Spring Arbor community in Middletown. Offering approximately 3,110 square feet of living space, this home features one of the largest floor plans in the neighborhood and a thoughtfully designed layout that blends comfort, flexibility, and convenient first-floor living. Step inside to an inviting foyer with beautiful hardwood flooring that flows throughout much of the main level. The heart of the home is the spacious family room, highlighted by a soaring ceiling, abundant natural light, and a striking floor-to-ceiling stone fireplace. The open layout connects easily to the dining area and kitchen, creating a comfortable space for both everyday living and entertaining. The kitchen offers plenty of cabinetry and counter space, stainless steel appliances, recessed lighting, and a large center island. An adjoining breakfast nook provides a casual dining option, while the separate dining room is ready for larger gatherings. Additional main-level living spaces include a formal living room and a separate sitting room, offering plenty of flexibility for a home office, reading room, or quiet retreat. The spacious primary suite is conveniently located on the main level and features a large walk-in closet and a private bath with dual vanities, ceramic tile, a relaxing garden tub, and a separate tiled shower. A second bedroom and full hall bath are also located on the main level, providing an excellent setup for guests or anyone looking for the convenience of first-floor living. Just off the main living area, the bright sunroom provides a wonderful place to enjoy views of the backyard throughout the seasons. Step outside to the hardscaped patio and spacious yard, offering an inviting setting for morning coffee, outdoor dining, or simply relaxing and enjoying the outdoors. Upstairs, the home continues to offer impressive flexibility with a third bedroom, full bath, spacious loft, and a separate bonus room or office that connects to the primary suite. Whether used for guests, hobbies, a home office, or additional living space, there are plenty of options to make the second floor fit your needs. A large floored attic storage room provides an abundance of easily accessible storage and even more versatility. Outside, attractive stone and siding accents, mature landscaping, and a two-car garage add to the home's curb appeal. Spring Arbor's convenient location adjacent to Westown Town Center puts groceries, shopping, dining, and everyday conveniences just minutes from home, while still offering the comfortable residential setting of an established 55+ community. With 3 bedrooms, 3 full baths, multiple living areas, a main-level primary suite, generous storage, and flexible spaces throughout, this Spring Arbor home offers plenty of room to enjoy today with the versatility to meet your needs for years to come. MAKE THIS YOUR NEW HOME TODAY!

13 Palisade Cir, Middletown
$675,000
5 Beds ⋅ 5 Baths ⋅ DENC2111004 MLS
Modern elegance meets effortless everyday living in this beautifully appointed home in the Preserve at Deep Creek. Built in 2022 and offering more than 4,000 square feet across three finished levels, this bright and contemporary residence features five bedrooms, four and a half bathrooms, sophisticated finishes, and an exceptionally versatile floor plan. <br><br> The main level welcomes you with a dedicated home office or den and a formal dining room before opening into an expansive living space designed for both gathering and entertaining. At the heart of the home, the sleek white kitchen features an oversized quartz island, crisp white cabinetry, stainless steel appliances, a subway tile backsplash, generous workspace, and an adjoining dining area. Abundant windows fill the main living spaces with natural light and offer views outside throughout. A walk in pantry, thoughtfully placed mudroom just off the garage, and powder room add everyday convenience. <br><br> Upstairs, you will find four spacious bedrooms, three full bathrooms, a versatile loft, and the conveniently located laundry room. Each bedroom features a walk in closet, while two enjoy private ensuite bathrooms. The impressive primary suite is one of them, offering its own private bath along with dual walk in closets. The remaining two bedrooms share the third full bathroom. The loft provides another inviting space for relaxing, working, studying, or play. <br><br> The finished lower level adds even more flexibility with a fifth bedroom and fourth full bathroom, creating an ideal arrangement for guests or extended stays. Multiple additional living areas can easily accommodate a game room, movie room, recreation space, or whatever best suits your lifestyle. Unfinished space provides abundant storage or the opportunity for a home gym. <br><br> Additional highlights include epoxy flooring in the garage and excellent storage throughout the home. <br><br> Life in the Preserve at Deep Creek offers amenities just beyond your front door, including a community pool, fitness center, basketball courts, playground, gathering spaces, planned activities, and community events and food trucks throughout the year. The HOA also handles lawn cutting for the property and common areas, leaving more time to simply enjoy it all. <br><br> Conveniently located near shopping, parks, golf, and major commuter routes, and within the Appoquinimink School District, this exceptional home offers an appealing combination of space, style, convenience, and flexibility.

