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Cheshire Homes for Sale

Newest Sharon Homes For Sale

$699,000
4 Beds ⋅ 2 Baths ⋅ 24193519 MLS
1900 Farm House Homestead on 6.9 Picture-Perfect Acres Enjoy 6.9 sprawling, gently sloping, sunlit acres of cleared meadows, mature landscaping, and Indian Lake Creek framing the back boundary line of the property. This gentleman's farm is fully set up for homesteading and equine enthusiasts. The impressive multi-use barn features two horse stalls, a chicken coop w/eight coops, hayloft, ample space for tractor, storage, & equipment. Barn is outfitted w/electricity & water & there is a run-in on each cleared meadow, plus 2 sheds. Back entrance to a large mud room/pantry area with washer/dryer leads to an open LR/DR/kitchen area combining rustic charm with beams, vaulted ceiling, new appliances, ceiling fans & an abundance of natural sunlight complimented by sky lights. An additional Family Room/Office w/hard wood floors and a Full Bath on main level. Upstairs are 4 Bedrooms & a 2nd Full Bath. A heated storage room separates the house from a 2 car attached, heated garage that includes a brand new, never used generator. Numerous cultural & recreational activities for every season - Sharon Playhouse, Lime Rock Park Racetrack, Mudge Pond, Hiking Trails, Ski Slopes & prestigious Private Schools. Open, enchanting vistas & many more amenities to experience in the precious NW corner of CT. 15 minutes to Metro North. Bring your horses, goats, & chickens & start a homestead, or simply enjoy the peace & beauty of the wide-open acreage. This turn-of-the century gem is ready for you

88 Sharon Valley Rd, Sharon
$575,000
2 Beds ⋅ 1 Baths ⋅ 24192359 MLS
Perched along a quiet country road and completely surrounded by the beauty of nature, this beautifully updated 2-bedroom, 1-bathroom home offers the perfect blend of modern luxury and peaceful rural living. Whether you are looking for a full-time sanctuary or a weekend getaway, this property delivers wide-open spaces and total serenity-all just minutes from town. The heart of the home features premium stainless steel appliances, sleek countertops, custom cabinetry, and a thoughtful layout designed for effortless entertaining and cooking. Step into a bright, airy living space framed by views of the surrounding landscape. The home boasts an inviting flow, highlighted by the stunning new kitchen that opens up to the main living areas. Both bedrooms offer cozy, peaceful retreats at the end of the day, accompanied by a well-appointed full bathroom. The detached 2-Car Garage with loft to Keep your vehicles protected from the elements, and utilize the expansive loft space above as a home office, artist studio, gym, or extra storage. Step outside onto your brand new, private deck. It's the ultimate spot for morning coffee, evening stargazing, or hosting summer barbecues against a backdrop of mature trees and wildlife. Outside, the acreage provides plenty of room to garden, play, or simply soak in the unobstructed views of the great outdoors. Schedule your private tour today and experience country living at its absolute finest.

94 Jackson Rd, Sharon
$680,000
7 Beds ⋅ 4 Baths ⋅ 24188982 MLS
Rare opportunity to own two homes on separate parcels, offering endless possibilities for multi-generational living, rental income, or investment. The main residence is a charming ranch-style home featuring a 2-car garage, beautiful hardwood floors, 2 cozy fireplaces, and a welcoming porch with scenic views, all situated on 1.52 acres. Also included in the sale is a ranch-style two-family home on its own 1.15-acre parcel. This property offers a 1-car garage, hardwood floors, first-floor laundry, and a covered porch, making it an excellent opportunity for additional income or extended family living. Adding to the property's character is a historic corn crib, one of the many unique features that make this offering truly special. Both homes are ready for a new owner to bring their vision and updates, creating an exceptional country estate or investment property. A rare chance to own over 2.6 acres with two homes and endless potential.

