Cheshire Homes for Sale

Welcome to Cheshire, Connecticut—an enchanting town nestled in New Haven County that perfectly blends suburban charm with modern convenience. Known for its picturesque landscapes and vibrant community spirit, Cheshire offers an idyllic setting for families, professionals, and retirees alike. With its rich history and an array of recreational activities, this town is a hidden gem in the heart of the Nutmeg State.

Cheshire boasts a strong sense of community, with friendly neighbors and excellent schools that make it a desirable place to raise children. The town is dotted with beautiful parks, scenic trails, and family-friendly amenities, ensuring that outdoor enthusiasts and nature lovers will find plenty to explore. From the tranquil beauty of the Cheshire Green to the expansive recreational facilities at Bartlem Park, there’s no shortage of ways to enjoy the great outdoors.

For those seeking homes for sale in Cheshire, you’ll discover a diverse array of properties that cater to various tastes and budgets. From charming colonial-style houses with timeless architecture to modern, energy-efficient new builds, there’s something for everyone. Many homes feature spacious yards, perfect for entertaining or enjoying peaceful evenings under the stars. With a strong real estate market, investing in a home here is not just a purchase; it’s a step into a welcoming community where you can create lasting memories.

Whether you’re drawn to Cheshire for its excellent schools, vibrant community, or beautiful homes, you’ll find that this charming town has all the elements for a fulfilling lifestyle. Come and explore the possibilities that await you in Cheshire, CT!

Newest Cheshire Homes for Sale

$850,000

4 Beds ⋅ 4 Baths ⋅ 24216993 MLS

It's here! 6 Mt Sanford is move-in ready showcasing all the newest designs for carefree living. Don't miss this brand new farmhouse style contemporary Colonial in south Cheshire. A picturesque country setting close to shopping & easy highway access.This stunning home blends modern elegance with exceptional craftsmanship throughout. Soaring 9-ft ceilings, 1.5" thick engineered HW floors throughout & a gas fireplace w/slate surround & wood mantle invites you into this bright open floor design. The gourmet kitchen features quartz countertops, subway tile backsplash, massive center island, stainless steel appliances, a custom chimney-style vented hood,& walk-in pantry. A perfect space for everyday living & entertaining. Step outside onto a private 20x16 back patio off the kitchen or to the welcoming front of the home which has a lovely lighted covered farmer's porch ideal for relaxing. A private office and separate mudroom complete the main floor. Upstairs a luxurious primary suite is joined by two additional bedrooms, which share a Jack-n-Jill bathroom, plus a private en-suite guest bedroom & bath. A second floor laundry adds extra convenience. Potential additional space in basement, that could be easily finished.Private backyard, protected from any future development.

6 Mount Sanford Rd, Cheshire

$595,000

4 Beds ⋅ 2 Baths ⋅ 24217571 MLS

A TRUE SHOWSTOPPER IN CHESHIRE! Welcome to 327 West Main Street, where timeless New England charm meets modern updates! This beautifully refreshed 4-bedroom, 2-full-bath home offers the character and craftsmanship you love in an older home, with the updates and conveniences today's buyers are looking for. From the moment you arrive, you'll appreciate the attention to detail throughout. Recent improvements include new windows, gutters, fresh interior paint, an on-demand hot water system, and a new mini-split system for year-round comfort and efficiency. Step outside and get ready to enjoy your own backyard retreat, complete with a brand-new above-ground pool and deck, perfect for summer entertaining! You'll also love the covered front and rear porches, ideal for enjoying your morning coffee or unwinding at the end of the day. And just when you think you've seen it all, there's MORE! The detached 3-car garage is an incredible bonus, featuring an epoxy floor and finished loft space above. Whether you're looking for a home office, fitness space, art studio, workshop, or simply extra room for your hobbies, the possibilities are endless! Homes offering this much character, versatility, and modern convenience don't come along every day. Move right in and start enjoying everything this unique Cheshire property has to offer!

