11,926

Cheshire, CT Homes

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  • /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. Best of all, it's move-in ready, allowing you to make thoughtful upgrades at your own pace. It has a private office with glass French doors and built-ins,

    Agent Photo

    Iris Meyer

    William Raveis Real Estate

    1 Mountaincrest Dr, 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

    1728 Highland Ave, 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 $673,352

    Last Listing Agent Jason Saphire www.HomeZu.com

    95 Orleton Ct, Cheshire, CT 06410
  • /29

    $455,000

    • 3 Beds
    • 1 Bath
    • 1,764 Sq Ft

    445 Lincoln Dr, Cheshire, CT 06410

    Welcome to 445 Lincoln Drive in Cheshire! This beautifully remodeled home offers the perfect blend of modern updates and comfortable living. Step inside to discover a bright, inviting interior featuring a renovated kitchen with stylish finishes, an updated bathroom, and thoughtful improvements throughout. The finished lower level provides valuable additional living space-perfect for a family

    Agent Photo

    Lucy Cordero

    KW Legacy Partners

    445 Lincoln Dr, Cheshire, CT 06410
  • /34

    Starting at $2,589

    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

    106 Stonebridge Ct, 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 $412,264

    Last Listing Agent Melanie Ricci Coldwell Banker Realty

    1364 Avon Blvd, 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

    5 Melrose 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

    10 Realty Dr, 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 $796,630

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

    458 Castle Glenn, Cheshire, CT 06410
  • /40

    $449,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,446 Sq Ft

    460 Oak Ave, Cheshire, CT 06410

    Highest and Best due by 5 pm Sunday 7/26. Welcome home to this well-maintained home offering comfort, convenience, and thoughtful updates throughout. The inviting family room features a cozy Vermont Castings wood stove, while mini-split systems provide efficient air conditioning on the first floor. Enjoy summer days in the 24' round above-ground pool (54" deep) with an deck that's just 5 years

    Agent Photo

    Cindy Forlenzo

    Coldwell Banker Realty

    460 Oak Ave, Cheshire, CT 06410
  • /35

    Starting at $1,794

    Total Monthly Price

    • Studio - 2 Beds

    50 Hazel Dr, Cheshire, CT 06410

    Lakeside of Cheshire

    50 Hazel 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 $244,678

    Last Listing Agent Katie Smith Berkshire Hathaway NE Prop.

    488 Radmere Rd Unit B, Cheshire, CT 06410
  • /33

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,323 Sq Ft

    448 Mixville Rd, Cheshire, CT 06410

    Welcome to your dream home, nestled in a serene wooded lot and perfectly located near the picturesque Mixville Park. This stunning residence features three spacious bedrooms and two and a half baths, offering ample space for relaxation and entertainment. As you step inside, you'll be greeted by hardwood floors that flow seamlessly throughout the main level, creating a warm and inviting

    Agent Photo

    Nick Prevost

    William Raveis Real Estate

    448 Mixville Rd, 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-- We have a 1 Bedroom now and we will have a 2 Bedroom for MID AUGUST. 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 parking. Storage included and

    356 Highland Ave, 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 $434,490

    Last Listing Agent Stacey Deangelis Calcagni Real Estate

    233 Mountain Rd, Cheshire, CT 06410
  • /40

    $579,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,758 Sq Ft

    335 Redwood Ln, Cheshire, CT 06410

    Highest &Best Monday 6/1 9PM. Beautifully updated 4-bedroom, 2.5-bath Raised Ranch ideally situated in a sought-after neighborhood setting with underground utilities & sidewalks. Set on a professionally landscaped, level yard designed for relaxation & entertaining, this move-in ready home blends timeless craftsmanship & modern sophistication. The stunning sun-filled kitchen features Omega solid

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    335 Redwood Ln, Cheshire, CT 06410
  • /13

    $2,300

    Total Monthly Price

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

    281 Spring St Unit All utilities included, Cheshire, CT 06410

    Cozy and Quiet Neighborhood in beautiful Cheshire and close to major highways, Colleges and Shopping malls

    281 Spring St Unit All utilities included, 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 $311,339

    Last Listing Agent Evan Johnson Coldwell Banker Realty

    204 Greens Loop Unit 204, Cheshire, CT 06410
  • /39

    $459,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,992 Sq Ft

    936 S Meriden Rd, Cheshire, CT 06410

    Welcome to 936 South Meriden Road - a classic Cheshire raised ranch that delivers the space, flexibility, and indoor-outdoor lifestyle today's buyers are looking for. The main level is made for living. A large family room anchors the space with a classic raised hearth fireplace, flowing seamlessly into a dining area with built-ins - perfect for everything from casual nights in to hosting a crowd.

