108 Houses For Sale in Cheshire, CT

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$329,900Est. Payment
4 Beds | 3 Baths | 2,238 Sqft

73 Pace Drive, Cheshire, CT 06410

House For Sale

Don't miss this Spacious 4 bedroom, 3 full bathroom raised ranch conveniently located in the south end of Cheshire! This home is on a level lot located on a quiet cul-de-sac, easy commute to New Haven and Hartford. Cheshire, Connecticut was recently named to Money's 2020 "Best Places to Live in the U.S. and is known for its' strong public schools. Roof and Central Air 2 years young, furnace and hot water tank, 8 years. This raised ranch won't last long! Call for your showing today!

$374,900Est. Payment
4 Beds | 2 Baths | 2,088 Sqft

140 Chipman Drive, Cheshire, CT 06410

House For Sale

Situated quietly off Rt 10, this spacious Ranch has plenty to offer aside from it's unique charm and endless surprises. With new major renovations including Kitchen, Dining/Family room, Bathrooms, and Bonus Room in basement - it's evident this home has received ample care over the span of it's current ownership. Among the many updates you will notice NEW windows, a NEW Roof (with a 50-year transferrable warranty) and many modern finishes throughout. Offering 4 neat bedrooms and 2 gleaming, chic bathrooms, you will have more than enough space to enjoy! Gather around the Stone-mantled fireplace or the inviting Dining room to create warm memories with your loved ones this season. You must see this gem for yourself and fall in love! Subject to Sellers Securing Suitable Housing. Total Sq ft does not include finished space in basement. See attachments for a list of updates.

$379,900Est. Payment
4 Beds | 3 Baths | 2,044 Sqft

305 Jinny Hill Road, Cheshire, CT 06410

House For Sale

Step into this classic New England 4 bedroom, 2.5 bath Colonial set on almost 2 acres with hardwood throughout. NEW SEPTIC AND WELL PUMP, just installed. The tiled kitchen has plenty of cabinets for all your storage needs. Have your morning coffee in the lovely sun porch with beautiful pine walls, pine ceiling and new windows. Walk onto the trek deck after a long day and view the open backyard. Upstairs you will find the master bedroom with a full bath. In the 3rd bedroom there are built-ins including 2 desks for all your work-at-home or home schooling needs. This room is the only bedroom carpeted but no worries, there are hardwood floors under. Don't miss this well maintained classic.

$382,000Est. Payment
3 Beds | 2 Baths | 2,191 Sqft

360 Wallingford Road, Cheshire, CT 06410

House For Sale

Discover this enchanting and charming property for you to make your own! 360 Wallingford Road is comfortably situated near the center of town, yet tucked away providing you with 3.32 acres of sanctity and the humbling comfort of nature. The expansive outdoor deck is the perfect place for stargazing or BBQ with friends and family. Walk-in to see the incredibly spacious living room w/ cathedral ceiling and fireplace- boasting a rustic, modern feel. Dining room is steps away from the living room flooded with natural light from the sliding glass doors giving one the impression of dining with nature. Family room nearby is the perfect place to kick back and relax with a movie after meals. The floor plan of this exceptional property leads you into the kitchen complete w/ granite countertops, ample cabinet space, and endless views of Connecticuts deciduous forests. First floor master bedroom provides convenience w/ hardwood floors and large windows. Additional bedroom next to master w/ hardwood floors and closet is conveniently located near a full bath. Upstairs, a large 3rd bedroom takes the floor with wall-to-wall carpeting and its own private bath. Bring your creativity for the downstairs- this area boasts custom masonry and a built-in bar. With much space for the ideal work from home environment and close proximity to schools, restaurants, farms, parks and more- come see why this property is perfect for you!

$394,900Est. Payment
4 Beds | 3 Baths | 3,311 Sqft

87 Thistle Court, Cheshire, CT 06410

House For Sale

Amazing space in this lovely 4/5 bedroom, 3 full bath home in desirable Strathmore Woods. Formal living room and dining room with built in china cabinets. Family room with fireplace and door leading out to large screened in porch. Hardwood floors throughout. Master bedroom with updated bathroom and 2 walk in closets. First floor room can be home office or can be a 5th bedroom. Main level updated full bathroom. If you need more space there is also a large finished lower level. New central air. Lovely lot on cul de sac. Association fee of $305 year for open space and playground areas.

