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$3,975
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24167323 MLS
Set on over 2.5 private acres with captivating views of Sharon Mountain, this beautifully furnished 1870 Colonial offers a rare blend of timeless charm and modern ease. Thoughtfully updated while preserving its character, the home features a renovated kitchen with modern appliances, warm wood floors throughout, and inviting, light-filled spaces designed for comfortable living. With 2/3 bedrooms and two full baths, the home is fully furnished and impeccably appointed so that everything you need is already in place. Whether enjoying quiet mornings overlooking the landscape or relaxed evenings at home, the setting is both serene and welcoming. Surrounded by protected land trust acreage, the property offers exceptional privacy and a true sense of escape. Scenic trails begin directly from the property, with nearby access to the Appalachian Trail. Ideally located, the home is also just moments from local amenities, including Lime Rock Park and the Sharon Playhouse, offering a perfect balance of seclusion and convenience. A two-car detached garage adds everyday ease to this turnkey offering. Private yet connected, this is a rare opportunity to experience the best of Sharon in a home that feels both elevated and entirely at ease.

163 East St, Sharon
$675,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
$610,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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
$1,250,000
ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
$3,999,000
6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24173869 MLS
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
$845,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24172218 MLS
Discover the timeless charm of this extraordinary circa 1755 Colonial estate in the heart of Sharon, Connecticut. Set on 1.6 picturesque acres surrounded by protected farmland, this distinguished historic home offers 3,846 square feet of living space and an exceptional opportunity to restore, renovate, or thoughtfully modernize while preserving its remarkable architectural heritage. Rich in authentic period details, the home showcases original wood floors, handcrafted moldings, five fireplaces, and enduring craftsmanship. Generously proportioned rooms reflect the elegance and character of the Colonial era. The main level features a library and formal dining room, each with custom built-ins and fireplaces, along with a spacious living room that opens to the patio. A large eat-in kitchen flows seamlessly into a cozy den with a wood-burning stove, French doors to the patio, a full bath, laundry area, and a rear staircase leading to a versatile upper-level bonus space. Upstairs, the primary suite includes a private full bath and fireplace, while three additional generously sized bedrooms offer ample accommodations. A walk-up attic, another full bath and a loft-style flexible space connected to the den by a secondary staircase. Complementing the residence are several substantial outbuildings, including a garage,workshop, and an office with two half baths.

28 Cole Rd, Sharon
$1,700,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24168858 MLS
Lovingly named "Nid D'Alcyon," French for Kingfisher Nest, by the current owner, this truly enchanting home is rich in history. This beautiful four-bedroom antique, dating to circa 1745, is set on one of Sharon's most scenic roads and tells a captivating story of life, travel, and love. Nestled within exquisite gardens and surrounded by a serene pond, mature trees, and perennial plantings, the setting is both peaceful and picturesque. The current owner has lovingly stewarded the property for 37 years, thoughtfully enhancing it while honoring its character. With great care, the home was renovated to maximize natural light-an exceptional quality for an antique-through raised ceilings where possible and thoughtfully designed additions that invite sunlight throughout the day. Improvements include central air conditioning, a full-house generator, and an expansion of the original petite footprint typical of antique homes. A first-floor primary suite with vaulted ceiling and en-suite bath featuring a custom fireplace was added, along with a mudroom, sunroom, and chef's eat-in kitchen. The formal living room offers another fireplace and beautifully crafted built-ins, creating a warm and inviting retreat. Every corner reflects exceptional care, seamlessly blending antique charm with modern comfort. This rare offering also includes a heated Gunite pool and barn, all set on five acres overlooking a dreamy pond.

130 Sharon Mountain Rd, Sharon
$1,065,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24167985 MLS
Set along one of Sharon's most scenic country roads, this inviting property offers a rare blend of country charm, flexible living space, and timeless Litchfield County appeal. Anchored by a 1948 main residence and complemented by an original guest cottage and substantial barn, the offering presents a versatile compound ideal for weekend living or full-time retreat. The main house is warm and welcoming, with four bedrooms and three baths, thoughtfully arranged to accommodate both gathering and privacy. The first-floor primary suite allows for easy, single-level living, while the open floor plan creates a natural flow between kitchen, dining, and living spaces. At the heart of the home, a generously sized kitchen island invites conversation and casual entertaining. A screened-in porch extends the living space outdoors, offering a peaceful setting for summer evenings, while a wood-burning fireplace adds a sense of comfort and tradition during cooler months. Just beyond, a classic barn provides two-car parking and ample additional space for storage, workshop use, or creative pursuits. The separate guest cottage, dating to the 1940s, remains a true time capsule-complete with three bedrooms, a full bath, kitchen, and a charming stone wood-burning fireplace. Preserved in its original condition, it offers a unique opportunity for restoration or continued use as a rustic retreat for guests.

