Middletown Homes under $500,000

Nestled on a generous 0.22-acre lot, this charming 5-bedroom, 3-bathroom ranch-style home offers a perfect blend of comfort and functionality. As you approach the residence, you'll appreciate the level lot, providing ample space for outdoor activities, gardening, or simply enjoying the fresh air. The well-maintained brick exterior not only adds to the home's curb appeal but also promises durability and low maintenance for years to come. Step inside to discover a cozy family room with a wood-burning fireplace. The main level features four spacious bedrooms, ensuring plenty of room for relaxation and privacy. The main floor has laundry hookups and two full bathrooms which provide convenience for busy mornings and gatherings, making this home perfect for entertaining. Gather around the fireplace on chilly evenings, creating lasting memories with loved ones in the heart of the home. Built in 1950, the property offers a great separate space for in-law quarters with a fully finished basement which includes a kitchen area, dining room, full bath, laundry area, and living room. The basement can only be accessed from the outside entrance. The inviting porch is an excellent spot for sipping morning coffee or unwinding after a long day, enhancing the overall sense of tranquility this property offers. Parking is a breeze with a detached garage that accommodates two vehicles, along with additional driveway and on-street parking options. This thoughtful design ensures that you and your guests will always have a place to park. Located in a peaceful area, this home provides a serene escape while still being conveniently close to schools, fire station, and local amenities. Whether you're looking for a quiet evening at home or a vibrant community to explore, this property meets a variety of lifestyle needs. This ranch-style home is ready to welcome you. Experience the comfort and warmth that this property has to offer and envision the countless memories waiting to be made within its walls. Don't miss the opportunity to make this delightful residence your own!

320 E Emaus St, Middletown

Listing courtesy of Iron Valley Real Estate Hanover. Contact:

$300,000

3 Beds ⋅ 2 Baths

INCREDIBLE INVESTMENT OPPORTUNITY IN MIDDLETOWN! Opportunity awaits at 312 W Windmill Way, where endless potential, an exceptional homesite, and an unbeatable price come together to create a rare opportunity in one of Middletown's established neighborhoods! Offered at just $300,000, this classic brick ranch is situated on a sprawling one-acre lot, surrounded by homes commanding significantly higher price points, making it an incredible opportunity for investors, renovators, or buyers looking to build equity and bring their vision to life. Set against a picturesque backdrop of open farmland, the property offers a peaceful setting, expansive outdoor space, and beautiful countryside views that are increasingly difficult to find at this price point. The timeless brick exterior provides a wonderful foundation for transformation, while the desirable single-story layout offers three bedrooms, two full bathrooms, a spacious family room with a charming wood-burning stove, and a generously sized kitchen with ample opportunity for reimagining. Downstairs, the massive basement presents another exciting opportunity, offering an abundance of square footage and the potential to create additional finished living space, recreation areas, or functional storage. While this home is ready for some TLC and a fresh vision, the possibilities are truly remarkable. Whether you're searching for your next renovation project, an investment opportunity, or a property to transform into your dream home, the combination of a classic brick ranch, expansive one-acre lot, breathtaking farmland backdrop, and desirable Middletown location creates an opportunity that's hard to overlook. With a $300,000 price tag and incredible potential for added value, this is your chance to turn vision into value. Don't miss it!

312 W Windmill Way, Middletown

Listing courtesy of Keller Williams Realty. Contact:

$293,500

2 Beds ⋅ 3 Baths

Welcome to 129 Rosie Drive, a well-maintained end-of-row home nestled in the heart of Middletown, Delaware. With more space, more light, and more privacy than a standard townhome, this property offers the perfect opportunity for a buyer ready to put their personal touch on a great foundation. Step inside and you’ll find hardwood floors flowing throughout the home, creating a warm and cohesive feel from room to room. The layout is functional and inviting, ideal for everyday living and easy entertaining. Upstairs, the primary bedroom impresses with a spacious walk-in closet, offering the storage and comfort you deserve. The additional bedroom and well-appointed bathrooms round out a thoughtful floor plan designed for modern living. Head outside and discover one of this home’s standout features: a large backyard that sets it apart from the typical townhome. Whether you envision weekend gatherings, a garden retreat, or simply room to breathe, this outdoor space delivers. 129 Rosie Drive is move-in ready and waiting for its next chapter. Schedule your private tour today and imagine the possibilities.

129 Rosie Dr, Middletown

Listing courtesy of Realty One Group Restore. Contact:

$80,000

3 Beds ⋅ 1 Baths

This property will be offered at Public Auction on Thursday, 12/3 at 6:00 PM. The listing price is the opening bid only and in no way reflects the final sale price. 10% down due at auction, 2% transfer tax and 3% buyer’s premium to be paid by the purchaser. Real estate taxes will be prorated.

