Cheshire, CT Homes

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  $890,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  1840 Blackberry Place, Cheshire, CT 06410

  Build the custom home of your dreams on ~ 1 acre of land in Blackberry Woods. Consider the Spruce model which offers 2,600 sqft of living space w/ 4 Bedrooms and 2 1/2 Baths. It includes a spacious foyer with double coat closets, mudroom, half bath & laundry off garage entry, an open floor plan between the family room, dinette & kitchen, gas log fireplace, and kitchen pantry. The formal dining

  

  Kathleen Maloney

  Coldwell Banker Realty

  (475) 447-1624

  1840 Blackberry Place, Cheshire, CT 06410
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  /10

  $1,895 per month plus fees

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  474 Oak Ave, Cheshire, CT 06410

  Welcome to your new home in the charming city of Cheshire, CT. This property offers an ideal location for those seeking comfort and convenience, with easy access to nearby restaurants, a department store, and family-friendly educational facilities such as Feldman Orthodontics and The Smart Start Preschool & Learning Center, both just a short drive away.The property features a centrall

  474 Oak Ave, Cheshire, CT 06410
• 

  $533,800 Sold Nov 18, 2025

  • 1,850 Sq Ft
  • $289/SF
  • 2 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2026

  126 Shea Cir Unit 126, Cheshire, CT 06410

  DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious exterior unit townhome in a desirable location. This maintenance-free community will have a covered pavilion, fire pit, walking loop, and trails. A convenient location offers

  Michael Helmuth EG Group Realty LLC

  126 Shea Cir Unit 126, Cheshire, CT 06410
• 

  Est $566,005 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,350 Sq Ft

  1645 Tuttle Ave, Cheshire, CT 06410

  1645 Tuttle Ave, Cheshire, CT 06410
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  /3

  $910,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  1711 Blackberry Place, Cheshire, CT 06410

  Welcome to the scenic Blackberry Woods in Cheshire. Build the custom home of your dreams on ~1 acre of land, on a lot with phenomenal views of Meriden Mountain. Consider the Spruce model with its 2,600 sqft of living space w/ 4 Bedrooms and 2 1/2 Baths. It includes a spacious foyer with double coat closets, mudroom, half bath & off garage entry, an open floor plan between the family room, dinette

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 496-4646

  1711 Blackberry Place, Cheshire, CT 06410
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  /17

  $3,000 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • House for Rent

  64 E Mitchell Ave Unit 27, Cheshire, CT 06410

  Welcome to Maplecroft Village! Nestled in the heart of Cheshire, our ranch-style apartment complex, built in 2024, boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments offer 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit offers beautiful

  Brette Stern Calcagni Real Estate

  64 E Mitchell Ave Unit 27, Cheshire, CT 06410
• 

  $650,000 Sold Nov 17, 2025

  • 2,215 Sq Ft
  • $293/SF
  • 47 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1938

  30 Elmwood Dr, Cheshire, CT 06410

  Stunning Custom Colonial w/ 3 beds & 2.5 baths, ideally located in the sought-after South End of Cheshire. This elegant home features over 2,200 sq ft of living space w/ abundant natural light, HW floors & custom details throughout. The formal living room showcases a beautiful wood-burning FP, custom built-in bookshelves, charming window seats & classic archways. A formal dining room provides an

  Jack Hill Seabury Hill REALTORS

  30 Elmwood Dr, Cheshire, CT 06410
• 

  Est $578,770 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 2,103 Sq Ft

  151 Corliss Ln, Cheshire, CT 06410

  151 Corliss Ln, Cheshire, CT 06410
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  /21

  $829,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,001 Sq Ft

  1517 Blackberry Place, Cheshire, CT 06410

  Exciting opportunity to build your very own 2001 sqft ranch with wonderful curb appeal. One level living at its finest, with 9ft ceilings throughout, custom kitchen w/granite countertops and center island, hardwood flooring in the main living areas, gas fireplace in the family room and a mudroom with half bath and laundry. Large Primary bedroom with bathroom en-suite, and walk-in closet. 2 guest

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 457-3624

  1517 Blackberry Place, Cheshire, CT 06410
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  /18

  $3,400 per month plus fees

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • House for Rent

  201 Elmwood Cir, Cheshire, CT 06410

  Completely renovated 3-bedroom, 1.5-bathroom home in the heart of Cheshire! This stunning property, located in a cul-de-sac, features all-new electrical, plumbing, and a state-of-the-art heating and air conditioning system with on-demand hot water. Landlord passes on propane savings to tenant (current contract at 1.75/gal). The modern kitchen is a chef's dream, boasting sleek quartz countertops

