Cheshire, CT Homes

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  /37

  $999,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 5,081 Sq Ft

  435 Maple Ave, Cheshire, CT 06410

  Your Dream Home in the Heart of Cheshire! Welcome to this stunning 5-bedroom/potential 7 bedroom, 5.5-bath Colonial located in the center of Cheshire. With over 5,000 sq. ft. of living space and set on more than an acre, this masterpiece offers the perfect blend of luxury, comfort, and convenience. The seller has spared no detail in the design and upkeep of this exceptional home. Main Floor

  Amy LaMaster The Bella Group, LLC

  435 Maple Ave, Cheshire, CT 06410
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  /18

  $2,000 per month

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

  1565 Byam Rd, Cheshire, CT 06410

  Come view this true oasis of a home right in Cheshire. This unit is the perfect mix of quaint, cozy, and roomy. Offering a main floor master bedroom, second floor full loft that can be used for office, storage, gym etc. 1 bathroom, a living space, kitchen, and in-unit laundry. The grounds are well kept and you have access to a beautiful backyard where you can make it your own! The owners have

  Alaina Capasso Advise Realty Services

  1565 Byam Rd, Cheshire, CT 06410
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  $426,500 Sold Jan 13, 2026

  112 Laurel Terrace, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1957

  Last Sold Summary

  • 2% Above List Price
  • $304/SF
  • 14 Days On Market

  Current Estimated Value $426,551

  Last Listing Agent Douglas Ledewitz Pulse Realty LLC

  112 Laurel Terrace, Cheshire, CT 06410
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  Est $743,936 Not Listed For Sale

  37 Warren St, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,492 Sq Ft
  • Built 2016

  37 Warren St, Cheshire, CT 06410

  Last Sold Summary

  • $299/SF
  • 7 Days On Market

  Last Sold Price $745,000

  Last Listing Agent Alex LaRosa Coldwell Banker
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  /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
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  /17

  $2,900 per month

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

  64 E Mitchell Ave Unit 49, Cheshire, CT 06410

  Now through April 30th - Special promotion on new 12-month leases only: New tenants get the choice of ONE of the following: A) Free storage unit for a year (any size, subject to availability), B) $1,000 flexible spending credit immediately applied to the tenant account (use toward rent, storage, pet fees at whatever time period tenant wants to use it during the lease - but does not apply to

  Brette Stern Calcagni Real Estate

  64 E Mitchell Ave Unit 49, Cheshire, CT 06410
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  $670,000 Sold Dec 29, 2025

  20 Bramble Way, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 3,591 Sq Ft
  • Built 2006

  Last Sold Summary

  • $187/SF
  • 6 Days On Market

  Current Estimated Value $674,636

  Last Listing Agent Karen Brimberg William Raveis Real Estate

  20 Bramble Way, Cheshire, CT 06410
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  Not Listed For Sale

  23 Wadsworth Ln Unit 23, Wallingford, CT 06492

  • 2 Beds
  • 2 Baths
  • 2,035 Sq Ft
  • Built 2006

  23 Wadsworth Ln Unit 23, Wallingford, CT 06492

  Last Sold Summary

  • $229/SF
  • 3 Days On Market

  Last Sold Price $465,000

  Last Listing Agent Roseann Ruocco HomeRun Realty LLC
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  /38

  $899,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 4,356 Sq Ft

  25 Surrey Dr, Cheshire, CT 06410

  The spectacular awaits in Cheshire - welcome to 25 Surrey Drive! This one-of-a-kind bespoke architectural masterpiece perfectly blends cosmopolitan design with a tranquil brook-side setting, creating a truly livable work of art. Inside, the dramatic, sculptural staircase immediately commands your attention, spanning 3 levels of striking proportions & walls of glass. The main level features

  Tommy Connors Redfin Corporation

  25 Surrey Dr, Cheshire, CT 06410
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  /17

  $2,800 per month

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

  64 E Mitchell Ave Unit 46, Cheshire, CT 06410

  Now through April 30th - Special promotion on new 12-month leases only: New tenants get the choice of ONE of the following: A) Free storage unit for a year (any size, subject to availability), B) $1,000 flexible spending credit immediately applied to the tenant account (use toward rent, storage, pet fees at whatever time period tenant wants to use it during the lease - but does not apply to

