Build Your Dream Home In Cheswold
As one of the original 13 colonies – and the first state in the union – Delaware is known for its history. It is also closely tied to the railroad industry, which helped the state to become a critical transportation corridor along the East Coast. Many Delaware towns sprang up around railroad stations, including the charming small town of Cheswold.
Located just north of Dover, Cheswold is a diverse, welcoming community with lots to offer. It is close to major cities like Wilmington, Philadelphia, and New York City while retaining its small-town atmosphere. If you are thinking about building a home in Cheswold, Carl Deputy & Son Builders can help you design and create a beautiful custom home to fit your lifestyle.
At Carl Deputy & Son Builders, we have earned a reputation for building high-quality, timeless custom and semi-custom homes in Kent and Sussex Counties in Delaware and the Eastern Shore of Maryland. We combine exceptional craftsmanship with outstanding customer service, helping each of our clients turn their vision for a dream home into reality. To learn more about building a new home in Cheswold, contact our team today.


About Carl Deputy & Son Builders
Founded in 1986, Carl Deputy and Son Builders is based in Felton, Delaware. For 40 years, we have helped homeowners build new homes and renovate existing houses. Our client-centered approach ensures that every home we build reflects the homeowner’s needs, preferences, and lifestyle.
What truly sets us apart from other builders is our dedication to customer service. Even under the best of circumstances, building a new home can feel overwhelming. Our goal is to make the process as smooth and stress-free as possible. We prioritize clear communication, promptly answering questions and addressing concerns so you always know what is happening with your construction project.
We also believe in building homes that last. That means using high-quality materials standard, with no upgrades required to get premium. We exclusively partner with trusted tradespeople and subcontractors who share our commitment to craftsmanship and exquisite attention to detail.
Your Cheswold custom home is more than just a building – it’s a place to relax, gather with loved ones, and enjoy everyday life. Our design team takes the time to make sure that your house plans are exactly what you want before construction begins. We will consult with you along each step of the process to make sure that your vision is fully realized.
Custom Home Builders in Cheswold, Delaware
Carl Deputy and Son Builders offer both custom and semi-custom homes in Cheswold. A fully custom home allows you to design every detail, from the layout to the finishes. A semi-custom home gives you the flexibility to choose from our extensive collection of floor plans and personalize the features and finishes to meet your needs.
The process begins with selecting a home site. We can build on land that you already own or on one of our available lots. If you haven’t purchased property yet, we can help you identify a lot that is suitable for residential construction.
Next comes the design phase. For semi-custom homes, you will start with a floor plan and then select finishes such as flooring, cabinetry, fixtures, and paint colors. For custom homes, our designers will work closely with you to develop a personalized floor plan before finalizing features and finishes. Once the design is complete, we’ll provide a detailed cost estimate and construction contract.
If you need financing, this paperwork can be used to secure a construction and/or land loan. If you don’t already have a lender, we’re happy to provide recommendations.
Once all of the paperwork is finalized and financing is secured, construction can begin. Before we break ground, we will review your plans one last time with you to make sure that everything meets your expectations. From there, construction will progress in carefully managed stages, from the foundation and framing to mechanical systems, flooring, and fixtures.
Throughout the construction process, we will coordinate all required inspections and approvals. We will also schedule “muddy boots” tours so that you can see your home taking shape. This is also a great time to ask questions and request any changes.
When construction is complete, we will conduct a final walkthrough of your home to review the various features and explain how to maintain your house. We will also complete any remaining punch list items. When everything is done to your satisfaction, we’ll schedule a closing and hand over the keys to your new Cheswold custom home.