  201 Elmwood Cir, Cheshire, CT 06410
• 

  $515,000 Sold Nov 14, 2025

  • 2,150 Sq Ft
  • $240/SF
  • 46 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1956

  240 Timber Ln, Cheshire, CT 06410

  This 5 Bedroom Colonial style home sits on a double lot ( 0.93 ) which the former owner merged together as 1 parcel and could possibly be subdivided again. The home has undergone newer changes including the Kitchen, Bathroom, Windows, Driveway & the road was just freshly paved with more draining added. The home Primary bedroom is on the main level. All the schools are close by with Doolittle

  Paul Ferreira RE/MAX Right Choice

  240 Timber Ln, Cheshire, CT 06410
• 

  Est $376,288 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,599 Sq Ft

  89 Corliss Ln, Cheshire, CT 06410

  89 Corliss Ln, Cheshire, CT 06410
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  /2

  $699,900 New Construction

  • 3 Beds
  • 3 Baths
  • 1,908 Sq Ft

  1600RR S Main St, Cheshire, CT 06410

  To be built. Modern Raised Ranch with plenty of room for all. Wonderful layout with endless possibilities. 3 large bedrooms and 3 full bathrooms, including one on the lower level allowing for easy accommodation of guests. Set on more than 2 acres. Open floor plan on the main level with sliders and lots of natural light. Finished basement area with sliders and a full bathroom offers flexible use

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 439-5995

  1600RR S Main St, Cheshire, CT 06410
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  /17

  $2,800 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • House for Rent

  64 E Mitchell Ave Unit 13, Cheshire, CT 06410

  Welcome to Maplecroft Village! Nestled in the heart of Cheshire, our ranch-style apartment complex, built in 2024, boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments offer 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit offers beautiful

  Nancy Lydell Calcagni Real Estate

  64 E Mitchell Ave Unit 13, Cheshire, CT 06410
• 

  $416,100 Sold Nov 14, 2025

  • 1,955 Sq Ft
  • $213/SF
  • 44 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  248 Mountain Rd, Cheshire, CT 06410

  Welcome to this beautifully updated home, offering a perfect blend of charm and modern comfort. Inside, you'll find a sun-filled layout with hardwood floors, a cozy fireplace, and a versatile sunroom-great for relaxing or working from home. The eat-in kitchen, complete with new stainless steel appliances (2023), connects effortlessly to the dining area, making it ideal for both everyday living

  Emily Lovejoy William Raveis Real Estate

  248 Mountain Rd, Cheshire, CT 06410
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  Est $689,925 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,677 Sq Ft

  30 Pine Brook Ct, Cheshire, CT 06410

  30 Pine Brook Ct, Cheshire, CT 06410
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  /2

  $899,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,718 Sq Ft

  1600 S Main St, Cheshire, CT 06410

  Build your own expanded Cape Cod inn the South End of Cheshire. Large lot of 2.96 acres. Convenient to Quinnipiac, Yale and New Haven. 4 bedroom, 2.5 bathroom Maple model with a primary bedroom on the main floor. Oversized family room with fireplace opens to a custom kitchen with island. Formal dining room for get togethers and events. The 1st floor hosts the primary suite with large walk in

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 885-1679

  1600 S Main St, Cheshire, CT 06410
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  /17

  $2,900 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • House for Rent

  64 E Mitchell Ave Unit 45, Cheshire, CT 06410

  Welcome to Maplecroft Village! Nestled in the heart of Cheshire, our ranch-style apartment complex, built in 2024, boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments offer 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit offers beautiful

  Brette Stern Calcagni Real Estate

  64 E Mitchell Ave Unit 45, Cheshire, CT 06410
• 

  $500,000 Sold Nov 14, 2025

  • 2,109 Sq Ft
  • $237/SF
  • 42 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1840

  353 Mount Sanford Rd, Cheshire, CT 06410

  Discover the character and charm of old New England in this colonial home built in 1840. This property is set on 3.08 acres in southern Cheshire countryside. With 4-bedrooms, 2-baths and 2,109 sq. ft. of living space this home blends historic charm with room for modern updates. The property includes a large 4-stall barn and workshop with loft, perfect for horses, hobbies, or additional storage.

