Middletown Real Estate

Middletown Real Estate

Welcome to Middletown, a charming city located in the heart of the United States. Nestled in the beautiful countryside, Middletown offers the perfect blend of small-town charm and modern amenities.

With a rich history dating back to its founding in the early 19th century, Middletown boasts a vibrant community and a strong sense of pride. The city is known for its picturesque landscapes, friendly residents, and bustling downtown area.

Middletown is a great place to call home for those looking for a peaceful and welcoming environment. The city offers a variety of housing options, from historic homes to newly built properties, catering to individuals and families of all sizes.

In addition to its residential appeal, Middletown provides residents with easy access to a range of amenities, including parks, shopping centers, restaurants, and top-rated schools. The city's convenient location also allows for quick commutes to nearby urban centers, making it an ideal choice for those seeking a balance between city living and suburban tranquility.

Whether you're looking to settle down or invest in real estate, Middletown has something to offer everyone. Come and discover the beauty and charm of this hidden gem in the heart of the United States.

Newest Listings in Middletown

$635,000
4 Beds 3 Baths
Just minutes from Chesapeake City, set on over an acre of flat, beautifully landscaped land in a well-established and sought-after neighborhood, this spacious 4-bedroom, 2.5-bath home offers the space and updates today's buyers are looking for. Upon entering, you're greeted by a formal dining room to the right, perfect for hosting holidays and special occasions, while a spacious room to the left offers an ideal home office or flex space to suit your needs. The kitchen was renovated in 2019 with crisp white cabinetry, granite countertops, stainless steel appliances, and a sleek induction cooktop. A charming bump-out creates the perfect spot for a sun-filled breakfast nook, ideal for casual everyday dining. The kitchen flows seamlessly into the adjoining family room, perfect for entertaining and everyday living alike, with a deck accessible from both the kitchen and family room, offering effortless indoor-outdoor living. Luxury vinyl flooring runs throughout, adding warmth and durability. Just off the kitchen, a convenient hallway houses the first-floor half bath, a dedicated laundry area, and direct access to the 2-car garage — everyday functionality designed for the way you live. Upstairs, you'll find all 4 bedrooms, including a spacious owner's suite complete with a walk in closet and a full bath featuring a soaking tub — your own private retreat at the end of the day. The partially finished basement offers flexible bonus living space, plus a large storage area housing the HVAC system — ideal for keeping things organized and out of sight. Outside, is a fully fenced backyard featuring mature landscaping and a cozy fireplace sitting area, perfect for relaxing evenings or entertaining guests year-round. A separate fully fenced area offers the perfect spot for a garden. With room to spread out both inside and on over an acre of land, this home combines comfort and updates throughout. Don't miss your chance to make it yours!

62 Millwood Dr, Middletown

Listing courtesy of Foraker Realty Co.. Contact: (484) 406-3004

$599,900
3 Beds 3 Baths
Escape the ordinary with this one-of-a-kind mountain-inspired retreat set on more than 5 secluded acres of mature woodland. Designed to embrace its natural surroundings, this distinctive chalet welcomes the outdoors in with dramatic vaulted ceilings, walls of windows, and multiple skylights that fill the home with sunlight while showcasing peaceful forest views from nearly every room. The inviting great room is centered around a beautiful fireplace, creating the perfect gathering place, while rich hardwood flooring and natural finishes enhance the home's warm, rustic charm. Step outside onto the expansive wraparound deck, where you can enjoy the sights and sounds of nature, entertain guests, or simply relax in complete privacy. The updated kitchen features granite countertops and stainless-steel appliances including gas cooking, offering modern functionality without sacrificing the home's unique character. An oversized detached two-car garage provides exceptional space for vehicles, a workshop, outdoor equipment, or additional storage. Offering the rare combination of privacy, distinctive architecture, and everyday convenience, this exceptional property feels like a secluded woodland retreat while remaining only about 15 minutes from Middletown's restaurants, shopping, and Middletown schools. Recent improvements include a new roof and skylights (2020), stove and microwave (2021), water softener and neutralizer (2022), and refrigerator (2025). Better see it soon before someone else gets to call it home!

