Cheshire, CT Homes

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  /40

  $295,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,132 Sq Ft

  70 Southwick Ct Unit 204, Cheshire, CT 06410

  Welcome to Southwick, Cheshire's Premier 55+ Community! This beautifully Remodeled 2 bedroom, 2 bath Ranch unit offers one-floor living and exceptional space in a peaceful, private community. Step into a sun-filled open layout featuring NEW laminate flooring throughout. Fully applianced Kitchen with Granite countertops and oak cabinets provide ample storage. Off the living/dining room is a large

  Julie Luchina Coldwell Banker Realty

  70 Southwick Ct Unit 204, Cheshire, CT 06410
• 

  $315,000 Sold Jul 28, 2025

  107 Greens Loop, Cheshire, CT 06410

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

  Last Sold Summary

  • $299/SF
  • 1 Day On Market

  Last Listing Agent Joel Grossman Lamacchia Realty

  107 Greens Loop, Cheshire, CT 06410
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  Est $1,092,136 Not Listed For Sale

  65 Mountain Brook Dr, Cheshire, CT 06410

  • 4 Beds
  • 5.5 Baths
  • 5,993 Sq Ft
  • Built 1983

  65 Mountain Brook Dr, Cheshire, CT 06410

  Last Sold Summary

  • 21% Above List Price
  • $150/SF
  • 325 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Iris Meyer William Raveis Real Estate
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  /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
• 

  $382,000 Sold Sep 08, 2025

  68 Woodland Dr, Cheshire, CT 06410

  • 4 Beds
  • 2 Baths
  • 2,227 Sq Ft
  • Built 1954

  Last Sold Summary

  • 12% Below List Price
  • $172/SF
  • 102 Days On Market

  Current Estimated Value $421,305

  Last Listing Agent Michael DelGreco New England Realty Assoc LLC

  68 Woodland Dr, Cheshire, CT 06410
• 

  Est $779,807 Not Listed For Sale

  215 Mountain Brook Dr, Cheshire, CT 06410

  • 5 Beds
  • 2.5 Baths
  • 3,266 Sq Ft
  • Built 1975

  215 Mountain Brook Dr, Cheshire, CT 06410

  Last Sold Summary

  • 13% Above List Price
  • $212/SF
  • 52 Days On Market

  Last Sold Price $691,000

  Last Listing Agent Sarah Kolman The Heritage Group, LLC
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  /31

  $419,900 Pending

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

  7 Bayberry Rd, Cheshire, CT 06410

  **MULTIPLE OFFERS - HIGHEST & BEST BY TUES 4/7 @ 10AM** Welcome to this well-maintained 3-bedroom, 1.5-bath home set on a level lot surrounded by mature trees in desirable Cheshire. Inside, you'll find hardwood floors throughout and freshly painted interiors that create a bright, move-in ready feel. The main living spaces offer a comfortable flow, while the partially finished basement provides

  Emily Viccaro Coldwell Banker Realty

  7 Bayberry Rd, Cheshire, CT 06410
• 

  $865,000 Sold Oct 29, 2025

  745 Cook Hill Rd, Cheshire, CT 06410

  • 4 Beds
  • 4.5 Baths
  • 4,654 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $186/SF
  • 100 Days On Market

  Current Estimated Value $867,100

  Last Listing Agent Anubha Agarwal Reddy Realty, LLC

  745 Cook Hill Rd, Cheshire, CT 06410
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  Not Listed For Sale

  660 Boulder Rd, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,843 Sq Ft
  • Built 1756

  660 Boulder Rd, Cheshire, CT 06410

  Last Sold Summary

  • $461/SF
  • 27 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Stacey Deangelis Calcagni Real Estate
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  /29

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,810 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
• 

  $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
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  Est $431,321 Not Listed For Sale

  1244 Half Moon Rd, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,052 Sq Ft
  • Built 1960

  1244 Half Moon Rd, Cheshire, CT 06410

  Last Sold Summary

  • 18% Above List Price
  • $347/SF
  • 5 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Mary Edeen Berkshire Hathaway Home Services
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  /36

  $635,000 Under Contract

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

  131 Merwin Cir, Cheshire, CT 06410

  Completely updated Cape Cod-style ranch, custom built with quality craftsmanship throughout! This beautifully maintained home features Marvin Windows and hardwood floors. The formal living room is an inviting space with a fireplace and a beautiful bay window that fills the room with natural light. The stunning kitchen features granite countertops, and stainless steel appliances including a

