Cheshire, CT Homes

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  /40

  $814,900

  • 4 Beds
  • 3.5 Baths
  • 2,709 Sq Ft

  10 W Ridge Ct, Cheshire, CT 06410

  Coming Soon - Exceptional 4-Bedroom 3.5 Bath Colonial. Built in 2017 and set on 2.5 acres in one of the area's most sought-after Quiet cul-de-sac neighborhoods, this stunning Colonial combines elegance, comfort, and modern convenience. Features include 9 foot ceilings, a grand two-story foyer welcomes you inside, where hardwood floors flow throughout the open and inviting floor plan. The spacious

  

  Ken Demirs

  Regency Real Estate, LLC

  (475) 472-9681

  10 W Ridge Ct, Cheshire, CT 06410
• 

  Explore Cheshire

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  /32

  $3,100 per month

  • 3 Beds
  • 2.5 Baths
  • 1,787 Sq Ft
  • House for Rent

  884 Highland Ave, Cheshire, CT 06410

  Move righrt into this turnkey remodeled Cape! Main level boasts open floor plan with stunning eating space kitchen appointed with Quartz counter tops, island, stainless appliances, bow window and sliding glass doors to deck, living room and dining room with hardwood flooring, main level bedroom and full updated bathroom complete this level. The upper level offers 2 addidtional bedrooms and second

  

  Linda Mayfield

  RE/MAX RISE

  (203) 601-7341

  884 Highland Ave, Cheshire, CT 06410
• 

  $585,000 Sold Sep 19, 2025

  • 1,826 Sq Ft
  • $320/SF
  • 99 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1982

  80 Jill Ln, Cheshire, CT 06410

  Move in Impeccably cared for w/ thoughtful upgrades, this 2/3 BR log home-highlighted by cathedral ceilings, exposed beams, large windows, and skylights that showcase its enduring beauty. Upgraded Kitchen - hickory cabinets, granite counters, a separate breakfast area with large windows overlooking nature, living room, 1st floor family room - all with soaring ceilings & skylights. Off of the

  Dawn D'Auria Coldwell Banker Realty

  80 Jill Ln, Cheshire, CT 06410
• 

  Est $188,687 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  484 Oak Ave Unit 53, Cheshire, CT 06410

  484 Oak Ave Unit 53, Cheshire, CT 06410
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  /14

  $529,999

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

  4 Soderman Way Unit 4, Cheshire, CT 06410

  Motivated Seller! Skip the wait on new construction and step into this upgraded end-unit townhome at The Reserve at Stonebridge Crossing. Featuring 2 bedrooms plus a flexible room with elegant French doors-perfect as a home office, guest space, or third bedroom. Inside you'll find GE Cafe appliances, upgraded flooring, trim, and premium hardware throughout. One of the few homes in the community

  

  Khaliq Brown

  CLMA Realty

  (203) 439-4822

  4 Soderman Way Unit 4, Cheshire, CT 06410
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  /22

  $2,650 per month

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft
  • Townhouse for Rent

  52 Currier Way, Cheshire, CT 06410

  Step into comfort and convenience with this spacious townhouse condo featuring an inviting open-concept first floor, perfect for entertaining or relaxing by the cozy chimney in the living room, which also opens onto a private deck-ideal for morning coffee or evening gatherings. Upstairs, you'll find two generously sized bedrooms and a full bath, offering plenty of room and comfort. The large

  

  Alex Rodrigues

  RE/MAX RISE

  (203) 751-1426

  52 Currier Way, Cheshire, CT 06410
• 

  $405,000 Sold Sep 17, 2025

  • 1,282 Sq Ft
  • $316/SF
  • 32 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1958

  125 Curve Hill Rd, Cheshire, CT 06410

  Charming 3-Bedroom Ranch with Screened-In sunroom in a wonderful Neighborhood. Welcome to this warm and inviting 3-bedroom, 1.5-bath ranch-style home offering over 1,200 square feet of comfortable living space. Nestled in a quiet, mature neighborhood, this property is full of charm and practical features that make it a perfect place to come home to! This home includes a 1-car garage and a full