21 & 15 Still Meadow Rd, Sharon
$675,000
2 Beds ⋅ 1 Baths ⋅ 24187245 MLS
This c. 1880 Colonial is nestled in the heart of the Village of Sharon. Thoughtfully restored from top to bottom, it is a truly turnkey offering that seamlessly blends Founding Era character with modern comfort. Inside, warm, inviting living spaces are filled with natural light and include a well-appointed kitchen with breakfast nook, two bedrooms, one beautifully finished bath, a living room and formal dining room. There is an additional room downstairs plus a dedicated laundry room. Every detail of the renovation was carefully executed to preserve the home's historic charm while introducing the quality, efficiency, and craftsmanship expected in a modern residence. Recent improvements include a new roof with custom gutters, new mechanical systems, fully restored windows, and a complete professional repaint. Designed to embrace its exceptional setting, the rear porch captures sweeping southern views across the surrounding landscape. Professionally landscaped grounds feature orchards, formal parterres, and mature gardens that provide year-round beauty and a peaceful sense of retreat. Rarely does a historic home offer such a complete restoration in one of Sharon's most desirable locations. With timeless architecture, beautifully curated gardens, and exceptional outdoor living framed by expansive southern views, this is a home of enduring beauty and effortless livability.

71 Hospital Hill Rd, Sharon
$265,000
2 Beds ⋅ 1 Baths ⋅ 24187482 MLS
Luna Sloop Cottage. Tucked into the hillside, this enchanting 2 bedroom bungalow with water access is the perfect wooded sanctuary situated near Mudge Pond. From the moment you step inside, you are enveloped in warmth by the gorgeous wood features that stretch across both the floors and in the distinctive ceiling mouldings, showcasing classic New England craftsmanship. The heart of the home is a beautiful open living and dining area centered around a rustic fieldstone fireplace, creating an inviting, cozy atmosphere perfect for crisp autumn evenings or peaceful winter nights. Beyond the main living space, a large, heated enclosed porch expands your square footage and offers an incredibly versatile bonus area. Flooded with natural light and usable all year round, it serves as the perfect sunlit home office, art studio, or peaceful secondary lounge overlooking the trees. Just outside your door, the magic continues. This location is perfect for outdoor enthusiasts, where you can easily launch your canoe or kayak for a quiet morning paddle, fish, or simply soak in the lakeside tranquility. Melding secluded privacy with easy access to Sharon's historic town center, this very special property is a rare find and ready for its next chapter. Minutes to the Sharon Land Trust hiking trails, farm to table restaurants, and endless outdoor activities - biking, skiing and much more. Close to area private schools. 2 hours to NYC.

22 Luta Hts, Sharon
$235,000
3 Beds ⋅ 1 Baths ⋅ 24186558 MLS
Opportunity awaits with this completely gutted home located directly across the street from Sharon Hospital. The current owner began renovations but is unable to complete the project, creating a blank canvas for investors, contractors, or buyers looking to customize a property to their exact specifications. Connected to town water and sewer, this property offers tremendous potential for renovation, resale, rental income, or owner occupancy. Convenient location with easy access to local amenities and healthcare facilities. Bring your vision and transform this property into something special-the possibilities are endless!

55 Hospital Hill Rd, Sharon
$1,395,000
3 Beds ⋅ 2 Baths ⋅ 24186400 MLS
Set along a quiet, dead-end road in the Ellsworth section of Sharon, this newly constructed shed-roof home was designed for simple, efficient living with a strong connection to the Earth. Solar panels and a heat pump system keep utility costs remarkably low, while expansive windows capture natural light and western sunset views. Thoughtful details include Bosch appliances, copper light fixtures, and a refined material palette that balances warmth with modern simplicity. The generous primary bedroom wing features a sauna, two separate dressing areas, and a bathroom finished with terrazzo tile. Two additional bedrooms occupy the opposite side of the home, creating a practical separation of spaces for family and guests. The exterior is clad in durable Hardie board siding, designed to age gracefully and require minimal maintenance. The landscape has been carefully planned and will continue to evolve with native wildflower meadow, apple trees, and maple, creating an ever-changing backdrop through the seasons. A detached two-car garage completes this understated and highly efficient modern home, offering a rare combination of Scandinavian design, low-maintenance living, and a peaceful country setting in one of Sharon's most desirable locations.

