Cheshire, CT Homes

• 

  Est $359,742 Not Listed For Sale

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

  28 Southwick Ct, Cheshire, CT 06410

  28 Southwick Ct, Cheshire, CT 06410
• 

  

  

  /40

  $1,200,000

  • 4 Beds
  • 4.5 Baths
  • 4,791 Sq Ft

  1 Mountaincrest Dr, Cheshire, CT 06410

  PREMIUM WOOD FLOORS JUST INSTALLED in this Mountaincrest custom colonial showcasing luxurious living & elegant entertaining. A dramatic two-story foyer sets a grand tone, leading to a private office. A stunning kitchen exudes sophistication-highlighting a massive center island seating 5, imported granite countertops, opulent backsplash, & top-tier Bosch appliances & Sub-Zero. The opulent kitchen

  Susan Santoro William Pitt Sotheby's Int'l

  1 Mountaincrest Dr, Cheshire, CT 06410
• 

  $500,000 Sold Oct 30, 2025

  • 1,375 Sq Ft
  • $364/SF
  • 34 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  64 Warren St, Cheshire, CT 06410

  ALL OFFERS DUE BY 4PM TODAY, SEPT. 30TH. Located right in the center of town, this beautifully updated home blends modern upgrades with neighborhood charm. Step inside to a fully remodeled kitchen featuring brand-new appliances, a large island with seating, sleek quartz countertops, and stylish finishes - perfect for cooking and entertaining. Enjoy peace of mind with a new roof and a new

  James Bulger Calcagni Real Estate

  64 Warren St, Cheshire, CT 06410
• 

  Est $275,576 Not Listed For Sale

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

  40 Southwick Ct Unit 310, Cheshire, CT 06410

  40 Southwick Ct Unit 310, Cheshire, CT 06410
• 

  

  

  /4

  $869,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,459 Sq Ft

  1511 Blackberry Place, Cheshire, CT 06410

  Can't wait ? Currently under construction! Blackberry Woods, located in the north end, is now building the gracious Charter Oak model which provides 2,459 sqft of thoughtful living space with 4 Bedrooms and 2 1/2 Baths. Desirable features of this plan include a spacious foyer entry with coat closet, mudroom off the garage entry w/ half bath and laundry, an open floor plan including a custom

  Phil Giampietro Coldwell Banker Realty

  1511 Blackberry Place, Cheshire, CT 06410
• 

  $865,000 Sold Oct 29, 2025

  • 4,654 Sq Ft
  • $186/SF
  • 100 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2004

  745 Cook Hill Rd, Cheshire, CT 06410

  Welcome to your dream Colonial in South Cheshire! This 3,561 sq ft Continental Colonial sits on 2.1 professionally landscaped acres at the end of a quiet cul-de-sac. A grand two-story foyer opens to formal living and dining rooms with tray ceilings and elegant millwork. The chef's kitchen features granite counters and stainless steel appliances, flowing seamlessly into a vaulted family room with

  Anubha Agarwal Reddy Realty, LLC

  745 Cook Hill Rd, Cheshire, CT 06410
• 

  Est $285,054 Not Listed For Sale

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

  40 Southwick Ct Unit 304, Cheshire, CT 06410

  40 Southwick Ct Unit 304, Cheshire, CT 06410
• 

  

  /40

  $849,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,815 Sq Ft

  1412 Marion Ave, Cheshire, CT 06410

  HOUSE IS FRAMED AND READY FOR BUYER CHOICES! GREAT NEW CONSTRUCTION READY FOR QUICK DELIVERY FOR NEW OWNERS!! Amazing open layout on this modern colonial. This home is perfect for entertaining with a huge kit island open to a spacious Family Room. The floor plan is versatile with 4 bedrooms on the second floor and a optional 5th bedroom/office on the main level. Perfect for a work from home

  Roy Evjen Evjen Agency

  1412 Marion Ave, Cheshire, CT 06410
• 

  $605,000 Sold Oct 28, 2025

  • 2,362 Sq Ft
  • $256/SF
  • 47 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1974

  31 Iris Ct, Cheshire, CT 06410

  Welcome to this beautiful colonial located in one of Cheshire's most desirable neighborhoods, within a nationally recognized Blue Ribbon school district. As you turn onto Iris Court, you'll be greeted by a quiet, tree-lined cul-de-sac that sets the stage for this charming home. Inside, you'll find spacious living areas with hardwood floors throughout. The bright, sun-filled kitchen features a