  Kelly Ryan William Raveis Real Estate

  353 Mount Sanford Rd, Cheshire, CT 06410
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  Est $452,980 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,772 Sq Ft

  1708 Orchard Hill Rd, Cheshire, CT 06410

  1708 Orchard Hill Rd, Cheshire, CT 06410
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  /3

  $987,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,821 Sq Ft

  1600 Blackberry Place, Cheshire, CT 06410

  Welcome to Blackberry Woods. Enjoy the Frasier model with 2,821 sqft of living space , w/ 4 Bedrooms and 2 1/2 Baths. This both elegant and practical model features a spacious Foyer with double coat closets, Mudroom and Half Bath off garage entry, open floor plan between the Family Room, Dinette & Kitchen, Gas Log Fireplace, Kitchen Pantry, and a backyard Patio with built-in Firepit! The formal

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 496-4049

  1600 Blackberry Place, Cheshire, CT 06410
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  /16

  $2,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  1142 Sperry Rd, Cheshire, CT 06410

  Remote 4BR/2BA unit on quiet farm adjacent to owner's residence. Cozy cottage feel with wood accents. Quiet, off-the-beaten-path setting surrounded by nature with room to garden. Long driveway leads to quiet location. Landlord lives in conjoining home and will handle plowing. Smoking outside only. No laundry, dishwasher or garage use. Pet upon approval with references and additional deposit. Do

  Kelly Ryan William Raveis Real Estate

  1142 Sperry Rd, Cheshire, CT 06410
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  $430,000 Sold Nov 14, 2025

  • 1,312 Sq Ft
  • $328/SF
  • 43 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1956

  21 Hawthorne Dr, Cheshire, CT 06410

  Inviting South Cheshire Ranch with Fireplace, Sunroom & Backyard Retreat! Lovingly cared for by just two owners in nearly 70 years, this 3-bedroom ranch offers the perfect blend of comfort and possibility. Imagine cozy evenings by the wood-burning fireplace, sunlit mornings in the heated addition with its oversized slider, and year-round enjoyment of a private, level backyard - perfect for

  Nicky Rubbo The Heritage Group, LLC

  21 Hawthorne Dr, Cheshire, CT 06410
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  Est $513,024 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,009 Sq Ft

  1700 S Main St, Cheshire, CT 06410

  1700 S Main St, Cheshire, CT 06410
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  /18

  $674,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,975 Sq Ft

  Carriage Home Plan at The Reserve at Stonebridge Crossing, Cheshire, CT 06410

  The Carriage Home offers 2,450 square feet of thoughtfully designed space with 3 bedrooms, 2.5 baths, and bright, open living areas made for modern comfort. The first-floor primary suite provides convenience and privacy, while the airy great room and designer kitchen with a large island and hardwood flooring create a welcoming flow for everyday living. Upstairs, a spacious loft adds versatility

  EG Home Builder

  31 Soderman Way Unit 36681016, Cheshire, CT 06410
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  /10

  $1,895 total monthly price

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  474 Oak Ave Unit 74, Cheshire, CT 06410

  Two Bedroom, Second floor at Birchwood, Upgraded-Hardwood floors, Available Immediately. HEAT, HOT WATER, SEWER & WATER INCLUDED! Two months Security, Condo monthly & Taxes paid by the Landlord, Credit and background check, Credit score of at least 725+! NO CO-SIGNERS, NO SMOKERS, NO PETS, One full bath and spacious bedrooms, There is coin operated laundry with an extremely reasonable price for

  Marty Rauch Marty Rauch Real Estate

  474 Oak Ave Unit 74, Cheshire, CT 06410
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  $360,000 Sold Nov 13, 2025

  • 1,658 Sq Ft
  • $217/SF
  • 63 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1976

  4 Currier Ct, Cheshire, CT 06410

  Currier Woods END UNIT condo is ready for new owners for the first time in 50 years ! Check out this floor plan like no other! The minute you enter this unit through the covered front porch you will feel at home. The main level is a space you can enjoy whether you want to dine in the eat in kitchen or invite others to join and expand into the formal dining room space. Adjacent to the dining room

  Donna Pellegrino Calcagni Real Estate

  4 Currier Ct, Cheshire, CT 06410
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  Est $423,078 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft

  107 Bradford Dr, Cheshire, CT 06410

  107 Bradford Dr, Cheshire, CT 06410
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  /37

  $778,572 Open Sun 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,975 Sq Ft

  81 Shea Cir, Cheshire, CT 06410

  Welcome to The Reserve at Stonebridge Crossing-Cheshire's premier low-maintenance community by EG Home. Recently elevated to a fully Designer Curated Quick Delivery Home, this residence now includes $103,672 of masterfully curated design elements, blending elevated contemporary style with timeless finishes-reflected in the updated price. Step through the grand entry foyer featuring crown molding,

  Felicity LeClair EG Group Realty LLC

  81 Shea Cir, Cheshire, CT 06410
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  /17

  $2,400 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,052 Sq Ft
  • Townhouse for Rent

  420 Greens Loop, Cheshire, CT 06410

  A terrific townhome near the pool and basketball courts at this wonderful location in the community. Country Village is minutes away from orchards, shopping, and the new Shops at Stone Bridge. Available for immediate move-in. Fully applianced, including washer and dryer. Security deposit, references required. A "screening fee" is required.

