Chester Homes with Colonial Style

Chester Homes with Colonial Style

Welcome to Chester, a charming gem nestled in the heart of the United States, where history meets modern living. Known for its picturesque landscapes and vibrant community, Chester offers a unique blend of small-town charm and urban convenience. With its tree-lined streets and welcoming neighborhoods, this city is perfect for families, professionals, and retirees alike.

One of the standout features of Chester is its rich architectural heritage, particularly the stunning Colonial-style homes that grace many of its streets. These homes are not only a nod to the past but also a testament to the timeless elegance and craftsmanship that defines this architectural style. Characterized by their symmetrical facades, gabled roofs, and classic brick exteriors, Colonial homes in Chester exude warmth and sophistication. Imagine sipping your morning coffee on a spacious front porch, surrounded by lush greenery and the gentle sounds of nature.

Living in a Colonial-style home in Chester means embracing a lifestyle steeped in tradition while enjoying the conveniences of modern amenities. Many of these homes have been thoughtfully updated to include contemporary features, making them ideal for today’s discerning buyers. The spacious layouts and inviting interiors provide ample room for family gatherings and entertaining friends.

Beyond the beautiful homes, Chester boasts an array of parks, local shops, and dining options, ensuring that everything you need is just a stone's throw away. With its strong sense of community and a commitment to preserving its historical charm, Chester is not just a place to live; it's a place to call home. Discover the allure of Chester and the enchanting Colonial homes that await you!

Newest Chester Homes with Colonial Style

4 Beds ⋅ 3 Baths

Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

313 Thomas White Blvd, Chester

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3848

4 Beds ⋅ 3 Baths

Welcome Home! JUST LISTED & OPEN Sunday 8/9 from 9am-11am OR by APPT DAILY! Barely lived in, this home still looks like new, offering all the benefits of new construction without the wait. The thoughtfully designed floor plan of the Simone model offers exceptional flexibility. The main level features a stunning gourmet kitchen with crisp white cabinetry, a large center island, stainless steel appliances, a wall oven/microwave combination, a propane gas range, all within an open-concept layout that flows into the light-filled dining room. The lovely living room is anchored by a cozy stone fireplace, while the screened porch provides the perfect place to relax and unwind. The main-level primary suite features tray ceilings and offers a spa-inspired bath with an expansive walk-in closet, dual vanities, and a large walk-in shower. One additional bedroom and a private office/den (or optional 5th bedroom), as well as a full bath and laundry room, are all located on the main level. Upstairs, you'll find a loft/family room, perfect for entertaining. Two additional bedrooms and a full bath accommodate family and guests. The attached garage provides added convenience and storage. Beyond the home, you'll enjoy an unmatched resort-style lifestyle with incredible community amenities, including a 23,000-square-foot clubhouse, gym, indoor and outdoor pools, billiard room, tennis and pickleball courts, a community pier, outdoor bar, fire pit, and a full calendar of social events. The nearby Cross Island Trail is perfect for walking, running, or biking, and you're just minutes from shopping, dining, and everything Kent Island has to offer. If you're looking for a home that combines luxury, space, and an exceptional lifestyle, 209 Harrier is one you won't want to miss.

209 Harrier Way, Chester

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

3 Beds ⋅ 3 Baths

Estate Sale! Incredible opportunity to own one of the best values on Kent Island. Priced well below its potential, this 3-bedroom, 2.5-bath Dundee Harbor townhome offers approximately 1,400 square feet with an excellent upside. An updated home in the community sold for $365,000 in 2025, and this property offers outstanding potential for investors, flippers, or buyers looking to build equity. Estimated rental potential of approximately $2,400 per month (buyer to verify). Enjoy relaxing or entertaining on the rear deck, then take advantage of Dundee Harbor's water privileges on Piney Creek, including a private community pier for fishing, kayaking, paddleboarding, crabbing, or simply enjoying the waterfront. Just minutes from Kent Narrows, you'll love the waterfront restaurants, marinas, boat ramps, tiki bars, live entertainment, and Chesapeake Bay lifestyle. Conveniently located near shopping, everyday conveniences, and Route 50, this home offers an easy commute while delivering the relaxed Eastern Shore lifestyle buyers are looking for. Whether you're searching for an investment property, primary residence, or weekend retreat, this Estate Sale is an opportunity you won't want to miss. Schedule your showing today!

