Chester Homes with Colonial Style

Welcome to Chester, Connecticut – a charming New England town that beautifully blends history, community, and natural beauty. Nestled in Middlesex County, Chester is known for its picturesque landscapes, vibrant arts scene, and a warm, welcoming atmosphere. With its quaint downtown area filled with unique shops, delightful eateries, and local galleries, Chester offers a small-town feel with big-city amenities just a stone's throw away.

One of the standout features of Chester is its stunning colonial-style homes, which reflect the town's rich heritage. These elegant residences, often adorned with classic architectural details such as gabled roofs, symmetrical facades, and charming front porches, transport you back to a time of grace and refinement. Each colonial home tells a story, offering a glimpse into the past while providing modern comforts for today’s discerning homeowner.

Living in Chester means immersing yourself in a community that values both tradition and innovation. Residents enjoy access to superb schools, beautiful parks, and a plethora of outdoor activities, from hiking along scenic trails to boating on the Connecticut River. The annual Chester Fair and various local festivals foster a strong sense of community and connection among residents.

Whether you're seeking a cozy colonial home with historical charm or a modern twist on classic architecture, Chester has something for everyone. Discover the beauty and warmth of this enchanting town, where every street corner feels like home, and every day offers the promise of new adventures. Come explore Chester – where history meets harmony in a vibrant community!

Newest Chester Homes with Colonial Style

$495,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192544 MLS

Discover the incredible potential of this custom-built Colonial, ready for your personal style and finishing touches. Designed with comfort and functionality in mind, the main level features a dedicated home office complete with extensive shelving and abundant storage, perfect for staying organized while working from home. Upstairs, you'll find three generously sized bedrooms and two full baths, including a beautifully glass tiled hall bath that adds beachy vibes. The spacious primary suite offers both a walk-in closet and an additional traditional closet, with ample room for a king-sized bed and your favorite furnishings. The bright, functional kitchen boasts an abundance of cabinetry, stainless steel appliances, and the convenience of a first-floor laundry room just steps away, between the kitchen and the powder room. The finished lower level provides valuable additional living space, ideal for a family room, recreation area, home gym, or hobby room, with direct access to the oversized two-car garage. With fresh paint and your personal decorating touches, this home can truly shine. Best of all, you're just a short walk from Chester's picturesque town center, where you'll enjoy charming shops, restaurants, galleries, and community events. Experience firsthand why Chester is consistently celebrated as one of Connecticut's most beloved small towns.

42 Straits Rd, Chester

$299,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24186867 MLS

Welcome to 92 Water St, a charming 1927 two-story Colonial offering a rare opportunity to own waterfront property in picturesque Chester, CT! This 3-bedroom, 1-bathroom home is perfectly situated right on the water, offering tranquil riverfront views and an unbeatable location just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining. Sitting on an 11,761 sq. ft. (0.27-acre) lot bounded directly by the water, this home features classic vinyl siding, a paved driveway, and a comfortable layout, making it a fantastic canvas for your dream riverfront retreat. Whether you are an investor seeking a value-add property or a homeowner looking for direct water access, the potential here is outstanding. Looking to expand your portfolio or create a larger waterfront compound? This property presents a unique dual-purchase opportunity: 92 Water St can be sold as a package with the neighboring property at 90 Water St. Buyers should note that the two properties conveniently share an existing septic system. This rare Chester waterfront offering is packed with potential and won't last long. Bring your vision and schedule your showing today!

92 Water St, Chester

$2,200,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24180698 MLS

A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American prosperity, craftsmanship, and vision. Listed on the National Registery of Historic Places, this exceptional Federal-style residence retains extraordinary architectural integrity with six fireplaces, original hardware, twelve-over-twelve windows, elegant period moldings, richly detailed mantels, and a commanding facade highlighted by Ionic columns, a Palladian window, fanlight entry, and granite foundation. A 19th-century carriage house on the property evokes the atmosphere of Warner's original gentleman-farmer estate. This historic landmark property sets the stage for unforgettable event possibilities on picturesque pastoral grounds. Revered by historians and preserved with exceptional care, this irreplaceable legacy property offers a rare opportunity to own one of Connecticut's most significant surviving Federal residences. Extensive original letters, bills, receipts, and construction records survived, documenting the artisans, materials, suppliers, and methods used to create this architectural masterpiece. Chester offer an abundance of amenities / local events, and borders the CT River.

47 E Kings Hwy, Chester

$3,150,000

4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24166793 MLS

Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.

288 Middlesex Ave, Chester

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