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Cheshire Homes for Sale

Newest Sharon Homes For Sale

$1,295,000
4 Beds ⋅ 3 Baths ⋅ 24165953 MLS
This 1768 antique Cape Cod is a masterclass in historic preservation meeting modern luxury. Set on 15+ sprawling acres of rolling pastures, this estate offers the ultimate in privacy and sophistication, just moments from Sharon's town center and the Metro-North line.The ResidenceSteeped in character, the home features exquisite original wood moldings and gleaming hardwood floors throughout. The heart of the home is a true chef's kitchen, anchored by professional-grade Viking and Traulsen appliances, sleek Corian surfaces, and a dedicated pantry. Entertaining is effortless in the formal dining room or the expansive living room, which features a custom wet bar and one of three wood-burning fireplaces. The flexible main-floor layout includes a media room, laundry suite, and a serene guest wing.The SanctuaryThe second level serves as a private retreat, highlighted by a meticulously renovated primary bath serving three sun-drenched bedrooms. Outside, a grand screened-in porch offers panoramic views of the estate's picturesque grounds. Step out to a resort-style, in-ground pool and pool house, perfectly positioned for summer afternoons in the Litchfield Hills.The Grounds & AmenitiesBeyond the main residence, a substantial heated outbuilding/barn provides versatile space for a studio, gym, or collector's gallery, complete with a walk-in cedar closet. The property also features a heated two-car attached garage.

Sharon
$3,999,000
6 Beds ⋅ 9 Baths ⋅ 24206049 MLS ⋅ Great Elm BLDG.
This exceptional residence, one of Sharon's most historic properties, occupies much of the original 1812 Georgian mansion, home to a notable family, including William F. Buckley, Jr., for over a century. The layout is spacious & flexible, offering multiple options for purchase: 1) purchase in its current layout as a spacious, 6-bedroom residence, 2) divide the current 6-bedroom residence into two spacious 3-bedroom residences, 3) additionally acquire the north wing to recreate a more complete version of the original mansion for use as an expansive single-family residence, a family compound, or separate residences for rental income. The current 6,716 sq ft home has been thoughtfully restored & offers 6 bedrooms with primary suites on both levels, 7 full baths, and 2 powder rooms. The kitchen opens to a stunning library & informal dining area, complemented by formal living & dining rooms, a family room, office, gym, den, laundry room and 7 fireplaces. At the center of the home, a dramatic three-story 1250 sq foot glass atrium (the 1,250 sq ft is not included in the 6,716 sq ft) - enclosing the 1929 courtyard - creates a year-round living space that brings light & openness into the core of the home. This is estate living with the ease of a managed community. Enjoy beautifully maintained grounds with specimen trees & beautiful plantings. Amenities include: junior Olympic-sized heated pool, pool house, tennis court & separate paddle/pickle courts and more. More info below.

1 Great Elm Dr, Sharon
$789,000
3 Beds ⋅ 3 Baths ⋅ 24204166 MLS
Surrounded by rolling farmland and open meadows, 16 Rhynus Road offers a peaceful country setting in beautiful Sharon, Connecticut. Set on 1.07 acres, the 3-bedroom, 3-bath main home offers 2,595 sqft, an in-ground pool and a separate cottage with dedicated parking. Hardwood floors run throughout, including antique hardwood floors in the original portion of the home. A large bay window fills the living room with natural light. The updated eat-in kitchen opens to the dining room and a spacious screened-in porch-an inviting extension of the living space overlooking the side yard. The family room features exposed beams and a wall of glass doors opening to the updated deck and pool area, while the primary suite has a private deck with stair access to the pool. Upstairs, the current laundry room offers flexible space for a home office or other use if laundry is relocated, and a floored, insulated attic provides generous storage. The renovated 475 sqft detached studio cottage, currently rented for the academic year, features a kitchen, full bath and open living/sleeping space. Updates include the cottage renovation, newly graveled driveway, kitchen upgrades, split heating/cooling, replacement windows and sliding doors, decks, front porch and electrical improvements. A new septic system serving the main house and cottage will be installed prior to closing. Enjoy a peaceful Northwest Connecticut lifestyle with nearby hiking, lakes, outdoor recreation, arts and culture.

