5,730 properties for sale in Cheshire Village, Cheshire town New Haven County Connecticut

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Exceptional, beautifully built, updated and maintained, custom center hall Colonial on over 1 acre of private, professionally maintained gardens and yard. Property abuts open space. Bluestone steps and stone walls surround this magnificent home. Hardwood floors throughout. Newer granite, tiled kitchen features large island,wet bar, wine cooler and window seat with storage. Kitchen by Gedney. Family room has white-washed brick, propane fireplace, built in cabinetry and slider to large deck. Front and rear paver walkways with stunning gardens. First floor laundry (12x9) has sink, under counter washer/dryer, built in hamper and ironing board. Formal living room (currently used as office)and formal dining room. Primary bedroom has remodeled bath with shower. 3 additional generous bedrooms and remodeled full bath. Lower level has over 500 sf - 2 carpeted rooms and fabulous wine cellar. Lower level has separate heat/ac zone 3 zones. Pull down stairs in garage for extra storage

Move In ready! Home Sweet Home! Look No Further! Tired of hearing the same old thing' 950 Peck Lane is so amazing, you will stop your search here! Come see for yourself what this 3 bedroom 1 1/2 bath ranch style home offers and watch your wish list dwindle to nothing. Outstanding features include beautiful hardwood floors throughout, updated kitchen and baths, a 1 car attached garage, central air. Outside welcomes you to a deck and gorgeous, level backyard with direct access to Farmington Canal Rail Trail where morning walks or bike rides start or end your day. Siding, Septic Tank, Driveway, Roof, Well Water Tank have all been replaced since 2013. Whole house generator and security system are additional features a new homeowner will inherit. See complete list of upgrades with dates in attachments. This home is 100% ready for a new homeowner to enjoy for years to come

Welcome to The Cheshire Estate on Whispering Hollow Court. Set on a private 1.84-acre lot in an intimate enclave of homes on a cul-de-sac, this modern brick Colonial offers over 10,000 sf of living space across three levels - a rare opportunity to live comfortably and entertain often. The two-story great room anchors the main level, with French doors opening to the patio, outdoor kitchen, and pool for effortless indoor/outdoor entertaining - enjoy quiet mornings by the water and evenings out back to socialize. The main level also features the primary suite, complete with a private sitting room and fireplace - a true retreat at the end of the day - along with a sunroom and a wood-paneled study. The finished lower level adds a home gym and an indoor basketball court, convertible to a squash or racquetball court, so game nights and workouts happen without ever leaving home. Adding rare flexibility, a semi-private au pair apartment (approx. 40' x 22') includes its own kitchen, full bath, l

Best and Final offers due Wednesday July 15th at Noon. *Welcome home to this beautifully maintained Cape offering 4 bedrooms, 2 full baths, and 1,678 square feet of comfortable living space on a level.48-acre lot. The inviting main level features a spacious family room with hardwood flooring that opens to the beautifully updated kitchen with granite countertops, creating the perfect space for everyday living and entertaining. The living room and dining room also feature hardwood floors, while a first-floor bedroom and full bath provide flexible living options. Enjoy year-round views of the picturesque backyard from the gorgeous sunroom with tile flooring and sliders leading to the expansive paver patio-ideal for outdoor dining, relaxing, and entertaining. Upstairs, you'll find three additional bedrooms and a second full bath. Additional highlights include an attached two-car garage, city water and city sewer, and a brand-new roof (2026). Conveniently located with sidewalks and just a s

Welcome to 380 Hitchcock Road, a beautifully maintained townhouse nestled in the highly desirable Countrywood Hills community. Offering the perfect blend of comfort, convenience, and value, this inviting townhome features 2 spacious bedrooms, 1 full bath, and 1 half bath. Step inside to a bright and airy living room highlighted by a charming bay window with built-in seating, creating the perfect place to relax, unwind, or enjoy your favorite book. The spacious eat-in kitchen offers ample cabinet space, a generous pantry, and easy access to the conveniently located half bath. Sliding glass doors lead to a large private deck, which overlooks a beautiful pond, providing the ideal setting for outdoor dining, entertaining guests, or enjoying your morning coffee. Upstairs, you'll find two generously sized bedrooms, each offering abundant closet space and plenty of natural light. Additional features include central air conditioning, an attached one-car garage, a dedicated laundry room with ex

