11,916

Cheshire, CT Homes

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  • 15 Shire Ct, Cheshire, CT 06410
    15 Shire Ct, Cheshire, CT 06410
    15 Shire Ct, Cheshire, CT 06410
    /39

    $1,085,000

    $40K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 4,437 Sq Ft

    15 Shire Ct, Cheshire, CT 06410

    Sophisticated elegance defines this 4,437 sq ft architect-designed Contemporary Colonial, featuring a luxurious first-floor primary suite with a custom closet, walk-in limestone shower, and separate soaking tub. The chef will appreciate the beautifully designed kitchen with a stainless-steel six-burner Viking gas range, double ovens, and expansive thick granite counters with seating. A charming

    Agent Photo

    Iris Meyer

    William Raveis Real Estate

    (475) 260-5765

    15 Shire Ct, Cheshire, CT 06410
  • 480 Radmere Rd Unit B, Cheshire, CT 06410
    480 Radmere Rd Unit B, Cheshire, CT 06410
    480 Radmere Rd Unit B, Cheshire, CT 06410
    /13

    $2,200 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,202 Sq Ft
    • Townhouse for Rent

    480 Radmere Rd Unit B, Cheshire, CT 06410

    Beautifully maintained condo located in quiet condominium community, conveniently located close to town center. The kitchen offers granite counter tops, pantry closet and an island, with a door to the shared back yard. There is a half bathroom on this level as well. The kitchen opens to an large living room/dining room combination. There are two spacious bedrooms and a full bathroom upstairs. The

    Agent Photo

    Jennifer D'Amato

    Real Broker CT, LLC

    (475) 270-7168

    480 Radmere Rd Unit B, Cheshire, CT 06410
  • 95 Orleton Ct, Cheshire, CT 06410

    $655,000

    Sold Feb 27, 2026

    95 Orleton Ct, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft
    • Built 1998

    Last Sold Summary

    • $227/SF
    • 124 Days On Market

    Current Estimated Value $662,726

    Last Listing Agent Jason Saphire www.HomeZu.com

    95 Orleton Ct, Cheshire, CT 06410
  • 1 Mountaincrest Dr, Cheshire, CT 06410
    1 Mountaincrest Dr, Cheshire, CT 06410
    1 Mountaincrest Dr, Cheshire, CT 06410
    /40

    $1,175,000

    $50K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,718 Sq Ft

    1 Mountaincrest Dr, Cheshire, CT 06410

    Majestically situated on a gentle hill designed to capture sweeping views of horses mountains and the picturesque countryside. This impressive 4,701 sq ft contemporary colonial is located in the highly sought after South Cheshire neighborhood. A dramatic two-story marble foyer with a sweeping staircase welcomes you into elegant formal spaces, including a private office with glass French doors and

    Agent Photo

    Iris Meyer

    William Raveis Real Estate

    (475) 244-8520

    1 Mountaincrest Dr, Cheshire, CT 06410
  • 1728 Highland Ave, Cheshire, CT 06410
    1728 Highland Ave, Cheshire, CT 06410
    1728 Highland Ave, Cheshire, CT 06410
    /4

    Starting at $2,595

    Total Monthly Price

    • 2 Beds

    1728 Highland Ave, Cheshire, CT 06410

    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. Please contact the Leasing Office for availability.

    Highland Farms

    (475) 244-8591

    1728 Highland Ave, Cheshire, CT 06410
  • 1364 Avon Blvd, Cheshire, CT 06410

    $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

    Current Estimated Value $405,225

    Last Listing Agent Melanie Ricci Coldwell Banker Realty

    1364 Avon Blvd, Cheshire, CT 06410
  • 28 E Ridge Ct, Cheshire, CT 06410
    28 E Ridge Ct, Cheshire, CT 06410
    28 E Ridge Ct, Cheshire, CT 06410
    /40

    $959,000

    Pending
    • 5 Beds
    • 2.5 Baths
    • 3,887 Sq Ft

    28 E Ridge Ct, Cheshire, CT 06410

    Submit HIGHEST & BEST by 4/14 at noon. Welcome to your bright and airy custom home inspired by the peaceful French countryside. Tucked away at the end of a private cul-de-sac, this sun-drenched home offers the perfect blend of class, comfort, and space. Step into the foyer and fall in love with the gleaming natural hardwood floors that flow throughout the main living areas. The living room