1025 Dundee Ct, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

4 Beds ⋅ 3 Baths

Welcome to this beautiful home in the desirable Brooks Chapel neighborhood! Offering 4 bedrooms, 2.5 bathrooms, and approximately 2,462 square feet of living space, this home combines a spacious floor plan with inviting indoor and outdoor features. The property offers excellent curb appeal with a full front porch featuring recessed lighting, a paved driveway, and a two-car attached garage. Inside, the open-concept main level features hardwood flooring, plantation blinds, and a private office or study—perfect for working from home. The spacious family room includes a ceiling fan and flows seamlessly into the gourmet kitchen, featuring granite countertops, stainless steel appliances, a tile backsplash, pantry, recessed lighting, and a center island with breakfast-bar seating. The bright and expansive morning room showcases a vaulted ceiling and provides direct access to the large composite deck with vinyl railings. Upstairs, the primary suite features a ceiling fan, walk-in closet, and private bathroom with tile flooring, a double vanity with granite countertop, jetted soaking tub, and separate tile shower. Three additional generously sized bedrooms offer carpeting, ceiling fans, and ample closet space. The fenced backyard provides plenty of room for entertaining, pets, and outdoor enjoyment. Beautifully maintained and move-in ready, this wonderful home is waiting for its next owner! Some images in this listing have been virtually staged. SCHEDULE SHOWINGS THROUGH SHOWINGTIME!

10007 Ethens Castle Dr, Chester

Listing courtesy of Move4Free Realty, LLC. Contact: 2023691460

5 Beds ⋅ 4 Baths

Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary suite. Designed for both luxury living and entertaining, the open floor plan features 7-inch wide plank flooring, a gas fireplace, entry-level guest suite, and high-end finishes throughout. The gourmet kitchen is the heart of the home, complete with shaker-style cabinetry, quartz countertops, an oversized island, premium ZLINE stainless steel appliances, upgraded custom lighting, and expansive water views. Upstairs, the spacious primary suite offers a peaceful waterfront retreat with a spa-inspired bath featuring a 6-foot tiled walk-in shower with dual shower heads, a built-in bench, double vanities, and generous closet space. Bedroom-level laundry and beautifully finished bathrooms with tile flooring add everyday convenience. Outdoor living is just as impressive, with an expansive rear deck and covered patio overlooking the creek—perfect for enjoying sunrises over the water or relaxing while watching local wildlife. Adding to the sense of privacy, approximately 181 acres of rural land zoned "Countryside District" stretch across the shoreline on the opposite side, preserving the natural views with protected land. For those who enjoy life on the water, this location is hard to beat. Launch a kayak, paddleboard, or small boat from your backyard and reach the Chester River in approximately one mile, with the Chesapeake Bay just 5 to 6 water miles beyond. Enjoy quick access to bay boating while returning home to the calm waters, privacy, and natural beauty of a protected creek. Combining quality craftsmanship, upscale finishes, and an exceptional waterfront setting, this newly completed home offers a rare opportunity to enjoy the best of Maryland's Eastern Shore lifestyle!

203 Riverside Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

3 Beds ⋅ 1 Baths

Investor potential! Edgemont Park Townhome, tenant occupied at $1200. per month. 1 Car built-in garage & 1 parking space in rear. On-street parking. Call for an appointment!

232 W 21st St, Chester

Listing courtesy of Sam Pace & Associates. Contact: 6105659040

5 Beds ⋅ 4 Baths

Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true centerpiece is the fully equipped gourmet kitchen, a masterpiece of design. A magnificent 10-foot Quartz center island takes center stage, surrounded by pristine cabinets, state-of-the-art appliances, and exquisite marble countertops. To top it off, the kitchen also boasts its own wet bar with a built-in beverage cooler. The open-concept layout seamlessly connects the kitchen to the living space, with a mesmerizing wall of oversized windows that offer breathtaking views of the expansive waterfront and private pier. Convenience is a priority in this home, with a three-car pull-through garage and a pier equipped with boat lift as well as dual Jetski lift for easy access to the water. Outdoor enjoyment is a given, with two waterfront decks, a screened-in patio, and a private en-suite deck for moments of relaxation. Privacy and the feeling of island-style living are abundant here. Located in the heart of Kent Island, this property provides effortless access to luxury dining options, waterfront restaurants, lively dock bars, and island-style entertainment. All while, being just 2 miles away from the Chesapeake Bay Bridge means seamless travel by land or sea. Welcome to your dream home, here on Kent Island where tranquility and luxury converge with Maryland's Eastern Shore and the Chesapeake Bay.

2702 Sherman Dr, Chester

Listing courtesy of Samson Properties. Contact: 7033788810

3 Beds ⋅ 1 Baths

Welcome to 1125 Remington Street, a well-maintained 3-bedroom, 1-bath twin home offering an excellent opportunity for first-time buyers or investors. Priced at just $135,000, this move-in-ready home features fresh paint throughout, an updated kitchen with modern finishes, and a brand-new water heater, providing comfort and value from day one. The main level offers a bright living space, functional layout, and an updated kitchen perfect for everyday living. Upstairs, you'll find three comfortable bedrooms and a full bath. Conveniently located just minutes from Memorial Park, residents can enjoy walking trails, playgrounds, sports fields, and open green space. Commuters will appreciate easy access to Interstate 95, making travel throughout the region a breeze. The home is also approximately 15 minutes from Philadelphia International Airport and about 20 minutes from Philadelphia, offering convenient access to employment, dining, entertainment, and major transportation hubs. Whether you're looking to add to your investment portfolio or purchase an affordable place to call home, 1125 Remington Street is one you won't want to miss!