16 Rhynus Rd, Sharon
$785,000
3 Beds ⋅ 2 Baths ⋅ 24202990 MLS
Picture starting your morning watching the sun rise over the water and ending your day with peaceful river views from almost every room in your home. Set on 2 acres along the majestic Housatonic river near Cornwall Bridge, 16 River Road has been completely transformed by a major renovation in 2024 into a modern waterfront sanctuary, while keeping its timeless antique character intact. Inside, refinished hardwood floors and classic antique detailing lead you to the open living and dining area, where a wood-burning fireplace creates a warm, cozy atmosphere. Large, new windows frame direct views of the river, pulling the beauty of the outdoors inside. For a closer look at the water, step out to the screened-in porch with its beautiful stone floor-an ideal setting for your morning coffee or evening wine. The brand-new chef's kitchen is a design masterpiece, combining custom cabinetry, quartz countertops, a bespoke stone backsplash, and a farmhouse sink. Equipped with a full suite of 2024 stainless-steel Frigidaire appliances (fridge-freezer, dishwasher, electric range, microwave, and hood), the kitchen also boasts a built-in wine fridge and a dedicated coffee station. Upgraded electrical systems with recessed lighting and dimmers allow you to set the perfect mood throughout. The main-level primary suite is your private oasis, complete with direct river views and an ensuite bath that rivals any spa.

16 River Rd, Sharon
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 24203533 MLS
Authentic c1966 Mid-Century Modern. Fully re-Built & Super Fab 3 Bedroom, 3 Bath Restored Modernist Set Near the End of a Quiet Country Road. Open Floor-Plan Living Features an Updated Kitchen Enveloped by Glass-Clad Living & Dining Area with Vaulted Ceiling & Fireplace. Large Main Level Primary with Updated Bath, Large Walk-in Closet & Access Outside. Prime Guest Bedroom with En-Suite Bath + 3rd Bedroom Served by Hall Bath. Additionally, A Cozy Den Serves as Quiet Retreat. 2-Car Attached Garage. Central AC & Full House Generator. Set Amongst the Backdrop of the Bucolic Ellsworth Section of Sharon, Less than 10 Min to the Village & 20 Min to Metro North Train.

29 Morey Rd, Sharon
$719,000
3 Beds ⋅ 3 Baths ⋅ 24203240 MLS
YOUR PRIVATE RETREAT AWAITS - RENOVATED, MOVE-IN READY & COMPLETE WITH AN ABOVE GROUND POOL! Welcome to this beautifully renovated 3 bedroom, 2.5 bath home offering the perfect combination of modern updates, comfort, and outdoor living. From the moment you arrive, you'll appreciate the fresh new siding and the attention given to updating this property throughout. Step inside to discover a refreshed interior with a bright and welcoming atmosphere, spacious bedrooms, two full bathrooms, and a convenient half bath. The renovations give this home a fresh, modern feel while providing plenty of space for everyday living, entertaining, working from home, or hosting family and friends. Major improvements include new siding, new propane tanks, and extensive renovations throughout, making this property truly move-in ready. The backyard is ready to become your favorite place to relax and entertain. Enjoy warm summer days by the above-ground swimming pool, host weekend barbecues, or simply unwind in your own outdoor space. With 3 bedrooms, 2.5 bathrooms, a renovated interior, important exterior upgrades, and a pool to enjoy, this home offers so much to its next owner. All you need to do is unpack and make it yours. Don't miss the opportunity to see this beautifully updated property schedule your private showing today!

497 Cornwall Bridge Rd, Sharon
$635,000
3 Beds ⋅ 3 Baths ⋅ 24201544 MLS
Set on two private acres just minutes from the village of Sharon, this inviting Colonial offers a wonderful blend of country privacy and everyday convenience. The main level features a spacious open-concept kitchen, living room, and dining area, complemented by a separate family room or home office. A whole-house media surround sound system enhances the living spaces throughout and an attached two-car garage provides added convenience. Upstairs, the generous primary suite offers multiple closets, including a walk-in, and a full bath with double vanity. Two additional bedrooms share a second full bath. The finished lower level provides flexible space for a recreation room, home gym, media room, or additional living area. Outside, a private back patio with a shade pergola creates an inviting setting for morning coffee, outdoor dining, or entertaining while enjoying the peaceful country surroundings. This property offers an exceptional location with easy access to the villages of Sharon, Millerton, Lakeville, and Salisbury, as well as the Wassaic train station with service to New York City. Nearby amenities include acclaimed private and public schools, scenic hiking trails and conservation areas, the Sharon Playhouse, and year-round recreation at Mohawk Mountain and Catamount Ski Area. A peaceful country setting with convenient access to the best of the Litchfield County and Hudson Valley region.