Welcome to The Cheshire Estate on Whispering Hollow Court. Set on a private 1.84-acre lot in an intimate enclave of homes on a cul-de-sac, this modern brick Colonial offers over 10,000 sf of living space across three levels - a rare opportunity to live comfortably and entertain often. The two-story great room anchors the main level, with French doors opening to the patio, outdoor kitchen, and pool for effortless indoor/outdoor entertaining - enjoy quiet mornings by the water and evenings out back to socialize. The main level also features the primary suite, complete with a private sitting room and fireplace - a true retreat at the end of the day - along with a sunroom and a wood-paneled study. The finished lower level adds a home gym and an indoor basketball court, convertible to a squash or racquetball court, so game nights and workouts happen without ever leaving home. Adding rare flexibility, a semi-private au pair apartment (approx. 40' x 22') includes its own kitchen, full bath, l

Everything you have been looking for is waiting for you in this fabulous home in great neighborhood in the desirable south end of Cheshire and is part of the Roaring Brook Association that offers amazing hiking trails and nature walks. Remodeled custom kitchen and bathrooms, open floor plan that walks out to bright sunroom with electric heat to extend season overlooking private yard with blue-stone patio and firepit. Beautifully decorated with neutral colors makes it easy to see yourself in this lovely home. Kitchen is open to great room with wood burning fireplace, large dining room, first floor office space, and welcoming foyer. Upstairs you have a large Primary suite and three additional bedrooms. Lower level includes a finished office, family room, and workout space. Just pack your boxes and move right in!

Set on a quiet cul-de sac on almost 2.5 acres, this spacious 4 bedroom, 2.5 bath colonial with lower level finished area and walk out, offers an exceptional opportunity to create something truly special in a highly desirable location. The setting- adorned with mature trees and flowering plants on a large parcel is just lovely, yet is close to all the everyday conveniences. This home features a Classical Colonial layout with generous sized rooms, many hardwood floors, a nice flow, and abundant potential to reimagine the space to your tastes and needs. Seize the opportunity to build equity in a prime town location. Recent updates include New primary bath shower, updates to half bath, painting, new kitchen slider, new lower level french door and more. (see list) Other updates 2023 well pump/ 2021 Trane A/C, 2019 HW heater/ 2016 Water softener/ newer washer dryer. Enjoy the amenities of the Town of Cheshire- Bartlem Park and Town Pool, Farmington Trail, Mixville Recreation area, open space

Exceptional, beautifully built, updated and maintained, custom center hall Colonial on over 1 acre of private, professionally maintained gardens and yard. Property abuts open space. Bluestone steps and stone walls surround this magnificent home. Hardwood floors throughout. Newer granite, tiled kitchen features large island,wet bar, wine cooler and window seat with storage. Kitchen by Gedney. Family room has white-washed brick, propane fireplace, built in cabinetry and slider to large deck. Front and rear paver walkways with stunning gardens. First floor laundry (12x9) has sink, under counter washer/dryer, built in hamper and ironing board. Formal living room (currently used as office)and formal dining room. Primary bedroom has remodeled bath with shower. 3 additional generous bedrooms and remodeled full bath. Lower level has over 500 sf - 2 carpeted rooms and fabulous wine cellar. Lower level has separate heat/ac zone 3 zones. Pull down stairs in garage for extra storage

Welcome to a truly unique opportunity in Cheshire! This legal two-family property offers exceptional versatility, space, and potential, making it ideal for extended family, an in-law arrangement, or generating additional rental income. Set on over 2 acres in a peaceful setting and located within Cheshire's award-winning school district, this property is a rare find. The main residence offers an inviting blend of character and functionality, featuring a wraparound porch, French doors, an open-concept kitchen and dining area, and a cozy living room highlighted by a beautiful stone fireplace. A wide, elegant staircase leads to the second floor, where you will find four generously sized bedrooms. The spacious primary bedroom features two walk-in closets and a private bath with a Jacuzzi tub. Three additional bedrooms offer generous proportions and ample closet space. Attached to the main home is a separate one-bedroom apartment with its own private entrance and porch, providing excellent f

