Chester Homes for Sale

Welcome to Chester, Connecticut – a hidden gem nestled in Middlesex County that beautifully marries the charm of small-town living with the vibrancy of modern conveniences. Known for its picturesque landscapes, Chester boasts a rich history that dates back to the 1700s, reflected in its well-preserved architecture and quaint downtown area. Stroll along Main Street, where you’ll discover an array of boutique shops, delightful eateries, and art galleries, all set against the backdrop of the stunning Connecticut River.

Chester is more than just a pretty face; it’s a community that thrives on connection and culture. With a calendar full of events, including farmers' markets and seasonal festivals, residents enjoy a close-knit atmosphere while benefiting from the conveniences of nearby larger towns. The town is also home to excellent schools and a variety of recreational activities, making it an ideal location for families, young professionals, and retirees alike.

For those considering a move, Chester offers a diverse selection of homes for sale, from charming historic properties to modern new builds. Whether you’re seeking a cozy cottage surrounded by nature or a spacious family home with room to grow, Chester has something to suit every taste and budget. With its stunning landscapes, friendly community, and an abundance of amenities, Chester is not just a place to live – it’s a place to thrive. Explore the homes for sale today and discover the perfect setting for your next chapter in this enchanting Connecticut town!

Newest Chester Homes for Sale

$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

$799,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24179377 MLS

Set on 33.97 private acres in beautiful Chester, CT, this inviting home offers space, privacy, and scenic views. The main level features a primary bedroom with a full bath, while upstairs you'll find 3 additional bedrooms with 2 full baths. The bright, open living room features soaring ceiling and a second floor balcony overlooking the main living space, creating an airy feel. Large south facing windows bring in abundant natural light and capture lovely views of the lightly wooded landscape. The home's attractive vertical wood siding adds character, while the expansive acreage provides a peaceful setting just minutes from the charm, shops and restaurants of Chester village.

88 Winthrop Rd, Chester

$499,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189125 MLS

NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away from; there's also sliders to the deck and a full bath. On the second floor there are three spacious bedrooms along with a second full bath. The whole house underwent full renovations between 2012-2013 including new kitchen, baths, gleaming oak flooring, foam insulation, new HVAC, new electrical; the updates continued along with a new roof in 2017, and just recently new carpeting on second floor, new stove and microwave plus a new dryer. Bring your creativity to finish the lower walk-out level with its charming brick architecture along with newer radiant-heated, poured concrete floors and french doors -- this could be an amazing walkout steps to the water! This house would be a perfect vacation rental.... Rent a few weeks/Stay a few weeks!

135 Middlesex Ave, 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

$274,900

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24186861 MLS

Rare waterfront opportunity! Nestled directly on the water, 90 Water St is a 1-bathroom Ranch currently configured as a 1-bedroom, but offering a spacious layout that easily converts to a 2-bedroom home. Built in 1950, the property provides a fantastic foundational footprint. It features a large 13'6" x 20'10" living room and a versatile 10'3" x 20'10" family room-the ideal space to partition into a second bedroom or home office. A combined 10'5" x 16'2" kitchen/dining area and a comfortable 12'5" x 10'3" primary bedroom complete the interior. Location is everything, and this property delivers. Situated right on the water, it offers tranquil views and the canvas for an incredible outdoor living space on the riverbank. Beyond the backyard, you are just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining. Looking to expand your portfolio or create a larger waterfront compound? This presents a unique dual-purchase opportunity: 90 Water St can be sold as a package with the neighboring property at 92 Water St (note: the two properties conveniently share an existing septic system). Whether you are an investor looking for a value-add rehab project or a buyer seeking a waterfront getaway with a vision to maximize this footprint, the possibilities are endless. Bring your contractor and imagination-schedule a showing today!

90 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

$900,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24172811 MLS

Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and entertaining. At the heart of the home is a spectacular chef's kitchen featuring an oversized island, quartz counters, stainless steel appliances, custom wet bar area, formal dining space, and inviting sitting area. Just beyond the kitchen, the great room showcases vaulted ceilings, a fireplace, and an abundance of natural light. The first-floor primary suite is a true retreat with a spacious walk-in closet, and a beautifully remodeled spa inspired bathroom. Upstairs, you'll find three additional bedrooms, another full bathroom, and a dedicated laundry room for added convenience. The finished lower level offers flexible space perfect for a media room, home gym, recreation area, or playroom. Step outside onto the oversized two-tier deck overlooking the expansive backyard - an ideal setting for entertaining or relaxing in total privacy. Additional upgrades include a new roof, windows, siding, HVAC system, and brand-new 5-bedroom septic system. Complete with a 2-car garage and set in a picturesque location, this turnkey property offers the perfect blend of luxury, comfort, and functionality.

136 Goose Hill Rd, 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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