$269,500Est. Payment
3 Beds | 1 Bath | 1,473 Sqft

323 Fenn Road, Cheshire, CT 06410

House For Sale

Quality built three bedroom ranch located in desirable south Cheshire. Bright home with hardwood flooring throughout majority of house. Spacious formal living room with gas fireplace. Formal dining room with ceiling fan and attractive built-ins. Fully applianced kitchen right next to laundry for your convenience. Abundance of closets with lots of shelving..great for storage! Three nicely sized bedrooms. Detached garage just steps from house. Picturesque lot abuts acres and acres of peaceful land trust property with acres of hiking trails. 16 x 28 patio with plenty of privacy. Many recent updates: New septic system just installed. New well pump and new well tank. Boiler-5 years old, Oil tank-3 years old, Shed-1 year old. Blue Ribbon Elementary School! City water in street. Convenient location to shopping and restaurants.

$399,900Est. Payment
4 Beds | 3 Baths | 2,032 Sqft

145 Round Hill Road, Cheshire, CT 06410

House For Sale

Pride of ownership abounds this fantastic home on desirable Round Hill Rd and walking distance to Chapman school. Recently updated the eat-in kitchen boasts oak cabinetry and corian countertops. Open to cozy family room with wood burning fireplace. Walk out to spacious deck and very private yard. The formal dining room and living room are great for entertaining. Upstairs is an oversized master bedroom with 2 closets and a new full bath with tiled shower, double sinks and quartz countertop. Three more bedrooms with a walk-up attic for easy storage. Entire house has hardwood floors!All mechanicals have been updated, including furnace and hot water heater(5 years old) Harvey windows were installed only 2 years ago throughout the home for the energy conscious buyer!

$499,900Est. Payment
3 Beds | 3 Baths | 2,860 Sqft

294 Wiese Road, Cheshire, CT 06410

House For Sale

Welcome home! Approaching this beautifully landscaped custom modern ranch, you will first notice the amazing 3-car garage with a wrap around sidewalk that welcomes you to your front door. Step inside to an elegant entrance way with cathedral ceiling that invites you to partake in all the details in your custom home. Walk into your formal living room, inviting you to sit down and enjoy the light from the beautiful windows. Head over to your great room which offers a beautifully rustic stonework gas fireplace that accents the beauty of this room. Step into a chefs dream with this gourmet kitchen with stainless steel appliances, double ovens, granite countertops, and a gas range built into the center island with a sweet breakfast nook which is a perfect spot to enjoy your morning coffee and watching the wildlife outside. Relax in your master bedroom en-suite. The en-suite contains a shower and a jacuzzi soaking tub, and is the perfect way to end a day. Included also in this beautiful home is a laundry room and an office. The 3-car attached garage has epoxy flooring and there is an additional detached 1 car garage that could be a garden, shed or a work space. Follow downstairs to the basement where youll find surprises behind every turn. It entertains a partially finished basement which would be ideal space for an in-law or a gaming room. Youll also discover a usable workroom for the craftsman in you. Close to Rts 10, 68, 70 and I-691 and I-84. This home offers it all!

$450,000Est. Payment
4 Beds | 3 Baths | 3,000 Sqft

495 Chestnut Street, Cheshire, CT 06410

House For Sale

READY SET MOVE! The dream home you've waited for is here. Enjoy the location of a quiet Cul de sac! Be greeted in to this beautiful 4 bedroom 2 & bath Colonial through the expansive front porch with mahogany decking it is a great additional space for outdoor living. The main level features a formal living room with crown moldings and a formal dining room with crown moldings and chair railing, recently painted and feature rich hardwood floors. The large family room offers plenty of living space with a cozy wood burning fireplace, new carpet and is recently painted. Enjoy a completely new kitchen. New cabinets, granite counter, appliances, tile flooring, multi-color under cabinet lighting, recessed lighting.it is all new. To top it off is an additional light filled sunroom right off the kitchen looking out at the beautiful backyard. Upstairs features 4 generous sized bedrooms with plenty of closet space. The en-suite master has hardwood floors and has been recently painted. A huge convenience is having the laundry on the 2nd floor. Never carry it up and down again! The finished basement adds a whole other dimension to the home. First is the large bright main room wired for surround sound. There is an office with custom built ins and an exercise room. Updates include new windows, A/C and a new driveway. Outside features a beautiful level backyard and it comes with a hot tub!...Homes like this do not come along every day. If you want to make it yours make it fast!