Build your dream Carriage Home from the ground up at The Reserve at Stonebridge Crossing-Cheshire's premier low-maintenance community by EG Home. This spacious 2,450 sq ft floor plan offers the perfect blend of comfort, flexibility, and energy efficiency, with the opportunity to personalize every detail. Create your ideal kitchen by selecting from EG Home's curated layouts, including our Pro Kitchen with 42 upper cabinets, 36 induction range, and professionally vented hood, or elevate your space with the Chef's Kitchen featuring a 36 cooktop and double-oven configuration. Choose a linear or classic electric fireplace to define your Great Room, and consider options such as a finished Rec Room adding 525 sq ft of living space, optional deck stairs for outdoor access, or plumbing for a future bath. Buyers also enjoy a private appointment in our 2,500 sq ft Design Center, where a certified interior designer helps bring each home's aesthetic vision to life with confidence and creativity. Ph

Fantastic location for this expansive ranch. Offering sunroom, hardwood flooring throughout the home, Fireplaced living room, open layout Flat yard unfinished lower level for even more expansion Updated heating, central air-conditioning. oversized 2/3 car garage. this home is in one of the most desirable locations in Cheshire Must see

Welcome home to 125 Wallingford Road in Cheshire, CT! Loaded with curb appeal from the moment you arrive, this sweet 1900s home welcomes you with a wonderful wrap-around porch and fenced-in back yard. Extensively renovated in 2009, this charming 3-bedroom, 2-bath home beautifully blends modern updates with the character of its era. Inside, natural light fills the open main level, where wide red oak hardwood floors run throughout. The updated kitchen features white cabinetry, granite countertops, stainless steel appliances and a butcher-block-topped island with seating-perfect for casual meals, working from home or gathering with friends. Two dining areas offer flexibility for everyday living and entertaining. A convenient entry by the back door helps keep things organized, while an office off the kitchen provides a dedicated workspace. There is a main level, beautifully updated full bath with tub/shower combination. Upstairs are three comfortable bedrooms with hardwood floors and anoth

Welcome to this stately 3,855 square-foot brick Colonial, perfectly situated on a beautifully level lot in a lovely neighborhood. This spacious 4-5 bedroom home offers timeless elegance and exceptional amenities designed for comfortable living and effortless entertaining. Inside, you'll find gleaming hardwood floors throughout most of the main level and a thoughtfully designed floor plan featuring a large eat-in kitchen with abundant cabinetry and workspace, ideal for everyday living and hosting family and friends. The home also features a spacious great room, perfect for gathering and relaxing, as well as a private home office that provides an ideal space for remote work or study. The convenience of an upper-level laundry room adds ease to daily living. Central air conditioning enhances comfort throughout the home. Step outside to your own private backyard retreat! Enjoy summers in the heated in-ground pool with an attached spa, relax on the expansive patio, or entertain guests in the

Charm abounds in this custom built reproduction Saltbox completely remodeled down to the studs featuring 5 bedrooms and 3 1/2 tiled baths. Home is in a picturesque setting with spring fed pond on almost 2 acres. Sparkling hardwood floors througout the home. Gracious large living room features hardwood floors, fireplace and wood storage box. Brand new kithen remodeled down to the studs, featuring quartz counters, retractable potfillers for both the GE glass cooktop and coffee bar. First floor laundry and half bath. 4 bedrooms each with ceiling fans on the 2nd floor including the Primary with full bath. 3d floor walk-up offers a 5th bedroom with full bath perfect for guests or an au-pair. Views to the pond from the 3-season porch. Additional space is in the finished basement area with a fireplace. Detached garage loft has electricity and potential for a separate work area