Cheswold Custom Home Features
When you choose Carl Deputy and Son Builders, many premium features come standard for both our custom and semi-custom homes. Depending on your selections, this may include:
- TV hookups in all bedrooms and living rooms
- Ceiling fan wiring in all bedrooms and living rooms
- Custom-built cabinets
- Built-in trash bin pull-out
- Granite countertops
- 50-gallon hot water heater
- Comfort height toilets
- Moen® fixtures
- Quiet bath exhaust vents
- 50-gallon hot water heater
- GAF Timberline® shingles with a 50-year warranty
- Seamless gutters and downspouts
- Pro Via® or Mastic® premium vinyl siding
- Insulation package with R-21 exterior walls and R-38 blown ceiling
- Insulated fiberglass doors with Schlage® interior door handles and exterior door locks
- Cased openings and windows with Sil
- Double hung vinyl windows with low-E argon gas
- 5-course block foundation
- Continuous footer system
- Engineered truss system
- Spray foamed cold floors areas
Homeowners also have the option to upgrade various finishes and features. Whether you want specialty countertops, custom tile work, or unique design elements like waterfall islands or built-in shower niches, we will work with you to explore options for making your house truly your own. We will also explain how the design choices that you make will impact your overall budget.
Our goal is simple: we want you to love both the process and the final product. By working closely with our clients, we have helped hundreds of homeowners achieve their vision. We’d love to do the same for you.
Recent Custom Home Builds

Custom Home – Smyrna
This custom 4,038 square-foot home flawlessly blends modern luxury with farmhouse charm, creating an inviting and elegant living experience. The exterior boasts striking charcoal straight siding accented with matching board and batten, complemented by expansive front and back porches ideal for relaxing and entertaining. The massive, hotel-inspired custom front door makes a grand entrance, hinting at the exquisite interiors within. Inside, the home offers six spacious bedrooms and four well-appointed bathrooms, ensuring ample space and comfort for family and guests. The heart of the home is the gourmet kitchen, featuring custom cabinets in stained white oak, elegant quartz countertops, and matching stained floating shelves, creating a stylish and functional space for cooking and gathering. The highlight of the home is the expansive two-story living room, anchored by a real wood-burning stone fireplace that adds warmth and rustic charm. The room’s soaring ceilings enhance the sense of grandeur while maintaining a cozy atmosphere. Above the living room, a loft provides a quiet sitting area, perfect for reading or unwinding. Every detail in this home has been meticulously designed to blend modern sophistication with farmhouse comfort, making it the perfect sanctuary for comfortable living.
4,038
sqft
6
Beds
4
Baths

Custom Home – Milford
This custom 3,200 square foot home is a masterpiece of design and craftsmanship. Its striking exterior features a harmonious blend of stone and board and batten, complemented by diamond-grilled windows that add a touch of classic elegance. Inside, the home offers four spacious bedrooms and four well-appointed bathrooms, each designed with attention to detail and comfort. The heart of the home is the kitchen, adorned with custom-stained cabinets and tile splashes throughout, creating a sophisticated and functional space for cooking and entertaining. The living area is anchored by a linear tiled fireplace with built-in shelving, providing both warmth and a stylish focal point. The master suite is a true retreat, featuring a tiled walk-in shower with inlaid mirrors and luxurious tiled walls. Coffered and vaulted ceilings throughout the home add a sense of grandeur and spaciousness. Each bathroom continues the theme of elegance with beautifully tiled splashes, ensuring a cohesive and refined aesthetic throughout the home. This residence is a perfect blend of modern luxury and timeless design, making it an ideal sanctuary for contemporary living.
3,200
sqft
4
Beds
4
Baths

Custom Home – Wild Quail
This custom two-story, 6,570 square foot home is a luxurious blend of elegance and functionality. Its striking stone exterior is complemented by sleek black windows, creating a modern yet timeless facade. Inside, the home features six spacious bedrooms and six well-appointed bathrooms, ensuring ample space and comfort for family and guests. The heart of the home is the gourmet kitchen, equipped with commercial-grade appliances, custom cabinets, and elegant quartz countertops and backsplash. A hidden cabinet door leads to a spacious pantry, providing both style and practicality. Two inviting fireplaces add warmth and ambiance to the living spaces, perfect for cozy gatherings. The master suite, located on the first floor, is a true retreat, featuring a walk-in shower, a luxurious soaking tub, and a walk-in closet with custom shelving and a convenient laundry area. Step outside to a large maintenance-free deck, perfect for outdoor entertaining, and a cozy screen room that allows you to enjoy the outdoors in comfort and style. The finished basement offers additional living and entertainment space, ideal for a home theater, gym, or recreation room. Every detail of this home has been thoughtfully designed to combine luxury, comfort, and functionality, making it the perfect place for modern living.