$369,900Est. Payment
4 Beds | 3 Baths | 2,598 Sqft

85 Brentwood Drive, Cheshire, CT 06410

House For Sale

Wonderful oversized ranch with in-law addition in South Cheshire, situated in a tranquil neighborhood with lights and sidewalks. Step into the bright open plan living room with hardwood floods, and enjoy the crisp white cabinetry and breakfast bar of your sunny kitchen. Laundry on the main level. The large master bedroom also has hardwood floors and a full bathroom. 2 guest bedrooms with ample closets complete the main home. The in law suite is on the same level with a small kitchenette living room, bedroom with full bath, and an enclosed sun room. Downstairs could be finished to provide even more living space if you need more than this huge ranch provides.

$289,900Est. Payment
3 Beds | 2 Baths | -- Sqft

171 Old Lane Road, Cheshire, CT 06410

House For Sale

Welcome yourself home to this beautiful and recently updated single story ranch. Features include a stunning open concept floor plan that you do not want to miss! Nestled quietly in the woods, this home has three nicely sized bedrooms, two full baths and an attached two car garage. Master bedroom includes full en suite. At the heart of the home is a stunning grand center island begging to be used for entertaining and a gorgeous stone fireplace perfect to keep you warm for those snowy New England evenings. Impeccable hardwood floors throughout the main living area. Separate laundry room off the kitchen. Lovely rear deck that brings you straight into a captivating view of nature eager to greet you with your morning coffee. Close proximity to Route 10, while maintaining your privacy. This awe-inspiring home will not last long-schedule your private showing! **Due to location, owner currently pays property taxes in Cheshire and Hamden: $1,125.50 for Cheshire and $8,241.44 for Hamden in 2020.**

$599,900Est. Payment
5 Beds | 4 Baths | 4,100 Sqft

635 Ashley Court, Cheshire, CT 06410

House For Sale

Centrally located on a cul-de-sac, this classic center hall colonial boarding privately wooded acreage that provides great versatility and comfort to live, work and play. The home offers 2,740 sq ft of living space. Nine-foot ceilings on the first floor with open kitchen, granite counters, stainless steel appliances, center island and open to front-to-back family room with fireplace for those cozy evenings to curl up by the fire. Hardwood floors throughout the main level. Large formal dining room with crown molding open to the living room for those holiday gatherings. Four spacious bedrooms on the second floor including the main en suite with walk-in closet and large attic space for storage. Lower level has a large rec room, plus exercise room or den, home office or craft room, 5th bedroom and full bath. Expansive multi-level patio surrounding an in-ground pool is fantastic for entertaining and provides a serene private outdoor space.

$650,000Est. Payment
4 Beds | 4 Baths | 4,204 Sqft

64 Clearbrook Place, Cheshire, CT 06410

House For Sale

Outstanding newer home set beautifully on a private drive end of a cul-de-sac! This custom-built 2005 home on 3.7ac offers 3704sf, 4 bed/3.5 baths with amazing pride of ownership, attention to detail, craftsmanship woodwork. Top of the line features begin when you enter the 2-story foyer w/ custom wainscoting, the office to the left with french doors & built-in cabinets. To the right is the living & dining room highlighted with custom trimmed columns. Gourmet kitchen w/ custom cherry cabinets, granite & corian counters is a chef's dream! The stainless appliances include tri-vection/convection built-in double ovens plus the 10ft center island offers refrigerator draws, gas 5-burner cooktop. This area opens into a spacious family rm w/ a gas fireplace, built-in cabinetry, surround sound system & speakers. The 1st flr offers hardwood throughout, 9' ceilings and crown moldings in every room. A gracious staircase takes you to the 2nd floor with master en-suite w/ large walk-in closet. Master bath offers double sinks, a walk-in tiled shower & jetted tub. 3 other bedrms include one w/ a full bath and two with built-ins. The 3rd full bath & laundry room complete the 2nd fl. The basement is partly finished with extensive space for storage. There's a lovely private backyard to enjoy serene moments, a pool for summer fun & cool down. Location-location-location, convenient to I84 & 691 highways, Cheshire schools & parks offers best experiences, Blue Ribbon Awards, Rails to Trail parks.