Temperately off market was to refinish the hardwood floors, the deck, and some additional work being done to the property. Located on a cul-de-sac in the desirable Nob Hill section of Cheshire, The main level has a huge front to back Family room with a fireplace, oversized windows, closet and sliders leading to a multi level IPE deck with benches and pergola. Formal dining room and living room also have oversized windows, crown molding. Remodeled kitchen with an island and eat-in area. Counters are white corian with black granite on the island. Stainless steel appliances. Entire first floor is hardwood except for tile floor in the kitchen. Large bedrooms and great closet spaces. All of the bedrooms have ceiling fans. The primary bedroom has walk-in closet, tiled stall shower with remodeled full bathroom. 2nd bedroom has a walk-in closet as well. Lower level has an office and a rec room. Furnace, C/A, Hot water heater and Oil tank were replaced in April 2025. Septic system is only 5 yea

Welcome to this exceptionally rare standalone condo in the highly desirable Copper Hill community of Cheshire. Perfectly situated in a premium location, this beautiful three bedroom, two full bath home offers the ease of one level living with an open, airy floor plan designed for today's lifestyle. The spacious living room features soaring vaulted ceilings that create a bright and inviting atmosphere, flowing seamlessly into the dining area and kitchen, ideal for everyday living and entertaining. The home has also been updated with newer windows and sliding doors (2023), Climatech A/C (2024) enhancing energy efficiency, comfort and natural light. The thoughtfully designed layout provides comfortable living spaces and generous natural light throughout. The finished lower level offers exceptional versatility, providing the perfect space for a family room, home office, fitness area or recreation room, along with a dedicated work area for hobbies, projects or additional storage. Whether yo

Seller is asking for highest and best Due 12 pm on Tuesday August 18th. * Welcome to 25 Stacy Court, a well-maintained raised ranch set on 0.92 acres in a desirable Cheshire cul-de-sac. Offered by the original owners after 55 years, this 1,905-square-foot home features three bedrooms, one full and one half baths, hardwood floors throughout the main level and plenty of indoor and outdoor living space. The living room has vaulted ceilings, a wood-burning fireplace and opens to the dining room, where a newer slider leads to the Trex deck. Three bedrooms and one full bath offering a tub, double-sink vanity and granite countertop complete the main level. Downstairs, the carpeted family room features a second wood-burning fireplace, along with a half bath, laundry area and access to the attached two-car with newer doors. Enjoy summer days around the in-ground vinyl pool with concrete surround and pool house. Additional features include a whole-house fan, gutter guards, paver side walk, and n

Welcome to the opportunity to build your dream home in a highly desirable location. Nestled on a secluded rear lot that is just under an acre, this thoughtfully designed 4-bedroom, 2.5-bath Colonial will offer 2,792 square feet of beautifully crafted living space with the perfect blend of privacy and modern comfort. Designed with today's lifestyle in mind, the open concept layout will seamlessly connect the kitchen, dining, and living areas-ideal for both everyday living and entertaining. The spacious primary suite will feature a private en-suite bath and generous closet space. With ample room for customization, buyers will have the opportunity to personalize finishes and selections to truly make this home their own. Enjoy the serenity of a tucked away setting while still being close to everything this sought after area has to offer. Don't miss the chance to create your perfect home from the ground up!

Beautifully designed home in desirable Stonebridge Riverside by EG Home, offering approximately 2,950 sq. ft. of total finished living space. This energy-efficient residence features 3 bedrooms, 2.5 baths, a dedicated office room, a versatile loft, and a finished basement with rough-in plumbing for a future full bathroom. The open-concept main level includes a spacious kitchen, dining area, and great room, while the first-floor primary suite offers a private bath and walk-in closet. Thoughtful upgrades include a private deck, attached 2-car garage, ceiling fans in all bedrooms, and a humidity control/ventilation system integrated with the home's high-performance HVAC setup. Enjoy low-maintenance living in a well-kept HOA community with exterior maintenance, landscaping, snow removal, trash service, and common area upkeep. Residents also have access to community recreation areas with grills, offering a great setting for relaxing and entertaining outdoors. High-performance construction,

