Cheshire Homes under $400,000

Welcome to Cheshire, Connecticut – a charming town nestled in New Haven County that perfectly blends suburban tranquility with vibrant community life. Known for its picturesque landscapes and friendly atmosphere, Cheshire offers residents a delightful lifestyle enriched by its rich history and modern amenities. With a population that values community spirit, this town is ideal for families, professionals, and retirees alike.

One of the standout features of Cheshire is its commitment to education, boasting top-rated schools that consistently rank among the best in the state. This focus on quality education makes it a sought-after destination for families looking to settle down in a nurturing environment. The town is also home to beautiful parks and recreational facilities, perfect for outdoor enthusiasts and those who enjoy an active lifestyle.

For homebuyers, Cheshire presents an exciting opportunity with a diverse range of properties available for under $400,000. Whether you’re searching for a cozy single-family home, a charming colonial, or a modern townhouse, Cheshire’s real estate market has something to suit every taste and budget. This affordability, combined with the town’s appealing lifestyle, makes it an attractive option for first-time buyers and those looking to invest in a growing community.

Explore Cheshire’s inviting neighborhoods, where tree-lined streets and friendly faces await. With its blend of small-town charm and convenient access to major highways, shopping, and dining, Cheshire is not just a place to live – it’s a place to call home. Discover your dream property today and become part of this thriving community!

Newest Cheshire Homes under $400,000

$335,000

2 Beds ⋅ 2 Baths ⋅ 24205596 MLS ⋅ Quarry Village BLDG.

This unit is located in the highly desirable Quarry Village complex, a quiet and exceptionally maintained residential community. Enjoy the proximity to the center of Cheshire, numerous parks and playgrounds, the Cheshire Community Pool, orchards, the Farmington Canal Heritage Trail, as well as extensive dining and shopping options. It is approximately 30 minutes to Hartford or New Haven. Your main level includes your living room with bay window and a gas fireplace, the kitchen with esthetically pleasing appliances and half bath. The double doors of the light-filled dining room lead to an updated Trex deck. The 2nd floor has two bedrooms with ample walk-in closet space, a full bath, as well as a bonus room that can be a third bedroom or home office. The basement is partially finished with a workshop room and extra humidity-controlled storage. The unit has an attached garage and driveway parking. Ample visitor and guest parking is available throughout the complex. Recent condo updates include: 2026 new roof depicted in aerial photos, new a/c compressor and fan (2026), updated Trex deck and new dishwasher (2025). The amenities & services covered by the low monthly Homeowners Assoc. include ground maintenance, snow removal, trash collection, and public water fee.

83 Quarry Village Rd Unit 83, Cheshire

$319,900

3 Beds ⋅ 2 Baths ⋅ 24208227 MLS

There's a lot to work with at 233 Forest Lane wether you're an investor or future owner occupant. This three-bedroom, one-and-a-half-bath ranch offers a practical single-level layout, hardwood floors, and the kind of footprint that gives its next owner plenty of options. The home has been well lived in and is ready for someone with a fresh vision to make it their own. Downstairs, the basement provides even more opportunity, with space that could potentially be finished into an additional living area, home office, gym, or playroom. Outside, a sizeable yard gives you room to spread out, while the carport adds everyday convenience. There's public sewer available in the street for those who may want that option in the future. Whether you update a little at a time or have bigger plans from day one, there's real potential here to create something that feels entirely your own.

233 Forest Ln, Cheshire

$384,900

3 Beds ⋅ 1 Baths ⋅ 24206787 MLS

Welcome to 374 Moss Farms Rd! This adorable ranch-style home is ready to begin its next chapter. Nestled in a desirable neighborhood on over an acre of land, this charming 3-bedroom, 1-bath home offers the perfect blend of character, comfort, and opportunity. Step inside to find a cozy living room featuring a fireplace and hardwood flooring, creating a warm and inviting space to relax and gather. One of the home's true highlights is the spacious 408-square-foot four-season porch-a wonderful spot to enjoy your morning coffee. The home also offers plenty of basement storage, providing room for all your seasonal items and more. Outside, enjoy the newer paver patio, perfect for entertaining or enjoying quiet evenings, along with a 2-car detached garage offering excellent parking and additional storage or workshop potential. Major updates offer added peace of mind, with the roof, furnace, and oil tank all less than 15 years old. With its generous lot, desirable location, cozy features, and plenty of potential to make it your own, this is an opportunity you won't want to miss. Located near Cheshires newly built schools. Easy access to shopping, library and local amenities. Subject to Probate Court Approval., Sold As-Is

374 Moss Farms Rd, Cheshire

$199,000

2 Beds ⋅ 1 Baths ⋅ 24203224 MLS ⋅ Birchwood BLDG.

Stylish, beautifully renovated and filled with natural light, this end-unit condominium is located in the well-maintained Birchwood community, surrounded by expansive green space and ample parking. Beautiful, move in condition! The open floor plan offers two spacious bedrooms, a large living room, and a stylish white kitchen with granite countertops, self-closing cabinets with lighting and stainless steel appliances. The beautifully remodeled bathroom features modern tile, a contemporary vanity, and a glass-enclosed shower. Additional amenities include a large private storage unit and shared laundry in the basement. The HOA fee covers water, heat, hot water, management, grounds and road maintenance - truly exceptional value. With no current special assessments and strong association reserves, this home provides peace of mind and affordability. Enjoy a prime Cheshire location with access to Farmington Canal Trail just minutes from excellent restaurants and charming cafes. New Stonebridge shopping center features Whole Foods, Barnes & Noble, TJ Maxx, J. Crew and other popular retailers. This is a wonderful opportunity to own a truly beautiful home and enjoy easy, no-maintenance living in one of Connecticut's most desirable towns with very good school system.

