Cheshire, CT Homes

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  $249,900 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  14 Woodridge Dr Unit 14, Cheshire, CT 06410

  Bright and cheerful condo in Cheshire, in a peaceful setting close to highway, and minutes from the town center. Step in to a spacious Living Room that opens to an updated kitchen with ample cabinetry and a very handy large pantry too. Access to a restful garden area to the back of the property. Upstairs are two large bedrooms, both with plenty of storage space. The primary bedroom has a gorgeous

  

  Kathleen Maloney

  Coldwell Banker Realty

  (475) 264-5624

  14 Woodridge Dr Unit 14, Cheshire, CT 06410
• Explore Cheshire

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  $2,495 total monthly price

  Highland Farms

  2 Beds

  1728 Highland Ave, Cheshire, CT 06410

  BRAND NEW APARTMENTS coming JANUARY 2026!Highland Farms combines a comfortable suburban location with access to nearby restaurants and services. Located less than a mile from The Shops at Stone Bridge, a brand new shopping center offering grocery, retail, and more. Property is under construction at this time. Please contact the Leasing Office to be added to the waitlist.

  1728 Highland Ave, Cheshire, CT 06410
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  $410,000 Sold Nov 03, 2025

  1364 Avon Blvd, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,142 Sq Ft
  • Built 1953

  Last Sold Summary

  • 8% Above List Price
  • $359/SF
  • 7 Days On Market

  Last Listing Agent Melanie Ricci Coldwell Banker Realty

  1364 Avon Blvd, Cheshire, CT 06410
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  Est $655,927 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,168 Sq Ft

  108 Old Farms Rd, Cheshire, CT 06410

  108 Old Farms Rd, Cheshire, CT 06410
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  $674,900

  • 4 Beds
  • 2.5 Baths
  • 3,205 Sq Ft

  721 Ives Row, Cheshire, CT 06410

  Spacious Four Bedroom Colonial! Nestled on a large level lot, this home delivers a great opportunity. Main level entry offers a sizeable foyer with double coat closets. The formal dining room displays attention to detail with crown molding and chair rail while the kitchen showcases stainless steel appliances, abundant cabinetry, pantry and center island w/breakfast bar. The Living room is

  

  Shane Kropo

  RE/MAX RISE

  (203) 457-8303

  721 Ives Row, Cheshire, CT 06410
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  $1,815 total monthly price

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

  64 E Mitchell Ave Unit 54, Cheshire, CT 06410

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

  Brette Stern Calcagni Real Estate

  64 E Mitchell Ave Unit 54, Cheshire, CT 06410
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  $865,000 Sold Nov 07, 2025

  458 Castle Glenn, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 3,646 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Above List Price
  • $237/SF
  • 1 Day On Market

  Last Listing Agent The Sally Bowman Team Berkshire Hathaway NE Prop.

  458 Castle Glenn, Cheshire, CT 06410
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  Est $917,184 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,834 Sq Ft

  679 Mountain Rd, Cheshire, CT 06410

  679 Mountain Rd, Cheshire, CT 06410
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  $335,000

  • 3 Beds
  • 2 Baths
  • 1,180 Sq Ft

  131 Wallingford Rd, Cheshire, CT 06410

  Charming, Close to town, 3 bedroom 2 bath Colonial. Hardwood floors, updated kitchen and bath. Front porch and rear deck. 2 car detached garage with loft.

  

  Steven Miller

  Coldwell Banker Realty

  (475) 267-5999

  131 Wallingford Rd, Cheshire, CT 06410
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  $1,570 - $2,800 total monthly price

  Lakeside of Cheshire

  Studio - 2 Beds

  50 Hazel Dr, Cheshire, CT 06410

  Ready to embrace vacation-inspired living in Cheshire, Connecticut? Our modern studio, 1 & 2 bedroom apartments offer spacious, pet-friendly floor plans for rent. This quiet suburban oasis is close to endless shops, dining, and recreation destinations. Live it up, wind it down, or take life at whatever pace you desire – Lakeside of Cheshire delivers the lifestyle you’ve been searching for. We

  50 Hazel Dr, Cheshire, CT 06410
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  $945,000 Sold Jul 17, 2025

  657 Tamarack Rd, Cheshire, CT 06410

  • 5 Beds
  • 7 Baths
  • 6,484 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $146/SF
  • 31 Days On Market

  Current Estimated Value $1,010,381

  Last Listing Agent Julie Luchina Coldwell Banker Realty

  657 Tamarack Rd, Cheshire, CT 06410
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  Est $392,321 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,303 Sq Ft

  57 Old Towne Rd, Cheshire, CT 06410

  57 Old Towne Rd, Cheshire, CT 06410
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  $929,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,794 Sq Ft

  1841 Blackberry Place, Cheshire, CT 06410

  Stunning 4 bedroom, 2.5 bathroom Colonial, The Birch offers gracious living and a wonderful floor plan. Culinary enthusiasts will love the large walk in pantry, granite-topped cabinetry with center island that opens to a spacious family room with vaulted ceiling. The wonderful layout for entertaining is completed by a formal dining room. Easily work from home with the main floor study. The