327 W Main St, Cheshire

$315,000

3 Beds ⋅ 1 Baths ⋅ 24216381 MLS

Opportunity meets location in Cheshire! Situated on just under a half acre corner lot with its very own brook running through the property, this 1920 Colonial offers charm, character, and the opportunity to make it your own. With approximately 1,400 square feet, 3 bedrooms, and 1 full bathroom, this home is ready for its next chapter. Bring your imagination and explore the possibilities! Update the kitchen with new cabinetry, countertops, and appliances, refresh the flooring, introduce modern lighting, or simply start with fresh paint and cosmetic improvements. Whether you envision preserving its vintage charm or creating a more contemporary feel, there's plenty of potential to personalize this home over time. The traditional layout provides a starting point for your ideas, while the unfinished basement offers additional storage and utility space. Outside, the corner lot offers opportunities for gardening, landscaping, and outdoor enjoyment, with the brook adding a distinctive natural feature. Conveniently located near Cheshire Academy, shopping, restaurants, and everyday amenities. If you've been looking for a property where you can build equity through thoughtful improvements rather than paying for someone else's renovations, this could be the opportunity you've been waiting for! Bring your vision and make this Cheshire Colonial your own. Sale is subject to probate approval.

135 Wallingford Rd, Cheshire

$889,000

5 Beds ⋅ 5 Baths ⋅ 24212574 MLS

Gracefully positioned within one of Cheshire's premier neighborhoods, this impressive 4,734 sf beauty features 5 beds, 5 baths, showcases classic architectural elegance, exceptional curb appeal and a picturesque, professionally landscaped grounds, designed for year-round enjoyment. A two-story foyer highlighted by an arched transom casts an abundance of natural light & introduces lovely architectural details and distinctive, colorful finishes throughout. Expansive kitchen with abundant cabinetry, generous counter space, breakfast bar, pantry, & sunny breakfast nook, along with a sunlit living room with fireplace, both offering convenient access to the rear deck for entertaining. The main level is further complemented by a formal dining room, convenient laundry room, 1/2 bath, & two private offices with custom built-ins & French doors, offering outstanding flexibility for remote work, guest room, study space, or additional living areas. Elegant open staircase to second level offers an exceptional primary suite featuring a spa-inspired full bath with a jetted tub, double vanity, stall shower & walk-in closet. Three generously sized secondary bedrooms & two well-appointed full baths, including a Jack-&-Jill bath, complete the upper level. Finished lower level with walk-out offers a full bath, abundance of storage & an adaptable floorplan with plenty of room to expand. Fabulous location to the new Stonebridge shops, parks, local farms, etc., A true must see to appreciate!

100 Scenic Ct, Cheshire

$579,900

4 Beds ⋅ 3 Baths ⋅ 24207101 MLS

Welcome to 42 Eastgate Drive, a spacious and well-cared-for 4 bedroom, 2-1/2 bath Colonial located in a desirable Cheshire neighborhood, just moments from Highland Elementary School. Offering 2,042 square feet of living space, this inviting home features a welcoming foyer, comfortable living room, formal dining room and a warm family room with fireplace and sliders leading to the screened porch. The eat-in kitchen features beautiful custom cherry cabinetry, granite countertops, a tile backsplash, hardwood flooring and generous pantry storage. Upstairs, the primary bedroom includes an updated private bath, while three additional bedrooms and a full hall bath provide plenty of space for family, guests or a home office. Hardwood flooring adds warmth and character throughout much of the home. The partially finished lower level offers additional flexible living space, a workshop, laundry and ample storage. Enjoy the screened porch overlooking a level backyard with established landscaping, colorful perennials and visiting birds throughout the seasons. Additional features include an attached two-car garage, vinyl siding, city water, city sewer, oil heat. Conveniently located near schools, shopping, restaurants and major highways. Come experience all that Cheshire offers, including the Farmington Canal Heritage Trail, Roaring Brook Falls, beautiful parks and open spaces, along with Whole Foods, Starbucks, Barnes & Noble and local shops and restaurants.

