Cheshire CT Real Estate & Homes for Sale

Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy, offer next-level efficiency, comfort, and durability. Standard features include a high-performance cold-weather heat pump, energy recovery ventilator (ERV) for real-time air quality control, rapid hot water delivery system, induction range, triple-pane windows, and spray foam insulation. Beyond your front door, enjoy community amenities like a covered pavilion with grills and firepits, a dedicated walking loop, and nearby trails, including the Farmington Canal Heritage Trail. Plus, explore nearby shopping, dining, and easy commuting routes. It's Time to Live Better! Better Process. Better Performance. Better Future.

Build your own expanded Cape Cod (or bring your own plans) on Blackberry Woods, Cheshire's newest development. 4 bedroom, 2.5 bathroom Maple model with a primary bedroom on the main floor. Oversized family room with fireplace opens to a custom kitchen with island. Formal dining room for get togethers and events. The 1st floor hosts the primary suite with large walk in closet and tile shower, and laundry room, making it a convenient option for those who prefer one level living. 3 Guest bedrooms upstairs ensure there is room for everyone. . The open floor plan Kitchen and Family Room look onto a deck with beautiful views.Walk out basement. Nature lovers will love that Blackberry Woods backs up to over 41 acres of protected, town-owned open space (donated by the developer) perfect for hiking. Easy access to highways, shopping and schools. (Other house models available to chose from. Pricing varies. Our local/custom builder can also price your own plans or help to create a plan that meets all your wishes!)

Welcome to this pristine 4-bedroom Colonial in the highly desirable Moss Farms Village development. This beautifully maintained home is situated on one of the neighborhood's largest lots and nestled on a quiet cul-de-sac. Remodeled kitchen with hardwood flooring, stainless steel appliances, and ceiling fan. Kitchen opens into a vaulted family room with matching hardwood floors, built-in entertainment nook and a cozy wood-burning fireplace. French doors lead to a bright, formal living room. The main room features an open dining area that is perfect for entertaining. Spacious mudroom/laundry room with bench seating sits just off the kitchen with access to the backyard and garage. Upstairs, you'll find four generously sized bedrooms, including a luxurious master suite with an updated bath featuring granite countertops and a stylish tiled tub, as well as a massive 22' x 20' bonus room with ceiling fan and decorative bench seat for extra storage. The lower level is full of natural light and is ready to be finished. Extra-deep two car garage offers plenty of storage. Recent updates include: 2010 gas furnace, 2017 HW heater, 2024 central air, 2012 roof. Enjoy peaceful outdoor living on the gorgeous deck overlooking a babbling brook and professionally landscaped yard with a six-zone irrigation system. This home truly has it all!

Welcome to 454 Castle Glenn-Cheshire's storybook stone castle with timeless charm and smart modern updates, nestled near the center of town on a private, tree-lined lot. Built in 1930 and beautifully updated over the years, this one-of-a-kind 2,803 sq ft home brings character, craftsmanship, and a calming retreat vibe all in one. From the turret and handcrafted stone details outside to the soaring vaulted ceilings and rich wood tones inside, this home is full of personality. The sunken living room feels like something out of a novel-dramatic beamed ceilings, tall windows, and a striking stone fireplace make it the heart of the home. The dining room continues the classic feel with a coffered ceiling, another stunning fireplace, and plenty of space to gather. The kitchen has been fully reimagined with warm terra cotta-style porcelain tile, a central island, and modern stainless appliances-all while keeping the historic feel intact. The layout also features a charming sunroom, walk-in pantry, mudroom, first-floor laundry area, and a cozy library with built-in shelving. Upstairs are four peaceful bedrooms, one with ensuite half bath, each filled with natural light, hardwood floors, and original solid wood doors that give a warm, grounded feel. The layout is ideal for everyday life, with one full bathroom nearby and central air on the second floor (2021) to keep things comfortable. With city water, city sewer, and oil heat, this home is as reliable as it is charming.

