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 rich history, vibrant community, and picturesque landscapes, Middletown offers an inviting atmosphere that makes it a perfect place to call home. With its friendly neighborhoods, diverse amenities, and a strong sense of community, this city is ideal for families, young professionals, and retirees alike.

One of the standout features of Middletown is its stunning homes with pools, providing the perfect oasis for relaxation and entertainment. Imagine stepping out into your own backyard paradise, where you can soak up the sun, host summer barbecues, or enjoy a refreshing dip after a long day. These homes offer not just a place to live, but a lifestyle that embraces outdoor living and leisure.

Middletown boasts a variety of architectural styles, from charming bungalows to modern estates, ensuring that there’s something for everyone. Many homes with pools are situated in family-friendly neighborhoods with easy access to parks, schools, and local shops, making daily life a breeze. Whether you’re looking for a cozy retreat or a spacious family home, Middletown’s real estate market has something to suit your needs.

In addition to its beautiful homes, Middletown offers a wealth of recreational opportunities. Explore the scenic parks, enjoy local festivals, or take a stroll through the historic downtown area, filled with delightful boutiques and eateries. With its vibrant community spirit and stunning homes with pools, Middletown is not just a place to live—it's a place to thrive. Come discover the charm of Middletown, where your dream home awaits!

Newest Middletown Homes with Pool

5 Beds ⋅ 4 Baths

This move-in ready, 3-year-old D.R. Horton home is a spacious two-story with five bedrooms, three and a half bathrooms. It also includes a game room with a wet bar, a media room, a workshop or exercise room, a full bathroom, and plenty of storage space in the basement, as well as a two-car garage and an oversized deck. The foyer features a coat closet and creates a welcoming flow for greeting guests. The front room is filled with natural light and is large enough to accommodate both a living and dining area. The spacious kitchen boasts beautiful birch cabinetry, granite countertops, stainless steel appliances, a pantry, and an island with seating. It opens to both the breakfast area and a sizable family room. A convenient powder room is located on the first floor, and the stairs to the second floor are tucked away in the family room, which also includes a cozy fireplace. Upstairs, the owner’s suite offers a large bedroom, two walk-in closets, and an oversized ensuite bathroom. The four additional generously sized bedrooms and a hall bathroom provide ample space for everyone. The first-floor laundry room is conveniently located near the garage, along with an additional coat closet. The property is vacant and ready to move in for the holiday.

1245 Pimpernell Path, Middletown

Listing courtesy of Realty Mark Associates-Newark. Contact: (888) 260-0040

4 Beds ⋅ 3 Baths

Welcome to this stunning Circa 1872 farmhouse nestled in the heart of Middletown with a stunning view! Situated on a gorgeous 1-acre lot on a quiet one-way street just off Main Street, this spacious property offers the perfect blend of peaceful living and everyday convenience, with easy access to I-81. Zoned B1, it offers many possibilities for either residential or commercial use, including a Bed and Breakfast! (see attached document). Step inside to discover timeless character and charm, featuring gorgeous period details including thick moldings, custom built-ins, decorative fireplaces, and beautiful hardwood floors. The impressive entrance foyer, featuring a grand spiral staircase, welcomes you and creates a memorable first impression. This home is absolutely perfect for entertaining, also featuring a grand dining room and details throughout that only a home of this era can offer. The thoughtfully designed second level offers four spacious bedrooms and two full bathrooms, providing privacy for family and guests. A convenient half bath on the main level is ideal for entertaining. Complete your journey to the third story overlook and enjoy the most beautiful sunsets you can imagine in the Shenandoah Valley - read, paint, meditate, or just relax and enjoy this very unique space. This exceptional home is ready to welcome its next owner.