  

  Kathleen Maloney

  Coldwell Banker Realty

  (475) 472-8934

  1841 Blackberry Place, Cheshire, CT 06410
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  $1,750 total monthly price

  • 1 Bed
  • 1 Bath
  • 10,780 Sq Ft
  • House for Rent

  63 Creamery Rd Unit 63, Cheshire, CT 06410

  Move right into this remodeled 1 bedroom apartment. Country setting in North Cheshire. Beautiful first floor unit with slider to patio. Excellent one floor living lifestyle with updated kitchen with stainless steel dishwasher, refrigerator, and stove. Updated bathroom! New laminate flooring, lots of closet space, off street parking, washer/dryer coin op in complex. Heat & hot water included!!

  The Sally Bowman Team Berkshire Hathaway NE Prop.

  63 Creamery Rd Unit 63, Cheshire, CT 06410
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  $240,000 Sold Nov 06, 2025

  488 Radmere Rd Unit B, Cheshire, CT 06410

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft
  • Built 1968

  Last Sold Summary

  • $200/SF
  • 49 Days On Market

  Last Listing Agent Katherine Smith Berkshire Hathaway NE Prop.

  488 Radmere Rd Unit B, Cheshire, CT 06410
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  Est $768,241 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 4,178 Sq Ft

  63 Trout Brook Rd, Cheshire, CT 06410

  63 Trout Brook Rd, Cheshire, CT 06410
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  $919,000 New Construction

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

  1800 Blackberry Place, Cheshire, CT 06410

  Build your own expanded Cape Cod (or bring your own plans) on Blackberry Woods, Cheshire's newest development. 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 closet and tile shower, and

  

  Kathleen Maloney

  Coldwell Banker Realty

  (475) 445-2914

  1800 Blackberry Place, Cheshire, CT 06410
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  $2,100 - $3,600 per month plus fees

  Riverpointe Cheshire

  Studio - 3 Beds

  106 Stonebridge Ct, Cheshire, CT 06410

  Riverpointe Cheshire encompasses 300 apartment homes within 10 buildings spread amongst beautifully manicured landscape. This stunning community features studios, one-bedroom (with option for a den), two-bedroom, and three-bedroom residences. The community will be completed with sophisticated unit and common area finishes as well as a robust amenity program for all residents to enjoy.Riverpointe

  106 Stonebridge Ct, Cheshire, CT 06410
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  $430,000 Sold Aug 22, 2025

  233 Mountain Rd, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 2,028 Sq Ft
  • Built 1963

  Last Sold Summary

  • 8% Above List Price
  • $212/SF
  • 43 Days On Market

  Current Estimated Value $424,161

  Last Listing Agent Stacey Deangelis Calcagni Real Estate

  233 Mountain Rd, Cheshire, CT 06410
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  Est $698,354 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,773 Sq Ft

  2 Stonegate Cir, Cheshire, CT 06410

  2 Stonegate Cir, Cheshire, CT 06410
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  $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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  $2,700 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,109 Sq Ft
  • House for Rent

  353 Mount Sanford Rd, Cheshire, CT 06410

  Spacious and charming farmhouse rental set on picturesque farmland, offering a peaceful rural setting in Cheshire. This unique home features 3-4 bedrooms and 2-1/2 baths with a flexible floor plan to suit a variety of needs. The eat-in kitchen boasts brand new appliances and opens to a convenient mudroom area with a full bath-perfect for everyday living. A separate laundry room, sunporch, and an

  The Sally Bowman Team Berkshire Hathaway NE Prop.

  353 Mount Sanford Rd, Cheshire, CT 06410
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  $317,000 Sold Oct 10, 2025

  204 Greens Loop Unit 204, Cheshire, CT 06410

  • 2 Beds
  • 1.5 Baths
  • 1,578 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Above List Price
  • $201/SF
  • 24 Days On Market

  Current Estimated Value $318,923

  Last Listing Agent Evan Johnson Coldwell Banker Realty

  204 Greens Loop Unit 204, Cheshire, CT 06410
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  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft

  11 Empire Ct Unit 18, Cheshire, CT 06410

  11 Empire Ct Unit 18, Cheshire, CT 06410
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  $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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  $1,238 - $2,650 per month plus fees

  Acclaim at Cheshire

  1 - 2 Beds

  10 Realty Dr, Cheshire, CT 06410

  Apartment Living Reinvented For The Twenty First CenturyAt Acclaim at Cheshire, youll discover the lifestyle youve been looking for has never been more within reach. Select your next residence from our spacious one or two-bedroom floor plans. Living at Acclaim at Cheshire offers a modern, efficient, and community-focused lifestyle. Designed with a blend of affordability, sustainability,