27 Morey Rd, Sharon
$925,000
2 Beds ⋅ 1 Baths ⋅ 24185728 MLS
Sixty-four years ago, an avid outdoor sportsman bought a large parcel of land on a gravel country road in Sharon, CT. Three years later he had split and sold some off, retaining 33.4+ acres for himself where he built the cabin of his dreams on the shore of a beautiful wetlands area with a pond along side. Bathed in peace, quiet, beauty, and serenity, he built a garage and a workshop, then later added some outbuildings to help with his affinity for collectibles. This was all he needed. The sportsman has passed, and today the home and property is being sold by his siblings. The peace, quiet, beauty, and serenity still remain. On the land and in the nearby water, nature awaits the next steward. The property has the potential for at least two additional home sites, and directly across the road is a large parcel owned by the Sharon Land Trust. The bones of the buildings are solid, and the land is a stunning mixture of native broad-leafed hardwoods and tall conifers. If you want to "get away from it all", this is the country place to get away to.

82 Westwoods, Sharon
$499,900
2 Baths ⋅ 24184967 MLS ⋅ Sharon-West Main Condominium BLDG.
Well established mix-use income producing property in the downtown center of Sharon, CT. Two separate buildings: Unit #1. a 1088 sf restaurant -kitchen, seating, ADA bathroom and outdoor seating all approved. Unit#2 a 1267 2 bedroom, 1.5 bath residence-with fireplace, hardwood floors, separate parking, back yard and patio. Both have long termed rental history. Attractive to Owner users or investors seeking quality real estate. Units are 49 percent ownership of Sharon West Main commercial condominium which incorporates one additional separately owned unit. See attached condo documents.

29 W Main St, Sharon
$625,000
3 Beds ⋅ 1 Baths ⋅ 24183989 MLS
Step inside the newly reborn 142 Gay Street. This village home, held by the same loving family for decades, has undergone a head-to-toe transformation. Forget the hassle of renovations. We're talking new plumbing, new wiring, fresh paint, refinished floors, and sleek new appliances throughout. But while the renovations are cutting-edge, the charm remains. You'll love the cozy layout, complete with an eat-in kitchen, a spacious living room centered around a classic wood-burning fireplace, and a versatile sunroom perfect for your home office or den. The 1.28-acre lot is a wide-open, level canvas just waiting for your landscaping vision (and maybe that pool you've always wanted!). With an unbeatable location steps away from the Sharon Farm Market, town lake, and local favorites like J. P. Giffords and Le Gamin restaurant, this is the fresh start you've been looking for. Don't wait-come see this Litchfield County treasure today!

142 Gay St, Sharon
$285,000
24183544 MLS
Perched high off the road in a large clearing this 7 acre building lot has all the advantages of the perfect country setting- privacy and views in an estate area. Atop a high open knoll one can spy long views east including, Dean and Coltsfoot Mountains as well as the the ski trails and Lookout Tower on Mohawk Mountain. A large open expanse makes ample room for a house, pool and barns should one wish to build. A well established driveway passes through thick forest is welcomed by a stone gate winding through a groomed wooded glade then gently up a slope to an sun-splashed open cleared building site. While there are neighbors, none are in sight as this property is surrounded on two sides by a large Sharon estate. The gravel road assures a low volume of traffic and noise. If your enjoyment of nature is derived with privacy and natural beauty, then you've found the spot. Priced $70,000 below what it was purchased for in 2021! Come see this amazing land and commune with nature for real country living!

