Cheshire, CT Homes

• 

  $670,000

  Sold Dec 15, 2025

  4 Brookfield Ct, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $291/SF
  • 39 Days On Market

  Current Estimated Value $671,371

  Last Listing Agent Brette Stern Calcagni Real Estate

  4 Brookfield Ct, Cheshire, CT 06410
• 

  Not Listed For Sale

  2 S Brooksvale Rd, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,578 Sq Ft
  • Built 2023

  2 S Brooksvale Rd, Cheshire, CT 06410

  Last Sold Summary

  • 378 Days On Market
• 

  

  

  /18

  $1,299,000

  New Construction Pending

  • 4 Beds
  • 3.5 Baths
  • 4,016 Sq Ft

  3 Melrose Dr Unit Lot 9, Cheshire, CT 06410

  Welcome to your Dream Home! This 4,016 sq ft TO BE BUILT colonial plan is nothing short of AMAZING!! This house plan offers many of today's Must Haves! Welcoming you in through the front door is a 2 story foyer, creating an grand entrance. Should you enter through the garage, you will walk through the desirable mudroom. The main living space on the first floor is a true open concept layout, from

  Dori Degennaro William Raveis Real Estate

  3 Melrose Dr Unit Lot 9, Cheshire, CT 06410
• 

  $565,000

  Sold Feb 19, 2026

  975 Wolf Hill Rd, Cheshire, CT 06410

  • 3 Beds
  • 3 Baths
  • 1,882 Sq Ft
  • Built 1947

  Last Sold Summary

  • 2% Below List Price
  • $300/SF
  • 10 Days On Market

  Current Estimated Value $560,196

  Last Listing Agent Rachel Wardwell Calcagni Real Estate

  975 Wolf Hill Rd, Cheshire, CT 06410
• 

  Est $751,517

  Not Listed For Sale

  265 S Brooksvale Rd, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft
  • Built 2023

  265 S Brooksvale Rd, Cheshire, CT 06410

  Last Sold Summary

  • 390 Days On Market
• 

  

  /15

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  401 Juniper Ln, Cheshire, CT 06410

  Set in a highly desirable neighborhood location, this charming ranch offers single-level living with a welcoming and functional floor plan. A spacious front-to-back living room presents plenty of room to gather, relax, or entertain includes a wood-burning fireplace and convenient access to the two-car garage with a separate enclosed storage room. The dedicated dining area provides the perfect

  Jessica Danard Coldwell Banker Realty

  401 Juniper Ln, Cheshire, CT 06410
• 

  $547,560

  Sold Apr 21, 2026

  135 Shea Cir Unit 135, Cheshire, CT 06410

  • 2 Beds
  • 2.5 Baths
  • 1,850 Sq Ft
  • Built 2025

  Last Sold Summary

  • 11% Above List Price
  • $296/SF
  • 32 Days On Market

  Last Listing Agent Michael Helmuth EG Group Realty LLC

  135 Shea Cir Unit 135, Cheshire, CT 06410
• 

  Est $438,695

  Not Listed For Sale

  1243 Avon Blvd, Cheshire, CT 06410

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft
  • Built 1954

  1243 Avon Blvd, Cheshire, CT 06410

  Last Sold Summary

  • 7 Days On Market
• 

  

  /40

  $449,900

  • 3 Beds
  • 1.5 Baths
  • 1,796 Sq Ft

  205 Mountain Rd, Cheshire, CT 06410

  Desirable three bedroom ranch set on a beautiful .84 acre lot backing to a wooded mountain setting, offering privacy and a peaceful natural backdrop. This well-built home features a spacious formal living room with built-ins and HW flooring beneath the carpet. Centrally located kitchen includes a newer refrigerator and is ready for your personal updates and design ideas. Impressive vaulted dining

  Stacey Deangelis Calcagni Real Estate

  205 Mountain Rd, Cheshire, CT 06410
• 

  $381,000

  Sold Jul 01, 2025

  48 Warren St, Cheshire, CT 06410

  • 3 Beds
  • 1 Bath
  • 1,198 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Above List Price
  • $318/SF
  • 39 Days On Market

