11,916

Cheshire, CT Homes

Section Image
  • 38 Mountain Rd, Cheshire, CT 06410
    38 Mountain Rd, Cheshire, CT 06410
    38 Mountain Rd, Cheshire, CT 06410
    /35

    $439,900

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,704 Sq Ft

    38 Mountain Rd, Cheshire, CT 06410

    Nicely maintained 4-bedroom, 2 full bath split-level home offering 1,488 sq. ft. of living space plus an additional 216 sq. ft. in the finished lower level with walk-out access. This home features hardwood flooring and a bright, inviting living room with a large bow window and a cozy brick-faced raised hearth fireplace with wood-burning insert. The spacious kitchen offers white cabinetry,

    Katie Smith Berkshire Hathaway NE Prop.

    38 Mountain Rd, Cheshire, CT 06410
  • 81 Shea Cir, Cheshire, CT 06410

    $758,572

    Sold Jan 28, 2026

    81 Shea Cir, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,975 Sq Ft
    • Built 2026

    Last Sold Summary

    • 13% Above List Price
    • $255/SF
    • 306 Days On Market

    Last Listing Agent Felicity LeClair EG Group Realty LLC

    81 Shea Cir, Cheshire, CT 06410
  • 140 Willow St, Cheshire, CT 06410
    140 Willow St, Cheshire, CT 06410
    140 Willow St, Cheshire, CT 06410
    /29

    $469,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,426 Sq Ft

    140 Willow St, Cheshire, CT 06410

    Come see this rare 2 family find in the heart of Cheshire. Both units have been fully updated with new kitchens, granite countertops, stainless steel appliances, updated baths, plumbing, electrical, and HVAC. Schedule your showing today

    Michael Dziedzic Precision Realty LLC

    140 Willow St, Cheshire, CT 06410
  • 40 Kensington Ct, Cheshire, CT 06410

    $900,000

    Sold Jun 27, 2025

    40 Kensington Ct, Cheshire, CT 06410

    • 4 Beds
    • 3.5 Baths
    • 3,459 Sq Ft
    • Built 2008

    Last Sold Summary

    • $260/SF
    • 2 Days On Market

    Current Estimated Value $945,692

    Last Listing Agent Elizabeth Urbanski Coldwell Banker Realty

    40 Kensington Ct, Cheshire, CT 06410
  • 95 Higgins Rd, Cheshire, CT 06410
    95 Higgins Rd, Cheshire, CT 06410
    95 Higgins Rd, Cheshire, CT 06410
    /40

    $759,000

    • 5 Beds
    • 3.5 Baths
    • 3,301 Sq Ft

    95 Higgins Rd, Cheshire, CT 06410

    Welcome to this beautifully maintained 5 bedroom, 3.5-bath Colonial, perfectly situated on 1.25 picturesque acres with its own private pond, creating a peaceful and private retreat right in your backyard. Designed with both comfort and entertaining in mind, this spacious home features an open-concept floor plan, soaring 9-foot ceilings, and gleaming hardwood floors throughout. The heart of the

    Shari DiDomenico Berkshire Hathaway NE Prop.

    95 Higgins Rd, Cheshire, CT 06410
  • 11 Fairway Dr, Cheshire, CT 06410

    $315,000

    Sold Sep 09, 2025

    11 Fairway Dr, Cheshire, CT 06410

    • 2 Beds
    • 1.5 Baths
    • 1,052 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $299/SF
    • 10 Days On Market

    Current Estimated Value $307,350

    Last Listing Agent Rosalia Casorla Premier Re Group LLC

    11 Fairway Dr, Cheshire, CT 06410
  • 886 Coleman Rd, Cheshire, CT 06410
    886 Coleman Rd, Cheshire, CT 06410
    /2

    $360,000

    $15K PRICE DROP
    • Land
    • 1.85 Acres
    • $194,595 per Acre

    886 Coleman Rd, Cheshire, CT 06410

    886 Coleman Road is a 1.85 acre mostly level and gently wooded parcel with mature trees. It offers natural beauty abundant with wildlife. Located in the South end of Cheshire- it is known as Lot 3 of The Carol Ridge Subdivision. The spot offers a respite from the day- yet it is conveniently located within an easy commute from New Haven, Quinnipiac University and Yale. This makes it well suited

    Donna Myjak CRS,SRES,SRS Berkshire Hathaway NE Prop.