  Brette Stern Calcagni Real Estate

  64 E Mitchell Ave Unit 46, Cheshire, CT 06410
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  $490,000 Sold Jul 07, 2025

  18 Hawthorne Dr, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • Built 1955

  Last Sold Summary

  • 17% Above List Price
  • $269/SF
  • 39 Days On Market

  Current Estimated Value $485,827

  Last Listing Agent Sarah Kolman The Heritage Group, LLC

  18 Hawthorne Dr, Cheshire, CT 06410
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  Est $770,432 Not Listed For Sale

  752 Ives Row, Cheshire, CT 06410

  • 5 Beds
  • 3.5 Baths
  • 3,265 Sq Ft
  • Built 2009

  752 Ives Row, Cheshire, CT 06410

  Last Sold Summary

  • 6% Above List Price
  • $224/SF
  • 48 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.
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  /37

  $974,263 Open Sat 12PM - 3PM

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

  31 Soderman Way Unit 31, Cheshire, CT 06410

  The Carriage Home floor plan combines architectural elegance with EG Home's high-performance building standards. Constructed with 2 X 6 exterior walls, double-pane double hung windows, and a layered insulation system of spray foam, batting, and blown-in insulation, each home is built for quiet comfort and lasting energy efficiency. A cold-climate heat pump and Energy Recovery Ventilator (ERV)

  Jason Helton EG Group Realty LLC

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

  $2,800 per month

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

  281 Spring St, Cheshire, CT 06410

  Discover comfort and convenience in this beautifully renovated rental located in the desirable town of Cheshire. This brand new one bedroom, one bathroom residence features a modern galley kitchen equipped with sleek stainless steel appliances, offering both style and functionality. Enjoy a private entrance for added peace and privacy, and step outside to a spacious backyard perfect for

  Matthew Olander KW Legacy Partners

  281 Spring St, Cheshire, CT 06410
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  $446,000 Sold Jan 06, 2026

  634 Cornwall Ave, Cheshire, CT 06410

  • 4 Beds
  • 3 Baths
  • 1,456 Sq Ft
  • Built 1952

  Last Sold Summary

  • 3% Below List Price
  • $306/SF
  • 83 Days On Market

  Current Estimated Value $449,335

  Last Listing Agent Owen Evans William Raveis Real Estate

  634 Cornwall Ave, Cheshire, CT 06410
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  Est $794,016 Not Listed For Sale

  18 Alyssa Dr, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 2,677 Sq Ft
  • Built 2008

  18 Alyssa Dr, Cheshire, CT 06410

  Last Sold Summary

  • 4% Above List Price
  • $284/SF
  • 38 Days On Market

  Last Sold Price $760,000

  Last Listing Agent Chris Jahn Showcase Realty, Inc.
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  /11

  $899,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,792 Sq Ft

  140 Willow Rear Lot St, Cheshire, CT 06410

  Welcome to the opportunity to build your dream home in a highly desirable location. Nestled on a secluded rear lot that is just under an acre, this thoughtfully designed 4-bedroom, 2.5-bath Colonial will offer 2,792 square feet of beautifully crafted living space with the perfect blend of privacy and modern comfort. Designed with today's lifestyle in mind, the open concept layout will seamlessly

  Michael Dziedzic Precision Realty LLC

  140 Willow Rear Lot St, Cheshire, CT 06410
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  /17

  $2,900 per month

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

  64 E Mitchell Ave Unit 27, Cheshire, CT 06410

  Now through April 30th - Special promotion on new 12-month leases only: New tenants get the choice of ONE of the following: A) Free storage unit for a year (any size, subject to availability), B) $1,000 flexible spending credit immediately applied to the tenant account (use toward rent, storage, pet fees at whatever time period tenant wants to use it during the lease - but does not apply to

  Nancy Lydell Calcagni Real Estate

  64 E Mitchell Ave Unit 27, Cheshire, CT 06410
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  $767,500 Sold Dec 09, 2025

  31 Nathan Hale Ct, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 3,427 Sq Ft
  • Built 1998

  Last Sold Summary

  • 7% Above List Price
  • $224/SF
  • 17 Days On Market

  Current Estimated Value $750,417

  Last Listing Agent Dorothy Karska-Piech Calcagni Real Estate

  31 Nathan Hale Ct, Cheshire, CT 06410
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  Est $1,015,866 Not Listed For Sale

