Cheshire Homes under $600,000

Welcome to Cheshire, Connecticut—a charming town nestled in New Haven County that beautifully blends suburban tranquility with convenient access to urban amenities. Known for its picturesque landscapes, friendly community, and rich history, Cheshire is a place where families thrive and individuals find their perfect home.

One of the most appealing aspects of Cheshire is its diverse range of housing options, particularly for those seeking homes under $600,000. Whether you’re a first-time homebuyer, looking to downsize, or seeking a cozy family abode, Cheshire offers a variety of properties that cater to different lifestyles and budgets. From quaint colonial-style houses with lush gardens to modern townhouses with updated amenities, you’ll find plenty of options that fit your needs.

Cheshire boasts excellent schools, making it a prime location for families. The town is also home to beautiful parks, recreational facilities, and a vibrant community life, ensuring that residents can enjoy an active and fulfilling lifestyle. The local farmers' market, seasonal festivals, and community events foster a strong sense of belonging among residents, making Cheshire feel like home.

With its strategic location, Cheshire provides easy access to major highways and public transportation, allowing for convenient commutes to nearby cities like New Haven and Hartford. This blend of suburban charm and urban accessibility makes Cheshire a highly desirable area for those seeking a balanced lifestyle.

Explore the wonderful homes available in Cheshire under $600,000 and discover why so many are choosing to call this delightful town home. Your dream home awaits!

Newest Cheshire Homes under $600,000

$419,900

3 Beds ⋅ 2 Baths ⋅ 24210609 MLS

Charming three bedroom ranch offering spacious living and a convenient location close to shopping, dining, schools and amenities. The large open kitchen features a generous dining area perfect for everyday meals and entertaining. Enjoy the inviting first floor family room with a cozy fireplace, creating a warm and comfortable gathering space. The primary bedroom includes it's own primary bath for added comfort and convenience. Beautiful hardwood floors run throughout much of the home adding character and appeal. An Unfinished lower level provides potential to nearly double the living space, offering endless possibilities for future expansion. Situated on a level lot, the property also features a lovely deck, ideal for relaxing.

388 Sharon Dr, Cheshire

$454,900

3 Beds ⋅ 2 Baths ⋅ 24210901 MLS

Welcome to this inviting three-bedroom, two full bath ranch offering comfortable one level living in a desirable neighborhood. With just over 1300 sq ft plus a finished basement it provides plenty of space for everyday living. This home features beautifully refinished floors throughout adding warmth and character. A generous size living room with a wood stove to provide warmth for those cold days ahead! Cheshire Mixville park is just steps away. Close to Rt10, Rt 84, shopping and so much more!

273 Winthrop Dr, Cheshire

$434,900

3 Beds ⋅ 2 Baths ⋅ 24210481 MLS

Welcome to this beautifully maintained 3-bedroom, 2-full-bath raised ranch tucked away on a quiet cul-de-sac, conveniently located near Mixville Recreation Area, Route 84, and area restaurants. The main level features HW floors throughout, recessed lighting, and a spacious living room with built-ins, ceiling fan, wood shutters, and a wall-mounted A/C unit replaced in 2026. The living room flows seamlessly into the dining area, where a slider leads to the deck overlooking the private backyard. The inviting eat-in kitchen features hardwood floors, stainless steel appliances, range hood, and ample cabinetry. The primary bedroom offers HW floors, recessed lighting, and ceiling fan, with convenient access to the Jack-and-Jill full bath. Two additional bedrooms feature hardwood floors, with one offering a ceiling fan. A pull-down attic provides additional storage. The finished lower level adds valuable living space with a comfortable family room featuring recessed lighting, beautiful exposed beams, stucco-style walls and ceiling, and built-in cabinetry. A slider leads to the area beneath the deck and private backyard. The lower level also includes a second full bath with a unique stone-accented shower and a dedicated laundry closet. Most windows were replaced approximately 5-8 years ago, and the roof is approximately one year old. Public water and sewer. A wonderful opportunity to enjoy comfortable living, great outdoor space, and a convenient location! Sold in AS IS condition.

980 Notch Rd, Cheshire

$525,000

4 Beds ⋅ 2 Baths ⋅ 24207733 MLS

A great opportunity to own this 4 Bedroom, 2 Bath Ranch in South Cheshire with a versatile open floor plan and one level living! A welcoming first impression can be felt as you enter the light and bright living room and continues into the Dining Area and Eat-in Kitchen with electric cooktop, built-in oven, pantry and stainless appliances. Conveniently off the Kitchen is the laundry/mud room with an entrance to the driveway for ease in carrying in groceries! A Family Room, with large picture window looking out to the yard, is the perfect spot for relaxing at the end of the day. A four season Sun Room, equipped with heat and A/C and statement skylight, provides access to the deck and yard making this the ideal spot for entertaining! Separate from the other bedrooms is the Primary Bedroom with attached full bath with walk-in shower. The additional 3 bedrooms and full Bath are located just down the hall. A walk up attic is positioned for future ease of expansion to the home. Full, unfished walk-out basement leads to a large shed area and the spacious, level back yard. Solar panels, central air, new roof, freshly painted throughout, updated baths, gutter guards, newer windows. Convenient to shopping, restaurants and highways. Don't miss your chance to make this spacious Ranch Style home your own!