222-224 W Cornwall Rd, Sharon
$2,300
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24167810 MLS
Spacious and bright second floor apartment in the Vicar's house-1880's Victorian building in the center of Sharon. There are two large bedrooms-one that once served as the Reverend's living quarters in this nearly 1400 sq. ft. apartment. The large kitchen with farmers' sink and room for a breakfast table. Full laundry room and a large storage closet. Full bathroom with shower. Antique floors, moldings and large windows make this a magical apartment to reside. Classic New England front porch is for private use. Includes most utilities-heat/electric. Ample parking and central to Sharon Hospital, restaurants, local shops and establishments. Owner/Landlord/Broker

33 W Main St Unit 3, Sharon
$8,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24165508 MLS
Over forty private wooded acres, a mountain stream, and hiking trails that lead to your own waterfall. This three-bedroom rustic stone cottage in the heart of the Litchfield Hills is the kind of country rental that's hard to find and harder to leave. A screen porch overlooks the running water, the living room has handsome exposed beams and opens to a covered porch, and wood-burning fireplaces make evenings in the formal dining room feel exactly right. One bedroom on the main level; the primary and third bedrooms up a level. The setting is quintessential Connecticut, located off a scenic country roads lined with antique homes. Macedonia Brook State Park at your doorstep, the village of Kent just minutes away, Metro-North is close by, and New York City just two hours away.

48 Keeler Rd, Sharon
$795,000
4 Beds ⋅ 1 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24164291 MLS
Nestled along a quiet country road in the charming town of Sharon, this circa 1848 home offers a rare chance to restore a piece of New England history. Rich with character and original detail, the 4-bedroom, 1-bath residence sits on a classic stone foundation and invites a thoughtful revival to bring it back to its full potential. The home retains its historic footprint, with a layout that speaks to a bygone era. While it will require a comprehensive restoration-including new roofing, siding repair, updated systems, and a reimagined kitchen and bath-the opportunity to preserve and enhance its authentic character is truly special. A newer boiler and hot water heater are already in place, providing a foundation to build upon. The property also includes an antique two-car carriage house, offering the possibility of restoration or replacement to complement the historic setting. Septic and well systems will likely require attention, and the basement shows signs of water infiltration consistent with a home of this age. For those drawn to historic homes and the beauty of country living, this property offers a meaningful canvas to create something lasting, rooted in history and place.

60 Millerton Rd, Sharon
$1,885,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24158388 MLS
Effortless elegance on seven acres directly across from protected conservation land. A dappled willow hedge and a classic pea stone driveway lead to this fully reimagined four-bedroom, three-and-a-half-bath retreat. Interiors are by Ellsworth Home, the New York and New England design studio behind the 2024 renovation - featured recently in Litchfield Magazine. Classic mouldings, high ceilings, and oversized windows carry through the first floor. The 13-foot kitchen island, AGA gas range, custom hood, and Bosch dishwasher make it a kitchen built for families who cook and entertain. It opens directly to a den with a soapstone gas fireplace and, beyond it, an east-facing screened porch. At the front of the house, a cozy living room - anchored by a brick wood-burning fireplace - sets an entirely different mood, while the dining room offers more traditional, sit-down entertaining. The main-level primary suite allows for the ease of one-floor living; upstairs, three more bedrooms include a second en-suite plus a third full bath. An approved pool site, attached two-car garage, and full unfinished basement leave room to grow into the property on your own timeline. Privacy reigns at the back of the property, where an old stone wall fades into the tree line and the woods take over.

200 Sharon Mountain Rd, Sharon
$1,195,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24156551 MLS
Nestled on 1.52 acres of meticulously landscaped grounds, this property features a Main Home along with a Guest Apartment, comprising 4 Bedrooms and 3.5 Baths. In addition to a gorgeous renovation that accommodates single-level living, this home features a new metal roof, Hardie board siding, new windows, a new septic system, and an automatic generator. Crafted for effortless living in the heart of Litchfield County, 331 Calkinstown Road exudes simplistic luxury. The Main Home is bathed in natural light and boasts a design that facilitates single-level living, highlighted by a luxurious Primary Bedroom Suite located on the First Floor. The well-appointed primary bathroom showcases an elegant aesthetic with double vanities, separate bath and shower facilities, and a dedicated dressing area. The primary Suite also includes a door that opens to the back deck, creating a private oasis. The kitchen, which features a seating island, is conveniently located next to the dining room that leads to the back deck, as well as a living room equipped with a wood-burning fireplace. On the upper level, two additional spacious bedrooms share a well-designed hall bathroom adorned with high-quality finishes. The 1-Bedroom Guest Apartment is positioned above the attached two-bay Garage, which can be accessed privately via an exterior door or through the Garage of the Main Home, providing flexible options for guests or a potential income source.