Spacious and grand contemporary colonial on a spectacular level one acre lot in a desirable, well-regarded neighborhood. This custom designed home offers a 2-story foyer and kitchen, 10-foot ceilings throughout most of first floor, and so much character. The grandiose entryway greets you with a curved double staircase leading to a bridged balcony overlooking the kitchen and foyer. The great room offers spectacular light and a full wall of beautiful and functional custom built-in cabinetry with window seats. This area is perfect for entertaining, relaxing, or gathering. It features a woodburning fireplace, French doors to a spacious composite deck, and an open layout that flows into the kitchen. The fully equipped kitchen features a spacious island, granite countertops, skylights, and plenty of room for cooking. Completing the first floor is a formal living and dining room along with a cozy, delightful three-season porch offer an ideal spot to relax and enjoy your morning coffee. The second floor offers 3 large bedrooms, and a spacious laundry room. The primary bedroom suite features a primary bath with a large soaking tub, two vanities, and a shower stall. The lower level offers a versatile living space, perfect for an in-law suite, teenager's retreat, playroom, or home gym. It includes a bedroom with a full bath, a family room with sliding doors to the backyard, and a wonderful wine cellar. This is an exceptional, one-of-a-kind and thoughtfully designed home.

Adventure meets opportunity in this well-cared-for 3-bedroom, 2-bath ranch with a finished walk-out basement and a backyard that's anything but ordinary. Backing up to protected land that offers both privacy and play, the current owner has spent years enjoying the outdoors-creating his own dirtbike track right out back. Inside, the home features a clean, well-maintained kitchen and bathrooms that are perfectly functional and ready for your personal touch. The finished lower level adds valuable living space, and with many neighbors having opened up their layouts, there's exciting potential to create a bright, modern open-concept design. A rare find with space to grow and room to ride! Viewings begin Saturday 4/26

Private Cape Estate on 6.53 Wooded Acres - Possibly Subdividable This stunning 14-room Cape offers a serene feel, space, and privacy, set on 6.53 wooded acres and abutting a land trust for even more seclusion. Inside, enjoy a distinct layout featuring 5 bedrooms, 4.5 bathrooms, a mudroom, and a cedar closet for added storage and convenience. Beautiful engineered hardwood flooring enhances the dining room and living room, while hardwood is found throughout most of the home, adding warmth and charm. The kitchen, features Dacor double ovens, quartzite countertops, gas cooktop and a stylish modern design, perfect for hosting and entertaining. The first-floor primary suite is a true retreat, boasting an en-suite bath with a soaking tub and an expansive walk-in closet. Upstairs, you'll find four additional bedrooms along with three full bathrooms, ensuring plenty of space for family or guests. Relax outdoors with a well-maintained in-ground heated pool, featuring a new liner installed in 2022, perfect for summer enjoyment. Equestrian enthusiasts will love the 4-stall barn, offering space for horses or additional storage. For those who need ample storage, in addition to the basement, the 4-car detached garage includes a storage area above-ideal for extra space. This property offers possible subdivision potential, creating exciting investment opportunities. Property being sold As Is.

****Sellers have requested that all - "Highest and Best Offers" be submitted by 6PM - Saturday April 26th, 2025 Who will be the first to find #259 and begin their "new life" in this perfect home...sitting pretty on .47 Acres with nearby neighbor pond perfect for winter ice skating! This home has been well maintained with many upgrades. Spacious formal living room with hardwood floors. Nice sized family room with cozy fireplace that leads into a sunroom/solarium featuring high vaulted ceilings and abundant natural light. The open kitchen/dining room features quartz countertops, tiled backsplash and stainless steel appliances. The center island offers an extra prep space or a quick sit down! Sliders lead to a spacious private patio- perfect for relaxing quietly or gathering to entertain. The entry hallway from the garage/driveway has a large coat closet and separate main level washer and dryer area. The floorplan nicely separates the bedrooms from the main living area. Master has its own bathroom! Downstairs has the best of both worlds, with newly renovated rec room - full carpet (play room, gym, hobbies, office) the unfinished section houses the 'systems'/work bench and extra bulk storage. Central Air to keep you cool... Security system. recently converted propane heat. Come see #259.

