Cheshire Homes under $750,000

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, friendly neighborhoods, and rich history, Cheshire offers residents a delightful place to call home.

One of the standout features of Cheshire is its exceptional quality of life. The town is renowned for its excellent school system, making it an ideal choice for families looking to provide their children with a top-notch education. With an array of parks, recreational facilities, and outdoor activities, residents can enjoy everything from hiking and biking to community events throughout the year.

For those seeking a home in Cheshire, you're in luck! The real estate market here boasts an impressive selection of homes under $750,000, providing a variety of options for first-time buyers, families, and retirees alike. From charming colonial-style houses to modern townhomes, there’s something to suit every taste and lifestyle. Many of these homes come with spacious yards, perfect for outdoor gatherings, gardening, or simply enjoying the serene surroundings.

Cheshire is also conveniently located, with easy access to major highways and the vibrant cities of New Haven and Hartford, making commuting a breeze. With its friendly atmosphere and beautiful scenery, Cheshire is not just a place to live—it's a community where you can thrive. Explore the opportunities waiting for you in this delightful town and discover why so many are proud to call Cheshire their home!

Newest Cheshire Homes under $750,000

$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

$725,000

4 Beds ⋅ 3 Baths ⋅ 24210753 MLS

Welcome to 21 Berkshire Court, a beautifully updated 4-bedroom, 2.5-bath Colonial offering 2,373 square feet of living space plus approximately 500 additional square feet in the beautifully finished lower level. Set on a manicured .59-acre lot, this impressive home features thoughtfully designed renovations, wonderful living spaces, and exceptional curb appeal. The heart of the home is the gorgeous expanded kitchen featuring a breakfast bar, abundant cabinetry, and custom built-ins, all opening seamlessly to the inviting family room with additional custom built-ins and French doors leading to the large deck. Just off the kitchen is a highly functional laundry area with additional cabinetry and a convenient coffee bar, along with access to the half bath and attached two-car garage. A formal dining room, spacious living room, and beautiful entryway complete the main level, which features hardwood flooring throughout. Upstairs, the primary suite offers a walk-in closet and beautifully appointed full bath with double sinks and a walk-in shower. Three additional bedrooms and a second full bath complete the upper level. The beautifully finished lower-level rec room is perfect for entertaining, a home gym, playroom, media room, or home office, while still offering plenty of storage. Outside, enjoy the beautifully manicured yard and large deck overlooking the private backyard. Conveniently located close to the center of town with easy access to parks, restaurants & shopping!!

21 Berkshire Ct, 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

$735,000

4 Beds ⋅ 3 Baths ⋅ 24209466 MLS

Nestled in a quiet neighborhood on a private, flat lot bordered by a peaceful treeline, this rare oversized 1963 ranch combines mid-century build quality with meticulous, thoughtful updates. Upscale exterior stonework, a custom stone walkway, and a welcoming threshold set an elegant tone that continues throughout the entire residence. Inside, rich hardwood floors flow through gracious rooms thoughtfully laid out to separate the sleeping quarters from the main living spaces. Storage is unmatched with 11 closets, including two cedar closets in the foyer, while every room offers scenic views-including serene pond views from the living room. Designed for seamless indoor-outdoor entertaining, the family room connects through French doors to the home's true showstopper: an expansive sunroom with radiant heat floors, cathedral ceilings, and windows on three sides. Warm up by two fireplaces or gather outside on the 20x18 stone back patio. All bedrooms are generously sized, featuring walk-in closets in two of the rooms, while first-floor laundry provides authentic one-level living ease. A massive basement offers endless potential to expand your living space, with city sewer available in the street. Maintained with extraordinary care, this exceptional home presents a unique opportunity to become only its third owner. Easy highway access for commuting and 8 minutes to new Shops at Stone Bridge. Located in Highland Elementary School district which is a National Blue Ribbon Sch