2239 Sixth St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

3 Beds ⋅ 2 Baths

Move right into this stunning K. Hovnanian Magnolia home located in the highly desirable Four Seasons at Silver Maple Farm community in Middletown! You will be immediately greeted by the stone front, lush curb appeal and charming covered front porch. Continue your tour inside where you’ll find your gourmet kitchen with luxury granite countertops, custom tile backsplash, recessed lighting, extended cabinets with crown molding, and upgraded stainless steel appliances. Solid hardwood flooring flows beautifully throughout all the living spaces. The open concept floor plan with recessed lighting is perfect for entertaining. Enter the living room that offers breathtaking vaulted ceilings and gas fireplace centerpiece. This home is perfect for one floor living with a main-floor laundry and a convenient office/third bedroom. Your spacious primary bedroom with massive wall-to-wall walk-in closet, en-suite with double vanities and extra wide tiled walk-in shower. A second bedroom and a full bathroom with tile surround are also on this level. The outdoor space offers an extended composite deck and backs up to private lush green space, perfect for relaxing or entertaining. Four Seasons at Silver Maple Farms amenities can’t be beat with an expansive clubhouse, a calendar of engaging activities for residents, along with indoor amenities that include community gathering space, kitchen, hearth room, fitness center, card room, yoga room, billiards room and ping-pong room. Outdoor amenities include the swimming pool with Tiki bar and BBQ area, tennis and pickle ball courts, bocce and horseshoe courts, miles of walking trails and a community garden. No need to worry about lawn care as it is included! Located a short drive to major highways like Route 1 and I-95, Delaware Beaches, main waterways, popular shopping, dining and more. Schedule your tour today!

239 Silky Dogwood Ln, Middletown

Listing courtesy of Crown Homes Real Estate. Contact: (302) 504-6147

2 Beds ⋅ 2 Baths

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

Listing courtesy of Coldwell Banker Realty. Contact: 3022341888

4 Beds ⋅ 3 Baths

Well cared for beautiful 4 Bedroom, 2 Bath Home on Nearly One Acre in Desirable Fox Hunter Crossing on almost an acre of land, with an inground pool and diving board. This elegant 4 bedroom home blends classic architectural details with warm, inviting spaces perfect for everyday living and memorable gatherings. In addition a new roof was installed 2 years ago. A two story foyer welcomes you with hardwood floors and a turned staircase that sets a gracious tone. The heart of the home is the beautiful eat in kitchen, offering 42" cabinetry, abundant workspace, and seamless flow into the step down family room. Here, cathedral ceilings, skylights, arched windows, and a wood burning fireplace create a bright, dramatic space ideal for relaxing or entertaining. The main level also features a formal living room, formal dining room, and a first floor study enhanced with french doors and crown molding, perfect for working from home. A convenient laundry and mudroom complete the first floor, with sliding doors leading to a large deck overlooking the private, fenced in backyard. Upstairs, the primary suite is truly a retreat. Enjoy a spacious bedroom with a separate sitting area, his and hers walk in closets, and a luxurious bath featuring a double vanity, soaking tub, and separate shower. Three additional comfortable bedrooms and a full hall bath complete the second floor. Additional highlights include a 3 car turned garage, extra large laundry room, 9' ceilings, and a welcoming front porch that adds charm and curb appeal. And we will save the best for last! Enjoy your new home with a beautiful INGROUND POOL installed in 2018. See it, you will want it.