    Agent Photo

    Cindy Gaioni

    KW Legacy Partners

    (475) 251-8853

    28 E Ridge Ct, Cheshire, CT 06410
  • 64 E Mitchell Ave, Cheshire, CT 06410
    64 E Mitchell Ave, Cheshire, CT 06410
    64 E Mitchell Ave, Cheshire, CT 06410
    /40

    Starting at $2,800 Plus Fees

    • 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

    Maplecroft Village

    (475) 405-1574

    64 E Mitchell Ave, Cheshire, CT 06410
  • 458 Castle Glenn, Cheshire, CT 06410

    $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

    Current Estimated Value $778,429

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

    458 Castle Glenn, Cheshire, CT 06410
  • 5 Melrose Dr, Cheshire, CT 06410
    5 Melrose Dr, Cheshire, CT 06410
    5 Melrose Dr, Cheshire, CT 06410
    /40

    $1,395,000

    Under Contract
    • 4 Beds
    • 4 Baths
    • 3,423 Sq Ft

    5 Melrose Dr, Cheshire, CT 06410

    Welcome to a home that perfectly balances proportions w/the warmth of a true family home! Built just 4years ago this stunning Cont/Col offers a new construction feel with all the extras usually added after closing!Step inside to find gleamingHW floors that flow seamlessly throughout.The dramatic two-story greatrm serves as the centerpiece,anchored by a cozy gas FP & flooded with natural light.It

    Agent Photo

    Iris Meyer

    William Raveis Real Estate

    (475) 265-2033

    5 Melrose Dr, Cheshire, CT 06410
  • 106 Stonebridge Ct, Cheshire, CT 06410
    106 Stonebridge Ct, Cheshire, CT 06410
    106 Stonebridge Ct, Cheshire, CT 06410
    /34

    Starting at $2,229

    Total Monthly Price

    • 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

    Riverpointe Cheshire

    (860) 899-1998

    106 Stonebridge Ct, Cheshire, CT 06410
  • 657 Tamarack Rd, Cheshire, CT 06410

    $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 $1,051,541

    Last Listing Agent Julie Luchina Coldwell Banker Realty

    657 Tamarack Rd, Cheshire, CT 06410
  • 139 Contour Dr, Cheshire, CT 06410
    139 Contour Dr, Cheshire, CT 06410
    139 Contour Dr, Cheshire, CT 06410
    /40

    $489,900

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,808 Sq Ft

    139 Contour Dr, Cheshire, CT 06410

    Welcome to this meticulously well-kept ranch, where comfort meets style in every corner! This delightful home boasts 3 bedrooms and 2.5 updated bathrooms, offering plenty of room for relaxation and family life. Step into the updated kitchen, complete with gorgeous granite countertops and stainless-steel appliances. Every bathroom in the house has been thoughtfully renovated, and the recently

    Agent Photo

    Tanya Uhelsky

    RE/MAX RISE

    (203) 601-7338

    139 Contour Dr, Cheshire, CT 06410
  • 10 Realty Dr, Cheshire, CT 06410
    10 Realty Dr, Cheshire, CT 06410
    10 Realty Dr, Cheshire, CT 06410
    /10

    Starting at $1,238 Plus Fees

    • 1 - 2 Beds

    10 Realty Dr, Cheshire, CT 06410

    Why compromise when you can have it all at Acclaim at Cheshire? Our affordable housing in Cheshire brings you the perfect blend of budget-friendly rates, modern amenities, and a convenient location. Whether you're seeking relaxation, exercise, or local exploration, our community has you covered. Beyond our apartments, you'll find close access to public transportation and an array of shopping,

    Acclaim at Cheshire

    (203) 760-0763

    10 Realty Dr, Cheshire, CT 06410
  • 488 Radmere Rd Unit B, Cheshire, CT 06410

    $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

    Current Estimated Value $248,761

    Last Listing Agent Katie Smith Berkshire Hathaway NE Prop.