6838 Mountain Church Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3016441086

$725,418
5 Beds 4 Baths
Introducing Freestone's largest floorplan, the Amesbury. Offering 5 bedrooms, 3.5 bathrooms, and over 3,400 square feet of thoughtfully designed living space. From the moment you step inside, you'll appreciate the open-concept layout, ideal for both everyday living and entertaining. The heart of the home is the gourmet kitchen, featuring quartz countertops, stylish Hazelnut cabinetry with a contrasting black island, a designer tile backsplash, and stainless-steel appliances. The spacious great room with a cozy fireplace flows seamlessly into the dining area, creating the perfect gathering space for family and friends. Upstairs, retreat to the luxurious owner's suite complete with a tray ceiling, dual walk-in closets, and a spa-inspired bathroom featuring a relaxing soaking tub. This home also includes the optional fifth bedroom, a private bath for Bedroom 2, and a convenient second-floor laundry room, offering flexibility for guests, multigenerational living, or a growing family. Additional highlights include elegant oak stairs with open railings, durable luxury vinyl plank flooring, and a walk-up basement ready for future expansion or storage. Located in Freestone Village, this exceptional home offers the perfect combination of modern design, quality finishes, and the convenience of living in the highly sought-after Appoquinimink School District. Schedule your tour today and discover everything this incredible home has to offer! *Pictures are artificially rendered and for representational purposes only. There is a sales trailer on-site. 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.

6033 Freestone Blvd, Middletown

Listing courtesy of Atlantic Five Realty. Contact: 8564243339

$649,900
4 Beds 4 Baths
***Solar panel is owned***Welcome to the sought after Middletown community of The Estates at Dove Run! Move right in, just in time to enjoy the heated fiberglass pool this summer! Enjoy this home all year long starting with the amazing outdoor space of the heated pool and hot-tub right off the updated Trex deck. There is a patio and a pool patio to accomodate all your guests. The front porch offers you an amazing pond view for those summer evenings. Upon entering the home, the two story freets you flanked by an open formal living room and dining room. Spacious family room with gas fireplace and eat in kitchen in the rear of the home. Updates on the main floor incude all flooring, paint, remodeled bath and laundry, remodeled fireplace hearth, updated lighting and a new back door to the deck. The kitchen offers oak 42" cabinets, granite countertops .Just behind the kitchen is the spacious laundry with mudroom and access to the 2-car garage.The garage offers EV charging station and an electric opener. On the second floor and you will find a surprising spacious loft next to the enormous master bedroom, three additional bedrooms, and unexpected closet spaces! The master bedroom features an expansive master closet, plenty of natural light from windows, and a luxurious bathroom with jetted tub and shower, it has been updated with new fixtures and lights. Finally , head downstairs to the finished basement with a full bathroom and wet bar, perfect for a game room, and additional entertaining space with double doors heading to your pool area. If this home doesn't catch your attention yet, the owned solar system and generator is sure to complete the desirable package! This home is spacious, updated, offers great space and features and is economical to live in!

313 Autumn Ct, Middletown

Listing courtesy of BHHS Fox & Roach - Hockessin. Contact: (302) 999-9999

$487,250
3 Beds 4 Baths
**October Move-In** Move right into this beautifully designed 2-story, 3 BR, 2 full and 2 half BA home offering plenty of room to gather, relax, and spread out. The open-concept main level creates a natural flow between the kitchen, dining area, and living space, making everything from holiday entertaining to weeknight dinners feel effortless. Just outside, the included deck extends your living space outdoors and provides the perfect spot for morning coffee, summer cookouts, or winding down at the end of the day. Upstairs, a versatile loft offers endless flexibility as a second living area, home office, playroom, or hobby space. Two secondary bedrooms share the level with the owner's suite, where a tray ceiling adds an elegant touch to the private retreat. The finished basement with powder room provides even more room to enjoy, whether you envision a media room, game room, fitness area, or the ultimate hangout space. Thoughtfully selected finishes include Carrara Breve quartz countertops in the kitchen and full baths, a timeless 3x6 Arctic White tile backsplash, and designer details throughout. This is the kind of home that gives you the space you need today with the flexibility to grow into tomorrow. With an October move-in, modern finishes, and low-maintenance living in Appoquinimink School District, this is the kind of opportunity buyers don’t wait on—be sure to take a closer look. Pictures are of model home from a sister community and for representational purposes only. There is a sales trailer on-site. 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.