109 Colonel Clayton Dr, Middletown

Listing courtesy of Patterson-Schwartz-Hockessin. Contact: 3022393000

3 Beds ⋅ 2 Baths

Welcome to this beautiful 3BR/2BA ranch home in one of Middletown's premier 55+ community at Four Season at Silver Maple. This K Hovnanian Martinique model features a spacious floor plan with 2372 sq ft of living space on the main level, and an additional 1178 sq ft in the partially finished basement. Curb appeal abounds with the stacked stone accents, modern carriage-style garage door, huge 16’ x 22’ maintenance-free deck with under-deck storage, an irrigation system to keep your grass looking green, and a premium lot backing to community open space. As you enter the home, you’ll be greeted with gleaming hardwood floors flowing throughout most of the main level, and a lots natural and recessed lighting. The gourmet kitchen boasts a stainless steel wall oven & microwave combo, gas cooktop, and a large angled island with sink and bar top seating opening up to the living room and dining areas. The perfect layout for entertaining family and friends and hosting holiday get-togethers. The extra-large primary bedroom suite has his/hers walk-in closets, double vanities separated by a makeup counter, tiled floors, and an enlarged tiled shower with a bench and glass shower doors. Additionally, there are 2 guest bedrooms, one with French doors, doubling as a convenient home office. Other features are a main floor laundry with included front-loading washer & dryer, 2-car garage with epoxy-coated floors, and the expansive recreation room in the finished basement. The unfinished areas offer ample storage, and 2 of the spaces currently act as a home gym and workshop. In 2025, New Timber Tech roof was placed. The community clubhouse provides a calendar of welcoming and engaging activities for residents, along with indoor amenities that include a café/kitchen, hearth room, fitness center, card room, yoga room, billiards room, ping-pong room, and a theater room. Outdoor amenities include the swimming pool with Tiki bar and BBQ area, tennis and pickle ball courts, bocce and horseshoe courts, several miles of walking trails and a community garden. Proximity to Rt 1 & Rt 13 make it within easy driving distance to everything Delaware has to offer – only 45 minutes to the Philly airport and less than an hour to sand-filled beaches.

171 Silver Maple Rd, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact: 3022855100

3 Beds ⋅ 2 Baths

Welcome home to this beautifully maintained 3-bedroom, 2-bath residence by K. Hovnanian, located in the highly desirable Silver Maple Farms community, formerly known as Four Seasons at Silver Maple. As you enter the neighborhood, you'll be greeted by a picturesque, tree-lined boulevard where mature trees create a lush canopy, preserving the timeless charm and character of the original farm. This welcoming entrance sets the tone for the peaceful surroundings and exceptional lifestyle that await. Designed for both comfort and entertaining, this home features an open-concept floor plan enhanced by beautiful hardwood flooring throughout the main living areas. The spacious owner's suite offers a large walk-in closet and a private en suite bath with a dual-sink vanity and oversized walk-in shower. Two additional bedrooms provide ample space for family or guests and share a well-appointed full bath with a marble vanity and tub/shower combination. The well-equipped kitchen is sure to impress with granite countertops, a tile backsplash, under-cabinet lighting, and a gas range. Adjacent to the kitchen, the generous dining room and inviting living room with a cozy gas fireplace create the perfect setting for entertaining or relaxing at home. Filled with natural light, the bright morning room overlooks the beautifully landscaped backyard and opens to a screened porch—an ideal place to enjoy your morning coffee or unwind in the evening. A spacious deck extends from the porch and leads to the lush green lawn, offering additional outdoor living space. Silver Maple Farms offers a lifestyle reminiscent of a private country club, with countless opportunities to socialize with neighbors or simply enjoy the tranquility of the community. Residents have access to miles of scenic walking trails, a community vegetable garden, pickleball and bocce courts, and a heated swimming pool equipped with a handicap-accessible lift, among many other amenities. Don't miss the opportunity to make this exceptional home your own. Schedule your private tour today and experience all that Silver Maple Farms has to offer.