This spectacular 4-bedroom Colonial is the BEST of the best!! Perfectly positioned on an expansive .88-acre corner lot in a sought-after, sidewalk-lined neighborhood. From the moment you arrive, you'll be WOWED by the fabulous updates, and spacious layout of this stunning home. Fully renovated from top to bottom, it boasts a sun-drenched living room and an elegant dining room with handsome wainscotting. The breathtaking kitchen is a true showstopper, featuring granite countertops, illuminated glass cabinets, abundant storage, a pantry, breakfast bar, and top-of-the-line stainless steel appliances. Flowing seamlessly from the kitchen, the inviting family room offers a gas fireplace and sliders leading to an oversized deck, ideal for outdoor gatherings. Upstairs, you'll find four generously sized bedrooms and two GORGEOUS remodeled full bathrooms. Gleaming hardwood floors throughout, and the freshly painted interior (all popcorn ceilings removed!) is complemented by beautiful new lighting fixtures. The lower level includes a newly updated playroom and laundry room. (adding an additional 500 sq ft of finished space)Enjoy peace of mind with a fenced-in, flat yard surrounded by pristine white vinyl fencing. With central air, newer roof, vinyl siding, new garage doors, and more, this home checks every box. Conveniently located to shopping and highways. An easy commute to Yale and Quinnipiac, this gem offers the lifestyle you've been dreaming of.

Fabulous south-end raised ranch convenient to shopping, top-rated schools, and the Farmington canal linear path. The heart of this home is a chef's dream kitchen featuring a professional 6-burner gas range with hood vent, stainless steel farmhouse sink, wine fridge, and sleek metallic stainless appliances. An oversized 8.5' x 5' island seats six comfortably and offers generous storage and working space. The open floor plan dining area offers plentiful light with modern light fixtures and a bay window. Off the kitchen is a sunny deck with pergola overlooking a delightful, fenced backyard with a newly lined in-ground pool. The remainder of the upstairs offers 3 generously sized bedrooms including one with an adjacent half bath, plus a full bath, and hardwood flooring throughout (even under the carpets). The lower level features an expansive bedroom with a home office and walk-in closet, plus a large family room with a cozy wood-burning fireplace-ideal for relaxing. All mechanicals and structural items have been updated within the last 2-8 years, including the roof. This home offers a large two car attached garage, and a gorgeous level lot and backyard just waiting for your summer gatherings. This home was built for entertaining! Don't miss your chance to own this spectacular residence.

Welcome to this charming Colonial nestled on a flat half-acre lot in the heart of Cheshire. Inside, you'll find beautiful hardwood floors throughout, four generously sized bedrooms, two and a half baths, and a fully applianced eat-in kitchen, plus classic formal dining and living rooms perfect for entertaining. Just off the family room is a new deck that overlooks a large private backyard complete with 2 storage sheds; an ideal space for relaxing or hosting summer gatherings. The full basement offers an abundance of storage and the opportunity to create even more living space in the future. The roof and driveway have been recently replaced, and the home has been freshly painted. This home is super convenient to local parks, schools, and even nearby orchards for those perfect fall weekends. While in need of some updating, this property offers great bones and a perfect layout, space and flow for today's modern living needs. Don't miss your chance to personalize and create the home you've been envisioning. This is an estate sale- no disclosures. Being sold in "as-is" condition.

Welcome to this centrally located, expanded cape with a park-like yard and updates throughout. Your everyday entrance from the garage provides quick access to the convenient laundry/mudroom (with shower!). The adjacent family room delivers on comfort with a wood beamed-ceiling, wide-plank hardwood floors, the warmth of the wood-burning, brick fireplace, and a delightful sunroom. Step into this sunny eat-in kitchen. You will love the abundance of cabinet space, stainless appliances, and granite counters. Sunlight streams in through the sliders which provide access to an multi-level deck and patio. A formal dining room and spacious living room, plus updated half bath complete the main level. Hardwood flooring throughout the entire home. The second floor delivers three unique bedrooms providing plenty of space, walk-in closets in each, and a delightful primary bedroom with architectural detail and renovated full bath. The renovated main bath is bright and light. The lower level provides finished space for hobbies and playtime. Plus, delight in all your summertime BBQ's and outdoor fun with this expansive backyard. 2-car oversized garage with walk-up ,floored attic. New roof & gutters, 2022.

Welcome to this beautiful updated ranch in the heart of Cheshire. This home has been extremely well cared for and is ready for its next family.This home is in move in ready condition with tons of amenities. The front entry brings you to a wide open living room/dining combo with hardwood floors and custom shelving that surround the propane fireplace insert. Large bay windows bring natural light. The remodeled kitchen with custom cabinets and large island, with built in appliances and cooktop, becomes the gathering space for all. Granite counters, flat cook top stove and built in microwave and oven are just some of the great features. The first floor laundry room brings convenience as its a short distance to the three bedrooms all on the main floor. A large updated full bath on the main level provides easy access for all. The lower level is 744 sq feet of living space with an attached full bath, providing a rec room or possible in law set up. Plenty of shelving and storage also creates an opportunity to use this room any way someone wants. Newer mechanicals include Furnace system, oil tank, in-direct water heater,Basement system with sump pump and back up pump, dehumidifier, central air, and reverse osmosis water system. The exterior of the home has vinyl siding, gutter guards, newer roof, repointed chimney with natural stone facade and s/s chimney liner for the fireplace, An irrigation system provides water for the yard and gardens. Two sheds are also included.