190 Cornwall Bridge Rd, Sharon
$5,250,000
2 Beds ⋅ 2 Baths ⋅ 24201909 MLS
The rarest luxury is seldom the land itself. It is the time already devoted to revealing its full potential. Set amidst protected land along the coveted Kent-Sharon border, RockOak offers the uncommon advantage of beginning years ahead on the construction of a legacy estate. The completed retreat allows the property to be enjoyed immediately, while the future estate evolves. Overlooking the orchard, gardens, woodlands and long views it offers refined, comfortable living from the very first day. The estate unfolds like a private park of meadows, woodlands, orchards, gardens, dramatic elevations and a sheltered seasonal brook. Sweeping western sunsets, expansive northern vistas, and carefully composed landscapes ensure every season reveals a new perspective. Two parcels define the property's flexibility. The principal Sharon homesite occupies a commanding elevation and includes architectural design plans by architect, Scot Samuelson, AIA, NCARB for a 5,000+ sq ft residence. The 2nd parcel is in Kent & Sharon, reached by its own private drive. It rests quietly on the edge of a woodland above the brook and in the meadow below the principal Sharon site. Throughout the estate, thoughtful infrastructure has been integrated into the landscape, while historic woodland roads, stone walls, specimen trees, perennial gardens, fountains, scenic overlooks, and a distinctive 40 tree orchard create a landscape of exceptional beauty and permanence. Convenient access to NYC by car or train.

Sharon
$525,000
4 Beds ⋅ 2 Baths ⋅ 24197961 MLS
An exceptional opportunity to own a move-in-ready four-bedroom home just around the corner from the heart of Sharon, offering the Litchfield County lifestyle at a price point increasingly difficult to find. Set on approximately three-quarters of an acre of level land, 120 Sharon Valley Road combines comfortable everyday living with an incredibly convenient location near Sharon's village center, Sharon Hospital, local shops, dining, recreation, and easy access to the New York border. The home is only about 15 minutes from the Metro-North station in Wassaic. Inside, light hardwood floors flow throughout the home, complemented by fresh interior paint and abundant natural light from replacement windows. The flexible four-bedroom layout provides room for family, guests, a home office, or creative space, giving the home functionality well beyond its footprint. The property has been thoughtfully refreshed with a newer driveway, updated landscaping, and a newer deck overlooking the fully fenced backyard-an ideal setting for pets, entertaining, gardening, or simply enjoying the peaceful surroundings. A large backyard shed provides exceptional additional storage for tools, outdoor equipment, bikes, or recreational gear. Downstairs, the walk-out lower level features impressively high ceilings and offers exciting potential for future finished living space, whether envisioned as a family room, home gym, office, workshop, or guest area.

120 Sharon Valley Rd, Sharon
$534,000
4 Beds ⋅ 2 Baths ⋅ 24199566 MLS
Welcome to 70 Gay St! Just minutes from Sharon's town center, this 1947, two-story charmer exudes peaceful and sun-filled vibes! Well sited on a beautiful, large 3.8-acre lot with equal parts wildflowers and lawn, the home is nicely nestled among mature trees, with just the right balance of sun and shade. And if you're an investor or developer, this property affords an excellent subdivision opportunity, with its 3/4-acre minimum zoning. You could consider subdividing the current 3.8 acres into potentially 4 or 5 separate building lots. Interior features: refinished, walnut-stained, oak floors...large living room with wood-burning fireplace...open kitchen/dining with three exposures and updated appliances...repainted interior...excellent closet space...full, dry basement with a Bilco door for easy exterior access...washer/dryer...and new hot water heater in 2023. Exterior features: new roof in 2021...detached, oversized, one-car garage with a connected, covered walkway from the house...large, flat lot with plenty of room to build, add a pool, tennis court, or whatever else your heart desires...and numerous landscaped flowerbeds.