1018 Applecross Dr, Middletown
$495,000
4 Beds ⋅ 4 Baths ⋅ DENC2110990 MLS
Welcome to this spacious 3-bedroom, 2.5-bath end-unit townhouse in the Canal View development. Ideally positioned with generous common grounds surrounding the home, this location offers an added sense of privacy and open space that many units in the community do not have. The extended kitchen features additional cabinetry and workspace, providing plenty of room for everyday living and entertaining. Step outside to the composite deck and enjoy peaceful views of the open common land. The finished basement adds exceptional versatility with an in-law suite that includes a family room, full kitchen, full bath, and bedroom. A walk-out door provides direct access to the stamped concrete patio, offering convenient outdoor access and additional living space. With its desirable end-unit location, expanded kitchen, composite deck, open views, and flexible finished basement, this Canal View townhouse offers a unique combination of space, privacy, and functionality.

138 Margaretta Dr, Middletown
$465,500
3 Beds ⋅ 3 Baths ⋅ DENC2110802 MLS
**Move-in ready new construction townhome in idyllic 55+ community** Now is the perfect time to buy your new 3BR/2.5BA home at The Venue at Winchelsea, Middletown, DE's premiere active adult community. This move-in ready two-story townhome offers low-maintenance living with sophisticated style and thoughtful design. Enter to find a dedicated study—perfect for a home office—and a convenient first-floor laundry. The gourmet kitchen shines with modern stainless steel appliances, sleek quartz countertops, 42” cabinetry, a wall oven, and gas cooktop. The open layout flows seamlessly into the dining and living areas, with an included patio to enjoy unwinding during the upcoming spring and summer months. The first-floor owner’s suite is a peaceful retreat with a private bath and spacious walk-in closet. Upstairs, two additional bedrooms, a full bath, and a versatile loft provide comfort and privacy for guests. Schedule your private tour today!! Community Highlights: This 55+ Active Adult neighborhood features a 5,400 sq. ft. clubhouse, pickleball, tennis, bocce, swimming pool, fitness center, and more. Lawn care, snow removal, trash, and recycling are all included—leaving you free to enjoy the lifestyle you’ve been waiting for. Pictures are of model home and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. Realtor representation must be acknowledged on the first interaction with Lennar, and the agent must accompany their client on the first visit. For tours and open houses, visit the model home at 2405 Greyfriar Loop.

3152 Pett Level Dr, Middletown
$398,000
2 Beds ⋅ 2 Baths ⋅ DENC2110800 MLS
Sensational Spring Arbor Community can accept 20% under age 55, no one under 18! Beautiful 2 bedroom, 2 bath, 2 car garage, 1800 SQ FT, open floor plan, 9FT ceilings and oversized paver patio. This well maintained carriage home offers one floor living! Recent Updates New Furnace January 2026, New Garage Door Opener July 2026 and New Roof October 2025! Entering the hardwood foyer to the Living Room which opens to Dining Room and Spacious Kitchen featuring an abundant cabinets, all appliances included, tile backsplash, extended granite counter space that seats four. Opens from the kitchen is a large and sunny family room with ceiling fan, fireplace and entry door to the paver patio and back yard. Laundry is complete with washer and dryer along with a stationary sink, shelving and large closet. The primary bedroom has a generously sized walk-in closet, private bath, vanity and shower. At the other end of the home is a roomy guest/2nd bedroom, adjacent to the full hall bath. Spring Arbor is a premier 55+ Community offering a clubhouse with a spacious gathering room that has kitchen facilities, game rooms, library, fitness room, salt water outdoor swimming pool, picnic area, bocce ball and shuffleboard courts. The Roofs and Siding are maintained by the association! Great location close to major roads and walking distance to restaurants, shopping and movie theater!

264 Trellis Ln, Middletown
$476,500
3 Beds ⋅ 3 Baths ⋅ DENC2110690 MLS
Located in The Grove at Bayberry in Middletown, Delaware, The Keaton blends contemporary comfort with everyday convenience in a way few homes can. Offering spacious rooms and open layouts with flexible living spaces, The Keaton is thoughtfully crafted for all that want room to live, work, and unwind. From its inviting main level master to its well-proportioned 3 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 Novella’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, lake, pool and courts in The Grove in addition to being surrounded by miles of walking trails throughout Bayberry.

353 Edgar Degas Lane Edgar Degas Unit #108, Middletown
$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
$389,900
4 Beds ⋅ 1 Baths ⋅ VAFV2044654 MLS
This charming ranch-style home, beautifully renovated in 2018, offers a perfect blend of comfort and modern living. Nestled on a serene half-acre lot, the property features a welcoming interior with four spacious bedrooms and a thoughtfully designed layout. Enjoy the warmth of hardwood floors throughout, complemented by upgraded countertops in the eat-in kitchen, which seamlessly connects to the dining area-ideal for gatherings. The main level includes a convenient entry-level bedrooms and a luxurious walk-in shower in the bathroom. Step outside to discover a private oasis with an above-ground pool, surrounded by lush landscaping and mature trees, providing a tranquil view of the pasture and woods. The exterior is enhanced by thoughtful features such as exterior lighting and flood lights, ensuring safety and ambiance. Located in a peaceful rural setting, this home is part of a friendly community that values connection and outdoor living. Nearby parks offer recreational opportunities, while local schools are known for their commitment to education. With easy access to public services and a gravel driveway accommodating up to four vehicles, convenience is at your fingertips. This property is not just a house; it's a place to create lasting memories. Experience the joy of living in a home that combines modern amenities with the charm of nature.