Welcome to 689 S Meriden Rd, This stunning 4 bedrooms and 2 bathrooms colonial is located on Tranquille neighborhood. The main floor features an open concept eat-in kitchen, dining area, and a family room. cozy living room with an inviting fireplace. Custom kitchen with white shaker cabinetry, granite countertop and stainless-steel appliances. The upper level has four large bedrooms with multiple closets and a full bathroom. The walk-out unfinished basement offers great storage and endless possibilities! this home boast New kitchen, new septic system, fresh paint throughout the house, new light fixtures, switch and outlet, and 2 car garages. Ready to move in. Don't miss the chance to make this property yours!

This open-concept ranch blends style, space, and smart updates in all the right ways. The main level features 3 bedrooms and 2 full bathrooms-including a recently updated bath-and a flowing layout anchored by a vaulted ceiling living room with a striking brick fireplace. The kitchen, dining, and living areas connect seamlessly, creating the perfect setup for everyday living and entertaining. Downstairs, a finished lower level adds space with a large family room and an extra bedroom-great for guests, hobbies, or a home office. Outside, enjoy a spacious, level backyard that's both private and perfect for entertaining, complete with an oversized deck. Major upgrades include a brand-new roof and gutters (Sept. 2024), central air with new compressor and lines (2017), there is a 2-car garage for added convenience. This home checks all the boxes-move-in ready and built for comfort.

This is a MUST-SEE PROPERTY. Nestled at the end of a quiet cul-de-sac, this home is the one you've been waiting for. Combining both privacy and a sense of community, it truly stands out in the Deaconwood neighborhood. The family room features a gas fireplace, creating a warm and cozy atmosphere perfect for relaxing with a book, watching TV, or playing board games. During warmer weather, you can enjoy the beautifully landscaped backyard from the patio. If you love cooking and entertaining, you'll appreciate the dream kitchen, which boasts an exceptional storage, an induction range, a trash compactor, double ovens, a large pantry, an expansive island, a full-size refrigerator, and a separate full-size freezer. The kitchen opens into a casual living room, fostering an open and inclusive environment for entertaining or simply unwinding. The second level has four bedrooms and a laundry closet. The primary bedroom features two closets, plus an additional walk-in closet. The en-suite bathroom has heated floors and a Bluetooth fan speaker system. Additionally, this home offers about 700 square feet of extra living space in the basement, ideal for a playroom, exercise area, movie room, or office. The unfinished portion of the basement offers extra space for storage.

Location, Location, Location! Nestled in the heart of town, this bright corner ranch-style condo on the second floor offers the perfect blend of convenience and comfort with easy walking distance to Farmington Canal Heritage Trail, schools, as well as only minutes from Route 10, 68, & shopping at Maplecroft Plaza. Enjoy one-floor living within a private complex that features serene courtyard views and abundant natural light. This gem boasts open living/dining area with new solid prefinished hardwood flooring, two spacious bedrooms with new rigid core vinyl plank flooring, and the bathroom with new shower area. HOA includes HEAT & HOT WATER! The shared basement provides coin-operated laundry and a 450 sq ft private storage area. The unit also has a newer roof with no special assessment! Don't miss this incredible opportunity, act quickly!

Charming Ranch-style home offering 3 bedrooms and 1-1/2 baths, including a convenient half bath in the primary bedroom. Beautiful hardwood flooring throughout enhances the home's warmth and character. The remodeled kitchen boasts sleek quartz countertops and custom built-ins, seamlessly opening into the dining room with charming corner cabinetry. Enjoy the cozy sunroom at the back of the house featuring a gas fireplace-perfect for relaxing year-round. The spacious living room is filled with natural light, featuring a bay window and another fireplace. A separate family room adds extra living space for all your needs. The finished lower level provides even more room for entertainment or storage. Outside, the beautifully manicured yard offers a peaceful retreat, and the home's central location provides easy access to Farmington Canal Walking Trail. A delightful and inviting property in the heart of town! Central air, city water, irrigation system. Home being sold as-is.