70 Gay St, Sharon
$1,550,000
5 Beds ⋅ 4 Baths ⋅ 24198204 MLS
Seeking a weekend getaway without a hassle? Just pop in the car or take Metro North to this private country home on a back road in Sharon CT. Built by a well regarded local contractor, it offers classic sensibilities with artistic country flair. The open floor plan concept feels anything but too formal or stuffy. Both home and property are warm, comfortable and wonderfully relaxing. The grounds are distinctively framed in moss covered stone walls. The residence is nestled on a large green lawn and beneath five acres of mature oaks and maples and enveloped in gardens cultured over 30 years. The home is classically infused with crown moldings, fluted columns and palladium style details though feature many traditional country touches of: sweeping porches; screened porch, large windows; native stone walls, nearby hiking trails and an open floor plan which is anything but too formal or stuffy. The family sized country kitchen is designed for large gathering of cooking, baking and just plain merry making. With three large surfaces of granite countertops, custom cabinetry, built-ins, prep sink, restaurant-quality appliances, a gas range, and a stainless-steel refrigerator, it has utilitarian cred of a New York City kitchen. While the wine fridge and Tuscan tile backsplash, three stool bar counter create the emotional heart of the home like an Neapolitan-style kitchen.

12 W Mountain Rd, Sharon
$585,000
2 Beds ⋅ 1 Baths ⋅ 24197956 MLS
Circa 1800s Colonial nestled on a picturesque two-acre parcel along a bucolic country road in Sharon, Connecticut, one of Litchfield County's most sought-after towns. Set back on a gentle rise, the property enjoys a peaceful setting with a backyard framed by mature trees. Rich in history and architectural character, this charming two-bedroom cottage showcases timeless craftsmanship and enduring New England appeal. The light-filled interior features a spacious great room with a wood-burning fireplace and a bay-windowed dining area ideal for gathering. A thoughtfully renovated country kitchen features butcher block countertops, a farmhouse sink with brass bridge faucet, and stainless-steel appliances. Recent improvements include freshly painted interiors and exterior, along with a new gravel driveway. A detached barn offers exceptional versatility as a studio, workshop, potting shed, or creative retreat-particularly appealing to the gardening enthusiast. This inviting country home offers a rare opportunity to enjoy the beauty, charm, and quintessential lifestyle of Litchfield County.

99 King Hill Rd, Sharon
$425,000
2 Baths ⋅ 24197331 MLS ⋅ Sharon-West Main Condominium BLDG.
NOW $425,000!! 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
$350,000
24196913 MLS
Rare investment opportunity on 3 acres of level, usable land with outstanding potential for redevelopment or a custom build. This property offers a strong foundation for your vision, featuring an existing foundation (in need of repair), private well, septic system, and electrical service already in place (currently not activated). The attached garage remains intact, providing immediate utility and added value. The home also features a chimney with fireplaces completely intact, offering a valuable structural element for future restoration or redesign. The original oversized ranch style (3220sq ft 3 bed 2 1/2 bath) home was lost to fire in 2011, and debris remains in the basement area requiring removal-creating a blank slate for renovation or new construction. With its generous acreage, level topography, and existing infrastructure, this property is ideal for investors, builders, or buyers looking to create significant equity. Sold strictly as-is. Buyers to perform all due diligence regarding condition and usability of all existing systems and structures. Do not go on property alone. Must be accompanied by an agent.

106 Lambert Rd, Sharon
$495,000
4 Beds ⋅ 4 Baths ⋅ 24194672 MLS
Exceptional Turnkey Investment Opportunity in Sharon, CT! Currently generating $3,700/month in immediate, documented income with active tenancies in place, this well-maintained side-by-side duplex is a rare, high-yielding Litchfield County asset. Each side features a nice 2-bedroom, 1.5-bathroom layout highlighting updated kitchens featuring stainless steel appliances, tile backsplashes, rich hardwood floors, and updated bath fixtures. Both units offer bright, inviting living spaces, dedicated basement laundry with included washers and dryers, and separate mechanicals. Tenants enjoy delightful outdoor living space, including shared, expansive covered front and rear porches. Unbeatable in-town location-situated just moments from the historic Sharon Town Green, local shops, cafes, Sharon Hospital, the Hotchkiss Library, and a short drive to The Hotchkiss School and Lakeville Lake. A seamless, low-maintenance addition to any investment portfolio offering proven cash flow and instant yield from day one!

39 Hospital Hill Rd, Sharon
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