Middletown Real Estate

This 3/4 Bedroom home has 2 Full Baths and sits in a country setting. It has been completely remodeled inside and out. New siding, new roof, new windows and landscaping on the outside. The inside has been freshly painted, all new flooring, kitchen has new stainless steel appliances and new cabinets. The eat-in kitchen also has new counter tops, beautiful backsplash and top of the line kitchen sink. The basement family room has built in book shelves and a full bath off of it. The office/ 4th bedroom has built in book shelves as well. There is plenty of storage and the laundry room in the basement too. Large rear yard! Convenient to shopping, schools, travel and historic sites.

323 S Jefferson St S, Middletown

Listing courtesy of Mackintosh , Inc.. Contact: 3017901700

$495,000

3 Beds ⋅ 2 Baths

Some homes simply have a soul—and this beautifully preserved 1920's Craftsman bungalow is one of them. Situated on a rare lot and a half in the heart of historic Middletown, this contributing home to both the National and Frederick Historic Registers has been lovingly cared for by just two families throughout its history. From the moment you arrive, you’ll notice the timeless character that sets this home apart. Tall original windows frame mature trees, gardens, and changing seasonal views from nearly every room, filling the home with natural light and creating a peaceful connection to the outdoors. Original wood floors, handcrafted trim work, pocket doors, custom storm windows, and historic architectural details blend seamlessly with thoughtful modern updates. The sellers have always appreciated the home’s solid clay block construction, which provides a remarkably quiet, comfortable feel and exceptional insulation rarely found in homes of this era. At the heart of the home is a beautifully renovated kitchen that has served as the gathering place for everything from weeknight dinners to holiday celebrations. A spacious island welcomes family and friends, while the thoughtful layout offers the perfect balance of openness and functionality. Upstairs, generously sized bedrooms, second-floor laundry, and an updated bath provide modern convenience while honoring the home’s historic roots. Outside, the property unfolds into a collection of extraordinary outdoor living spaces. Enjoy sunrise views from the backyard, summer sunsets from the welcoming front porch, abundant gardens, mature trees, a kitchen garden, and a private backyard retreat complete with a pergola and gas firepit. Every outdoor space offers its own unique experience, creating a rare sense of privacy and connection to nature in the heart of town. Major improvements include a renovated kitchen and baths, NTI combi-boiler, roof, insulation, updated electrical, propane installation, custom storm windows, and asbestos remediation. Perhaps most special of all are the home’s original handcrafted windows and custom-built storm windows—an increasingly rare treasure that has been lovingly maintained and thoughtfully restored. Throughout their stewardship, the sellers viewed themselves less as owners and more as caretakers of something truly special, dedicated to preserving the integrity and craftsmanship the original builders intended. The result is a home that honors its past while offering the comfort, beauty, and functionality today’s buyers desire. A rare opportunity to own a piece of Middletown history—where historic craftsmanship, thoughtful updates, beautiful gardens, and small-town charm come together to create something truly exceptional. Showings to begin August 1st, not before.

106 Prospect St, Middletown

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005

$379,000

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

7927 Main St, Middletown

Listing courtesy of Coldwell Banker Premier. Contact:

$379,000

4 Beds ⋅ 2 Baths

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

7927 Main St, Middletown

Listing courtesy of Coldwell Banker Premier. Contact:

$621,619

2 Beds ⋅ 2 Baths

2817 Bernstein Cir, Middletown

Listing courtesy of Blenheim Marketing LLC. Contact: 3022540100

$429,500

Rarely does a property offer this much versatility, whether you're a multigenerational family, an investor, or simply someone who wants room to spread out, 105 Oak Hill Drive delivers two fully functional homes on one spacious corner lot. The main residence is a classic Cape Cod brimming with character and move-in ready condition. Featuring 3 bedrooms, 1.5 baths, it includes a large upstairs den that works beautifully as a bedroom or home office, the layout is both flexible and functional. Enjoy a welcoming living room, a separate dining area, and an eat-in kitchen. The crown jewel of this property is the fully renovated detached ranch-style home, now featuring a brand-new mini-split HVAC system, updated throughout, and completely move-in ready. With its own bedroom and bathroom, this second dwelling is perfect as an in-law suite, a private residence, or a rental unit generating immediate income. It also offers a spacious bathroom with a walk-in shower. Additional highlights include new appliances, a large two-car detached garage with a loft, and a rear storage/workshop — all set on a generous corner lot with mature trees and lush yard space. The possibilities here are truly unique: live in the main house and rent the ranch for passive income, house multiple generations under one address while maintaining privacy, or use the entire property as a compound. All of this in an established Middletown neighborhood close to schools, shopping, and major commuter routes. This is not just a home, it's an investment in flexibility, family, and lifestyle.