  Stacey Deangelis Calcagni Real Estate

  131 Merwin Cir, Cheshire, CT 06410
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  $525,000 Sold Apr 21, 2025

  299 Greenbriar Dr, Cheshire, CT 06410

  • 4 Beds
  • 2 Baths
  • 2,186 Sq Ft
  • Built 1959

  Last Sold Summary

  • 5% Above List Price
  • $240/SF
  • 46 Days On Market

  Current Estimated Value $540,806

  Last Listing Agent Brette Stern Calcagni Real Estate

  299 Greenbriar Dr, Cheshire, CT 06410
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  Est $925,326 Not Listed For Sale

  445 Wild Flower Place, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 3,460 Sq Ft
  • Built 1997

  445 Wild Flower Place, Cheshire, CT 06410

  Last Sold Summary

  • 9% Above List Price
  • $246/SF
  • 126 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Betsy Purtell Purtell Realty LLC
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  /32

  $529,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,696 Sq Ft

  346 Village Dr, Cheshire, CT 06410

  Classic Colonial * 0.92-acre private lot * 4 BR, 2.1 BA * 1,696 sf * Quartz kitchen * Hardwood floors throughout * Fireplace family room * French doors to patio * Roof 2022 * Thermopane windows * Electric baseboard heat * Split system * 2-car garage Set on a peaceful 0.92-acre setting in the Town of Cheshire, 346 Village Drive offers classic New England style with thoughtful updates. The

  The Sally Bowman Team Berkshire Hathaway NE Prop.

  346 Village Dr, Cheshire, CT 06410
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  $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 $306,079

  Last Listing Agent Rosalia Casorla Premier Re Group LLC

  11 Fairway Dr, Cheshire, CT 06410
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  Not Listed For Sale

  1330 Sperry Rd, Cheshire, CT 06410

  • 4 Beds
  • 2 Baths
  • 2,686 Sq Ft
  • Built 1948

  1330 Sperry Rd, Cheshire, CT 06410

  Last Sold Summary

  • 4% Above List Price
  • $143/SF
  • 57 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Katie Smith Berkshire Hathaway Home Services
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  /21

  $324,900 Pending

  • 2 Beds
  • 1 Bath
  • 822 Sq Ft

  34 Lakeview Ave, Cheshire, CT 06410

  Welcome to this charming ranch style single family home, thoughtfully updated and conveniently located just minutes from I84 and Route 8, with easy access to the Merritt Parkway and I91 for an easy commute. From the moment you walk in, you will appreciate the bright and refreshed feel throughout. The kitchen has been updated with quartz countertops, stainless steel appliances, and brand new

  Eric Chou eXp Realty

  34 Lakeview Ave, Cheshire, CT 06410
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  $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 $929,526

  Last Listing Agent Elizabeth Urbanski Coldwell Banker Realty

  40 Kensington Ct, Cheshire, CT 06410
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  Est $388,361 Not Listed For Sale

  63 Southwick Ct, Cheshire, CT 06410

  • 2 Beds
  • 2.5 Baths
  • 1,450 Sq Ft
  • Built 1999

  63 Southwick Ct, Cheshire, CT 06410

  Last Sold Summary

  • 9% Above List Price
  • $245/SF
  • 4 Days On Market

  Last Sold Price $355,000

  Last Listing Agent Sarah Murphy William Raveis Real Estate
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  /2

  $360,000

  • 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
• 

  $880,000 Sold Jun 06, 2025

  805 E Johnson Ave, Cheshire, CT 06410

  • 5 Beds
  • 4.5 Baths
  • 4,189 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $210/SF
  • 10 Days On Market

  Current Estimated Value $905,602

  Last Listing Agent Cindy Forlenzo Coldwell Banker Realty

  805 E Johnson Ave, Cheshire, CT 06410
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  Est $266,148 Not Listed For Sale

  70 Southwick Ct Unit 302, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft
  • Built 1998

  70 Southwick Ct Unit 302, Cheshire, CT 06410

  Last Sold Summary

  • 18% Above List Price
  • $205/SF
  • 65 Days On Market

  Last Sold Price $226,000

  Last Listing Agent Phil Giampietro Coldwell Banker
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  /31

  $395,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,491 Sq Ft

  840 Westside Rd, Cheshire, CT 06410

  Inquire immediately-ask your agent to secure this one before it's gone. Welcome to 840 Westside Road in Cheshire, a beautifully updated and meticulously cared-for home set on a prime lot in one of the area's more desirable neighborhoods. From the moment you arrive, you'll notice the curb appeal and thoughtful landscaping. Inside, the home features a stylish NEW kitchen opening seamlessly to the

  Sam Ratner Keller Williams Realty Prtnrs.