  Heather Cretella Calcagni Real Estate

  125 Curve Hill Rd, Cheshire, CT 06410
• 

  Est $791,890 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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  /34

  $525,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,330 Sq Ft

  1013 Wallingford Rd, Cheshire, CT 06410

  Experience Tranquil Rural Living in Your Multi-Generational Dream Home! This stunning property offers a blend of modern amenities and serene rural living, perfect for households of all sizes. Step into a cozy sunken living room, featuring elegant French doors that open to a spacious patio, ideal for indoor-outdoor entertaining. Enjoy cooking in a sleek, modern kitchen equipped with quality

  

  Mark Mnich

  Coldwell Banker Realty

  (475) 281-3540

  1013 Wallingford Rd, Cheshire, CT 06410
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  /2

  $1,078 - $2,495 per month

  Highland Farms

  1 - 2 Beds

  1728 Highland Ave, Cheshire, CT 06410

  1728 Highland Ave, Cheshire, CT 06410
• 

  $450,000 Sold Sep 16, 2025

  • 1,706 Sq Ft
  • $264/SF
  • 27 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1956

  136 Crescent Cir, Cheshire, CT 06410

  Welcome Home! This beautifully updated 3 bedroom, 1.5 bath home is situated on a prime corner lot in a quiet, desirable Cheshire neighborhood. Just a short walk to top-rated schools, this location is ideal for those seeking community, convenience, and charm. You'll love strolling the sidewalk-lined streets and coming home to a property that blends timeless character with thoughtful modern

  Mela Veltri Case KW Legacy Partners

  136 Crescent Cir, Cheshire, CT 06410
• 

  Est $835,743 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,488 Sq Ft

  125 N Timber Ln, Cheshire, CT 06410

  125 N Timber Ln, Cheshire, CT 06410
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  /24

  $449,500

  • 3 Beds
  • 2 Baths
  • 1,985 Sq Ft

  1715 Musso View Ave, Cheshire, CT 06410

  Welcome home to this gorgeous ranch-style gem in desirable Cheshire! Nestled on a beautifully landscaped 0.64-acre lot, this 3-bedroom, 2-bath home offers 1,540 sq ft on the main level and an additional 445 finished sq in the basement, ideal for versatile living. Step into a spacious living room with a cozy fireplace and gleaming hardwood floors that extend throughout the main level, including

  

  Zachary Nichols

  West View Properties, LLC

  (203) 872-9531

  1715 Musso View Ave, Cheshire, CT 06410
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  /11

  $3,150 per month

  • 2 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Apartment for Rent

  217 Old Towne Rd, Cheshire, CT 06410

  Welcome to Old Towne Commons - Enjoy easy living in this centrally located complex withing walking distace from coffee shops, cafes, local favorites, shopping & more. Located on the second floor, this unit features two bedrooms with the option for a third or a home office/study, along with two full bathrooms. There is hardwood flooring throughout the spacious living areas and bedrooms, central

  Ian Mackie Berkshire Hathaway NE Prop.

  217 Old Towne Rd, Cheshire, CT 06410
• 

  $357,000 Sold Sep 16, 2025

  • 1,450 Sq Ft
  • $246/SF
  • 37 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1998

  67 Southwick Ct Unit 67, Cheshire, CT 06410

  Maintenance-Free Living in the Heart of Cheshire! Welcome to this beautifully maintained RARELY AVAILABLE Manor House end-unit condo in the sought-after Southwick 55+ community, where comfort, convenience, & serenity come together seamlessly. Perfectly located just minutes from shopping, dining, medical facilities, and more, this light-filled home offers an exceptional lifestyle w

  Mela Veltri Case KW Legacy Partners

  67 Southwick Ct Unit 67, Cheshire, CT 06410
• 

  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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  /33

  $469,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  403 Juniper Ln, Cheshire, CT 06410

