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

$495,000

2 Beds ⋅ 2 Baths ⋅ DENC2108110 MLS

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

$675,000

6 Beds ⋅ 5 Baths ⋅ DENC2107494 MLS

Welcome to 1032 Applecross Drive, an exceptional residence in Middletown's highly sought-after Preserve at Deep Creek, where modern luxury, thoughtful design, and incredible space come together in one unforgettable home. Built in 2022 and offering over 4,450 square feet of beautifully finished living space, this rare opportunity features 6 bedrooms and 5 full bathrooms—a combination seldom available at this price point. From the moment you arrive, impressive curb appeal sets the tone. Stone accents, manicured landscaping, and a spacious two-car garage create a warm welcome before you even step inside. Fresh paint and luxury vinyl plank flooring immediately showcase the home's modern elegance, while the expansive layout offers flexibility for every stage of life. Just off the foyer, a private main-level bedroom suite with a walk-in closet and adjoining full bath creates the perfect retreat for guests, multigenerational living, or a quiet home office. Across the hall, the formal dining room is ready to host everything from holiday celebrations to intimate dinner parties before opening into the true heart of the home. Designed for gathering, the expansive family room is filled with natural light from oversized windows and flows effortlessly into a stunning open-concept kitchen that was built to impress. Crisp white cabinetry, gleaming quartz countertops, a timeless tile backsplash, upgraded appliances, and an oversized center island create a space that is as beautiful as it is functional. Just beyond, a custom butler's pantry and prep area, an oversized walk-in pantry, and abundant storage make everyday living remarkably convenient. Upstairs, a spacious loft offers the perfect second living area—ideal for movie nights, a playroom, homework space, or additional office. The conveniently located second-floor laundry room adds even more practicality to this thoughtfully designed floor plan. The luxurious primary suite is a true sanctuary, featuring two walk-in closets and a spa-inspired ensuite with dual vanities, a beautifully tiled walk-in shower with bench seating, and a private water closet. A second bedroom enjoys its own private ensuite and walk-in closet, while two additional generously sized bedrooms share a beautifully appointed hall bath, providing comfort and privacy for family and guests alike. The finished basement extends the home's versatility even further. Whether you envision a recreation room, home theater, fitness studio, or game room, this expansive lower level delivers. It also includes a sixth bedroom with an egress window and closet, a full bathroom with a walk-in shower, and generous unfinished storage space to keep everything organized. Beyond your front door, The Preserve at Deep Creek offers a lifestyle as impressive as the home itself. Residents enjoy beautifully maintained open green spaces, lawn care and landscaping services, and planned amenities including a clubhouse, fitness center, swimming pool, sports courts, and playgrounds. Directly across the street, Charles Price Memorial Park provides even more opportunities for recreation and outdoor enjoyment. Perfectly positioned in the heart of Middletown, you'll enjoy quick access to everything the area has to offer, including Middletown's vibrant Main Street, Silver Lake Park, Charles Price Memorial Park, The Everett Theatre, Dutch Country Farmers Market, countless restaurants, boutique shopping, and everyday conveniences. Nearby Route 1, Route 301, and Route 896 make commuting to Wilmington, Newark, Dover, and beyond effortless. Offering the rare combination of 6 bedrooms, 5 full bathrooms, over 4,450 finished square feet, modern 2022 construction, and an exceptional location, this home presents an incredible opportunity to own one of the area's most spacious and thoughtfully designed residences. Homes that offer this much space, flexibility, and value are exceptionally hard to find. Schedule your private showing today!

1032 Applecross 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

$445,000

3 Beds ⋅ 3 Baths ⋅ DENC2104592 MLS

Welcome to 376 Goodwick Drive in the Highly Desirable Preserve at Deep Creek Community in Middletown! Built in 2020, This Beautifully Maintained Townhome Offers 3 Bedrooms, 2.5 Bathrooms, and Approximately 2,575 Square Feet of Thoughtfully Designed Living Space. Step Inside to an Open-Concept Floor Plan Filled With Natural Light, Creating the Perfect Setting for Both Everyday Living and Entertaining. The Spacious Kitchen Flows Seamlessly into the Dining and Living Areas, While the Finished Basement Provides Flexible Space for a Home Office, Media Room, Fitness Area, or Playroom. Upstairs, the Generously Sized Primary Suite Features a Walk-In Closet and Private En-Suite Bath, Complemented by Two Additional Bedrooms and a Full Bathroom. Enjoy a Low-Maintenance Lifestyle With HOA Services That Include Common Area Maintenance, Lawn Maintenance, Snow Removal, and Access to Outstanding Community Amenities. Residents of The Preserve at Deep Creek Have Access to a Swimming Pool, Fitness Center, Clubhouse, Community Center, Recreational Center, Basketball Courts, Billiard Room, Meeting Room, Party Room, Picnic Area, Dog Park, Tot Lots/Playground, and Beautifully Maintained Common Grounds, Offering Something for Every Lifestyle. A One-Car Attached Garage Adds Everyday Convenience, While the Home's Location Within the Highly Sought-After Appoquinimink School District Places You Just Minutes from Shopping, Dining, Parks, and Major Commuting Routes. This Move-In-Ready Home Offers the Perfect Combination of Comfort, Convenience, Modern Living, and Exceptional Community Amenities. Don't Miss Your Opportunity to Own in One of Middletown's Most Popular Communities!