614 Red Maple Rd, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact: 3022855100

3 Beds ⋅ 3 Baths

Welcome to Comfort, Convenience & Low-Maintenance Living in The Preserve at Deep Creek! Why wait for new construction when you can own this beautifully maintained, just 4-year-old ranch home situated on a premium lot backing to peaceful open space? Located in the highly desirable 55+ active adult community of The Preserve at Deep Creek, you'll enjoy resort-style amenities including a clubhouse, fitness center, swimming pool, pickleball courts, walking paths, and open green space. Even better, lawn maintenance and snow removal are included, allowing you to spend more time enjoying life and less time on home maintenance. From the moment you step inside, you'll appreciate the bright, open floor plan featuring 9-foot ceilings and luxury vinyl plank flooring that flows throughout the foyer, kitchen, and great room. Designed for both everyday living and entertaining, the gourmet kitchen is the gathering space of the home and boasts a large center island with seating and pendant lighting, 42-inch cabinetry, gorgeous countertops, tiled backsplash, stainless steel appliances, gas cooking, a vented range hood, and upgraded LED lighting. The spacious dining area easily accommodates a large table and opens through sliding glass doors to the enclosed porch, creating a seamless indoor-outdoor living experience. The inviting great room provides the perfect space for entertaining, while the private owner's suite offers a relaxing retreat complete with a tray ceiling, crown molding, ceiling fan, walk-in closet, and a beautifully appointed en-suite bath featuring dual vanities, upgraded cabinetry, tile flooring, and a large tiled shower. Two additional generously sized bedrooms, a full hall bath, a convenient laundry room, and a practical mud space area just off the garage complete the main level. Step outside and discover one of this home's standout features—the enclosed porch overlooking scenic open space, making it the perfect spot to enjoy your morning coffee or unwind in the evening. Just beyond, the maintenance-free composite deck with its spacious gazebo/pergola provides an ideal setting for outdoor dining, entertaining, BBQs, or simply relaxing while taking in the peaceful backyard views. The finished lower level dramatically expands your living space and offers endless possibilities for a recreation room, media room, home office, fitness area, or hobby space. A full bathroom and an expansive unfinished storage area provide exceptional flexibility and convenience. Additional upgrades include a tankless water heater, irrigation system, security alarm, and an attached two-car garage. Conveniently located just minutes from grocery stores, restaurants, parks, shopping, Christiana Care's emergency facility, and major highways, this exceptional home combines modern comfort with an unbeatable location. If you're looking for a move-in ready home with outstanding amenities and truly maintenance-free living, this one checks every box. Schedule your private tour today and experience everything this exceptional home has to offer!

272 Anglesey Dr, Middletown

Listing courtesy of RE/MAX Advantage Realty. Contact: 3023788700

3 Beds ⋅ 4 Baths

Welcome home! Fall in love with 585 Canal Drive! This is perhaps the best end unit in Canal View, that has actual canal views! This modern townhome is located on one of the largest lots in the community. (Lot premium) With three bedrooms, two full baths and two half baths this home has it all. The bright first floor includes hardwood floors, an open floor plan and access to the rear deck- a great spot for get togethers, entertaining, or just enjoying morning coffee. The kitchen has granite countertops and a stainless-steel appliance package. Finished great room/TV room in the basement includes outside access to rear patio and a half bath. Upstairs has three bedrooms, with a full bath in the primary suite, and a full hall bath. Second floor laundry. Large primary bedroom including full bath and large walk-in closet. Fenced yard. The two-car garage with door openers and inside access.

585 Canal Dr, Middletown

Listing courtesy of Keller Williams Realty Wilmington. Contact: 3022991100

4 Beds ⋅ 4 Baths

6 Green Meadow Blvd, Middletown

Listing courtesy of HERITAGE HOUSE SOTHEBY`S INT`L REALTY. Contact: (732) 946-9200