    488 Radmere Rd Unit B, Cheshire, CT 06410
  • 20 Stacy Ct, Cheshire, CT 06410
    20 Stacy Ct, Cheshire, CT 06410
    20 Stacy Ct, Cheshire, CT 06410
    /40

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,140 Sq Ft

    20 Stacy Ct, Cheshire, CT 06410

    This cul-de-sac gem has to be the 2026 Curb Appeal Winner! Beautifully maintained gardens bursting w/ seasonal color, a lush green lawn, & attractive landscaping create a welcoming first impression. A stone paver driveway & gorgeous pathway lead to the inviting entrance. Soaring cathedral ceilings & gleaming hardwood floors create a wonderful first impression. The living room w/ fireplace flows

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 937-2923

    20 Stacy Ct, Cheshire, CT 06410
  • 50 Hazel Dr, Cheshire, CT 06410
    50 Hazel Dr, Cheshire, CT 06410
    50 Hazel Dr, Cheshire, CT 06410
    /32

    Starting at $1,794

    Total Monthly Price

    • Studio - 2 Beds

    50 Hazel Dr, Cheshire, CT 06410

    Welcome Home to Lakeside at Cheshire. New Apartments.

    Lakeside of Cheshire

    (475) 405-1923

    50 Hazel Dr, Cheshire, CT 06410
  • 233 Mountain Rd, Cheshire, CT 06410

    $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 $429,061

    Last Listing Agent Stacey Deangelis Calcagni Real Estate

    233 Mountain Rd, Cheshire, CT 06410
  • 568 Wiese Rd, Cheshire, CT 06410
    568 Wiese Rd, Cheshire, CT 06410
    568 Wiese Rd, Cheshire, CT 06410
    /40

    $540,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,633 Sq Ft

    568 Wiese Rd, Cheshire, CT 06410

    Welcome to 568 Wiese Rd in the heart of Cheshire, a beautifully maintained home set in one of the town's most desirable areas. From the moment you arrive, you'll notice the thoughtfully designed landscaping that creates incredible curb appeal and a true sense of privacy. Step into the backyard and discover your own private sanctuary. Lush greenery, mature plantings, and carefully curated outdoor

    Agent Photo

    Rudy Pierre

    YellowBrick Real Estate LLC

    (475) 242-6022

    568 Wiese Rd, Cheshire, CT 06410
  • 356 Highland Ave, Cheshire, CT 06410
    356 Highland Ave, Cheshire, CT 06410
    356 Highland Ave, Cheshire, CT 06410
    /7

    $1,600

    Total Monthly Price

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

    356 Highland Ave, Cheshire, CT 06410

    Amazing property and a great place to make a home-- Check for Available units as we DO NOT HAVE ANYTHING AT THIS TIME!!! AUGUST 2026 IS THE NEXT APARTMENT. Don't wait to get in touch with us about these Great units in a fantastic location- No smoking, No pets-- Good credit and Good income needed to qualify. Heat and Hot water, cold water, sewer, trash included in the rent. Super onsite, ample

    356 Highland Ave, Cheshire, CT 06410
  • 204 Greens Loop Unit 204, Cheshire, CT 06410

    $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 $306,544

    Last Listing Agent Evan Johnson Coldwell Banker Realty

    204 Greens Loop Unit 204, Cheshire, CT 06410
  • 27 S Pond Cir, Cheshire, CT 06410
    27 S Pond Cir, Cheshire, CT 06410
    27 S Pond Cir, Cheshire, CT 06410
    /40

    $675,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    27 S Pond Cir, Cheshire, CT 06410

    HIGHEST AND BEST BY 5/12/2026 NOON. Welcome to this classic Colonial located in the highly desirable South Pond subdivision, offering sidewalks, underground utilities, and a scenic neighborhood pond with benches. This spacious vinyl-sided home features beautiful hardwood floors, a flexible floor plan, and an ideal location close to schools, shopping, major highways, and the bus line. The

    Agent Photo

    Marc Seigel & Lauren Seigel-Gross

    RE/MAX RISE

    (475) 265-3051

    27 S Pond Cir, Cheshire, CT 06410
  • 941 Waterbury Rd Unit 2nd Floor, Cheshire, CT 06410
    941 Waterbury Rd Unit 2nd Floor, Cheshire, CT 06410
    941 Waterbury Rd Unit 2nd Floor, Cheshire, CT 06410
    /8

    $1,325

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 572 Sq Ft
    • Condo for Rent

    941 Waterbury Rd Unit 2nd Floor, Cheshire, CT 06410

    Pets allowed with restrictions. Renters insurance required. All utilities paid by tenant.