  Current Estimated Value $386,763

  Last Listing Agent Kelly Ryan William Raveis Real Estate

  48 Warren St, Cheshire, CT 06410
• 

  Est $396,018

  Not Listed For Sale

  200 Bates Dr, Cheshire, CT 06410

  • 2 Beds
  • 1 Bath
  • 1,096 Sq Ft
  • Built 1954

  200 Bates Dr, Cheshire, CT 06410

  Last Sold Summary

  • 4 Days On Market
• 

  

  /39

  $599,900

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  620 Riverside Dr, Cheshire, CT 06410

  Nestled in prestigious Nob Hill neighborhood, this stately Georgian Colonial showcases timeless elegance with a striking brick facade, twin brick lamp posts, and a convenient side-entry garage. Situated on private 1.22-acres, this beautifully maintained home has only been used part of the year by its snowbird owners. Inside, the formal living room features gleaming HW floors, abundant natural

  Stacey Deangelis Calcagni Real Estate

  620 Riverside Dr, Cheshire, CT 06410
• 

  $552,500

  Sold May 06, 2026

  107 Country Club Rd, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 2,088 Sq Ft
  • Built 1975

  Last Sold Summary

  • 9% Above List Price
  • $265/SF
  • 36 Days On Market

  Current Estimated Value $507,093

  Last Listing Agent Frank Lazowski Laz Real Estate, LLC

  107 Country Club Rd, Cheshire, CT 06410
• 

  Est $579,152

  Not Listed For Sale

  86 Hawthorne Dr, Cheshire, CT 06410

  • 4 Beds
  • 3 Baths
  • 2,449 Sq Ft
  • Built 1955

  86 Hawthorne Dr, Cheshire, CT 06410

  Last Sold Summary

  • 4 Days On Market
• 

  

  /38

  $430,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  39 Fernwood Ln, Cheshire, CT 06410

  **Best and final requested by Wednesday, May 20 at 8pm.** Nestled on a quiet cul-de-sac in desirable South Cheshire, 39 Fernwood Lane offers exceptional privacy and seclusion on over 2 acres of picturesque property. Surrounded by mature trees and a natural landscape, the expansive yard creates a peaceful retreat with endless possibilities for outdoor living, entertaining, gardening, recreation,

  Mark Hodges Carl Guild & Associates

  39 Fernwood Ln, Cheshire, CT 06410
• 

  $785,000

  Sold Jul 17, 2025

  33 Roxbury Ct, Cheshire, CT 06410

  • 5 Beds
  • 4.5 Baths
  • 3,671 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $214/SF
  • 121 Days On Market

  Current Estimated Value $796,244

  Last Listing Agent Kori Gauvin KW Legacy Partners

  33 Roxbury Ct, Cheshire, CT 06410
• 

  Est $767,055

  Not Listed For Sale

  8 Inverness Ct, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,868 Sq Ft
  • Built 1968

  8 Inverness Ct, Cheshire, CT 06410

  Last Sold Summary

  • 3 Days On Market
• 

  

  /35

  $364,900

  Pending

  • 2 Beds
  • 2.5 Baths
  • 1,486 Sq Ft

  10 Ives Hill Ct Unit 10, Cheshire, CT 06410

  Welcome to this move-in ready condo in the highly sought-after Ives Hill community in Cheshire! Thoughtfully updated throughout, this home offers the perfect blend of modern finishes, flexible living space, and a prime location. Step inside to an open-concept main level featuring a spacious living room with a cozy wood-burning fireplace, a separate dining area, and a beautifully updated kitchen

  Jill Rubino Century 21 AllPoints Realty

  10 Ives Hill Ct Unit 10, Cheshire, CT 06410
• 

  $350,000

  Sold Apr 28, 2026

  66 Old Towne Rd, Cheshire, CT 06410

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $228/SF
  • 96 Days On Market

  Current Estimated Value $365,184

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

  66 Old Towne Rd, Cheshire, CT 06410
• 

  Est $1,515,165

  Not Listed For Sale

  65 Abrams Rd, Cheshire, CT 06410

  • 6 Beds
  • 9 Baths
  • 8,099 Sq Ft
  • Built 1988

  65 Abrams Rd, Cheshire, CT 06410

  Last Sold Summary

  • 163 Days On Market
• 

  