1035 Plane St, Middletown

Listing courtesy of Cavalry Realty LLC. Contact:

$379,900

3 Beds ⋅ 2 Baths

Nestled in a serene setting, this charming 3-bedroom, 1.5-bathroom home offers a unique blend of history, character, comfort, and functionality. Originally built as a single-room schoolhouse known as Coble School, this distinctive property offers a rare opportunity to own a piece of local history while enjoying the conveniences of today. With its commercial zoning, the property also provides added flexibility and potential for business, investment, or residential use. As you step inside, you'll be greeted by a warm and inviting atmosphere that flows throughout the 1,768 square feet of living space. The heart of the home features a kitchen that seamlessly connects to the living areas, making it easy to entertain guests or enjoy everyday living. The three generously sized bedrooms provide comfortable retreats, each offering natural light and room for personalization. The home includes one full bathroom and an additional half bath for added convenience. Upstairs, you'll find a huge bonus room complete with a bar, making it the perfect space for entertaining, hosting gatherings, creating a game room, or designing your own private retreat. This additional space adds even more versatility and character to an already unique property. Outside, the property offers approximately 0.54 acres, providing plenty of room to enjoy the outdoors, expand, or explore additional possibilities. A standout feature is the 30' x 60' detached garage, offering substantial space for vehicles, equipment, storage, a workshop, or potential business-related uses. The property also features an attached garage, providing even more parking and storage options. The home's brick construction offers durability and classic appeal, while the spacious grounds provide a blank canvas for gardening, outdoor entertaining, or simply enjoying the peaceful surroundings. One of the property's most unique advantages is its commercial zoning, offering flexibility for those looking to combine residential living with business opportunities, subject to applicable zoning requirements. Whether you're searching for a distinctive home, business location, investment property, or a combination of uses, this property presents an opportunity that's hard to find. Conveniently located within a short drive of local amenities, shopping, and dining, this historic former schoolhouse combines small-town charm with tremendous potential. From its history as Coble School to its impressive detached garage, spacious bonus room with bar, and versatile commercial zoning, this property is full of possibilities. Don't miss your chance to own this one-of-a-kind property! Schedule your showing today and discover all the character, space, and opportunity this unique property has to offer.

1235 N Union St, Middletown

Listing courtesy of Union Realty, Inc.. Contact:

$299,900

3 Beds ⋅ 3 Baths

Nestled in the charming Tartan Court community, this exquisite townhouse offers a harmonious blend of traditional elegance and modern comfort. Built in 2003, this meticulously maintained residence spans 1,725 square feet, providing ample space for relaxation and entertaining. Step inside to discover a warm and inviting interior, where natural light dances across the laminate plank and plush carpet flooring. The heart of the home is the spacious eat-in kitchen, equipped with high-end appliances including a self-cleaning oven, dishwasher, and disposal, making meal preparation a delight. The adjoining dining area flows seamlessly into the living space, perfect for hosting gatherings or enjoying quiet evenings at home. The primary suite is a true retreat, featuring an en-suite bath that offers both luxury and convenience. With two additional well-appointed bedrooms and an additional full bath. The full basement, accessible from both inside and outside, is a versatile space that can be transformed to suit your lifestyle-whether as a home gym, entertainment area, or additional storage. The walkout level provides easy access to the beautifully landscaped rear yard, which backs onto an open common area, offering a serene backdrop for outdoor activities or peaceful moments in nature. Outside, the property boasts a charming deck, ideal for morning coffee or evening gatherings under the stars. The level lot features both a front and rear yard, providing a perfect balance of privacy and community. The paved driveway leads to an attached garage, ensuring convenience and security for your vehicles. Located in the middle of the block, this home enjoys a peaceful setting while remaining close to essential amenities. With a bus stop less than a mile away, commuting and exploring the surrounding area is effortless. This property is not just a house; it's a lifestyle. Experience the perfect blend of comfort, style, and community in this exceptional townhouse, where every detail has been thoughtfully designed to create a welcoming and luxurious living environment. Embrace the opportunity to make this exquisite residence your new home.

