Middletown Crossing Real Estate

Middletown Crossing Real Estate

Welcome to Middletown Crossing, a charming subdivision nestled in the heart of Middletown, Delaware. This vibrant community offers a perfect blend of suburban tranquility and convenient access to urban amenities, making it an ideal place for families, professionals, and retirees alike.

Middletown Crossing is characterized by its beautifully designed homes, featuring a variety of architectural styles that cater to diverse tastes. The well-maintained streets are lined with lush landscaping, creating a picturesque environment that residents are proud to call home. With a range of housing options, from cozy single-family homes to more spacious properties, there's something to suit every lifestyle and budget.

The community is strategically located, providing easy access to major highways and nearby cities, making commutes to Wilmington or Newark a breeze. Residents can enjoy the charm of small-town living while still being just a short drive away from shopping, dining, and entertainment options. The nearby Middletown Village offers a delightful selection of boutiques, restaurants, and parks, perfect for family outings or a leisurely afternoon stroll.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a quality education. The community also boasts a variety of recreational facilities, including parks, playgrounds, and walking trails, promoting an active and healthy lifestyle.

Discover the warmth and camaraderie of Middletown Crossing, where neighbors become friends and community spirit flourishes. Whether you’re looking to plant roots or simply explore the area, Middletown Crossing is a place where you can truly feel at home. Come and experience the charm of this delightful subdivision today!

Newest Listings in Middletown Crossing

4 Beds ⋅ 3 Baths

Nestled in the charming community of Middletown Crossing, this exquisite Colonial-style residence offers a perfect blend of elegance and comfort. Built in 2006, this detached home exudes timeless appeal with its classic vinyl siding and inviting curb appeal. Spanning a generous 0.23 acres, the property provides ample space for outdoor enjoyment and relaxation. Step inside to discover a thoughtfully designed layout that seamlessly combines functionality with sophistication. With four spacious bedrooms, 2.5 baths, this home is ideal for those who appreciate room to breathe and grow. The primary bedroom, a true sanctuary, features an en-suite bathroom that promises a spa-like experience, complete with modern fixtures and ample natural light. The open-concept design allows for effortless flow between the living room, dining area, and kitchen, making it perfect for entertaining. The unfinished basement presents a blank canvas, offering endless possibilities for customization-imagine a home theater, gym, or additional living space tailored to your lifestyle. The exterior of the property is equally impressive, featuring a front-entry attached garage that provides convenience and security. The driveway offers additional parking for guests, ensuring that entertaining is always a breeze. The surrounding community amenities and nearby parks provide plenty of opportunities for outdoor recreation and leisure. Enjoy the tranquility of suburban living while being just a short drive away from vibrant shopping, dining, and entertainment options. Whether you're hosting a lively gathering or enjoying a quiet evening at home, this residence is designed to cater to your every need. Don't miss the opportunity to make this exceptional property your own. Schedule appointments today!

4 W Shakespeare Dr, Middletown

Listing courtesy of RE/MAX Edge. Contact: 3024424200

3 Beds ⋅ 4 Baths

Welcome to 40 S Cummings Dr in Middletown Crossing! This spacious 3-bedroom twin offers a comfortable layout, flexible living space and plenty of opportunity to make it your own. The main living area is warm and inviting, with a cozy fireplace and plenty of room to relax or entertain. With two full baths, two half baths, and a 1 car garage, the home is designed to make everyday life a little easier. The partially finished basement adds valuable extra space and can easily work as a family room, home office, gym, playroom or whatever best fits your needs. Outside, the manageable yard offers just enough space for a patio, garden, entertaining or simply enjoying some time outdoors without a ton of upkeep. An attached garage and driveway provide convenient off-street parking and additional storage. Located in Middletown Crossing with easy access to shopping, dining, parks and major routes, this home offers a great combination of space, convenience and flexibility. If you're looking for a home you can settle into now while still having room to make it your own, this one is worth a look! Please note - this property was incorrectly reported as sold in August of 2026. Listing agent is working with the MLS to rectify.

40 S Cummings Dr, Middletown

Listing courtesy of Real Broker LLC. Contact: 8554500442

3 Beds ⋅ 4 Baths

Welcome to 17 Browning Circle — where modern comfort, spacious living, and exceptional outdoor entertaining come together beautifully. This well-maintained home features 3 bedrooms and 3.5 bathrooms, including a convenient first-floor primary suite designed for everyday comfort and accessibility. Bay windows in the dining area fill the home with natural light, creating a warm and inviting atmosphere throughout. A standout feature of this home is the expansive oversized Trex deck, offering the perfect outdoor retreat for entertaining, dining, or simply relaxing while overlooking the professionally landscaped backyard. Complete with a natural gas grill and a 6-zone irrigation system, the outdoor space is designed for both enjoyment and easy maintenance. The fully finished basement significantly expands the living space and offers endless possibilities for a media room, game room, fitness area, guest suite, or private retreat. With a full bathroom included, the lower level delivers both flexibility and functionality. Additional upgrades and features include: New roof (2 years old) New HVAC system (2 years old) Electric vehicle charging station Upgraded garage electrical receptacles Motorized foyer chandelier Spacious upgraded garage Thoughtfully designed layout with modern conveniences throughout 17 Browning Circle offers the perfect blend of indoor comfort, finished lower-level living, and exceptional outdoor entertaining space — a true lifestyle home ready for its next owner.

17 Browning Cir, Middletown

Listing courtesy of English Realty. Contact: 3022954845

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Lisa Mathena

Meet Lisa Mathena | Top Delaware Real Estate Expert & Luxury Home Specialist With 34+ years of experience in the Delaware real estate market, Lisa Mathena is one of the most trusted and accomplished REALTORS® serving Southern Delaware. A lifelong resident of the state, Lisa brings unmatched local knowledge and deep expertise across New Castle County, Kent County, and Sussex County, helping buyers and sellers navigate every stage of the real estate process with confidence and clarity. Recognized throughout her career as a top-producing REALTOR®, Lisa has built a reputation for delivering results through strong negotiation skills, strategic marketing, and a deep understanding of Delaware’s real estate laws, contracts, and local regulations. Her clients benefit from her ability to coordinate trusted vendors, manage complex transactions, and provide step-by-step guidance designed to make every sale or purchase as smooth and stress-free as possible. Lisa’s primary goal is always to help clients make informed decisions that are truly in their best interest. Whether assisting first-time buyers, move-up homeowners, investors, or clients facing short sales or foreclosure situations, she provides honest advice, clear communication, and expert-level market insight throughout the entire process. Lisa holds the Certified Residential Specialist (CRS) designation, as well as the Short Sales and Foreclosure Resource (SFR®) and Real Estate Negotiation Expert (RENE®) certifications. Lisa has been ranked in the Top 1% of realtors nationwide, and she has also achieved Five Star Professional Status every year since 2019. Lisa has received consistently high rankings from RateMyAgent on both local and state levels, and achieved Agent of The Year for the State of Delaware & Sussex County in 2023. Alignable also named her Local Businessperson of the year in 2023, 2024 & 2025. In 2023, Lisa was appointed to the Delaware State Real Estate Commission and became a certified National Association of REALTORS (NAR) mediation officer. In 2009, Lisa founded The Lisa Mathena Group to bring together a team of highly skilled professionals who share her commitment to exceptional service and client success. Since its formation, the team has consistently ranked among the top real estate groups in the state of Delaware, known for its professionalism, responsiveness, and results-driven approach. Today, Lisa and her team proudly serve clients throughout Delaware, helping families buy and sell homes with confidence while maintaining a reputation built on trust, performance, and long-term relationships.

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