331 Calkinstown Rd, Sharon
$429,000
ACTIVE Status ⋅ 24141835 MLS
Rarely will you find a property surrounded by state forest with usable access, buried utilities, cleared pasture, woods and views of the Connecticut hills. There are two abutting parcels which could also be purchased. Please ask.

39 Swaller Hill Rd Unit lot 3, Sharon
$395,000
ACTIVE Status ⋅ 24141946 MLS
Discover a rare opportunity to own over 21 acres of private forestland with potential views overlooking the Housatonic River Valley, directly adjoining hundreds of acres of Connecticut State Forest. Tucked away on a private road, this secluded property features a network of wood roads and hiking trails, perfect for exploration and outdoor adventure. A rustic campsite complete with a lean-to and small seasonal cabin offers an ideal base for recreation while you develop your future homesite. The land also borders a picturesque mountain stream, adding to its natural charm and tranquility. Located just minutes from the village of West Cornwall, fly fishing on the Housatonic River, and skiing at Mohawk Mountain, this property is a true country retreat-a peaceful haven for nature lovers and outdoor enthusiasts.

Swaller Hill Rd, Sharon
$419,000
ACTIVE Status ⋅ 24141828 MLS
LOT 1 - 26.72 ACRES - $419,000 The Build-Ready Opportunity Nestled on scenic Swaller Hill Road, this exceptional 26.72-acre parcel offers mountain views, privacy, and valuable infrastructure already in place. The property has been cleared to showcase potential homesites, with underground utility conduit installed and an established utility easement, reducing future development uncertainty. A rare opportunity to build your dream home on a beautiful estate parcel in one of Sharon's most desirable locations. Key Features: * 26.72 acres * Mountain views * Cleared homesite area * Underground utility conduit installed * Established utility easement * Privacy and natural beauty Rare opportunity! Lot directly abuts 1000's of acres of state forest with some cleared pasture and remarkable views over the NW CT hills. Many potential home sites: either in the pasture, over looking the pasture or higher up in woods. Utility pipes are buried but wires not yet pulled until closing.

39 Swaller Hill Rd Unit 1, Sharon
$139,000
ACTIVE Status ⋅ 170559925 MLS
Wonderful Opportunity for an affordable 2 Acre Lot in the heart of the Litchfield Hills. Country setting with South Westerly exposure, mature trees and stone setting on a lovely scenic road, conveniently located near the center of Sharon, Ct. close to neighborhood schools, and downtown shopping and restaurants. Use your plans or your own builder when envisioning your dream home. Map/Lot 13/26/1. Deep Hole and Percolation test done in 2006

Cornwall Bridge Rd, Sharon
$859,000
ACTIVE Status ⋅ 24065338 MLS
This listing is a combination of three legal lots: Lot # 1, 26.72 acres, Lot #3, 25.36 acres, and Lot #4, 10.1 acres, totaling 62.18 acres. This beautiful parcel is surrounded by thousands of acres of state forest. Spectacular views, cleared pastures, woods and total privacy. Driveway is roughed in and drivable.

Swaller Hill Rd, Sharon
$750,000
ACTIVE Status ⋅ 170425303 MLS
This property offers the opportunity to build a home in Sharon that features both privacy and the enjoyment of a wildlife sanctuary. The site of the original farm house has long views over the wetlands and pond. Most importantly this parcel is protected by adjoining lands with conservation easements. 25 Bowne Rd has available a Phase 1 review, survey, wetlands survey, etc. Also included is the 11 acre parcel off of Butter Rd.

25 Bowne Rd, Sharon
$1,000,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24096674 MLS
Discover Timeless Elegance and Potential at 400 Gay Street, Sharon CT Situated on the edge of over 20 acres of picturesque land, this 1940 hand-built brick house awaits a visionary's touch to update the interior. There are several possible building sites that would accommodate a large Main house. This estate presents a rare chance to own a piece of Sharon's history and to craft a sanctuary tailored to your lifestyle. Property Highlights: * Historic Brick House: Built with care by the original owner, this home offers a solid foundation for restoration and customization. * Expansive Acreage: Over 20 acres of diverse landscapes, featuring open meadows and partially wooded areas with nature trails, perfect for outdoor enthusiasts. * Breathtaking Views: Enjoy serene long views of Mudge Pond, complemented by the enchanting spectacle of sunsets. * Privacy Meets Convenience: Positioned adjacent to protected lands, ensuring tranquility, yet conveniently close to the charming village of Sharon and the esteemed Hotchkiss School. * Additional Structures: Several outbuildings present on the property offer a multitude of uses, from workshops to storage or a number of garage bays. Whether you're drawn to the allure of a restoration project or the appeal of the land's natural beauty, 400 Gay Street is a canvas for your imagination.

400 Gay St, Sharon

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