  /40

  $579,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,937 Sq Ft

  76 Glenbrook Dr, Cheshire, CT 06410

  Highest and Best Tuesday, 5/19/26 by noon please. Welcome to this exceptional home, thoughtfully designed for easy one-level living and built with quality craftsmanship throughout. A charming covered front porch creates a warm first impression and sets the tone for the inviting interior beyond. The bright and airy updated kitchen features a marble-top island with seating for 4, quartz

  Kristen Butts Century 21 Clemens Group

  76 Glenbrook Dr, Cheshire, CT 06410
• 

  $646,500

  Sold Mar 13, 2026

  25 Goldenrod Ct, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,311 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $280/SF
  • 171 Days On Market

  Current Estimated Value $668,532

  Last Listing Agent Mark Gracia William Raveis Real Estate

  25 Goldenrod Ct, Cheshire, CT 06410
• 

  Est $893,003

  Not Listed For Sale

  647 Tamarack Rd, Cheshire, CT 06410

  • 4 Beds
  • 4 Baths
  • 3,703 Sq Ft
  • Built 1997

  647 Tamarack Rd, Cheshire, CT 06410

  Last Sold Summary

  • 33 Days On Market
• 

  

  /33

  $685,000

  New Construction $104K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,506 Sq Ft

  1050 Jarvis St, Cheshire, CT 06410

  Brand-new construction completed on 12/12/2025 and currently receiving final finishing touches by the owner. This beautiful home offers 4 spacious bedrooms, 3 full bathrooms, and a 2-car garage with an additional 506 square feet of garage space. The Town has issued the Certificate of Occupancy (CO). Thoughtfully designed layout with modern finishes throughout. A rare opportunity to own a newly

  Carlos Ventura Ventura Group Realty LLC

  1050 Jarvis St, Cheshire, CT 06410
• 

  $710,000

  Sold Jun 30, 2025

  671 Cortland Cir, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 2,750 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Above List Price
  • $258/SF
  • 3 Days On Market

  Current Estimated Value $707,762

  Last Listing Agent Cheri Paulsen Advise Realty Services

  671 Cortland Cir, Cheshire, CT 06410
• 

  Est $672,838

  Not Listed For Sale

  36 Wildlife Ct, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 2,672 Sq Ft
  • Built 2010

  36 Wildlife Ct, Cheshire, CT 06410

  Last Sold Summary

  • 4 Days On Market
• 

  

  /3

  $949,000

  Coming Soon

  • 5 Beds
  • 3.5 Baths
  • 5,187 Sq Ft

  85 Scenic Ct, Cheshire, CT 06410

  A private hilltop retreat with over 5,000 square feet of finished living space, an in-ground pool, walk-out lower level, and secluded resort-style setting- Welcome to 85 Scenic Court. This custom-built 5 bedroom, 3.5 bath colonial is set back on a private, beautifully landscaped lot and offers an exceptional blend of space, comfort, privacy, and luxury. The main level features a private office

  Jeffrey Puciato Puciato Altieri Realty Group

  85 Scenic Ct, Cheshire, CT 06410
• 

  $400,000

  Sold Dec 04, 2025

  1325 Avon Blvd, Cheshire, CT 06410

  • 3 Beds
  • 1 Bath
  • 1,316 Sq Ft
  • Built 1953

  Last Sold Summary

  • $304/SF
  • 69 Days On Market

  Current Estimated Value $396,404

  Last Listing Agent Cindy Forlenzo Coldwell Banker Realty

  1325 Avon Blvd, Cheshire, CT 06410
• 

  Est $539,851

  Not Listed For Sale

  28 Wildlife Ct, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 1,563 Sq Ft
  • Built 2010

  28 Wildlife Ct, Cheshire, CT 06410

  Last Sold Summary

  • 2 Days On Market
• 

  

  /22

  $519,900

  • 4 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  2175 Plank Rd, Cheshire, CT 06410

  Tucked away on a private 5.57-acre rear lot, this spacious 4 BR 2 1/2 bath Colonial in need of some renovation offers a rare opportunity in desirable Cheshire! Built in 2007 and set far back from the road on a long private driveway, the property offers exceptional privacy and a peaceful setting surrounded by nature. Offering approximately 2,496 square feet, the home features high ceilings, and a