376 Goodwick Dr, Middletown

$590,000

2 Beds ⋅ 3 Baths ⋅ DENC2104738 MLS

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

$411,000

2 Beds ⋅ 2 Baths ⋅ DENC2098306 MLS

New Garage Door Opener Installed July 2026. New Furnace January 2026. New Roof October 2025. What More Does Anyone Need! This townhouse gem is the shortest drive to all Middletown shops & restaurants! Monthly HOA fee and $2K Initial Contribution covers replacement and insurance of the roof, siding, driveway, interior (builder specs) and more - all that the responsibility of the HOA (that's what you get for the HOA contribution(s)). Also community private heated salt water pool. Driveway sealed this summer by the HOA. This cozy Townhome is nestled in THE BEST Community of the Middletown area, SPRING ARBOR (no one under 18 may reside more than 30 days). Location, Location, Location! Nestled in the charming Spring Arbor community, conveniently close to all Middletown has to offer, this delightful twin/semi-detached residence offers a serene retreat designed for those seeking a vibrant yet peaceful lifestyle. Built in 2007, this home boasts a spacious 1,800 square feet of living space, providing ample room for relaxation and entertaining. As you step inside, you'll be greeted by an inviting atmosphere with a gas fireplace - perfect for cooler evenings. The layout allows for personal touches to create a space that feels like home. With a new roof, new furnace, new garage door opener and owner-upgraded granite countertop, you can live worry-free - the HOA insurance covers the exterior and interior builder-grade installations - that is worth something. The home's attached garage and driveway provide parking options and shelter from the weather. Lightly touched, almost-new furnishings are negotiable upon request. The move-in ready condition of the property ensures that you can quickly start enjoying all that this community has to offer. Spring Arbor is more than just a place to live; it's a lifestyle. The home's convenient location close to the Spring Arbor Clubhouse allows quick, easy access in mere minutes via a short walk without getting in and out of the car. The Clubhouse is larger than others and easily rented for your family & friends events. Social activities & gaming weekly, also group trips. The community is thoughtfully designed with a variety of amenities that cater to an active and engaging lifestyle. Residents can enjoy the heated outdoor salted swimming pool, perfect for a refreshing dip, or gather with friends in the clubhouse for games and social events. The fitness center's exercise room provides opportunities to stay healthy, while the library and game rooms offer quiet spaces for relaxation and leisure. For those who love the outdoors, the community features sidewalks, a walking path and a picnic area, shuffleboard and bocce courts, horseshoe pits and billiard room. With a strong sense of community, there are plenty of opportunities to connect with neighbors and make lasting friendships. The association fee includes comprehensive services such as lawn care, snow removal, and common area maintenance, allowing you to spend more time enjoying your home and less time on upkeep. The management office is staffed five days per week. Spring Arbor is the 55-or-better community in the location closest of all to local shops, dining, and entertainment options, making it easy to enjoy the best of what the area has to offer. With a welcoming atmosphere and a focus on community, this residence is perfect for those looking to embrace a fulfilling lifestyle in a beautiful setting. Experience the warmth and comfort of Spring Arbor, where every day feels like a getaway. New Guaranteed Roof was installed in Fall of 2025 and New Furnace was installed in late-January 2026. New Garage Door Opener ($1000) installed July 2026. Shortest drive to Middletown shops and restaurants, and the Community Clubhouse. WHAT MORE DOES ONE NEED?

264 Trellis Ln, 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

$804,900

4 Beds ⋅ 3 Baths ⋅ DENC2093610 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 Waterford – Two-story home with a first-floor owner’s suite and 3,642+ sq. ft. Includes 4 bedrooms and 3.5 baths. Features an open kitchen with island seating, breakfast nook, spacious great room, and flex room. A first-floor guest bedroom with full bath adds convenience. Upstairs offers 2 bedrooms, a loft, full bath, and unfinished bonus room. 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.

2200 Early Ct, Middletown

$789,900

4 Beds ⋅ 4 Baths ⋅ DENC2093606 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 Bridgeport is a two-story home starting at 3,500 sq. ft., featuring a first-floor secondary owner’s suite, 4 bedrooms, and 3.5 baths. Open kitchen with island, breakfast nook, walk-in pantry, and flex room. Upstairs includes the Owner’s suite, 2 bedrooms, loft, 2 baths, and laundry. Optional layouts available for additional bedrooms, baths, and outdoor living. 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.

1135 Majesty Ln, Middletown

$629,900

3 Beds ⋅ 2 Baths ⋅ DENC2093608 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 Newport – Single-level ranch home with 1,662+ sq. ft., 3 bedrooms, and 2 baths. Features a spacious kitchen with island seating open to the dining area and great room. Options include an added second-floor bedroom and bath, unfinished storage, 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.

2202 Early Ct, Middletown

$669,900

3 Beds ⋅ 2 Baths ⋅ DENC2093528 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 Whimbrel is a ranch home starting at 1,971 sq. ft., with 3 bedrooms, 2 baths, and a flex space ideal for a home office. Open kitchen with island flows to dining and great room. Options available for extra bedrooms, baths, loft, and outdoor living. 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.

2204 Early Ct, Middletown

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.