    Agent Photo

    Carly Kirsch

    Lamacchia Realty

    936 S Meriden Rd, Cheshire, CT 06410
  • /11

    $3,150 Per Month

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

    219 Old Towne Rd, Cheshire, CT 06410

    First floor ranch-style unit available at Old Towne Commons - Enjoy easy living in this centrally located complex within walking distance from coffee shops, cafes, local favorites, shopping & more. 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.

    219 Old Towne Rd, 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
  • /2

    $850,000

    New Construction Pending
    • 4 Beds
    • 2.5 Baths
    • 2,536 Sq Ft

    6 Mount Sanford Rd, Cheshire, CT 06410

    A rare find!Brand new farmhouse style contemporary Colonial being constructed at the south end of town in a picturesque country setting close to shopping & easy highway access.The home is available to customize & make changes while under construction & should be ready for late summer occupancy.The home offers HW floors on the main level & landing,2zone gas heat & central air,9' ceilings on the

    Agent Photo

    Iris Meyer

    William Raveis Real Estate

    6 Mount Sanford Rd, Cheshire, CT 06410
  • /35

    $3,440

    Total Monthly Price

    • 5 Beds
    • 3.5 Baths
    • 2,392 Sq Ft
    • House for Rent

    205 Jinny Hill Rd, Cheshire, CT 06410

    Experience comfort, privacy, and flexible living in this distinctive Frank Lloyd Wright–inspired home. Featuring five bedrooms, 3.5 bathrooms, abundant storage, and mini-split systems for year-round comfort, the home blends architectural character with thoughtful modern updates.The remodeled kitchen offers granite countertops, stainless steel appliances, and radiant heated floors.

    205 Jinny Hill Rd, 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 $406,381

    Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

    239 Bates Dr, Cheshire, CT 06410
  • /2

    $1,109,410

    New Construction Pending
    • 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

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    1811 Blackberry Place, Cheshire, CT 06410
  • /2

    $3,995 Per Month

    • 5 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • House for Rent

    170 Creamery Rd, Cheshire, CT 06410

    Lovely and inviting home. Spacious, airy rooms. Central pleasant landlord maintains the lawn and plows the driveway in a timely way. Leafy and tranquil neighborhood with great neighbors. Walk or bike to Cheshire Park for tennis, basketball, soccer, softball, nice playscape. Short drive to charming colonial era town green. Hit the beach or drop a line at Mixville Pond. Explore the Historic

    Joel Matson Coldwell Banker Realty

    170 Creamery Rd, Cheshire, CT 06410
  • 20 Watch Hill Rd, Cheshire, CT 06410

    $466,000

    Sold Jul 17, 2026

    20 Watch Hill Rd, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,086 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Above List Price
    • $223/SF
    • 50 Days On Market

    Current Estimated Value $601,725

    Last Listing Agent Karen Brimberg William Raveis Real Estate

    20 Watch Hill Rd, Cheshire, CT 06410
  • /3

    $890,000

    New Construction Pending
    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    1840 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

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    1840 Blackberry Place, Cheshire, CT 06410
  • /21

    $2,500 Per Month

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

    1335 Wolf Hill Rd, Cheshire, CT 06410

    Renovated rental available in desirable Cheshire!

    George Daniolos eRealty Advisors, Inc.

    1335 Wolf Hill Rd, 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 $584,381

    Last Listing Agent Felipe Segura Coldwell Banker Realty

    106 Woodland Dr, Cheshire, CT 06410

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$531,002
Median Single Family Sale Price
$557,000
Median Townhouse Sale Price
$530,855
Median 2 Bedroom Sale Price
$330,000
Median 1 Bedroom Sale Price
$171,000
Average Price Per Sq Ft
$292
Number of Homes for Sale
34
Last 12 months Home Sales
320
Months of Supply
1.30
Median List Price
$529,900
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
1%
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