Delaware, the second smallest state in the United States, holds a significant place in American history. Beyond its beautiful coastline and charming towns, the state boasts a collection of remarkably old homes that stand as silent witnesses to centuries of change. These architectural treasures, some dating back to the 17th and 18th centuries, offer a tangible connection to the lives and times of Delaware’s early settlers and prominent figures. Exploring these twelve oldest standing homes is like stepping back in time, each structure whispering stories of colonial life, pivotal historical events, and the enduring spirit of the First State. From grand Georgian mansions to humble farmhouses, these well-preserved residences showcase the craftsmanship and evolving architectural styles of bygone eras, providing invaluable insights into Delaware’s rich heritage.

1. Georgian Colonial Home in Middletown, Delaware (1714)

Built in 1714, the Dilworth House is one of Delaware’s earliest surviving homes, constructed by Swedish colonist Olla Jansen during the 1600–1700 Native American Period. Nestled on 12.25 acres beside the Augustine Wildlife Preserve, this rare property blends historical legacy with natural beauty. The home features exceptional early masonry, including glazed brick “diapering” patterns, stepped belt courses, and exposed framework. Inside, original beams and brick fireplaces recall a time when a single chimney heated the home. With six bedrooms, three full baths, two half baths, and a finished attic, it offers generous space and preserved charm. While much of the home remains in original condition and needs restoration, updates have enhanced its function. Outbuildings like a silo, barn-turned-workshop, and cow shed make it ideal for farming, hobbies, or a unique retreat.

2. Rustic American Barn in Newark, Delaware (1726)

Built in 1726, this historic home sits on a lush 0.7-acre lot backing up to the scenic White Clay Creek, offering peaceful views and a serene atmosphere. Bursting with character, the structure presents a rare opportunity to be reimagined as a stunning single-family home, a series of townhomes, or even a creative studio or workshop. Its rustic charm makes it ideal for artisans or hobbyists seeking a space that inspires. Already connected to public sewer and electric, the mill offers a solid foundation for redevelopment, with fewer hurdles to start your vision. Whether for living, working, or creating, this property is a blank canvas with rich historic roots.

3. Colonial Revival Home in Christiana, Delaware (1750)

Built in 1750, the Brinkle-Maxwell House is a remarkable piece of Delaware’s heritage, listed on the National Historic Register and located in the Historic Village of Christiana—one of the state’s earliest settlements. With ties to Col. John Read and his son George Read, a signer of the Declaration of Independence, this home holds deep historical significance. Set on 1.5 acres of lush, private land bordered by the Christiana River and Lewden-Green Park, it offers a scenic and secluded setting ideal for a Bed & Breakfast or special events. The home features 6 bedrooms, 3 baths, and 4 fireplaces, with original wide-plank floors and a grand staircase adding to its timeless charm.

4. American Colonial Home in Newark, Delaware (1800)

Built in 1800, this home offers a rich blend of history and modern living, originally serving as a mill before its transformation into a charming three-bedroom, three-bathroom home. A former barn now serves as a guest house with a full suite including kitchen, living room, and loft. The main home features flagstone floors, exposed beams, stone walls, and elegant fireplaces, while the renovated kitchen boasts quartz countertops and a breakfast bar. Upstairs, the primary suite includes vaulted ceilings, French doors, and a private balcony, with additional bedrooms and baths on the upper levels. The guest house, currently used as an Airbnb, retains historic character with original shiplap walls, a wood stove, and skylit loft. Set on over an acre, the property includes multiple patios, a garage, pool, and stunning grounds.

5. Colonial Revival Home in Wilmington, Delaware (1810)

Built in 1810, the J. McCormick Farmhouse nestled on a 2/3-acre lot at the end of a cul-de-sac in the Breckenridge community, this home has been thoughtfully renovated, preserving original features like molded mantels and built-ins. The property, once owned by John Mitchell, a local property “flipper,” was saved from demolition in the 1990s. The home offers a spacious main floor with living areas and a well-equipped kitchen, while the upstairs includes a primary suite, two bedrooms, and a versatile finished attic. Beautiful gardens, raised bed gardens, and a front porch swing provide a peaceful, scenic retreat.