6,570
sqft
6
Beds
6.5
Baths
About Cheswold
Located in Kent County, Cheswold is part of the Dover metropolitan area. A small town of just .4 square miles, Cheswold is home to approximately 2,000 residents. It is a diverse town that was originally inhabited by members of the Lenape Indian tribe, Scottish immigrants, and enslaved people. To this day, the Lenape Indian Tribe maintains a presence in Cheswold.
Cheswold’s origins can be traced back to the mid-1800s, when the town was incorporated in 1856, shortly after the construction of the Delaware railroad. At this time, the Leipsic Station was established as a stop along the railroad (named for the nearby town of Leipsic). This railroad stop became an important depot for transportation, particularly for mail and agricultural products such as grain and fruit.
By 1860, the town of Cheswold had grown to 35 houses, 3 general stores, a brickyard, a wheelwright, and a grain warehouse. Later, the Leipsic Station’s name was changed to Moorton after John S. Moor, who owned most of the land in the region, operated a general store, and was the first postmaster for this area of Kent County. However, the dual names created some confusion because other towns in Delaware and Pennsylvania had similar names.
In 1888, the town held a contest for residents to come up with a new name. The winning name, Cheswold, came from a combination of “Chess” for the chestnut trees near the train depot and “wold,” which means forest or trees. In later years, the town’s name was shortened to Cheswold.
Cheswold is one of the smaller municipalities in Delaware. It sits at the intersection of U.S. Route 13 and Delaware Route 42. It is just 14 miles from the state capital of Dover. In addition to numerous highways, residents can get around using the DART First State bus, which heads south to Dover and north to Smyrna. The Delmarva Central Railroad also passes through Cheswold, and the Delaware Airpark is located right outside of town.
Cheswold has multiple neighborhoods, including Old Town, Main Street, Nobles Pond, Fox Pointe, Cheswold Village, Parkers Run, and Leyland Village. As a small town, Cheswold doesn’t have a large park within its boundaries. However, residents visit many nearby parks in Kent County, such as Brecknock Park, Fork Branch Preserve, Killens Pond, Fort Delaware State Park, and Cape Henlopen State Park. Cheswold is also a short drive to many of Delaware’s best beaches, including Broadkill Beach, Rehoboth Beach, Dewey Beach, and Lewes Beach.
There is an array of stores and services located in Cheswold, including Redner’s Market, Cheers Wine and Spirits, Cheswold News and Tobacco, Fabulous Nail Bar, Shore Stop, Tattoo Mafia, and State Line Building Supply. When it comes to restaurants, residents enjoy Poliseno Pizza in Cheswold, and nearby Stonerail Market, Grey Fox Grille, Pleasanton’s Seafood, Bul Jang BBQ, and Rail Haus (all in Dover).
Cheswold is part of the Capitol School District. Students in the area attend North Dover Elementary, Fairview Elementary, or Hartley Elementary before moving on to William Henry Middle School (5th and 6th grades) and Central Middle School (7th and 8th grades). They can then attend Dover High School.
There are many public libraries near Cheswold. This includes the Kent County Public Library in Dover, the Dover Public Library, and the Smyrna Public Library. There are also several institutes of higher education in the region, including Delaware State University, Wesley College, Delaware Technical and Community College, and Wilmington College.
While Cheswold is a small town, it has a lot going for it. It offers historic charm and friendly neighbors, all in close proximity to bigger cities like Dover. This makes Cheswold a great place to build a new custom home.
Ready to Build a Custom Home in Cheswold? Give Us a Call!
Cheswold is a beautiful small town with a rich history. It offers the perfect combination of proximity to beaches and major cities, a close-knit community, and a short commute to Dover. If you are looking for a slower pace of life without sacrificing accessibility to all that Delaware has to offer, Cheswold might be the ideal place to build your custom home.
With four decades of experience in the industry, Carl Deputy and Son Builders is known for quality construction and exceptional service. We work closely with homeowners to make the building process efficient, transparent, and enjoyable.
To learn more about custom home construction in Cheswold or to schedule a consultation with a member of our design and building team, call 302-284-3041 or fill out our online contact form.