  10 Realty Dr, Cheshire, CT 06410
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  $370,000 Sold Oct 09, 2025

  239 Bates Dr, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 1,646 Sq Ft
  • Built 1956

  Last Sold Summary

  • 6% Above List Price
  • $225/SF
  • 70 Days On Market

  Current Estimated Value $374,037

  Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

  239 Bates Dr, Cheshire, CT 06410
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  Est $787,406 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,492 Sq Ft

  37 Warren St, Cheshire, CT 06410

  37 Warren St, Cheshire, CT 06410
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  $859,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,459 Sq Ft

  1600 S Main St Unit Model A (Charter Oak, Cheshire, CT 06410

  Wonderful opportunity to build in the south end of Cheshire. The custom built gracious Charter Oak model provides 2,459 sq ft of thoughtful living space with 4 Bedrooms and 2 1/2 Baths. Desirable features of this plan include a spacious foyer entry with coat closet, mudroom off the garage entry w/ half bath and laundry, an open floor plan including a custom kitchen, dinette & family room, gas log

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 806-9529

  1600 S Main St Unit Model A (Charter Oak, Cheshire, CT 06410
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  /22

  $5,000 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,371 Sq Ft
  • House for Rent

  50 Heritage Dr, Cheshire, CT 06410

  For Rent: Beautifully updated, freshly painted, 4-bedroom, 2.5-bath Colonial set in a desirable neighborhood just minutes from Route 10. The first floor offers a classic and functional layout featuring a formal dining room, formal living room, and a spacious family room with a wood burning fireplace. The recently renovated kitchen is a standout, boasting brand-new appliances, new countertops, and

  Annie Dillon William Raveis Real Estate

  50 Heritage Dr, Cheshire, CT 06410
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  $970,000 Sold Apr 04, 2025

  31 Harvest Ct, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 4,422 Sq Ft
  • Built 1992

  Last Sold Summary

  • 1% Below List Price
  • $219/SF
  • 39 Days On Market

  Current Estimated Value $970,855

  Last Listing Agent Beverly Thorne Coldwell Banker Realty

  31 Harvest Ct, Cheshire, CT 06410
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,035 Sq Ft

  23 Wadsworth Ln Unit 23, Wallingford, CT 06492

  23 Wadsworth Ln Unit 23, Wallingford, CT 06492
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  $1,060,000 New Construction

  • 4 Beds
  • 3 Baths
  • 3,029 Sq Ft

  1500 Blackberry Place, Cheshire, CT 06410

  Welcome to Blackberry Woods, Cheshire's newest development. Consider The Willow, with its 3,029 sqft of Living Space on just over 1.36 Acres of Land. Fabulous Floor Plan includes an impressive 2 Story Foyer, First-Floor Full Bath, Large Kitchen Pantry, and Private Office on the Main Level. The Master Suite will "WOW" You with a Walk-In Closet, Double Vanities, Water Closet, and a Luxurious

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 427-0372

  1500 Blackberry Place, Cheshire, CT 06410
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  $1,895 total monthly price

  • 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
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  $570,000 Sold Dec 04, 2025

  241 Beacon Hill Dr, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 3,500 Sq Ft
  • Built 1967

  Last Sold Summary

  • 5% Below List Price
  • $163/SF
  • 61 Days On Market

  Last Listing Agent Kelly Ryan William Raveis Real Estate

  241 Beacon Hill Dr, Cheshire, CT 06410
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  Est $786,100 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,265 Sq Ft

  752 Ives Row, Cheshire, CT 06410

  752 Ives Row, Cheshire, CT 06410
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  $1,109,410 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,036 Sq Ft

  1811 Blackberry Place, Cheshire, CT 06410

  New construction in a neighborhood setting. Cheshire's newest development. Blackberry Woods, has a wonderful range of lot types including those with beautiful views of Meriden Mountain, those with plenty of privacy, and those with wonderful backyard options. The Montgomery Model features 9' ceilings and hardwood flooring on the main floor, a custom-designed kitchen opening to family room with gas

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 463-4250

  1811 Blackberry Place, Cheshire, CT 06410
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  $1,945 total monthly price

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

  494 Oak Ave Unit 33, Cheshire, CT 06410

  First floor-Two Bedroom Condo at Birchwood, Upgraded-Just completely painted-New shower and bathtub, 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

  Marty Rauch Marty Rauch Real Estate

  494 Oak Ave Unit 33, Cheshire, CT 06410
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  $1,500,000 Sold Jan 22, 2025

  408 Mount Sanford Rd, Cheshire, CT 06410

  • 5 Beds
  • 6 Baths
  • 6,161 Sq Ft
  • Built 2022

  Last Sold Summary

  • 9% Below List Price
  • $243/SF
  • 171 Days On Market

  Current Estimated Value $1,570,825

  Last Listing Agent Iris Meyer William Raveis Real Estate

  408 Mount Sanford Rd, Cheshire, CT 06410
• 

  Est $819,114 Not Listed For Sale

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

  18 Alyssa Dr, Cheshire, CT 06410

  18 Alyssa Dr, Cheshire, CT 06410

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