8 Applewood Dr, Cheshire

$645,000

3 Beds ⋅ 4 Baths ⋅ 24209218 MLS

Welcome to 531 Blacks Road, a spacious and distinctive split-level home set on a beautiful, level 1.93 acre property. A broad front lawn creates a generous set back from the street, while the park-like backyard provides an exceptional amount of usable outdoor space. From the covered front porch, double-entry doors welcome you into a dramatic, light-filled two-story foyer with soaring windows and an open staircase, an impressive introduction to the home's multi-level layout. Hardwood floors and abundant windows enhance the main living areas and bedrooms. The kitchen, with side door access, features abundant cabinetry, Corian countertops, and a generously proportioned dining area with plenty of room for everyday dining and entertaining. The adjoining living room is anchored by a full-wall brick fireplace, while two sets of glass doors open to the screened porch and frame views of the grounds. Upstairs are three bedrooms, including a primary with a private full bath, along with a versatile flex room ideal for a den, home office or hobby space. The walkout lower-level family room includes a half bath and access to the backyard and two-car garage. Recent improvements include a new roof and new gutters. Cheshire is known for its well-regarded public schools, extensive walking trails, parks, and wide selection of shopping and dining destinations, including The Shops at Stone Bridge. This home offers easy access to recreation, everyday amenities, and major commuter routes.

531 Blacks 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

$695,000

4 Beds ⋅ 3 Baths ⋅ 24205288 MLS

OWNER MOTIVATED! Great Opportunity. Beautiful setting. Come see! Welcome to 1100 Coleman Rd, a charming, timeless Colonial nestled on a peaceful, private 1.85-acre lot in the heart of Cheshire, CT. Built in 1957, this home combines classic architectural craftsmanship with 2,280 square feet of functional living space, highlighted by beautiful hardwood floors throughout. The main level features a formal living room anchored by a fireplace with a custom-built mantel, traditional dentil crown molding, built-in bookcases, and convenient wood storage. Host large gatherings in the formal dining room, or relax in the eat-in kitchen and family room combination, which features two beautiful bay windows, a main-floor powder room, and direct access to an expansive deck that spans nearly the entire back of the home. This massive outdoor living space flows effortlessly into a park-like backyard, creating an ideal setting for seamless indoor-outdoor entertaining, gardening, or quiet relaxation. The second floor hosts 4 spacious bedrooms and 2 full bathrooms, offering plenty of room for family, guests, or a dedicated home office. The lower level maximizes every square foot, starting with a convenient underhouse side-load garage that opens into a finished, generous laundry room. Down the hall past the utility room, you will find a versatile finished bonus room with its own cozy fireplace-perfect for a playroom, media room, or art studio.

1100 Coleman Rd, Cheshire

$649,900

3 Beds ⋅ 3 Baths ⋅ 24208189 MLS

Welcome to 70 Heritage Drive, a beautifully maintained 3-bedroom, 2.5-bath home offering 2,080 sq. ft. of living space plus an additional 525 sq. ft. in the finished lower level. Set on .35 acres with wonderful curb appeal, this inviting home offers a spacious and versatile floor plan. The welcoming entry leads to a beautiful kitchen featuring granite countertops, stainless steel appliances, and an eat-in area with sliders to a large deck with awning-perfect for outdoor dining and entertaining. A formal dining room with bay window and formal living room, currently used as a home office, provide additional flexible living space. At the back of the home, the expanded family room is a standout, featuring a gas fireplace and a wall of windows that fills the room with natural light. A half bath completes the main level. Upstairs, the spacious primary bedroom features a beautifully updated private bath. Two additional bedrooms and a second full bath complete the upper level. The finished lower level adds approximately 525 sq. ft. of additional living space with a rec room, plus a laundry area and additional storage. Outside, enjoy the large deck, patio, irrigation system, and nicely maintained yard. Additional features include a 2-car garage, city water and sewer, a new roof (2026), Central Air on 2nd floor and a ductless split in Living Room & Family Room. Conveniently located just a short walk from in-town activities, this home combines space, comfort, and a great location

70 Heritage Dr, 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

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