105 Oak Hill Dr, Middletown

Listing courtesy of Straub & Associates Real Estate. Contact: (717) 612-9901

$429,500

4 Beds ⋅ 3 Baths

Rarely does a property offer this much versatility, whether you're a multigenerational family, an investor, or simply someone who wants room to spread out, 105 Oak Hill Drive delivers two fully functional homes on one spacious corner lot. The main residence is a classic Cape Cod brimming with character and move-in ready condition. Featuring 3 bedrooms, 1.5 baths, it includes a large upstairs den that works beautifully as a bedroom or home office, the layout is both flexible and functional. Enjoy a welcoming living room, a separate dining area, and an eat-in kitchen. The crown jewel of this property is the fully renovated detached ranch-style home, now featuring a brand-new mini-split HVAC system, updated throughout, and completely move-in ready. With its own bedroom and bathroom, this second dwelling is perfect as an in-law suite, a private residence, or a rental unit generating immediate income. It also offers a spacious bathroom with a walk-in shower. Additional highlights include new appliances, a large two-car detached garage with a loft, and a rear storage/workshop — all set on a generous corner lot with mature trees and lush yard space. The possibilities here are truly unique: live in the main house and rent the ranch for passive income, house multiple generations under one address while maintaining privacy, or use the entire property as a compound. All of this in an established Middletown neighborhood close to schools, shopping, and major commuter routes. This is not just a home, it's an investment in flexibility, family, and lifestyle.

105 Oak Hill Dr, Middletown

Listing courtesy of Straub & Associates Real Estate. Contact: (717) 612-9901

$465,999

4 Beds ⋅ 3 Baths

Welcome to this move-in ready Cedar model in the Villages at Middletown—where modern design meets everyday convenience. Offering 4 bedrooms, 2.5 bathrooms, and approximately 1,900 square feet, this home delivers stylish living with an open-concept layout ideal for today’s lifestyle. The main level impresses with a sleek kitchen featuring upgraded mocha cabinetry, stainless steel appliances, and a seamless flow into the living and dining areas—perfect for both relaxing and entertaining. A versatile flex space provides options for a home office, study, or creative use. Upstairs, the spacious primary suite serves as a private retreat, complete with an oversized walk-in closet and a well-appointed ensuite bath with double vanity and a large shower. Three additional bedrooms, including two with walk-in closets, offer flexibility for a variety of needs. The conveniently located upper-level laundry room adds everyday ease. Enjoy the outdoor setting with a backyard that backs to scenic green space, providing a peaceful backdrop. The walk-out basement offers endless potential for customization—ideal for expanding your living space. A perfect blend of style, space, and opportunity—schedule your tour today.

145 Dursley Cir, Middletown

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

$269,900

3 Beds ⋅ 2 Baths

"Investers Alert" - This property has been damaged by fire and needs entire Interior renovation including HVAC, Electrical, Drywall, Fixtures, Etc. Priced Accordingly. Buyer has approved plan for extension details can be provided upon request.This home is ready for whole renovation ,buyer can design and upgrade according to their desire.Property contains a direct access garage, enjoy outdoor gatherings on the beautifully landscaped lot with a private backyard—perfect for summer barbecues or peaceful evenings. Located minutes from Route 1, shopping centers, restaurants, and parks, this home combines suburban tranquility with convenient access to everything Middletown has to offer. Seller will accept higher and best offer (if acceptable to seller) as this conditions CASH offers only, no inspections or contigency. Don’t miss this chance to invest in one of Delaware’s most desirable markets!

945 Lansdowne Rd, Middletown

Listing courtesy of Real Broker, LLC. Contact: 3025567215

Middletown Real Estate

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