  Mikell Foggitt Margaret Bennett Realty

  31 Iris Ct, Cheshire, CT 06410
• 

  Est $230,693 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft

  40 Southwick Ct Unit 303, Cheshire, CT 06410

  40 Southwick Ct Unit 303, Cheshire, CT 06410
• 

  /2

  $825,000 New Construction

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

  Lot 3 Mount Sanford Rd, Cheshire, CT 06410

  Great opportunity to build your dream home on a wonderful level lot in new three-house subdivision in the desirable South end of Cheshire. Award winning builder, Ricci Construction Group, Inc., will build this fabulous home, and you can make all your selections, or use their design team to help make decisions. Builder has a plan that can be customized to meet your needs. Schedule appointment

  Melanie Ricci Coldwell Banker Realty

  Lot 3 Mount Sanford Rd, Cheshire, CT 06410
• 

  $570,000 Sold Oct 27, 2025

  • 1,620 Sq Ft
  • $352/SF
  • 73 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  1016 Split Rock Rd, Cheshire, CT 06410

  Perched gracefully on a gentle knoll, this beautifully maintained 3-bedroom, 2-bath Ranch blends comfort and character in a sought-after neighborhood. The classic brick front adds timeless curb appeal, while vinyl siding on the sides and back ensures low-maintenance living. A spacious composite deck, accessible from sliding doors off the kitchen, provides the perfect setting for outdoor

  Heidi Weed Lamacchia Realty

  1016 Split Rock Rd, Cheshire, CT 06410
• 

  Est $281,736 Not Listed For Sale

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

  40 Southwick Ct Unit 111, Cheshire, CT 06410

  40 Southwick Ct Unit 111, Cheshire, CT 06410
• 

  

  /38

  $675,000 Pending

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

  4 Brookfield Ct, Cheshire, CT 06410

  Nestled in desirable and centrally located Cheshire neighborhood, this beautifully maintained and thoughtfully updated 4-bedroom, 2.5-bath center hall colonial blends timeless elegance with modern comfort. The heart of the home is a stunning remodeled kitchen featuring custom cabinetry, gorgeous pearlescent backsplash, granite counters, stainless steel appliances, a professional vented range

  Brette Stern Calcagni Real Estate

  4 Brookfield Ct, Cheshire, CT 06410
• 

  $427,000 Sold Oct 27, 2025

  • 1,349 Sq Ft
  • $317/SF
  • 51 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1945

  471 Spring St, Cheshire, CT 06410

  HIGHEST AND BEST TOMORROW, 9/12 AT 2 PM. School's back in session, and this Cape is handing out straight A's: A brand-new deck, Beautiful updates, and Convenience with sidewalks leading to coffee, shops, and trails. (Recess = your private patio and level yard, completely fenced in so pets can join the fun.) Inside, the remodeled galley kitchen is sharp with granite counters, custom cabinets, and

  Kim Dawson Real Broker CT, LLC

  471 Spring St, Cheshire, CT 06410
• 

  Est $236,067 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft

  40 Southwick Ct Unit 104, Cheshire, CT 06410

  40 Southwick Ct Unit 104, Cheshire, CT 06410
• 

  

  /40

  $675,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft

  118 Harrison Rd, Cheshire, CT 06410

  This 2,676 sq. ft. colonial offers space, versatility, and privacy on over an acre of beautifully landscaped property. The home features four generous bedrooms and two and a half baths, plus an additional accessible full bath with a shower, toilet, and sink conveniently located in the front office; ideal for in-home care or extended guest accommodations. The first floor showcases hardwood

  Nicole Staples Coldwell Banker Realty

  118 Harrison Rd, Cheshire, CT 06410
• 

  $510,000 Sold Oct 24, 2025

  • 3,416 Sq Ft
  • $149/SF
  • 11 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1962

  332 Academy Rd, Cheshire, CT 06410

  Architecturally designed Contemporary home on 2.83 scenic acres! Mid century Modern style! Located close to town in a country setting. Bright & sunny with beautiful backyard views. Open floor plan, a stone fireplace, wood parquet floors & 3 bedrooms on the main floor. 32 x 7 foot deck off living & dining rooms with views! The lower level walk-out can be a possible in-law apartment with another

  Laura Bitondo Berkshire Hathaway NE Prop.