The Carriage Home floor plan combines architectural elegance with EG Home's high-performance building standards. Constructed with 2 X 6 exterior walls, double-pane double hung windows, and a layered insulation system of spray foam, batting, and blown-in insulation, each home is built for quiet comfort and lasting energy efficiency. A cold-climate heat pump and Energy Recovery Ventilator (ERV) system provide exceptional air quality and consistent year-round performance. Residents at The Reserve at Stonebridge Crossing enjoy a 1/4-mile walking loop surrounding a covered pavilion with gas fire pits, grills, picnic tables, and power outlets-perfect for gatherings in every season. The loop connects directly to a walking trail leading to the new Shoppes at Stonebridge for convenient dining, coffee, and shopping. The HOA covers exterior maintenance, landscaping, snow removal, and trash service, offering a truly low-maintenance lifestyle. Passive solar installations help offset monthly HOA due

Temperately off market was to refinish the hardwood floors, the deck, and some additional work being done to the property. Located on a cul-de-sac in the desirable Nob Hill section of Cheshire, The main level has a huge front to back Family room with a fireplace, oversized windows, closet and sliders leading to a multi level IPE deck with benches and pergola. Formal dining room and living room also have oversized windows, crown molding. Remodeled kitchen with an island and eat-in area. Counters are white corian with black granite on the island. Stainless steel appliances. Entire first floor is hardwood except for tile floor in the kitchen. Large bedrooms and great closet spaces. All of the bedrooms have ceiling fans. The primary bedroom has walk-in closet, tiled stall shower with remodeled full bathroom. 2nd bedroom has a walk-in closet as well. Lower level has an office and a rec room. Furnace, C/A, Hot water heater and Oil tank were replaced in April 2025. Septic system is only 5 yea

Beautifully updated, move-in-ready ranch tucked away on a quiet cul-de-sac in desirable Cheshire! Offering 3 bedrooms and 2.5 bathrooms, this home combines modern updates and comfortable single-level living in a perfect location. Refinished hardwood floors lead to a spacious living room with a cozy fireplace and an inviting dining room with direct access to the oversized deck. The updated kitchen showcases white shaker soft-close cabinetry, quartz countertops, a tiled backsplash, and brand-new stainless steel appliances. Down the hall, you'll find two generously sized bedrooms and a full bathroom, along with a private primary suite featuring double closets and its own beautifully updated full bathroom. The fully finished lower level provides even more living space, featuring luxury vinyl flooring, a large open area ideal for a family room, a half bathroom with modern finishes, and a versatile bonus room that could serve as a 4th bedroom, home office, gym, or guest space. The lower leve

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 old, perfect for entertaining. Recent improvements include Andersen replacement windows, a new boiler, 2022 Smart indirect hot water tank, upgraded 200-amp electrical service, new oil tank, insulated Bilco basement door, and a 2-year-old driveway. A Generac whole-house generator (2021), fueled by leased propane, provides added peace of mind. With open fields directly across the street, this home offers enhanced privacy, beautiful open views, and the opportunity to enjoy birds, deer, and other local wildlife right from your front yard. Conveniently located within walking distance of Doolittle Schoo

Welcome to this stately 3,855 square-foot brick Colonial, perfectly situated on a beautifully level lot in a lovely neighborhood. This spacious 4-5 bedroom home offers timeless elegance and exceptional amenities designed for comfortable living and effortless entertaining. Inside, you'll find gleaming hardwood floors throughout most of the main level and a thoughtfully designed floor plan featuring a large eat-in kitchen with abundant cabinetry and workspace, ideal for everyday living and hosting family and friends. The home also features a spacious great room, perfect for gathering and relaxing, as well as a private home office that provides an ideal space for remote work or study. The convenience of an upper-level laundry room adds ease to daily living. Central air conditioning enhances comfort throughout the home. Step outside to your own private backyard retreat! Enjoy summers in the heated in-ground pool with an attached spa, relax on the expansive patio, or entertain guests in the