  Highest and Best Tuesday 8/19 12pm. This well-maintained home is situated on a lovely 1/2 acre lot surrounded by beautiful perennial garden beds. Minutes to the center of town, this 3-bedroom, 2-bath home has room for everyone. Enter into the large, sun-filled living room with hardwood floors, a wood-burning fireplace, and a new 9'x4' picture window. Open to the dining room, this makes for easy

  

  Kathleen Maloney

  Coldwell Banker Realty

  (203) 349-6311

  403 Juniper Ln, Cheshire, CT 06410
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  /35

  $2,760 - $2,900 per month

  Maplecroft Village

  2 Beds

  64 E Mitchell Ave, Cheshire, CT 06410

  Nestled in a prime, central location in the heart of Cheshire, these apartments are crafted to offer a harmonious blend of style and functionality. From the moment you enter, you'll be greeted by spacious layouts adorned with upscale finishes and contemporary touches.The open-concept living areas provide the perfect backdrop for entertaining guests or unwinding after a long day. Each

  64 E Mitchell Ave, Cheshire, CT 06410
• 

  $670,000 Sold Sep 15, 2025

  • 3,020 Sq Ft
  • $222/SF
  • 45 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1989

  12 N Pond Rd, Cheshire, CT 06410

  Looking for a spacious colonial in the desirable Pondside subdivision? Here is your opportunity! This Colonial offers flexible living space, classic style and room to grow. The open-concept dining room flows seamlessly into a comfortable living area with wood burning fireplace, while the front-facing office and inviting foyer offer a warm welcome and a versatile work-from-home arrangement. The

  Heidi Weed Lamacchia Realty

  12 N Pond Rd, Cheshire, CT 06410
• 

  Est $835,042 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
• 

  /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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  /40

  $3,100 per month

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • House for Rent

  316 Jinny Hill Rd, Cheshire, CT 06410

  Discover your dream home in the heart of Cheshire! This stunning 3-bedroom, 2-bathroom single-family ranch sits on a private 0.92-acre sloping lot, offering ultimate seclusion just 3 minutes from South Main Street's shops, dining, and daily essentials. Nestled in privacy, it's the perfect blend of tranquility and convenience-enjoy peaceful BBQs on your expansive deck without sacrificing easy

  George Daniolos eRealty Advisors, Inc.

  316 Jinny Hill Rd, Cheshire, CT 06410
• 

  $780,000 Sold Sep 12, 2025

  • 4,059 Sq Ft
  • $192/SF
  • 55 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1956

  430 Cook Hill Rd, Cheshire, CT 06410

  Welcome to 430 Cook Hill Rd - a private retreat in the heart of Cheshire! This stunning home offers over 4,000 sq ft of finished living space on a 3.64-acre open and level lot, just minutes from top-rated schools, shopping, restaurants, and town amenities. The property is expansive with open land ready for entertaining, gardening, or a future pool. Step inside to discover a thoughtful layout,

  Kyle Howles Better Living Realty, LLC

  430 Cook Hill Rd, Cheshire, CT 06410
• 

  Est $1,070,970 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,404 Sq Ft

  50 Kensington Ct, Cheshire, CT 06410

  50 Kensington Ct, Cheshire, CT 06410
• 

  /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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  $2,100 - $3,625 per month

  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
• 

  $175,000 Sold Sep 12, 2025

  • 810 Sq Ft
  • $216/SF
  • 76 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1964

  1105 Waterbury Rd Unit 1B, Cheshire, CT 06410

  Located in the desirable town of Cheshire, this updated first-floor 1-bedroom ranch-style condo offers the perfect mix of style, comfort, and convenience. Inside, you'll find easy-care flooring, fresh paint, and a private deck-making it truly move-in ready. Heat and hot water are included in the HOA fee, adding extra value and ease to your monthly budget. A major highlight of this property is

  Amber Fischer Lewis Real Estate Services

  1105 Waterbury Rd Unit 1B, Cheshire, CT 06410
• 

  Est $667,207 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,764 Sq Ft

  28 Alison Ave, Wallingford, CT 06492

  28 Alison Ave, Wallingford, CT 06492
• 

  