Sunny ranch lovingly by one family on a quiet street right near Dodd Middle school. The potential is incredible in this sweet home offering high ceilings, a spacious eat-in kitchen, hardwood under carpeting in living room, cork flooring and hardwood in the bedrooms. Laundry was moved up for convenience. Downstairs you'll find a fun heated rec room for pool or a family room. Vinyl windows and natural gas heating/cooking are a few more perks. Let's not forget the perfectly level lot! Not far from all the wonderful shops and restaurants Cheshire has to offer.

Stylish & Fully Renovated 2 Bedroom Condo in a Peaceful Neighborhood! Look no further, this beautifully remodeled condo is move-in ready! Featuring brand-new windows, modern laminate flooring, updated kitchen and bath, and freshly painted walls. Step into the kitchen boasting quartz countertops, marble backsplash, new cabinetry, and new appliances, a perfect blend of style and functionality. The bathroom has been completely redesigned, showcasing a marble-tiled shower, sophisticated double-sink vanity and new flooring. Enjoy low-maintenance living with just $158/month, covering both oil heat and water. Nestled in a quiet wooded location, this condo offers the perfect balance of tranquility and convenience. Don't miss out, schedule your showing today!

Welcome to 336 Peck, a well-maintained 3 bedroom, 1 bath home that's full of quality features and thoughtful updates. The beautifully remodeled kitchen offers granite countertops, a spacious island and ample cabinetry, flowing seamlessly into a new dining room addition with cathedral ceilings, recessed lighting and plenty of space for gatherings. A dedicated pantry area provides extra storage, while the inviting living room with hardwood floors leads to the bedrooms, including a primary with a stunning new walk-in closet. The finished lower level adds approximately 500 sq ft of versatile living space, perfect for entertaining or a home office. Enjoy newer central air, a backyard patio for outdoor living and a charming playhouse. This home truly has it all!

Inspiring country home. Inground pool, tennis court and equestrian features.

Welcome to Blackberry Woods. Enjoy the Frasier model with 2,821 sqft of living space , w/ 4 Bedrooms and 2 1/2 Baths. This both elegant and practical model features a spacious Foyer with double coat closets, Mudroom and Half Bath off garage entry, open floor plan between the Family Room, Dinette & Kitchen, Gas Log Fireplace, Kitchen Pantry, and a backyard Patio with built-in Firepit! The formal Dining Room and Office perfectly complete the main level. Beautiful Hardwood Flooring is included for the main level living areas and the 2nd floor hallway. Upstairs features the spacious Primary Bedroom with En-suite and walk-in closet, 3 additional Bedrooms (1 with a walk-in closet), Full Bathroom with linen closet, Bonus/Rec Room, and a conveniently located second-floor Laundry Room. Nature lovers will love that Blackberry Woods backs up to over 41 acres of protected, town-owned open space (donated by the developer) perfect for hiking. Easy access to highways, shopping and schools. (Other house models available to chose from. Pricing varies. Our local/custom builder can also price your own plans or help to create a plan that meets all your wishes!)

Welcome to Blackberry Woods, Cheshire's newest neighborhood! This private, secluded lot presents a rare opportunity to build your dream home with a respected local builder known for quality craftsmanship, meticulous attention to detail, and energy-efficient design. The Magnolia model showcases 9' ceilings, hardwood flooring in the main living areas, and a custom-designed kitchen that seamlessly flows into the family room, where a gas fireplace adds warmth and charm. The primary suite offers an en-suite bath and a spacious walk-in closet for ultimate comfort. Tucked away in one of the most private locations within the community, this lot delivers the perfect balance of neighborhood living and serene retreat. Photos shown are of a previously built Magnolia model and include upgrades not reflected in the base price. Make this home truly your own-schedule a consultation today!

Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy, offer next-level efficiency, comfort, and durability. Standard features include a high-performance cold-weather heat pump, energy recovery ventilator (ERV) for real-time air quality control, rapid hot water delivery system, induction range, triple-pane windows, and spray foam insulation. Beyond your front door, enjoy community amenities like a covered pavilion with grills and firepits, a dedicated walking loop, and nearby trails, including the Farmington Canal Heritage Trail. Plus, explore nearby shopping, dining, and easy commuting routes. It's Time to Live Better! Better Process. Better Performance. Better Future.