190 Remus Rd, Cheshire

$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

$439,900

3 Beds ⋅ 2 Baths ⋅ 24208667 MLS

Welcome to 122 Green Hill Lane, a beautifully updated 3-bedroom, 1.5-bath ranch offering 1,572 square feet of comfortable living space in desirable South Cheshire. Step inside to gleaming new hardwood floors throughout and an updated kitchen featuring stainless steel appliances. The spacious family room is a standout, with vaulted ceilings, a ceiling fan, and an impressive wood-burning stone fireplace. Step outside to the private rear deck, perfect for relaxing or entertaining. Additional features include thermopane replacement windows, ceiling fans in all three bedrooms, a covered front porch, and a one-car underneath garage. The expansive 1,056-square-foot unfinished basement offers tremendous potential for additional finished living space, potentially bringing the home to approximately 2,500 square feet. Situated on .42 acres with convenient access to Quinnipiac University, Sleeping Giant State Park, Yale University, shopping, dining, and major commuting routes. Move-in ready with room to grow!

122 Green Hill Ln, Cheshire

$429,900

3 Beds ⋅ 3 Baths ⋅ 24207116 MLS ⋅ Old Towne BLDG.

Welcome to 58 Old Towne Rd. This rare 3 bedroom 3 bath unit is located in the highly sought after Old Towne Condos. It is an end unit in what some say is the best location in the complex. It sits adjacent to a wooded area with views of nature all around. There is ample parking directly in front of the unit along with its one car attached garage. The home has a first floor bedroom with bath. The kitchen has been remodeled and there is plenty of room in the eat in kitchen/dining room space. The living room has a wood burning fireplace and an elevated deck located off the rear for those comfortable nights. The upper level has two large bedrooms with a bath, giving this unit tons of space. The lower level has both a partial finished area as well as an unfinished area with laundry hook up and plenty of storage. There is also a walk out slider from the lower level giving you the ability to enjoy the wooded lot and quiet outdoor space. If that's not enough, there is a community pool. The complex is next to a local favorite coffee house, and is close to Rt 10 giving you access to the center of Cheshire. This well established complex is near all amenities and only a few miles from the new Shopping plazas just built in the wonderful town of Cheshire. Home of award winning schools, and a regular as one of the best places to live in Connecticut.

58 Old Towne Road Unit 58, Cheshire

$449,900

3 Beds ⋅ 2 Baths ⋅ 24207039 MLS

Welcome to this beautifully maintained, freshly painted, move-in-ready home offering the perfect blend of one-level living, modern style, and convenience. This property features 3 bedrooms and 2 full bathrooms, highlighted by an open and inviting floor plan with gleaming hardwood floors throughout. Enjoy a beautifully updated kitchen (2016) featuring a functional breakfast bar that flows seamlessly into the main living spaces. For ultimate daily convenience, one of the main-level full bathrooms features a dedicated laundry setup. The attached oversized garage also offers excellent extra storage space. Step outside to your private, fully fenced backyard-the perfect secure space for outdoor entertaining, gardening, or pets Experience true peace of mind with extensive mechanical and structural upgrades completed in 2016, including a newer roof, durable siding, a high-efficiency HVAC system, updated plumbing, and a brand-new 200-amp electrical service panel. The home is connected to public water and public sewer. Ideally situated just minutes away from Cheshire's vibrant town center, premier parks, schools, local shopping, and a fantastic dining scene. This turnkey property is ready for its next owner. Please reach out directly to the owner for more information.

80 Contour Dr, Cheshire

$599,900

4 Beds ⋅ 3 Baths ⋅ 24205796 MLS

Enjoy spacious ranch living and beautiful outdoor surroundings at 98 Merwin Circle in South Cheshire! A welcoming front porch, lovely gardens, and professionally landscaped grounds create an inviting setting for this home, offering 1,848 square feet on the main level plus approximately 900 square feet of finished living space in the walkout lower level. The generous living room features a fireplace and slider to the large deck, while the large eat-in kitchen provides plenty of room for everyday meals and gatherings. Three main-floor bedrooms include a primary bedroom with its own full bath and two additional bedrooms served by a second full bath. Downstairs, the finished lower level offers a family room with a second fireplace, a large bedroom or office with exterior windows, and an additional full bath. Laundry is also in the finished lower level. An exceptionally spacious deck provides room for outdoor dining, entertaining, and relaxing while enjoying the gardens. Awnings shade the home's south-facing windows, and a two-car attached garage adds everyday convenience. Features include central air (2021) three-zone oil-fired baseboard heat (2008), Well water with a water softener, and City sewer. Windows, vinyl siding, and the roof were replaced in 2006, Comfortable main-floor living, flexible additional space, and beautiful grounds make this South Cheshire home a wonderful place to call your own!

98 Merwin Cir, Cheshire

$497,700

3 Beds ⋅ 2 Baths ⋅ 24207223 MLS ⋅ Copper Hill BLDG.

DESIRABLE COPPER HILL STAND-A-LONE RANCH CONDO in Cheshire on a Cul-de-sac Setting !!! BRING your vision to life at 2 Saxon Woods Court. This home offers great bones and a flexible layout, ready for your personal touch. With some updating, this home presents a wonderful opportunity to create the home of your dreams in a peaceful, private setting. This spacious standalone condo is tucked away on a quiet cul-de-sac in Copper Hill community. Offering 2459 square feet of living space, three bedrooms, two full baths and an open floorplan, that's ideal for both everyday living and entertaining. The finished lower level adds valuable bonus space, complete with a cozy fireplace and bar area-perfect for game nights, gathering or a relaxing retreat. REMEMBER there is no age restriction, making this home a perfect fit for buyers of all ages.

2 Saxon Woods Ct, 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

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