1810 Chapel Rd, Middletown
$749,999
4 Beds ⋅ 3 Baths ⋅ DENC2110610 MLS
Welcome to the Village of Bayberry South! Boasting pride of ownership both inside and out, this beautifully maintained home offers the rare opportunity to enjoy a home that feels like new. This home features thoughtful upgrades and established landscaping that makes it feel like your new home. Built in 2018 and beautifully appointed with a neutral interior throughout, it provides the perfect blank canvas for your own creative touches. Situated in the Village of Bayberry South, this exceptional home is set on a premium $30,000 lot that backs to trees and open space beside the property, creating a peaceful setting with a wonderful sense of privacy. An inviting front porch and mature landscaping enhance the home's curb appeal, welcoming you into a property that has been lovingly cared for. Inside, you'll find 4 bedrooms, including a main-level primary suite with a 2-foot extension, upgraded primary bath featuring upgraded hardware, tile flooring, vanity, and shower, plus a spacious walk-in closet. The main level also offers a sunroom extension, recessed lighting, and a family room with a fireplace accented by a granite surround. The designer kitchen is a standout, featuring upgraded appliances, cabinetry with pull-out trays, and upgraded hardware. Beautiful 5-inch Hickory hardwood flooring extends through the foyer, dining room, sunroom, kitchen, and breakfast area, complemented by upgraded carpet throughout the home. Upstairs, the spacious loft includes a separate HVAC zone, along with a fourth bedroom and upgraded bath, offering a wonderful private retreat for guests or additional living space. This home includes an impressive $118,871 in builder options, reflecting the thoughtful upgrades and attention to detail throughout. The Village of Bayberry South is a distinguished 55+ community offering an elegant setting, beautiful homes, and a welcoming atmosphere. With its established streetscapes, attractive surroundings, and impressive amenities, it provides a wonderful place to enjoy the next chapter of life. The impressive clubhouse serves as the heart of the community, offering a spacious gathering room, bar, fitness center, exercise studio, billiards room, meeting room, and a beautiful outdoor patio overlooking a tranquil pond with a fire pit. A vibrant social calendar featuring clubs, events, and activities makes it easy to stay active, meet neighbors, and enjoy the lifestyle you've been looking for. Conveniently located with easy access to the brand-new Bayberry Town Center, you'll enjoy nearby shopping, restaurants, fitness centers and healthcare facilities. Come discover the pride of ownership, exceptional upgrades and stately community setting that make this Village of Bayberry South home such a wonderful place to call your own!

642 Vivaldi Dr, Middletown
$749,000
4 Beds ⋅ 3 Baths ⋅ DENC2110562 MLS
Stunning property available in the much sought after 55+ community of The Ponds at Bayberry. An opportunity to own this beautiful home for a fraction of new construction costs with upgrades and it is competitively priced for sale. A beautiful premium lot that is professionally landscaped with an underground irrigation system. This lot provides privacy with incredible views to be enjoyed from the screened porch and patio. This expanded ranch offers 4 spacious bedrooms with 3 full upgraded baths. The spacious primary suite is your personal retreat, with an ensuite bath and large walk-in closet. A fabulous gourmet chef's kitchen with a gas cook top, microwave, 2 wall ovens, vented range hood, dishwasher (2026), refrigerator (2022), upgraded cabinetry with soft close drawers, pull out drawers, beautiful granite with counter seating, upgraded stainless appliances. Featuring an open floor plan. A conveniently located mud room with newer washer and dryer leads to a full two-car garage. Full daylight walkout basement with 9ft ceilings. New sump pump (2026) and replaced the garage door cables which have a warranty. There is a whole home surge suppressor, coated concrete on the front and back porches and a whole house humidifier. This 55+ resort-style community offers luxury amenities for a low monthly HOA fee that includes landscaping, snow plowing and trash removal. There is an outdoor heated pool, pickle ball courts, tennis courts, bocce courts, and walking trails. Inside the large 10,000 sq ft clubhouse features a large community room, bar, fitness room, exercise room, billiards room, meeting rooms and a large patio overlooking one of the large outdoor ponds with a fire pit. There is an active social scene full of activities for many interests.

2744 Van Cliburn Cir, Middletown
Start Your Search