  /3

  $890,000 New Construction

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

  1517A 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

  (203) 590-8495

  1517A Blackberry Place, Cheshire, CT 06410
• 

  

  /23

  $2,395 per month

  • 2 Beds
  • 1 Bath
  • 1,316 Sq Ft
  • House for Rent

  53 Horton Ave Unit 2, Cheshire, CT 06410

  Spacious rental in the center of town! Two family house. The main level in this unit offers a functional kitchen, dining room, living room, and family room, providing plenty of space to spread out. Upstairs you'll find 2 bedrooms, an office, and a full bath. Features include wall-to-wall carpet, large windows that let in natural light, washer/dryer hookup in the basement, and both a covered front

  The Sally Bowman Team Berkshire Hathaway NE Prop.

  53 Horton Ave Unit 2, Cheshire, CT 06410
• 

  $315,000 Sold Sep 09, 2025

  • 1,052 Sq Ft
  • $299/SF
  • 10 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  11 Fairway Dr, Cheshire, CT 06410

  Welcome to this well-maintained 2-bedroom, 1.5-bath end unit condo offering comfortable living in a desirable community with great amenities. The main level features a spacious living room, a functional eat-in kitchen with new stainless steel appliances, quartz countertops, and a convenient half bath. Upstairs you'll find two generously sized bedrooms and a full bath. Enjoy outdoor space on your

  Rosalia Casorla Premier Re Group LLC

  11 Fairway Dr, Cheshire, CT 06410
• 

  Est $545,044 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  1435 Tuttle Ave, Wallingford, CT 06492

  1435 Tuttle Ave, Wallingford, CT 06492
• 

  

  /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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  /35

  $2,266 - $2,800 per month

  Lakeside of Cheshire

  1 - 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
• 

  $382,000 Sold Sep 08, 2025

  • 2,227 Sq Ft
  • $172/SF
  • 102 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1954

  68 Woodland Dr, Cheshire, CT 06410

  Charming Oversized Cape in Idyllic New England Setting! Discover the potential of this well-built, expansive Cape Cod home nestled in a picturesque, quintessential New England neighborhood on a non-through street. This super charming residence offers generously sized rooms throughout, perfect for comfortable living and entertaining. The main level features a spacious living room with a cozy

  Michael DelGreco New England Realty Assoc LLC

  68 Woodland Dr, Cheshire, CT 06410
• 

  Est $525,216 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,528 Sq Ft

  16 Wadsworth Ln, Wallingford, CT 06492

  16 Wadsworth Ln, Wallingford, CT 06492
• 

  

  /3

  $950,000 New Construction

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

  1600 S Main St Unit BFraser Model, Cheshire, CT 06410

  Wonderful opportunity to build in the south end of Cheshire. Consider 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

  

  Kathleen Maloney

  Coldwell Banker Realty

  (475) 445-1113

  1600 S Main St Unit BFraser Model, Cheshire, CT 06410
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  /14

  $2,900 per month

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

  64 E Mitchell Ave Unit 7, 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 7, Cheshire, CT 06410
• 

  $528,000 Sold Sep 05, 2025

  • 1,248 Sq Ft
  • $423/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  20 Club Ln, Cheshire, CT 06410

  HIGHEST & BEST DUE BY WEDNESDAY, JULY 23RD AT 9:00AM. Welcome to this beautifully updated and impeccably maintained 3-bedroom, 2 full bath Ranch style home, perfectly situated on a desirable corner lot in a lovely neighborhood. The bright and airy interior features an updated kitchen with stainless steel appliances, 2 recently renovated bathrooms with custom tilework and stunning hardwood floors

  James Bulger Calcagni Real Estate

  20 Club Ln, Cheshire, CT 06410
• 

  Est $468,798 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,758 Sq Ft

  78 Woodland Rd, Guilford, CT 06437

  78 Woodland Rd, Guilford, CT 06437

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