  332 Academy Rd, Cheshire, CT 06410
• 

  Est $279,664 Not Listed For Sale

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

  70 Southwick Ct Unit 211, Cheshire, CT 06410

  70 Southwick Ct Unit 211, Cheshire, CT 06410
• 

  

  /38

  $714,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,427 Sq Ft

  31 Nathan Hale Ct, Cheshire, CT 06410

  Multiple offers, deadline 10/6, 5:00 PM. Tucked away on 3.5 beautiful acres this spectacular home welcomes you with timeless elegance & thoughtful design. From custom millwork & charming wainscoting, to detailed floor inlays & crafted ceiling, every detail was curated to impress. Fabulous, open floor plan flows effortlessly from the modern kitchen-with a large center island, sleek granite

  Dorothy Karska-Piech Calcagni Real Estate

  31 Nathan Hale Ct, Cheshire, CT 06410
• 

  $180,000 Sold Oct 24, 2025

  • 870 Sq Ft
  • $207/SF
  • 99 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1964

  1109 Waterbury Rd Unit 1A, Cheshire, CT 06410

  Step into modern comfort with this well-maintained 870 sq ft single-level condo featuring two bedrooms, a full bath, and open living/dining area. Enjoy a spacious kitchen and attached basement garage. Nestled in a serene, lightly wooded complex with shared laundry, coin-op basement facilities, and pet-friendly rules (cats only). Just minutes from I84/I691, top-rated schools, shopping, and

  George Noujaim Dave Jones Realty, LLC

  1109 Waterbury Rd Unit 1A, Cheshire, CT 06410
• 

  Est $224,158 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft

  70 Southwick Ct Unit 209, Cheshire, CT 06410

  70 Southwick Ct Unit 209, Cheshire, CT 06410
• 

  

  /4

  $825,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,419 Sq Ft

  Lot 1 Mount Sanford Rd, Cheshire, CT 06410

  Everything you have been waiting for in this new construction home on beautiful lot in the South end of Cheshire. Great open floor plan with office, flex room, mud room, custom kitchen with walk in pantry and island, hardwood floors throughout except tile in baths, Four bedrooms, dining room, great room with propane fireplace, and lovely back yard patio. Don't wait, you can still make custom

  Melanie Ricci Coldwell Banker Realty

  Lot 1 Mount Sanford Rd, Cheshire, CT 06410
• 

  $1,500,000 Sold Oct 23, 2025

  • 4,981 Sq Ft
  • $301/SF
  • 57 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  50 Abrams Rd, Cheshire, CT 06410

  Welcome to a spectacular retreat in Southern Cheshire's coveted Mountaincrest neighborhood. This stunning 4-bedroom home is filled with natural light, thanks to oversized windows & skylights throughout. A dramatic two-story foyer leads into a spacious living room with cathedral ceilings and a cozy fireplace, setting the tone for a warm, inviting layout. The living room flows beautifully into a

  Susan Santoro William Pitt Sotheby's Int'l

  50 Abrams Rd, Cheshire, CT 06410
• 

  Est $353,039 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft

  102 Southwick Ct, Cheshire, CT 06410

  102 Southwick Ct, Cheshire, CT 06410
• 

  

  /20

  $529,900 Pending

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

  136 Shea Cir Unit 136, Cheshire, CT 06410

  DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious exterior unit townhome in a desirable location. This maintenance-free community will have a covered pavilion, fire pit, walking loop, and trails. A convenient location offers

  Michael Helmuth EG Group Realty LLC

  136 Shea Cir Unit 136, Cheshire, CT 06410
• 

  $750,000 Sold Oct 21, 2025

  • 2,345 Sq Ft
  • $320/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  625 Tamarack Rd, Cheshire, CT 06410

  This immaculate 3 bedroom, 2 bath split-level ranch sits on a well-manicured 1.84 acre lot, lined with luscious trees in the backyard for extra privacy. 625 Tamarack Rd's open floor plan with floor-to-ceiling windows allows for a flood of natural light all throughout the house! Gleaming hardwood floors throughout this main level with granite accents offer a luxurious vibe without being

  Peter Digangi Dow Della Valle

  625 Tamarack Rd, Cheshire, CT 06410
• 

  Est $588,995 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  87 S Brooksvale Rd, Cheshire, CT 06410

  87 S Brooksvale Rd, Cheshire, CT 06410
• 

  

  /20

  $524,900 Pending

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

  132 Shea Cir Unit 132, Cheshire, CT 06410

  DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious exterior unit townhome in a desirable location. This maintenance-free community will have a covered pavilion, fire pit, walking loop, and trails. A convenient location offers

  Michael Helmuth EG Group Realty LLC

  132 Shea Cir Unit 132, Cheshire, CT 06410
• 

  $547,500 Sold Oct 21, 2025

  • 2,783 Sq Ft
  • $197/SF
  • 72 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1947

  1681 Orchard Hill Rd, Cheshire, CT 06410

  Expansive Cape on a quiet neighborhood street in the south end of Cheshire. Welcome to 1681 Orchard Hill Road - a beautifully expanded Cape Cod-style home nestled on a landscaped .45 acre lot. This exceptional property blends classic charm with modern updates offering the perfect balance of comfort, space, and privacy. Inside, the home features an updated kitchen with SS appliances, granite