  840 Westside Rd, Cheshire, CT 06410
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  $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 $699,074

  Last Listing Agent Heidi Weed Lamacchia Realty

  12 N Pond Rd, Cheshire, CT 06410
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  Est $352,452 Not Listed For Sale

  28 Southwick Ct, Cheshire, CT 06410

  • 2 Beds
  • 2.5 Baths
  • 1,379 Sq Ft
  • Built 1998

  28 Southwick Ct, Cheshire, CT 06410

  Last Sold Summary

  • 5% Above List Price
  • $243/SF
  • 88 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Norinne Byrne Calcagni Real Estate
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  /40

  $509,000 Under Contract

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

  107 Country Club Rd, Cheshire, CT 06410

  Open Saturday 4-4-26 12-2pm Desirable Cheshire neighborhood. Step into this inviting 3bedroom, 2.5bath home and feel the possibilities open up. The moment you walk in, you're greeted by a bright open floor plan that's perfect for everyday living and effortless entertaining. Updated kitchen and bathrooms. The primary bedroom offers comfort and convenience with its own full ensuite bath. Head

  Frank Lazowski Laz Real Estate, LLC

  107 Country Club 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 $420,651

  Last Listing Agent Jessica Danard Coldwell Banker Realty

  1775 Orchard Hill Rd, Cheshire, CT 06410
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  Est $276,571 Not Listed For Sale

  40 Southwick Ct Unit 310, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 1,132 Sq Ft
  • Built 2000

  40 Southwick Ct Unit 310, Cheshire, CT 06410

  Last Sold Summary

  • 20% Above List Price
  • $203/SF
  • 31 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Mollie Abend Berkshire Hathaway Home Services
• 

  /2

  $385,000

  • 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
• 

  $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 $429,954

  Last Listing Agent Phil Giampietro Coldwell Banker Realty

  19 Heath Ct, Cheshire, CT 06410
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  Est $280,743 Not Listed For Sale

  40 Southwick Ct Unit 304, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 1,132 Sq Ft
  • Built 2000

  40 Southwick Ct Unit 304, Cheshire, CT 06410

  Last Sold Summary

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

  Last Sold Price $230,000

  Last Listing Agent Leanne Delrosso Lamacchia Realty
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  /39

  $359,900 Pending

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

  66 Old Towne Rd, Cheshire, CT 06410

  Welcome to Old Towne Condos, a highly desirable center-of-town community offering convenience & walkability. This spacious 1,536 sq. ft., 2-bedroom, 2-1/2 bath Townhouse unit features a welcoming eat-in kitchen at the front of the home, a formal dining room, and a sunken living room complete with a wood-burning fireplace and French doors leading to a covered sun porch. The porch overlooks a very

  The Sally Bowman Team Berkshire Hathaway NE Prop.

  66 Old Towne Rd, Cheshire, CT 06410
• 

  $550,000 Sold Jun 03, 2025

  614 Wiese Rd, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 1,926 Sq Ft
  • Built 1968

  Last Sold Summary

  • 10% Above List Price
  • $286/SF
  • 37 Days On Market

  Last Listing Agent Brette Stern Calcagni Real Estate

  614 Wiese Rd, Cheshire, CT 06410
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  Est $219,104 Not Listed For Sale

  80 Southwick Ct Unit 202, Cheshire, CT 06410

  • 1 Bed
  • 1 Bath
  • 813 Sq Ft
  • Built 2006

  80 Southwick Ct Unit 202, Cheshire, CT 06410

  Last Sold Summary

  • 4% Above List Price
  • $258/SF
  • 22 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Jessica Danard Coldwell Banker
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  /20

  $225,000

  • 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
• 

  $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 $464,209

  Last Listing Agent Karen Klein Coldwell Banker Realty

  202 Mountain Rd, Cheshire, CT 06410
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  Est $284,872 Not Listed For Sale

  40 Southwick Ct Unit 111, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 1,151 Sq Ft
  • Built 2000

  40 Southwick Ct Unit 111, Cheshire, CT 06410

  Last Sold Summary

  • 16% Above List Price
  • $213/SF
  • 45 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Stacey Deangelis Calcagni Real Estate
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  /26

  $849,900

  • 5 Beds
  • 3 Baths
  • 4,352 Sq Ft

  1731 Marion Rd, Cheshire, CT 06410

  Unique Multi-Home Property on Over 3 Private Acres! A rare opportunity to own two homes on one beautiful property in a peaceful, private setting. Property Highlights: Over 3 acres of land R-40 zoning - ideal for farming, gardening, horses, or hobby farm potential Quiet country setting surrounded by nature Endless possibilities for multi-generational living, rental income, or guest house Main

  Nancy Newman LPT Realty

  1731 Marion Rd, Cheshire, CT 06410

Showing Results 161 - 200, Page 5 of 18