6038 Freestone Blvd, Middletown

Listing courtesy of Atlantic Five Realty. Contact: 8564243339

$752,487
4 Beds 5 Baths
Welcome to 6035 Freestone Boulevard at Freestone Village, where luxury, space, and thoughtful design come together in one exceptional home. This beautifully upgraded Grier floorplan offers over 3,000 square feet of living space plus a finished basement with its own full bath, making it ideal for growing families, entertaining, or multigenerational living. The open-concept main level is designed for everyday living and hosting alike, featuring a gourmet kitchen, quartz countertops, soft close cabinetry, and a spacious island. The morning room extension off the kitchen fills the home with natural light and creates additional living and gathering space overlooking the backyard. Upstairs, the luxurious owner's suite provides a relaxing retreat with an oversized walk-in closet. Three additional bedrooms, including a secondary bedroom with its own private en-suite bath, plus a centrally located laundry room completes the second floor. The finished basement adds even more flexible living space with a large recreation room and a full bathroom—perfect for a home theater, fitness area, game room, or additional guest accommodations. Additional premium features include oak stairs with open railing, designer tile selections, stainless-steel appliances including refrigerator, washer, and dryer, and a prime location in the award-winning Appoquinimink School District with easy access to shopping, dining, and major commuter routes. *Pictures are of model home from a sister community and for representational purposes only. There is a sales trailer on-site. 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.

6035 Freestone Blvd, Middletown

Listing courtesy of Atlantic Five Realty. Contact: 8564243339

$825,000
6 Beds 4 Baths
Discover a rare opportunity to own an exceptional custom residence where timeless craftsmanship, refined comfort, and peaceful natural surroundings come together. Nestled on five picturesque wooded acres within an exclusive lake community in Middletown, this remarkable estate offers over 4,700 square feet of beautifully designed living space, creating the perfect balance of luxury, privacy, and everyday functionality. Thoughtfully designed, the home features six bedrooms and three-and-a-half bathrooms, providing exceptional flexibility. A dedicated office on the main level creates an elegant work-from-home space, while an expansive loft offers endless possibilities as a library, media lounge, or additional gathering area. The spacious primary suite is conveniently located on the first floor, featuring access to the deck, a stone fireplace and private ensuite bathroom. At the heart of the home, the chef-inspired kitchen is equipped with newer appliances—all less than five years old—and seamlessly flows into generous living and dining spaces designed for effortless entertaining. The walk-out lower level is partially finished and already plumbed for a future full bath, offering exceptional potential to create a luxury guest suite, fitness studio, wine cellar, home theater, or recreation space tailored to your vision. Step outside to experience the home's true sanctuary. A custom multi-level deck overlooks the wooded landscape, providing multiple outdoor living spaces for entertaining or quiet relaxation. A reinforced section has already been engineered to accommodate a hot tub, creating the perfect setting for enjoying peaceful evenings beneath the stars. Exceptional features continue with an oversized two-car garage and the added confidence of a whole-home gas generator, ensuring comfort and peace of mind in every season. Residents enjoy access to the community's private lake, offering opportunities for fishing, kayaking, and embracing the beauty of the surrounding countryside. Despite its serene setting, the property remains conveniently located near commuter routes, historic Middletown, wineries, outdoor recreation, and all that the Shenandoah Valley has to offer. Offering an extraordinary combination of luxury, privacy, and room to grow, this distinguished estate is more than a home—it's a lifestyle.

816 Great Lake Dr, Middletown

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

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