    886 Coleman Rd, Cheshire, CT 06410
  • 7 Bayberry Rd, Cheshire, CT 06410

    $462,000

    Sold May 12, 2026

    7 Bayberry Rd, Cheshire, CT 06410

    • 3 Beds
    • 1.5 Baths
    • 1,341 Sq Ft
    • Built 1957

    Last Sold Summary

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

    Current Estimated Value $418,327

    Last Listing Agent Emily Viccaro Coldwell Banker Realty

    7 Bayberry Rd, Cheshire, CT 06410
  • 456 Castle Glenn, Cheshire, CT 06410
    456 Castle Glenn, Cheshire, CT 06410
    456 Castle Glenn, Cheshire, CT 06410
    /40

    $769,900

    $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,740 Sq Ft

    456 Castle Glenn, Cheshire, CT 06410

    Nestled in the desirable Castle Glenn community, this beautifully maintained detached home offers the ease of community living with the privacy of a single-family residence. Built in 1989, this home features 2,840 sq ft plus an additional 900 sq ft in the finished lower level. A standout feature is the first-floor primary suite, complete with walk-in closet and en-suite bath with jetted tub,

    The Sally Bowman Team Berkshire Hathaway NE Prop.

    456 Castle Glenn, Cheshire, CT 06410
  • 12 N Pond Rd, Cheshire, CT 06410

    $670,000

    Sold Sep 15, 2025

    12 N Pond Rd, Cheshire, CT 06410

    • 4 Beds
    • 3.5 Baths
    • 3,020 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $222/SF
    • 45 Days On Market

    Current Estimated Value $711,893

    Last Listing Agent Heidi Weed Lamacchia Realty

    12 N Pond Rd, Cheshire, CT 06410
  • 58 Old Towne Rd, Cheshire, CT 06410
    58 Old Towne Rd, Cheshire, CT 06410
    58 Old Towne Rd, Cheshire, CT 06410
    /38

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    58 Old Towne Rd, Cheshire, CT 06410

    Welcome to this spacious end-unit townhouse located in the heart of Cheshire, offering both privacy and convenience. The oversized living room opens directly to a private outdoor deck, creating the perfect space for relaxing or entertaining. The updated kitchen features a breakfast bar, upgraded vented range hood exhausting to the exterior, and hardwood flooring that continues through the main

    Dan Xu Vision Real Estate

    58 Old Towne Rd, Cheshire, CT 06410
  • 131 Merwin Cir, Cheshire, CT 06410

    $706,000

    Sold May 29, 2026

    131 Merwin Cir, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • Built 1959

    Last Sold Summary

    • 11% Above List Price
    • $310/SF
    • 27 Days On Market

    Current Estimated Value $633,977

    Last Listing Agent Stacey Deangelis Calcagni Real Estate

    131 Merwin Cir, Cheshire, CT 06410
  • 15 Philson Ct, Cheshire, CT 06410
    15 Philson Ct, Cheshire, CT 06410
    /2

    $385,000

    $15K PRICE DROP
    • Land
    • 2 Acres
    • $192,500 per Acre

    15 Philson Ct, Cheshire, CT 06410

    15 Philson Court is a 2 acre lightly wooded parcel- also known as Lot 5 of The Carol Ridge Subdivision- which is a quiet established cul de sac in the south end of Cheshire. This lot is highlighted on this picture-it is to the left-large rectangle shaped. The location is ideal for those who value convenience and ease of commuting to New Haven, Yale, QU, and Tweed Airport for quick weekend jaunts.

    Donna Myjak CRS,SRES,SRS Berkshire Hathaway NE Prop.