  Julie Luchina Coldwell Banker Realty

  1681 Orchard Hill Rd, Cheshire, CT 06410
• 

  Est $363,538 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,556 Sq Ft

  7 Brubaker Rd, Cheshire, CT 06410

  7 Brubaker Rd, Cheshire, CT 06410
• 

  

  /34

  $670,000

  • 3 Beds
  • 2.5 Baths
  • 3,591 Sq Ft

  20 Bramble Way, Cheshire, CT 06410

  Exceptional offering in the highly desirable community of Cheshire Crossing! Elegant 2 story entry foyer, 1st floor office, classic open living room and dining room defined by decorative columns. Gracious 2 story Family room has propane fireplace w marble hearth and is flanked by two windows. The beautifully remodeled and fully applianced kitchen features honed marble island and counters, tiled

  Karen Brimberg William Raveis Real Estate

  20 Bramble Way, Cheshire, CT 06410
• 

  $350,000 Sold Oct 20, 2025

  • 1,512 Sq Ft
  • $231/SF
  • 174 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1947

  3 Cedar Ln, Cheshire, CT 06410

  Recently reduced!!! Motivated seller!!! Welcome to this spacious 8-room, multifunctional ranch, featuring 3 bedrooms and perfectly designed for a home-based office or business. The inviting living room, complete with a wet bar and fireplace, is ideal for entertaining. A doorway leads to the business wing, consisting of three rooms, a kitchen nook, and a half bath. This area also has a separate

  Colleen Caron Barrieau Realty Signature Prop

  3 Cedar Ln, Cheshire, CT 06410
• 

  Est $802,252 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,648 Sq Ft

  50 Harrison Rd, Cheshire, CT 06410

  50 Harrison Rd, Cheshire, CT 06410
• 

  

  /23

  $275,000

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  445 Lincoln Dr, Cheshire, CT 06410

  Three Bedroom raised ranch for sale in desirable Cheshire. Home being sold as-is, where-is. See the upside potential, see the resale value and/or rental value, and make your offer. Come see the tranquil neighborhood and nearby area, and fully enjoy. Investors, and those seeking a home that is not over-priced; come make this yours.

  Justin Marino Marino Realty LLC

  445 Lincoln Dr, Cheshire, CT 06410
• 

  $610,000 Sold Oct 17, 2025

  • 1,854 Sq Ft
  • $329/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1971

  751 Rustic Ln, Cheshire, CT 06410

  Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the heart of Cheshire! This spacious property features numerous recent upgrades, including Gorilla Plank siding, a Trex deck, updated heating and cooling systems, and refinished hardwood floors on the second level. Plus, a hot water tank, EV charger, electric panel and energy-efficient solar panels were all installed this year. The

  Philip Unger LPT Realty

  751 Rustic Ln, Cheshire, CT 06410
• 

  Est $500,479 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  55 Brentwood Dr, Cheshire, CT 06410

  55 Brentwood Dr, Cheshire, CT 06410
• 

  

  /30

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 2,052 Sq Ft

  15 Quarry Village Rd Unit 15, Cheshire, CT 06410

  Discover this beautifully maintained 3-bedroom, 1.5-bathroom condominium located in the desirable Quarry Village subdivision of Cheshire. Built in 1985, this home offers a perfect blend of comfort and convenience. Inside, you'll find a freshly painted interior that creates a bright and welcoming atmosphere. Enjoy modern living with central air conditioning and efficient gas heat, ensuring

  Vincent Masotta Pearce Real Estate

  15 Quarry Village Rd Unit 15, Cheshire, CT 06410
• 

  $199,000 Sold Oct 17, 2025

  • 900 Sq Ft
  • $221/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1966

  478 Oak Ave Unit 68, Cheshire, CT 06410

  Welcome to this inviting second-floor ranch-style condo offering 900 sq. ft. of comfortable living space. This freshly painted unit features two bedrooms, bright living areas, and professionally cleaned carpeting, making it move-in ready. Located in a well-maintained building with a new roof, residents also enjoy convenient shared laundry facilities and a private basement storage unit. Perfect

  Leanne Delrosso Lamacchia Realty

  478 Oak Ave Unit 68, Cheshire, CT 06410
• 

  Est $695,810 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,587 Sq Ft

  5 Brittany Ct, Cheshire, CT 06410

  5 Brittany Ct, Cheshire, CT 06410

Showing Results 121 - 160, Page 4 of 18