1125 Remington St, Chester

Listing courtesy of Century 21 Emerald. Contact: 3027981000

3 Beds ⋅ 1 Baths

Turnkey investment opportunity at 2605 Swarts St! This income-producing property is currently tenant-occupied and generating approximately $1,450 per month in rental income. A great addition to any investor's portfolio with immediate cash flow and established tenancy. Don't miss this opportunity to own a performing rental property. NEW roof - all renovated including bathroom

2605 Swarts St, Chester

Listing courtesy of Keller Williams Liberty Place. Contact: 6093995454

4 Beds ⋅ 3 Baths

NEW PRICE—An Unbelievable Value on Kent Island! Built in 2020, this gorgeous, like-new home offers approximately 1,974 square feet of beautifully maintained living space, a spacious yard backing to trees, and a desirable Kent Island location. An assumable VA loan at an attractive 2.75% interest rate may be available to qualified buyers, subject to lender and VA approval. Fresh interior paint and new carpeting throughout make this home truly move-in ready. The spacious living and dining areas provide plenty of room for everyday living and entertaining, while the inviting fireplace adds warmth and character. The kitchen features a breakfast bar, granite, pantry, abundant cabinetry, and generous storage. The spacious owner’s suite offers two walk-in closets and a private en-suite bath, creating a comfortable retreat. Step outside to enjoy the private backyard backing to trees, ideal for relaxing, entertaining, or enjoying peaceful evenings outdoors. Ccnvenient access to nearby boat ramps. Ideally located near shopping, dining, golf, pickleball, waterfront parks, walking trails, beaches, a dog beach, marinas, boat storage, Queenstown Premium Outlets, and popular local restaurants and entertainment. Experience the best of Kent Island living in this beautifully updated home. Some rooms have been virtually staged, including the owner’s suite, living room, and dining room.

124 Riverside Dr, Chester

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937

3 Beds ⋅ 1 Baths

Welcome to this beautifully updated 3-bedroom, 1 full bath home that combines modern upgrades with comfortable living. The heart of the home is the stunning renovated kitchen, featuring amazing appliances, stylish finishes, and plenty of space for cooking and entertaining. The bathroom was also completely updated in 2023, offering a fresh feel. Enjoy peace of mind with new windows installed throughout the home, enhancing both energy efficiency and natural light. The finished basement provides valuable space and features new flooring installed in 2023. This move-in-ready home offers comfort, convenience, and exceptional value. Don't miss the opportunity to make this wonderful property your new home!

309 W 21st St, Chester

Listing courtesy of CG Realty, LLC. Contact: 6105665182

2 Beds ⋅ 3 Baths

Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both style and functionality. Step inside to discover a thoughtfully designed interior that boasts hardwood and pine flooring, creating a warm and inviting atmosphere throughout. The combination kitchen and dining area is perfect for entertaining, featuring ample space for gatherings and culinary creations. Natural light floods the home, enhancing the inviting ambiance and highlighting the quality craftsmanship that defines this property. One year old HVAC and four year old hot water heater. The outdoor spaces are equally impressive, with a charming deck and porch that invite you to relax and enjoy the serene surroundings. Imagine sipping your morning coffee while taking in the gentle sounds of nature or hosting evening gatherings under the stars. The community pool and recreational facilities provide additional opportunities for leisure and relaxation, ensuring that every day feels like a vacation. Located just blocks from the Chester River, this property offers water-oriented living at its finest. Enjoy easy access to the river, perfect for kayaking or leisurely strolls along the waterfront. The community amenities, including a clubhouse, exercise room, and jogging paths, cater to an active lifestyle, while the meticulously maintained common grounds provide a picturesque backdrop for your daily activities. Parking is a breeze with a detached garage that offers additional storage space, ensuring that your home remains clutter-free. The association fee includes lawn care, snow removal, and trash services, allowing you to spend more time enjoying the luxurious lifestyle this community has to offer. Gibsons Grant is not just a place to live; it's a lifestyle choice that embraces the beauty of nature while providing modern conveniences. With its prime location, high-end features, and a strong sense of community, this townhouse is a rare gem that promises to be a cherished home for years to come. Experience the perfect blend of luxury and comfort in this stunning property, where every detail has been designed with your enjoyment in mind.

115 Gibson Cir, Chester

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

Start Your Search