    15 Philson Ct, Cheshire, CT 06410
  • 1775 Orchard Hill Rd, Cheshire, CT 06410

    $420,000

    Sold Aug 25, 2025

    1775 Orchard Hill Rd, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,301 Sq Ft
    • Built 1940

    Last Sold Summary

    • 8% Above List Price
    • $323/SF
    • 36 Days On Market

    Current Estimated Value $416,706

    Last Listing Agent Jessica Danard Coldwell Banker Realty

    1775 Orchard Hill Rd, Cheshire, CT 06410
  • 15 Melrose Dr, Cheshire, CT 06410
    15 Melrose Dr, Cheshire, CT 06410
    /2

    $1,300,000

    New Construction Pending
    • 4 Beds
    • 5 Baths
    • 4,379 Sq Ft

    15 Melrose Dr, Cheshire, CT 06410

    Last lot at the Orchard View Subdivision! Currently under construction! At 3,579 square feet, there's a space for everyone! On the main level you'll find hardwood floors throughout and an open concept kitchen and family room. While all the ceilings on the main level are 9ft, the family room is open to the second floor creating an incredible airy and open feel. You'll also have a study/office to

    Dori Degennaro William Raveis Real Estate

    15 Melrose Dr, Cheshire, CT 06410
  • 19 Heath Ct, Cheshire, CT 06410

    $430,000

    Sold Jan 05, 2026

    19 Heath Ct, Cheshire, CT 06410

    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Built 1964

    Last Sold Summary

    • 1% Above List Price
    • $205/SF
    • 50 Days On Market

    Current Estimated Value $434,051

    Last Listing Agent Phil Giampietro Coldwell Banker Realty

    19 Heath Ct, Cheshire, CT 06410
  • 422 N Brooksvale Rd, Cheshire, CT 06410
    422 N Brooksvale Rd, Cheshire, CT 06410
    422 N Brooksvale Rd, Cheshire, CT 06410
    /20

    $225,000

    Pending
    • 3 Beds
    • 1,562 Sq Ft

    422 N Brooksvale Rd, Cheshire, CT 06410

    Investors take notice. House needs total renovation.Being sold as is where is including contents. Cash Offers Only Highest and best offers by 4:00pm on Monday 3/30/2026

    Phil Giampietro Coldwell Banker Realty

    422 N Brooksvale Rd, Cheshire, CT 06410
  • 202 Mountain Rd, Cheshire, CT 06410

    $457,000

    Sold Jul 18, 2025

    202 Mountain Rd, Cheshire, CT 06410

    • 3 Beds
    • 1.5 Baths
    • 1,356 Sq Ft
    • Built 1948

    Last Sold Summary

    • 4% Above List Price
    • $337/SF
    • 42 Days On Market

    Current Estimated Value $458,902

    Last Listing Agent Karen Klein Coldwell Banker Realty

    202 Mountain Rd, Cheshire, CT 06410
  • 21 Fawn Dr, Cheshire, CT 06410
    21 Fawn Dr, Cheshire, CT 06410
    21 Fawn Dr, Cheshire, CT 06410
    /29

    $375,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,404 Sq Ft

    21 Fawn Dr, Cheshire, CT 06410

    Highest and Best due by 3pm May 23,2026. Great opportunity to own this 3 Bedroom, 1 Bath Ranch style home conveniently located in South Cheshire! The spacious Living Room is warm and inviting with a wood burning brick fireplace and slider that leads to the backyard deck. Kitchen has wood cabinetry and tile flooring with room for family dinners at your kitchen table. Easy access to the light and

    Phil Giampietro Coldwell Banker Realty

    21 Fawn Dr, Cheshire, CT 06410
  • 747 W Main St Unit F, Cheshire, CT 06410

    $357,500

    Sold Aug 29, 2025

    747 W Main St Unit F, Cheshire, CT 06410

    • 2 Beds
    • 1.5 Baths
    • 1,908 Sq Ft
    • Built 1983

    Last Sold Summary

    • 10% Above List Price
    • $187/SF
    • 34 Days On Market

    Last Listing Agent Robin Thurston Coldwell Banker Realty

    747 W Main St Unit F, Cheshire, CT 06410
  • 305 Richmond Glen Dr, Cheshire, CT 06410
    305 Richmond Glen Dr, Cheshire, CT 06410
    305 Richmond Glen Dr, Cheshire, CT 06410
    /40