  50 Kensington Ct, Cheshire, CT 06410

  • 5 Beds
  • 4.5 Baths
  • 5,404 Sq Ft
  • Built 2008

  50 Kensington Ct, Cheshire, CT 06410

  Last Sold Summary

  • 13% Above List Price
  • $167/SF
  • 0 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Nicole Staples Coldwell Banker Milford
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  /37

  $779,900 Pending

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

  46 Soderman Way Unit 46, Cheshire, CT 06410

  Welcome to this stunning, practically brand-new 2,975 sq. ft. condo, built in 2024 and thoughtfully designed for modern living. Over $150,000 of upgrades! Immaculate and move-in ready, this open-concept home offers the perfect blend of style, comfort, and convenience in a fantastic location. The spacious first-floor primary suite features an elegant tray ceiling, a generous walk-in closet, and a

  Stanley Martone Lamacchia Realty

  46 Soderman Way Unit 46, Cheshire, CT 06410
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  $350,000 Sold Apr 21, 2025

  91 Southwick Ct, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Above List Price
  • $345/SF
  • 3 Days On Market

  Current Estimated Value $344,902

  Last Listing Agent Robin Thurston Coldwell Banker Realty

  91 Southwick Ct, Cheshire, CT 06410
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  Est $681,856 Not Listed For Sale

  28 Alison Ave, Wallingford, CT 06492

  • 3 Beds
  • 4 Baths
  • 2,764 Sq Ft
  • Built 1986

  28 Alison Ave, Wallingford, CT 06492

  Last Sold Summary

  • 22% Above List Price
  • $203/SF
  • 3 Days On Market

  Last Sold Price $560,000

  Last Listing Agent Roberta Havlick William Raveis Real Estate
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  /39

  $849,000

  • 4 Beds
  • 2.5 Baths
  • 2,904 Sq Ft

  131 Paulney Rd, Cheshire, CT 06410

  This classic 1927 brick home in the perfect Cheshire location stuns with details and design that are both elegant and practical. This nearly 3000 SQ FT house with 4 bedrooms and 2.5 baths is sited on just about an acre lot on a quiet and friendly cul-de-sac, just a short walk to the town center, library, and great restaurants and coffee shops. This home will delight year round as you enjoy your

  Jack Hill Seabury Hill REALTORS

  131 Paulney Rd, Cheshire, CT 06410
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  $455,000 Sold Sep 30, 2025

  161 Laurel Terrace, Cheshire, CT 06410

  • 3 Beds
  • 3 Baths
  • 2,808 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 34 Days On Market

  Current Estimated Value $462,954

  Last Listing Agent Anshuman Singh LPT Realty - IConn Team

  161 Laurel Terrace, Cheshire, CT 06410
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  Est $523,740 Not Listed For Sale

  1435 Tuttle Ave, Wallingford, CT 06492

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1975

  1435 Tuttle Ave, Wallingford, CT 06492

  Last Sold Summary

  • 10% Above List Price
  • $170/SF
  • 77 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Jessica Boswell LPT Realty
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  /39

  $799,900 Open Sun 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 3,984 Sq Ft

  773 Devonwood Dr, Cheshire, CT 06410

  Pride of ownership shines in this beautifully maintained Colonial. A spacious foyer with hardwood floors welcomes you into a thoughtfully designed eat-in kitchen featuring a cherry wood island with leathered granite, abundant cabinetry, stainless steel appliances, and under-cabinet lighting. The sun-filled family room offers vaulted ceilings and a brick wood-burning fireplace with a rustic barn

  Daniela Volo Calcagni Real Estate

  773 Devonwood Dr, Cheshire, CT 06410
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  $944,660 Sold Dec 05, 2025

  1611 Blackberry Place, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,459 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Above List Price
  • $384/SF
  • 10 Days On Market

  Last Listing Agent Kathleen Maloney Coldwell Banker Realty

  1611 Blackberry Place, Cheshire, CT 06410
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  Est $485,415 Not Listed For Sale

  16 Wadsworth Ln, Wallingford, CT 06492

  • 2 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 2007

  16 Wadsworth Ln, Wallingford, CT 06492

  Last Sold Summary

  • 6% Above List Price
  • $299/SF
  • 3 Days On Market

  Last Sold Price $456,500

  Last Listing Agent Emily Lovejoy William Raveis Real Estate
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  /40

