Chester Homes under $400,000

Welcome to Chester, Connecticut – a charming town nestled in the heart of Middlesex County, where picturesque landscapes and a vibrant community come together to create an idyllic living environment. Known for its rich history and small-town charm, Chester boasts a delightful blend of scenic beauty and modern amenities. With its quaint downtown area filled with unique shops, art galleries, and delightful eateries, residents enjoy a lifestyle that celebrates both culture and community.

Chester is surrounded by lush greenery, offering ample opportunities for outdoor enthusiasts to explore its many parks, trails, and the stunning Connecticut River. The town is also home to several annual events that foster a strong sense of community, making it easy to connect with neighbors and friends alike.

For those seeking a home in this enchanting town, Chester offers a range of options under $400,000. Whether you’re a first-time homebuyer, looking to downsize, or searching for a cozy retreat, you’ll find a variety of charming properties that fit your budget. From historic homes with character to modern townhouses with contemporary finishes, there’s something for everyone.

Living in Chester means embracing a lifestyle that balances tranquility with access to nearby urban conveniences. With its excellent schools, friendly atmosphere, and a strong sense of community, Chester is more than just a place to live; it’s a place to call home. Discover the beauty of Chester, CT, and find your perfect abode today!

Newest Chester Homes under $400,000

$379,900

3 Beds ⋅ 2 Baths ⋅ 24210808 MLS

One floor living in a quiet neighborhood just outside Chester Village. The main floor has a large Living Room, Kitchen and Dining Room, 3 bedrooms, 1 bathroom. The partially finished basement has 2 addional rooms, and storage. Some unfinished projects! Ready for your updating!

40 Castle View Dr, Chester

$269,900

3 Beds ⋅ 1 Baths ⋅ 24198196 MLS

Charming 1927 Colonial offering a rare chance to own directly on the water in the heart of Chester. This 3-bedroom, 1-bath home spans 1,217 sq ft across two stories, with a classic layout featuring a living room and dining room on the main level and three bedrooms upstairs. Set on a 0.27-acre lot with vinyl siding and a paved driveway, the home sits right on the water with tranquil river views - a fantastic canvas for a riverfront retreat, whether you're an investor or a homeowner seeking direct water access. Just a short stroll to downtown Chester's boutiques, art galleries, and acclaimed dining. This property can also be purchased together with the adjacent 90 Water St for a larger waterfront compound (the two share an existing septic system). Bring your vision - this rare Chester waterfront offering won't last long! One of the parties to the LLC has an active real estate license

92 Water St, Chester

$254,900

1 Beds ⋅ 1 Baths ⋅ 24198111 MLS

Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and comfortable primary bedroom round out the interior. Step outside to direct river frontage with sweeping water views and endless potential for outdoor living on the riverbank. All of this just a short stroll from downtown Chester's boutiques, galleries, and acclaimed restaurants. This property can also be purchased together with the adjacent 92 Water St for a larger waterfront compound (the two share an existing septic system). A fantastic value-add opportunity for an investor or a buyer with vision - bring your contractor and imagination! One of the parties to the LLC has an active real estate license.

90 Water St, Chester

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