502 Oak Ave Unit 17, Cheshire

$160,000

1 Beds ⋅ 1 Baths ⋅ 24202177 MLS ⋅ Cheshire Hillside Village BLDG.

Welcome to easy, one-level living in Cheshire Hillside Village, a desirable 62+ active adult community. The standout feature of this inviting one-bedroom condo is its large, open floor plan with generously sized rooms and a beautiful vaulted ceiling in the living room, creating a spacious, airy setting that is ideal for entertaining and everyday living. Located on the upper level, this sought-after style unit has no neighbors above, allowing for added privacy and helping create the wonderful sense of openness and natural brightness throughout. Despite being an upper-level unit, there are no stairs to enter the building, thanks to the convenient layout of the complex. Brand-new flooring throughout, fresh paint, in-unit washer and dryer and a slider that leads from the living room to the private deck with convenient exterior storage add to the appeal. The monthly HOA fee includes heat and hot water, offering added convenience and helping make monthly expenses more predictable. Ideally located in the center of Cheshire, near the Stop & Shop plaza, with easy access to I-84, I-91, and Route 691, and just a quick ride down Route 10 to the new shops at Stonebridge Crossing. Nearby recreational facilities are also easily accessible, making this a wonderful opportunity for comfortable, convenient, and low-maintenance living in the heart of Cheshire.

459 E Mitchell Ave Unit 459, Cheshire

$199,900

1 Beds ⋅ 1 Baths ⋅ 24201442 MLS ⋅ Cheshire Hillside Village BLDG.

This beautifully renovated condo features a versatile flex/bonus room and is located in a desirable 62+ community nestled within the town of Cheshire. The bright and inviting first floor unit has been completely updated from top to bottom, featuring brand-new stainless-steel appliances, tiled backsplash, crown molding, modern fixtures, new flooring, paint, a custom feature wall, and a fully refreshed kitchen and bathroom. Hardwood flooring is throughout this condo. The primary bedroom includes a well-designed closet system offering ample storage. The spacious flex room offers endless possibilities perfect for a home office, guest space, hobby room, or second bedroom. Your new sliders open to a back patio where you can relax with your morning coffee and watch the birds. The HOA includes heat and hot water, making this a truly affordable, and complete turnkey living within the town of Cheshire. There is easy parking and mailbox access. Just pack your suitcases and enjoy comfortable, low maintenance living in this well-kept community designed for active adults. Welcome home!!!

443 E Mitchell Ave Unit 443, Cheshire

$329,900

2 Beds ⋅ 2 Baths ⋅ 24200337 MLS ⋅ Country Village BLDG.

Location! Location! Location! Easiest in and out from the Country Club Rd entrance (Fairway Dr), just a few feet from the mail, pool, clubhouse, and basketball courts-wooded rear yard. Beautifully updated, featuring new hardwood floors and carpet. Refreshed kitchen cabinets with quartz counters and new appliances. All new bathrooms! Freshly painted throughout. Great location close to orchards, shopping, and "The Shops at Stone Bridge." Plenty of fun can be found nearby, including the Linear Trail and the Farmington Canal Heritage Trail, Bartlem Recreation Area, and Cheshire Park.

418 Greens Loop, Cheshire

$349,900

3 Beds ⋅ 3 Baths ⋅ 24192035 MLS ⋅ Currier Woods BLDG.

One of the many advantages of purchasing a home in Currier Woods is its location directly across the street from the brand-new Norton Elementary School. This beautifully designed, state-of-the-art K"6 school is a convenient neighborhood amenity within feet of the community. Currier Woods offers the benefits of modern living in a desirable location with easy access to local schools, parks, shopping and other everyday conveniences.

54 Currier Pl Unit 54, Cheshire

$359,900

2 Beds ⋅ 2 Baths ⋅ 24186242 MLS

House in now available to be shown anytime! Discover this charming two-bedroom ranch located in the heart of Cheshire. As you step inside, you'll immediately be impressed by the hardwood floors that span the living room, family room, and both bedrooms. Beautiful built-in bookshelves and crown molding add a classic touch. The master bedroom has its own private full bathroom, ensuring convenience and privacy. On those rainy days, retreat to the enclosed, heated rear porch - a cozy spot perfect for relaxation or an extra living space. The lower level features a washer and dryer, along with ample storage space to meet all your needs. The property also offers a detached garage with an overhang. The level, open yard is perfect for both play and entertaining. Located just a short distance from the center of Cheshire, you'll enjoy easy access to top-rated schools, local shopping, and the scenic Farmington Canal Trail. This home truly offers the best of both worlds: a peaceful, private setting with convenient access to everything you need. Sold in AS IS condition.

393 S Meriden Rd, Cheshire

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