$679,900Est. Payment
5 Beds | 5 Baths | 4,556 Sqft

5 Mountaincrest Drive, Cheshire, CT 06410

House For Sale

Set back on 4.24 acres, this sprawling contemporary located in Mountaincrest has much to offer: lots of living space for the entire family and guests, with generous-sized rooms. 4 bedrooms and 4 full baths, large bright living room with lots of windows, vaulted ceiling & fireplace for those nice, cozy evenings. Updated eat-in kitchen with large stainless steel appliances & pantry overlooking dining room, perfect for hosting & entertaining. The first floor has two rooms and full bath, perfect for a home office, den, kids playroom or additional bedrooms. Attached is a three-room in-law apartment with large eat-in kitchen, laundry, living room with stone fireplace, one bedroom and a full bath. This house has two attached garages to accommodate 3 cars. Possible subdivide opportunity for the large lot, as per engineers.

$1,250,000Est. Payment
5 Beds | 3 Baths | 5,615 Sqft

1181 Sperry Road, Cheshire, CT 06410

House For Sale

GRACIOUS LIVING COLONIAL Welcome home to a peaceful sanctuary on over 3 acres of land including a wooded pasture overlooking the Cheshire Land Trust. This inviting house exudes classic New England style with updated finishes for comfortable living. In the custom kitchen, Viking and SubZero appliances together with Cherry Kennebec Cabinetry and an expansive dining space, make entertaining a dream. Enjoy the convenience of a main level Magnolia-inspired laundry room, true home office, plus space for a home gym or yoga studio. There are three fireplaces, true divided sunny windows, wide plank hardwood floors, abundant storage and handcrafted millwork throughout. Weekend guests are welcomed in 5 bedrooms plus additional spaces that may be closed off for privacy. The open floorplan is flexible to meet your personal needs. Enjoy abundant parking, grassy play spaces, a three car garage, and a delightful potting shed for gardening or passion projects. Your summer days will be spent relaxing in the backyard at your own gunite swimming pool. An Au pair or in-law arrangement has been thoughtfully designed as a two-room space with adjoining bathroom. Cheshire, Connecticut was recently named to Money's 2020 "Best Places to Live in the U.S." Between New York City and Boston, the town is known for strong public and private schools, access to outdoor activities, short commutes to Hartford, New Haven, and institutions of higher learning. Possible horse property. Owner/Agent related.

$689,900Est. Payment
4 Beds | 3 Baths | 4,500 Sqft

929 Summit Road, Cheshire, CT 06410

House For Sale

Outstanding custom home built in 2008. Beautifully set on 1.95 acres, adjacent to nearly 80 acres of open space. Center hall Colonial has wonderful open floor plan with 9ft. ceilings on both floors with 2nd story access via rear staircase. Custom craftsmanship throughout including elegant crown molding on 1st and 2nd floors. Wrap around custom stamped concrete patio with built in firepit, perfect for private outdoor entertaining. Over 1,000 square foot Great Room on walk out lower level with custom Granite top wet bar. Amazing Master bedroom chamber with sitting area and master bath suite that includes Jacuzzi, vaulted ceiling, and upscale lighting. Extra-large Family room offers cozy fireplace with mantle and marble surround. 10 speaker audio system throughout great room and patio.

$439,900Est. Payment
4 Beds | 3 Baths | 2,554 Sqft

265 Sorghum Mill Drive, Cheshire, CT 06410

House For Sale

Welcome to 265 Sorghum Mill Drive! You are immediately welcomed by the warmth of this 4 bed, 2.1 bath colonial set on just over a half acre in an established South Cheshire neighborhood. The entry way with large closet initially greets you with the staircase to the left and to the right is the formal living room with hardwood flooring and french doors connecting to the dining room. Straight ahead is the eat-in kitchen with gleaming white quartz counters with breakfast bar, subway tiled backsplash, beautiful cabinetry & stainless steel appliances. An amazing all season sun porch is just off the eat-in area with access to the deck & a large bay window overlooking the private yard. The sunken family room with continued hardwood flooring has large windows, raised hearth fireplace, a slider leading out to the deck and pool and access to the two car attached garage. A half bath off the front hallway & laundry is tucked away in the kitchen. Upstairs you'll find the bright & spacious bedrooms all carpeted with wonderful closets in each room. There is also linen closet & full bath with a double vanity. The master bedroom suite offers two separate closets and bathroom with double vanity sinks & a shower. The basement offers plenty of storage space with some initial framing for potential finishing. Outside living is easy on the trex decking that offers entertaining space with steps down to the yard as well as decking around the above ground pool.

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