    941 Waterbury Rd Unit 2nd Floor, Cheshire, CT 06410
  • 83 Shea Cir Unit 83, Cheshire, CT 06410

    $765,735

    Sold Feb 24, 2026

    83 Shea Cir Unit 83, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • Built 2026

    Last Sold Summary

    • 14% Above List Price
    • $313/SF
    • 55 Days On Market

    Last Listing Agent Jason Helton EG Group Realty LLC

    83 Shea Cir Unit 83, Cheshire, CT 06410
  • 43 Hawthorne Dr, Cheshire, CT 06410
    43 Hawthorne Dr, Cheshire, CT 06410
    43 Hawthorne Dr, Cheshire, CT 06410
    /39

    $519,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,346 Sq Ft

    43 Hawthorne Dr, Cheshire, CT 06410

    Welcome to 43 Hawthorne Drive - a well-maintained Cheshire home that truly shows beautifully. This home offers three bedrooms, two full baths and flexible living spaces. The main level offers a spacious and bright living room, full bath, bedroom and office and eat-in kitchen. The updated eat-in kitchen features beautiful cabinetry and counters for everyday meals with a slider to the deck- perfect

    Agent Photo

    Carly Kirsch

    Lamacchia Realty

    (475) 259-7391

    43 Hawthorne Dr, Cheshire, CT 06410
  • 13 Warren St, Cheshire, CT 06410
    13 Warren St, Cheshire, CT 06410
    /2

    $3,495

    Total Monthly Price

    • 4 Beds
    • 1.5 Baths
    • 1,887 Sq Ft
    • House for Rent

    13 Warren St, Cheshire, CT 06410

    13 Warren St, Cheshire, CT 06410
  • 239 Bates Dr, Cheshire, CT 06410

    $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 $400,909

    Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

    239 Bates Dr, Cheshire, CT 06410
  • 643 Maple Ave, Cheshire, CT 06410
    643 Maple Ave, Cheshire, CT 06410
    643 Maple Ave, Cheshire, CT 06410
    /35

    $575,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,722 Sq Ft

    643 Maple Ave, Cheshire, CT 06410

    *** Highest and Best Deadline Monday 5/11 at 7:00 pm.***. This is the one you've been waiting for-fully remodeled, absolutely move-in ready, and not a detail overlooked. Homes like this in Cheshire rarely come to market, combining timeless charm with today's most sought-after updates. Renovated top-to-bottom between 2020-2022, this home offers true peace of mind-there is nothing left to do but

    Agent Photo

    Sarah Andrea

    Coldwell Banker Realty

    (203) 935-8966

    643 Maple Ave, Cheshire, CT 06410
  • 83 Poplar Dr, Cheshire, CT 06410
    83 Poplar Dr, Cheshire, CT 06410
    83 Poplar Dr, Cheshire, CT 06410
    /16

    $3,400 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,436 Sq Ft
    • House for Rent

    83 Poplar Dr, Cheshire, CT 06410

    A rare opportunity to rent a fully updated 3 br 1.5 bath home in Cheshire. Spacious and bright open floor plan for easy and functional everyday living. A lovely updated kitchen with stainless appliances and convenient laundry. Hardwood flooring. Combination living room and dining room with additional space for work area . Oversized 2 car garage included. A fenced in backyard perfect for a furry

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

    83 Poplar Dr, Cheshire, CT 06410
  • 106 Woodland Dr, Cheshire, CT 06410

    $605,000

    Sold Apr 01, 2026

    106 Woodland Dr, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 2,247 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Above List Price
    • $269/SF
    • 11 Days On Market

    Current Estimated Value $580,748

    Last Listing Agent Felipe Segura Coldwell Banker Realty

    106 Woodland Dr, Cheshire, CT 06410
    • 37 Warren St, Cheshire, CT 06410

      Est $759,982

      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

      • 7 Days On Market

Showing Results 1 - 40, Page 1 of 18

Connecticut New Haven County Cheshire

Real Estate & Homes

Home Prices in Cheshire, CT

The median home sale price in Cheshire, CT is $525,000, up 1% year-over-year. Homes in Cheshire sell in 54 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$525,000
Median Single Family Sale Price
$549,900
Median Townhouse Sale Price
$533,230
Median 2 Bedroom Sale Price
$327,444
Median 1 Bedroom Sale Price
$192,000
Average Price Per Sq Ft
$289
Number of Homes for Sale
25
Last 12 months Home Sales
311
Months of Supply
1.00
Median List Price
$510,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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