4 Beds ⋅ 3 Baths

Welcome to 4534 Cagney Lane, a beautiful, like-new Cape Cod-style home located in the highly sought-after 55+ luxury community of Village of Bayberry South. Offering 4 bedrooms, 3 full bathrooms, a 2-car garage, and backing to open common space, this exceptional home combines elegant design, thoughtful functionality, and low-maintenance living. Step inside the inviting foyer, where rich hardwood flooring flows throughout the main living areas. Elevated ceilings and an open-concept floor plan create a bright and airy atmosphere. Just off the foyer, the formal dining room provides an elegant space for hosting guests, while the spacious living room showcases dramatic vaulted ceilings that open to the second-story loft above. The gourmet kitchen features granite countertops, double wall ovens, a gas cooktop, a large center island with breakfast bar seating, pantry, recessed lighting, and beautiful crown molding on the cabinetry. Sliding glass doors lead directly to the backyard, where you can relax and enjoy peaceful views of the open community space. The main level offers the convenience of single-floor living with three bedrooms, including the spacious primary suite. The primary bedroom features two walk-in closets and an ensuite bath complete with tile flooring and a double vanity. Two additional bedrooms share a hall bath, while the generously sized laundry room provides direct access to the attached two-car garage. Upstairs, you'll find a versatile loft overlooking the living room below, along with a private fourth bedroom featuring its own ensuite bathroom - an ideal setup for overnight guests or a home office. The expansive unfinished basement offers endless possibilities for future living space, recreation, or storage, and already includes a plumbing rough-in for a fourth full bathroom. Additional highlights include dual-zoned HVAC, an irrigation system, blackout shades in bedrooms, and all appliances included, making this home truly move-in ready. Life at Village of Bayberry South means enjoying an outstanding array of resort-style amenities, including a heated outdoor pool, pickleball and tennis courts, bocce courts, basketball court, walking trails, a private clubhouse with fitness center, billiards room, meeting spaces, and a scenic patio overlooking the lake. An active social calendar provides endless opportunities to connect with neighbors and enjoy community events. Best of all, the HOA handles lawn care, landscaping, and trash service, allowing you to enjoy the very best of low-maintenance living. Don't miss the opportunity to make this exceptional home yours and experience the lifestyle you've been waiting for. Schedule your tour today!

4534 Cagney Ln, Middletown

Listing courtesy of Compass. Contact: 3022029855

3 Beds ⋅ 4 Baths

*MOVE IN READY* Introducing the 3034 Ivyhouse Lane, the Tuscany Luxe, a beautifully appointed home offering 2,151 square feet of thoughtfully designed living space, plus a partially finished basement with endless potential. This elegant residence blends open-concept living with private retreats, perfect for both everyday comfort and entertaining. The main level features a spacious family room anchored by a cozy gas fireplace, flowing seamlessly into the dining area and gourmet kitchen complete with upgraded quartz countertops, stylish backsplash, premium gray cabinetry, and stainless-steel appliances. A dedicated home office provides the ideal space for remote work or quiet study. The luxurious owner’s suite offers a spa-like bath and his and her closets, while a secondary bedroom and full bath add flexibility for guests or family. Expanding the living space, the home includes a stunning sunroom extension with ample windows and a high ceiling that fills the interior with natural light and opens to a composite deck, perfect for relaxing or entertaining outdoors. Upstairs, a third bedroom, full bath, and loft create a private retreat for guests or additional living space. Additional highlights include a 2-car garage, convenient first-floor laundry, upgraded flooring throughout, and an partially finished basement with full bath ready for future customization. The Tuscany Luxe offers timeless style, modern comfort, and flexible living—all in a beautifully crafted home designed to fit your lifestyle. To top it off, this community offers a stunning 5,400 square foot clubhouse, pickleball courts, tennis courts, bocce, a swimming pool, fitness center, and so much more! Relax and enjoy the peace of mind that your lawncare, snow removal, and trash/recycle are all taken care of for you. Prices, dimensions, and features may vary and are subject to change. Photos are for illustrative purposes only. To top it off, this community offers a stunning 5,400 square foot clubhouse, pickleball courts, tennis courts, bocce, a swimming pool, fitness center, and so much more! Relax and enjoy the peace of mind that your lawncare, snow removal, and trash/recycle are all taken care of for you. *Prices, dimensions, and features may vary and are subject to change. Photos are for illustrative purposes only. Taxes to be assessed after settlement. If using a Realtor: the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit. For appointments and open houses, please visit the welcome home center located at 2405 Greyfriar Loop.*

3034 Ivyhouse Ln, Middletown

Listing courtesy of Atlantic Five Realty. Contact: 8564243339

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