6. American Foursquare Home in Rehoboth Beach, Delaware (1820)

Built around 1820, this unique property offers a blend of historical charm and modern convenience, ideally situated east of Coastal Highway for easy access to downtown Rehoboth Beach and the Junction & Breakwater trails. Imagine biking or hiking the 14+ miles of trails at nearby Cape Henlopen State Park via the Wolfe Neck Tract. The spacious .46-acre GR-zoned lot provides ample room for all your recreational vehicles. The remodeled farmhouse features three bedrooms and two baths, including a convenient first-floor bedroom suite. A detached 20′ x 34′ garage with two large bays and finished spaces, along with a frame shed and tackle shack, caters to hobbyists and collectors.

7. Italianate Home in Smyrna, Delaware (1833)

Built in 1833, this property at first glance presents a stately appearance with its Italianate architectural influences, including a bracketed cornice and tall windows. The welcoming wrap-around porch adds to its charm and offers outdoor living space. The residence also holds potential within the historic context of Smyrna. Its presence on Main Street suggests a central location within the town. Located at a prime location within Smyrna, it offers walkability to local amenities and a connection to the town’s character

8. Italianate Home in Delaware City, Delaware (1855)

Built in 1855, this captivating residence welcomes you through grand 9ft doors into a foyer showcasing a stunning three-story staircase. Soaring 10-foot ceilings on the first level create an immediate sense of spaciousness, complemented by 9-foot ceilings on the second and 8-foot ceilings on the third. To the right, an enormous eat-in kitchen awaits, featuring granite countertops, a large island, and 42-inch soft-close solid wood cabinets, along with a convenient 9ft pantry. The main level also offers a half bath and access to a basement with a modern concrete floor, revealing the original stone foundation. To the left of the foyer, a generously sized living space mirrors the kitchen in size, flowing into a bright sitting or breakfast room with access to the rear patio, all enhanced by large windows and recessed lighting.

9. Federal Vernacular Home in Delaware City, Delaware (1857)

Built around 1857, this charming home welcomes you from the driveway porch into a foyer with a staircase leading to upper levels. To the left, a hall connects to the dining room, while the right leads to a spacious kitchen featuring granite countertops and 42-inch soft-close cabinets, both flowing into an open floor plan encompassing the dining and living areas. Large windows flood the space with natural light, and double doors open to a generous patio overlooking the property. The main level also includes a convenient half bath and a tankless hot water heater. Upstairs, the second floor hosts the primary bedroom with an en-suite bathroom, walk-in shower, multiple closets, and a laundry room, while the third floor offers two additional bedrooms connected by a Jack & Jill bathroom.

10. Colonial Revival Home in Little Creek, Delaware (1860)

Built in 1860, this fully remodeled 4-bedroom, 2.5-bathroom home resides in the charming town of Little Creek, a short distance from Dover. Step inside to discover vinyl plank flooring throughout and a bright, inviting white kitchen. The convenience of a first-floor primary bedroom adds to the appeal, while three additional spacious rooms await on the second floor. Its location offers proximity to the bay and a fishing pier, perfect for enjoying the coastal lifestyle.

11. Italianate Home in Wilmington, Delaware (1860)

Built in 1860, this historic duplex is offering a prime investment opportunity. This 1,500 sq ft Colonial-style townhouse comprises two 2-bedroom units—one currently rented, providing immediate income, and one vacant, ready for your next tenant or updates. The property features a full basement, forced air heating powered by natural gas, and on-street parking. Situated on a 1,742 sq ft lot in the Trinity Vicinity neighborhood, it falls within the Christina School District. With its convenient location and income-generating potential, this property is ideal for investors looking to maximize rental returns.

12. Greek Revival Home in Milford, Delaware (1866)

Built in 1866, this stunning Greek Revival home sits atop a picturesque hill in downtown Milford, exuding timeless elegance and rich history. Set on over half an acre, the property features a detached two-car garage/carriage house, wrought iron fencing, and ample off-street parking—an uncommon luxury in the area. Inside, freshly painted rooms, sunlit windows, and original hardwood floors blend seamlessly with modern updates, including a fully renovated kitchen. With six bedrooms across three spacious stories, plus bonus areas and a separate office entrance, the home is ideal for live-work flexibility. Its prime downtown location, historic pedigree (including a spot on the National Register), and potential for business or short-term rental use make it an incredibly versatile opportunity. Whether as a grand residence, a home-based business hub, or an income-generating property, this one-of-a-kind Milford landmark offers endless possibilities.