411 Tartan Dr, Middletown

Listing courtesy of Iron Valley Real Estate at The Beach. Contact:

$249,900

3 Beds ⋅ 2 Baths

OFFERS RECEIVED - DEADLINE SET FOR 11/2/2026 3 PM - Solid bones, incredible setting, and tons of upside. This 3-bedroom, 2-bath ranch sits on a quiet .93 acre country lot with gorgeous, wide-open views of neighboring farmland. The home features a practical single-level layout, an attached 2-car garage, and some hardwood flooring waiting to be brought back to life. There's no sugarcoating it, the seller has moved to a senior living facility so please forgive the yard sale treasures in the photos but they will all be removed from the home. There is a good bit of work and TLC from top to bottom needed. But for an investor looking for their next flip, or a handy buyer wanting to build instant sweat equity, the fundamentals are all here. Between the peaceful setting and great location, the finished product will have serious appeal. Add this to your tour list and bring your contractor and your vision. Cash or conventional financing only and sold as-is.

2830 Orchard Ln, Middletown

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

$410,000

3 Beds ⋅ 2 Baths

Open House, Sunday Nov. 1 12:00-2:00 PM Welcome to this beautifully updated 3-bedroom, 1.5-bath split foyer in Fountaindale South. The home offers fresh paint, new waterproof laminate plank flooring, updated lighting and bath/kitchen fixtures, and a renovated kitchen featuring all-new appliances, quartz countertops, tile backsplash, and a walk-in pantry. The renovated full bath is finished in clean, neutral tones. Off the kitchen enjoy relaxing outdoor living from the spacious deck and screened porch overlooking the 0.34-acre lot. The main level features bright, comfortable open living spaces, while the finished walkout lower level offers a large additional bedroom, half bath, and more flexible space that could be enjoyed as a home office, recreation room, or guest area. The unfinished portion of the lower level has a second refrigerator and standing freezer which convey, and modular and built in shelving with ample space for organized storage. Additional excellent improvements include a new roof in 2024 with warranty, and new HVAC in 2019. The very large 2-car garage attached at the breezeway provides convenient access to the breezeway and backyard. Located on a quiet cul-de-sac with convenient access to Historic Middletown, shopping, dining, commuter routes, and highly rated Middletown-area schools, this affordable move-in-ready home offers an appealing combination of updates, space, and location.

4397 Agate Ct, Middletown

Listing courtesy of Samson Properties. Contact:

$279,900

3 Beds ⋅ 2 Baths

First Look Initiative for home buyers until 11/27/26. This ranch style home has lots of space with a family room, living room, and bonus room above the garage. Enjoy the nice 1 acre lot with a large detached garage and covered back porch. Schedule a showing today and see how you can make this home your own!

86 Water Plant Rd, Middletown

Listing courtesy of Braddock Realty Inc. Contact:

$199,900

3 Beds ⋅ 1 Baths

Cute and well-maintained 3BR, 1BA ranch home featuring convenient one-floor living! Spacious oversized living room, some updated flooring (2024), and an architectural shingle roof installed in 2021. Enjoy the fenced backyard, perfect for pets and outdoor activities, plus a storage shed for added convenience. Driveway provides off-street parking. Efficient natural gas heat and gas cooking. Easy-to-maintain property that's ideal for first-time buyers, downsizers, or investors. Don't miss this great opportunity in Middletown!

1057 N Pine St, Middletown

Listing courtesy of Iron Valley Real Estate of Central PA. Contact:

$400,000

3 Beds ⋅ 4 Baths

This property will be offered at Public Auction on Saturday, November 21, 2026 at 10am. The listing price is the opening bid only and in no way reflects the final sale price. 10% down due at auction, 2% transfer tax to be paid by the purchaser, real estate taxes prorated. Parcel 1: This spacious home offers a functional layout with plenty of room to enjoy. The first floor features an entryway, living room, eat-in kitchen, dining room, laundry room, family room, and full bathroom. The second floor includes a primary bedroom with a private bathroom, two additional bedrooms, a full bathroom, a half bathroom, and a finished bonus room above the garage. Additional amenities include an unfinished basement and an oversized two-car garage with a dedicated workshop area.

396 Woodland Ave, Middletown

Listing courtesy of Cavalry Realty LLC. Contact:

$50,000

3 Beds ⋅ 1 Baths

This property will be offered at Public Auction on Saturday, November 21, 2026 at 12pm. The listing price is the opening bid only and in no way reflects the final sale price. 10% down due at auction, 2% transfer tax to be paid by the purchaser, real estate taxes prorated. Parcel 3: This three-bedroom home offers a full bathroom, an unfinished basement, and an exterior shed for additional storage. The property is in need of cosmetic updating, offering an opportunity to make improvements to suit your preferences.

120 S Lawrence St, Middletown

Listing courtesy of Cavalry Realty LLC. Contact:

Middletown Homes under $500,000

Newest Middletown Homes under $500,000

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