42 Eastgate Dr, Cheshire

$389,900

2 Beds ⋅ 1 Baths ⋅ 24214222 MLS

Welcome to 45 Broadview Road, a charming ranch with easy one-level living on a level 0.48-acre lot in a convenient Cheshire neighborhood. Hardwood floors run through the main level, where the bright living/dining room centers on a brick fireplace with an insert. The updated kitchen has Corian counters, a skylight, a pantry and plenty of cabinet space. Two bedrooms, the second ideal as a home office, and a tiled full bath complete the main level, with ceiling fans throughout. Downstairs, the finished family room with a wood stove adds cozy living space, along with laundry, a workshop and abundant storage. A floored attic with pull-down stairs offers even more room. A brand-new roof is being installed in early November 2026. Other features include an attached one-car garage with an automatic opener, 200-amp electrical service, wood shingle siding, city water and sewer, oil heat, 1992 Steam Boiler and a 2012 indirect hot water heater. Outside, relax on the oversized deck with a hot tub, or enjoy the patio and gazebo. The beautifully landscaped yard is filled with unusual plants, mature trees and established gardens, and two sheds give you plenty of space for tools and equipment. This sweet, well-loved home offers character and possibilities for its next owner. It's close to Cheshire's shops, restaurants and parks, and you can walk to the Farmington Canal Heritage Trail and town. Come take a look!

45 Broadview Rd, Cheshire

$675,000

4 Beds ⋅ 3 Baths ⋅ 24215798 MLS

Welcome to 35 Brookside Place, a spacious and inviting four-bedroom Colonial offering comfortable living, thoughtful updates, and exceptional spaces for entertaining. Set on a beautifully landscaped property in Cheshire, this home combines classic New England charm with the features today's buyers appreciate. Step inside to discover a versatile floor plan with generous living areas, hardwood flooring, and abundant natural light. The welcoming living room features a beautiful bay window, while a separate den with a fireplace provides a cozy place to relax. The updated eat-in kitchen is the heart of the home. Sliding glass doors lead to one of the property's most distinctive features-a spectacular sunroom with soaring curved wood framing and expansive glass walls and ceiling. Filled with natural light and overlooking the backyard, this wonderful space is perfect for morning coffee, entertaining, or simply enjoying the changing seasons. Upstairs, four generously sized bedrooms provide comfortable accommodations, including a spacious primary bedroom with ample closet space and ensuite bathroom. Another full bathroom completes the second level, while a convenient half bath and laundry area are located on the main floor. The finished lower level adds additional square feet of flexible recreation space.

35 Brookside Pl, Cheshire

$479,900

4 Beds ⋅ 5 Baths ⋅ 24216201 MLS

Investors and Contractors take notice. This 3,839 Colonial is ready to be brought back to life. Features include a huge Family Room with cathedral ceilings and a fireplace with an open floor plan that includes the large eat-in kitchen, dining area, and slider to the back deck. Outside there is an inground pool with spa and outdoor kitchen area. Prior water damage led to this property being stripped to the studs awaiting your custom re-build. As-Is Sale.

7 Edith Pl, Cheshire

$839,900

4 Beds ⋅ 3 Baths ⋅ 24214742 MLS

This stunning home feels brand new, with extensive updates and impeccable attention to detail. Newly refinished HW floors, fresh paint including ceilings, newer roof and siding, and beautifully remodeled kitchen and baths make this home move-in ready. The custom kitchen features new cabinetry, quartzite countertops, stainless steel appliances, a center island, built-in desk area, spacious dining space, skylights that bring in morning sun, and one of the home's three fireplaces. The dining space of the kitchen showcases a vaulted cedar-lined ceiling, more skylights, and a beautiful copper fireplace. Just off the kitchen, the family room has a dramatic vaulted ceiling, palladium windows, built-in bookshelves, and another fireplace. The inviting living room offers a decorative fireplace, custom built-in bookcases, and French doors leading to a sun-filled all-season room with a propane stove. A convenient 1st floor laundry room adds everyday practicality. Upstairs, you'll find 4 updated bedrooms, including a spacious primary suite with a remodeled bath, along with a fully renovated guest bathroom. Outdoor living is equally impressive, featuring an expansive brick patio overlooking a lush lawn and established perennial gardens, creating the perfect setting for relaxing, entertaining, and enjoying the seasons. Located in Cheshire's desirable Beacon Hill neighborhood, this exceptional home offers timeless charm with modern updates in one of the town's most sought-after settings!