    $839,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,625 Sq Ft

    305 Richmond Glen Dr, Cheshire, CT 06410

    Welcome to Richmond Glen, a sought-after 55+ community offering comfort, style and easy living. This stunning free-standing condo features an expansive open floor plan designed for both everyday living and entertaining. A tastefully decorated formal dining room perfectly adaptable as a den, adds flexibility to the space while a convenient butler's pantry enhances functionality. The gourmet

    Beverly Welch Calcagni Real Estate

    305 Richmond Glen Dr, Cheshire, CT 06410
  • 3 Cedar Ln, Cheshire, CT 06410

    $350,000

    Sold Oct 20, 2025

    3 Cedar Ln, Cheshire, CT 06410

    • 3 Beds
    • 1.5 Baths
    • 1,512 Sq Ft
    • Built 1947

    Last Sold Summary

    • 18% Below List Price
    • $231/SF
    • 174 Days On Market

    Current Estimated Value $393,631

    Last Listing Agent Colleen Caron Barrieau Realty Signature Prop

    3 Cedar Ln, Cheshire, CT 06410
  • 115 Thorn Hollow Rd, Cheshire, CT 06410
    115 Thorn Hollow Rd, Cheshire, CT 06410
    115 Thorn Hollow Rd, Cheshire, CT 06410
    /31

    $599,900

    Under Contract
    • 2 Beds
    • 2 Baths
    • 2,077 Sq Ft

    115 Thorn Hollow Rd, Cheshire, CT 06410

    Desirable Redbridge model in Cheshire Crossing set on a premium lot with wooded rear exposure! Beautifully maintained home offers an open-concept layout with vaulted ceilings, HW flooring, recessed lighting, and abundant natural light. The eat-in kitchen features granite countertops, stainless steel appliances including double wall ovens, cooktop, refrigerator, tile backsplash, and slider to Trex

    Stacey Deangelis Calcagni Real Estate

    115 Thorn Hollow Rd, Cheshire, CT 06410
  • 295 Hotchkiss Ridge, Cheshire, CT 06410

    $660,000

    Sold Nov 07, 2025

    295 Hotchkiss Ridge, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,848 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $232/SF
    • 102 Days On Market

    Current Estimated Value $677,039

    Last Listing Agent Carly Kirsch Lamacchia Realty

    295 Hotchkiss Ridge, Cheshire, CT 06410
  • 28 Tamarack Ct Unit 28, Prospect, CT 06712
    28 Tamarack Ct Unit 28, Prospect, CT 06712
    28 Tamarack Ct Unit 28, Prospect, CT 06712
    /40

    $635,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 2,005 Sq Ft

    28 Tamarack Ct Unit 28, Prospect, CT 06712

    HIGHEST AND BEST DUE BY 5 PM 4/27/26! Welcome to Regency at Prospect, an elite 55+ sanctuary set upon 182 acres of serene landscape. This custom-built Alder model masterfully balances rural tranquility with urban convenience, located just minutes from I-84, The Merritt, and Route 8. Artistry Design-Experience with an unparalleled level of quality in this custom-built Alder model. Boasting over

    Deborah Ridolfi Pavlik Real Estate LLC

    28 Tamarack Ct Unit 28, Prospect, CT 06712
  • 15 Royalwood Ct, Cheshire, CT 06410

    $675,000

    Sold Aug 29, 2025

    15 Royalwood Ct, Cheshire, CT 06410

    • 5 Beds
    • 3 Baths
    • 2,845 Sq Ft
    • Built 1975

    Last Sold Summary

    • 8% Above List Price
    • $237/SF
    • 3 Days On Market

    Current Estimated Value $675,655

    Last Listing Agent Tracie Sires Press/Cuozzo Realtors

    15 Royalwood Ct, Cheshire, CT 06410

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