  $699,900 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,144 Sq Ft

  1609 Sturbridge Ct, Cheshire, CT 06410

  Some homes just feel right the moment you walk in - and this is one of them. Nestled on a quiet cul-de-sac in south Cheshire, this beautiful colonial offers the perfect blend of classic charm, thoughtful updates, and everyday comfort. Sun-filled living spaces, hardwood floors throughout, and a flowing layout create an inviting setting for both daily living and entertaining. The updated eat-in

  Cheri Paulsen Advise Realty Services

  1609 Sturbridge Ct, Cheshire, CT 06410
• 

  $555,000 Sold Jan 05, 2026

  160 Willow St, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $318/SF
  • 69 Days On Market

  Current Estimated Value $545,846

  Last Listing Agent Melissa Kearns Great Estates, CT

  160 Willow St, Cheshire, CT 06410
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  Est $468,276 Not Listed For Sale

  78 Woodland Rd, Guilford, CT 06437

  • 3 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • Built 1959

  78 Woodland Rd, Guilford, CT 06437

  Last Sold Summary

  • 10% Above List Price
  • $242/SF
  • 44 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Rose Ciardiello William Raveis Real Estate
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  /14

  $1,120,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,731 Sq Ft

  6 Melrose Dr Unit Lot 10, Cheshire, CT 06410

  Have you been searching for a new construction home that will provide you with one level living?? 6 Melrose Drive is the perfect solution to your search! This To Be Built Ranch plan is a spacious 2,731 sq ft of living space. It provides wonderful outdoor living spaces starting with a covered front porch welcoming you and your guests through the front entry and a screened porch at the back of the

  Dori Degennaro William Raveis Real Estate

  6 Melrose Dr Unit Lot 10, Cheshire, CT 06410
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  $683,000 Sold Feb 03, 2026

  462 Castle Glenn, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 3,290 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Below List Price
  • $208/SF
  • 49 Days On Market

  Current Estimated Value $687,473

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

  462 Castle Glenn, Cheshire, CT 06410
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  Est $660,188 Not Listed For Sale

  108 Old Farms Rd, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 3,168 Sq Ft
  • Built 1995

  108 Old Farms Rd, Cheshire, CT 06410

  Last Sold Summary

  • 10% Above List Price
  • $189/SF
  • 65 Days On Market

  Last Sold Price $599,900

  Last Listing Agent Myla Chadwick Real Broker CT, LLC
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  /40

  $769,900 Under Contract

  • 2 Beds
  • 4 Baths
  • 2,948 Sq Ft

  151 Victoria Dr, Cheshire, CT 06410

  This exceptional home, in the multi-award-winning 55(+) community of Castle Heights, blends striking architecture, sophisticated design & effortless elegance throughout. A charming front porch welcomes you into a dramatic two-story foyer & an elegant living room adorned with decorative columns, soaring cathedral ceilings & a gas fireplace - perfect for grand entertaining or intimate gatherings.

  Dorothy Karska-Piech Calcagni Real Estate

  151 Victoria Dr, Cheshire, CT 06410
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  $410,000 Sold May 09, 2025

  102 Flagler Ave, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft
  • Built 1955

  Last Sold Summary

  • $221/SF
  • 64 Days On Market

  Current Estimated Value $429,346

  Last Listing Agent Steven Vastola KW Legacy Partners

  102 Flagler Ave, Cheshire, CT 06410
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  Est $410,337 Not Listed For Sale

  1751 S Main St, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 2,002 Sq Ft
  • Built 1937

  1751 S Main St, Cheshire, CT 06410

  Last Sold Summary

  • 35% Above List Price
  • $152/SF
  • 56 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Amber Bova William Raveis Real Estate
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  /3

  $904,200 Pending

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

  209 Memory Ln, 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

  Phil Giampietro Coldwell Banker Realty

  209 Memory Ln, Cheshire, CT 06410
• 

  $285,000 Sold Sep 04, 2025

  52 Currier Way, Cheshire, CT 06410

  • 2 Beds
  • 1.5 Baths
  • 1,408 Sq Ft
  • Built 1980

  Last Sold Summary

  • 14% Above List Price
  • $202/SF
  • 33 Days On Market

  Current Estimated Value $282,741

  Last Listing Agent Beverly Welch Calcagni Real Estate

  52 Currier Way, Cheshire, CT 06410

Showing Results 81 - 120, Page 3 of 18