Westwoods Rd Unit #2, Sharon
$1,250,000
24089909 MLS
NO NEED TO WAIT FOR TOWN APPROVALS! Design development plans with project entitlements in place for a spectacular, modern, 5-bedroom, 5,400 sq. ft. two-level home-featuring an indoor pool, sauna, multiple attic areas and attached garage are paired with this expansive 33.73-acre parcel in Sharon's desirable West Woods section. Nestled amidst tranquil nature, this remarkable property offers an unmatched blend of privacy and accessibility, ideal for a serene retreat, equestrian estate, or exceptional investment. Boasting 443 feet of frontage on a bucolic country road, the building site is set back along the road. Behind the building site, an old wood road crosses a private pond, leading to your own hiking trail along the babbling Macedonia Brook to a higher open area which includes a proposed 4.52 acres of open meadow on the higher side of Macedonia Brook. I The property is bordered by protected land trust, ensuring a forever-preserved natural backdrop. Enjoy easy access to local amenities, located just 7 miles from Kent's vibrant town center, shops, and restaurants, and minutes from The Kent School, Macedonia State Park, Skiff Wildlife Preserve and the Appalachian Trail. Buyers may choose to streamline their build with the included, fully approved designs and entitlements or pursue their own custom vision subject to local approval.

44 Keeler Rd, Sharon
$785,000
3 Beds ⋅ 3 Baths ⋅ 24181959 MLS
This 3 bedroom,3 full bath home has a 2 car garage. There is a modern kitchen with quartz counter tops. All of the bathrooms have been updated. The septic system has also been updated with a new 4 bedroom tank. There is a private backyard bordering a stream with perennial gardens. Just a short stroll to the Market.

40 Calkinstown Rd, Sharon
$299,000
2 Beds ⋅ 1 Baths ⋅ 24181104 MLS
Set on a level parcel within walking distance to the heart of Sharon, this enchanting 1875 antique home blends timeless New England character with inviting, livable comfort. Wrapped in natural wood siding and rich with rustic detail the home welcomes you with a covered front porch an ideal spot for a rocking chair & morning coffee. Inside offers warm authentic spaces highlighted by beautiful hardwood floors, wood accents, and exposed beams. The country kitchen serves as the heart of the house and opens to a cozy, sunlit sunroom overlooking the rear outdoor space, creating a wonderful peaceful spot. Off the kitchen is a separate entrance leading to a mudroom and dedicated laundry area, adding everyday practicality and ease. The home features two bedrooms, two living areas and a beautifully renovated, light-filled full bath-thoughtfully updated while honoring the home's historic character. Outdoors the backyard unfolds as a unique summer retreat-a private-feeling oasis- a wood burning oven anchors the space all set within a manageable 0.20-acre lot. Perfectly suited as a summer retreat or full time living. Warm, rustic & historic, it offers a rare opp to own a lovingly preserved home in a quintessential high end New England community. Residents enjoy hiking/canoeing at the 452-acre Housatonic State Park. Sharon Town Beach. Yr-round entertainment at the Sharon Playhouse. Local farm-to-table dining. Short drive to train into NYC. Audubon Center-1,147-acre sanctuary + low taxes

91 Amenia Rd, Sharon
$1,950,000
7 Beds ⋅ 7 Baths ⋅ 24174774 MLS
Set in a private, elevated setting along the banks of the Housatonic River, this property offers a rare waterfront retreat with a main house, guest house, and pool shed surrounding an in-ground gunite pool. The main residence includes an attached two-car garage, fireplace, and a dedicated woodworking/crafts shop in the basement with its own private entrance, along with a beautiful stone terrace overlooking the Housatonic River. The guest house features its own attached one-car garage, fireplace, and a charming porch with river views, providing both comfort and convenience for family and guests alike. All structures are thoughtfully positioned above the riverfront to capture the beauty and tranquility of the natural surroundings. Enjoy direct access to the river for fly fishing, kayaking, or tubing right from your own property. Located in close proximity to the Appalachian Trail, this exceptional compound is ideal for outdoor enthusiasts seeking privacy, recreation, and scenic riverfront living in the heart of Litchfield County. Perfectly situated for four-season enjoyment, the property is just 5 minutes to Mohawk Mountain for downhill skiing and snow tubing, and less than 10 minutes to Kent Falls State Park. The quintessential village of Cornwall Bridge is less than 5 minutes away, offering charming local shops, dining, and small-town New England character.

35 River Rd, Sharon
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