256 Beacon Hill Dr, Cheshire

$469,000

4 Beds ⋅ 3 Baths ⋅ 24214579 MLS

Welcome to 68 Pleasant Drive, where a potential in-law suite with its own private entrance offers flexibility for extended family or guests. Hardwood floors, a spacious floor plan, and a convenient Cheshire location create a wonderful place to call home. Sidewalks line the road, adding to the appeal of this walkable setting close to shopping and local restaurants. The large backyard offers plenty of room for outdoor entertaining, gardening, or simply relaxing in privacy. Enjoy space, versatility, and everyday convenience in an established neighborhood. Showings begin tomorrow! NOTE: the square footage reflected in the MLS is based on town assessor records. SELLER BELIEVES it may not accurately represent the home's actual living space. The property offers additional living area beyond what is recorded. Buyers and their agents are encouraged to independently verify total square footage.

68 Pleasant Dr, Cheshire

$589,900

3 Beds ⋅ 2 Baths ⋅ 24213428 MLS

CHARMING CHESHIRE CAPE ON A NEAR-ACRE LOT - welcome to 178 Harrison Road, a well-loved three-bedroom, two-bath Cape Cod set on 0.97 lightly-wooded acres in a quiet, tree-lined neighborhood. The kitchen features granite counters, stainless appliances and timeless brick accents, flowing seamlessly to a sun-filled eat-in dining area with vaulted ceiling and walls of windows framing peaceful views of the private backyard. Multiple distinct living spaces give you room to spread out: a formal living room with tile-surround fireplace, a cozy family room with pellet stove, and a formal dining room with built-in cabinets. Hardwood flooring throughout the first-floor living areas. Three generous bedrooms including a main-floor primary, two full baths, and 2,054 square feet above grade, plus a built-out finished lower level ideal as a home gym, playroom, or office. Major capital improvements already addressed: 2024 ROOF, 2025 OWNED solar panels (no lease/loan to transfer), 2021 HVAC/Central Air, 2023 chimney liner, and underground irrigation. Oversized 2-car under-house garage offers abundant storage. Step outside to a versatile outdoor retreat with zones for every season - generous back deck, flagstone patio at the front entrance, dedicated children's play area with playscape, and plush lawn framed by stacked stone retaining walls and mature landscaping. Short distance to Cheshire schools, parks, and shopping. DONT MISS OUT!

178 Harrison Rd, Cheshire

$579,900

4 Beds ⋅ 3 Baths ⋅ 24213826 MLS

Welcome to 450 Cardinal Lane! This well-maintained 4-bedroom, 2.5-bath Colonial offers 2,042 square feet of living space on a beautifully landscaped .46-acre lot in Cheshire. The spacious first floor features a large living room, formal dining room, and a beautifully remodeled kitchen with white cabinetry, stainless steel appliances, and a comfortable eat-in area. Just off the kitchen is the inviting family room with a fireplace, access to the attached two-car garage, and direct access to the backyard. You'll also appreciate the convenience of an updated half bath on the main level. Upstairs, you'll find a generously sized primary bedroom with direct access to the full hall bathroom, along with three additional bedrooms. Hardwood flooring throughout adds warmth and character to the home. The partially finished lower level offers plenty of storage space, laundry area and a second full bathroom that has not been used in many years. Step outside to enjoy the beautiful, oversized patio overlooking the private, nicely manicured backyard, perfect for outdoor entertaining, dining, or simply relaxing. Additional highlights include a two-car attached garage with new door openers, replacement windows (2017), a brand-new roof (2026), and a newer oil tank (2020). Conveniently located near Cheshire's shopping, restaurants, parks, and recreational amenities, this lovely home offers a wonderful combination of space, comfort, and location. Don't miss this opportunity to make it your own!

450 Cardinal Ln, Cheshire

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Cheshire Homes for Sale

Newest Cheshire Homes for Sale

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