  Joel Grossman Huntsman,Meade & Partners Comp

  420 Greens Loop, Cheshire, CT 06410
• 

  $490,000 Sold Nov 13, 2025

  • 1,786 Sq Ft
  • $274/SF
  • 54 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1967

  294 Greenwood Dr, Cheshire, CT 06410

  Perfectly positioned in a desirable neighborhood with sidewalks and a welcoming sense of community, this beautiful home blends timeless charm with thoughtful modern updates. As you step inside, you're greeted by a bright, open floor plan where ample natural light pours through the newer windows. The spacious, remodeled kitchen is thoughtfully designed with central island, cabinet organizers and

  Dorothy Karska-Piech Calcagni Real Estate

  294 Greenwood Dr, Cheshire, CT 06410
• 

  Est $543,550 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,548 Sq Ft

  1450 S Main St, Cheshire, CT 06410

  1450 S Main St, Cheshire, CT 06410
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  /13

  $669,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,450 Sq Ft

  83 Shea Cir Unit 83, Cheshire, CT 06410

  Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy,

  Jason Helton EG Group Realty LLC

  83 Shea Cir Unit 83, Cheshire, CT 06410
• 

  

  /22

  $2,400 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,578 Sq Ft
  • Townhouse for Rent

  745 Greens Loop Unit 745, Cheshire, CT 06410

  Beautiful townhouse condominium in quiet, country setting! Just Painted White Kitchen Cabinets with New Hardware. New Granite Countertops in Kitchen, Stainless Steel Appliances, French Doors to Deck. Hardwood Floors just refinished on first floor. Half Bath on First Floor. Two Bedrooms, One full bath on second floor, with access from Master Bedroom and Hallway. Two Large Closets in Master

  Joan Kranyak Coldwell Banker Realty

  745 Greens Loop Unit 745, Cheshire, CT 06410
• 

  $465,000 Sold Nov 13, 2025

  • 1,248 Sq Ft
  • $373/SF
  • 40 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1969

  70 Warren St, Cheshire, CT 06410

  Welcome to 70 Warren Street, a beautifully updated ranch home set on a desirable corner level lot in the heart of Cheshire. Recent upgrades include a full basement remodel with an additional full bathroom, hardwood flooring throughout and modern lighting. Comfort and efficiency come with a new central air conditioning system and natural gas heat updated in 2018. The exterior has been refreshed

  Tanya Uhelsky RE/MAX RISE

  70 Warren St, Cheshire, CT 06410
• 

  Est $794,506 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,594 Sq Ft

  3 Mulberry Ct, Cheshire, CT 06410

  3 Mulberry Ct, Cheshire, CT 06410
• 

  

  /20

  $504,900 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  135 Shea Cir Unit 135, Cheshire, CT 06410

  DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious exterior unit townhome in a desirable location. This maintenance-free community will have a covered pavilion, fire pit, walking loop, and trails. A convenient location offers

  Michael Helmuth EG Group Realty LLC

  135 Shea Cir Unit 135, Cheshire, CT 06410
• 

  

  /8

  $1,575 total monthly price

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • House for Rent

  2144 Waterbury Rd Unit 7, Cheshire, CT 06410

  Recently renovated 1 bed, 1 bath ranch-style end unit condo in desirable Cheshire. Bright and comfortable layout with on-site laundry. Conveniently located near major highways, offering easy access for commuting and everyday needs.

  Mary Sutera Carbutti & Co., Realtors

  2144 Waterbury Rd Unit 7, Cheshire, CT 06410
• 

  $520,000 Sold Nov 12, 2025

  • 2,236 Sq Ft
  • $233/SF
  • 150 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1960

  791 Ives Row, Cheshire, CT 06410

  Opportunity is knocking!! Don't miss out. This Classic Colonial is located in the heart of Cheshire. Discover timeless elegance in this beautifully maintained 4 / 5 bedroom, 3 full bath Colonial. This spacious home offers the perfect blend of character and comfort with a traditional layout, sun-filled rooms, and hardwood floors throughout. The updated kitchen (with a walk in pantry) opens to a

  Debora Masotta Pearce Real Estate

  791 Ives Row, Cheshire, CT 06410
• 

  Est $424,465 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,473 Sq Ft

  323 Fenn Rd, Cheshire, CT 06410

  323 Fenn Rd, Cheshire, CT 06410

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