  Lisa McCarthy Coldwell Banker Realty

  2175 Plank Rd, Cheshire, CT 06410
• 

  $710,000

  Sold Jan 08, 2026

  440 Mount Sanford Rd, Cheshire, CT 06410

  • 4 Beds
  • 4 Baths
  • 3,816 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $186/SF
  • 16 Days On Market

  Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

  440 Mount Sanford Rd, Cheshire, CT 06410
• 

  Est $652,107

  Not Listed For Sale

  15 Wildlife Ct, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 2,639 Sq Ft
  • Built 2010

  15 Wildlife Ct, Cheshire, CT 06410

  Last Sold Summary

  • 14 Days On Market
• 

  

  /40

  $559,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,462 Sq Ft

  230 Wallingford Rd, Cheshire, CT 06410

  **Highest and Best Saturday, 5/23/26 by 3 PM please**. Well-maintained and classic, this 3-bedroom, 2.5-bath Dutch Colonial set on a nice .77-acre corner lot in Cheshire and offers 1,994 square feet of living space plus 468 square feet in the finished walkout lower level. The family room features a raised-hearth gas fireplace, bay window, and French doors to a true three-season porch, creating a

  The Sally Bowman Team Berkshire Hathaway NE Prop.

  230 Wallingford Rd, Cheshire, CT 06410
• 

  $507,500

  Sold Oct 09, 2025

  236 Mountain Rd, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 1,619 Sq Ft
  • Built 1948

  Last Sold Summary

  • 4% Below List Price
  • $313/SF
  • 54 Days On Market

  Last Listing Agent Elise Kamp Press/Cuozzo Realtors

  236 Mountain Rd, Cheshire, CT 06410
• 

  Est $565,262

  Not Listed For Sale

  122 Thorn Hollow Rd, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 2,032 Sq Ft
  • Built 2008

  122 Thorn Hollow Rd, Cheshire, CT 06410

  Last Sold Summary

  • 83 Days On Market
• 

  

  /37

  $659,900

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,124 Sq Ft

  59 Williams Rd, Cheshire, CT 06410

  Some homes check the boxes. This one checks them all and then pulls you in with something harder to quantify: the feeling that you've found exactly where you're supposed to be. Tucked away on a private rear acre in one of Cheshire's most coveted in-town locations, this beautifully maintained 3-4 bedroom, 2.5-bath colonial offers the rare combination of peaceful seclusion and unbeatable

  Leanne Delrosso Lamacchia Realty

  59 Williams Rd, Cheshire, CT 06410
• 

  $285,000

  Sold Jan 27, 2026

  40 Southwick Ct Unit 201, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 954 Sq Ft
  • Built 2000

  Last Sold Summary

  • $299/SF
  • 52 Days On Market

  Current Estimated Value $280,645

  Last Listing Agent Julie Luchina Coldwell Banker Realty

  40 Southwick Ct Unit 201, Cheshire, CT 06410
• 

  Est $592,606

  Not Listed For Sale

  105 Thorn Hollow Rd, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 2006

  105 Thorn Hollow Rd, Cheshire, CT 06410

  Last Sold Summary

  • 6 Days On Market
• 

  

  /40

  $949,900

  Under Contract

  • 4 Beds
  • 4 Baths
  • 4,154 Sq Ft

  699 Andrea Ct, Cheshire, CT 06410

  Perfectly maintained and beautifully appointed Colonial set at the end of a cul-de-sac in one of Cheshire's most desirable neighborhoods. Surrounded by higher-end homes on 1.86 private, park-like acres, this property is ideal for both everyday living and entertaining. The eat-in kitchen features granite countertops, center island, stainless steel appliances, double wall ovens, cooktop, built-in

  Stacey Deangelis Calcagni Real Estate

  699 Andrea Ct, Cheshire, CT 06410
• 

  $590,000

  Sold Feb 13, 2026

  100 Lynwood Drive Extension, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft
  • Built 1955

  Last Sold Summary

  • 10% Above List Price
  • $434/SF
  • 4 Days On Market

  Current Estimated Value $565,248

  Last Listing Agent Julie Corrado Coldwell Banker Realty

  100 Lynwood Drive Extension, Cheshire, CT 06410

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