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A rare opportunity to own a private woodland retreat at the base of Sharon Mountain! Set on 3.84 picturesque acres, this distinctive 3-bedroom, 2-bath log chalet offers the perfect blend of rustic elegance, natural beauty, and peaceful seclusion. Tucked away at the end of a winding driveway, this first-time-offered home features soaring wood ceilings, exposed beams, a dramatic stone fireplace, and warm natural wood finishes that capture the charm of mountain living. An expansive elevated deck overlooks beautifully established perennial gardens, traditional stone walls, and surrounding woodlands. The partially finished walk-out basement features a wood stove and an additional 365 square feet of versatile space overlooking the yard, ideal for recreation, hobbies, or relaxation. Explore private walking paths, relax by the fire pit, or enjoy the open grassy clearing that once formed part of the historic Sharon Mountain Ski Area. Recent improvements include exterior painting and updated deck boarding. Perfect as a primary residence or countryside retreat, the property offers convenient access to Wassaic Metro-North Station with service to Grand Central Terminal, the region's many renowned independent schools, charming villages, fine dining, hiking, skiing, and outdoor recreation. Experience the tranquility of the Litchfield Hills while remaining connected to New York City and Hartford. A truly special property offering privacy, character, tranquility and four-season enjoyment!

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24216195 MLS

A rare opportunity to own a private woodland retreat at the base of Sharon Mountain! Set on 3.84 picturesque acres, this distinctive 3-bedroom, 2-bath log chalet offers the perfect blend of rustic elegance, natural beauty, and peaceful seclusion. Tucked away at the end of a winding driveway, this first-time-offered home features soaring wood ceilings, exposed beams, a dramatic stone fireplace, and warm natural wood finishes that capture the charm of mountain living. An expansive elevated deck overlooks beautifully established perennial gardens, traditional stone walls, and surrounding woodlands. The partially finished walk-out basement features a wood stove and an additional 365 square feet of versatile space overlooking the yard, ideal for recreation, hobbies, or relaxation. Explore private walking paths, relax by the fire pit, or enjoy the open grassy clearing that once formed part of the historic Sharon Mountain Ski Area. Recent improvements include exterior painting and updated deck boarding. Perfect as a primary residence or countryside retreat, the property offers convenient access to Wassaic Metro-North Station with service to Grand Central Terminal, the region's many renowned independent schools, charming villages, fine dining, hiking, skiing, and outdoor recreation. Experience the tranquility of the Litchfield Hills while remaining connected to New York City and Hartford. A truly special property offering privacy, character, tranquility and four-season enjoyment!

480 Cornwall Bridge Rd, Sharon

$830,000

This is a special, protected, and unique setting in the middle of a beautiful area of Sharon.The charming, well-maintained Cape home is on almost fifty acres, with approximately 46 conserved acres in Sharon Land Trust. The Land Trust properties also extend beyond the property's boundaries to hundreds more acres of Jackson-Peck properties. The property is mostly forest land, with mixed, mature hardwoods, and a small meadow -- and easily walkable. The home is listed on the Sharon "field card" as 1-bedroom and 1-bath. There are two full baths and an additional, possible bedroom. The combination dining room/living room has a fireplace and wood floors. Central air on the first level and a split system/AC on the 2nd floor. Plus there's a full basement, detached two-car garage and whole house generator. New roof in 2025. Importantly, it's a town maintained road. The property offers the ultimate privacy, a true sanctuary, in a peaceful setting surrounded by endless nature and the occasional wildlife.

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24215197 MLS

This is a special, protected, and unique setting in the middle of a beautiful area of Sharon.The charming, well-maintained Cape home is on almost fifty acres, with approximately 46 conserved acres in Sharon Land Trust. The Land Trust properties also extend beyond the property's boundaries to hundreds more acres of Jackson-Peck properties. The property is mostly forest land, with mixed, mature hardwoods, and a small meadow -- and easily walkable. The home is listed on the Sharon "field card" as 1-bedroom and 1-bath. There are two full baths and an additional, possible bedroom. The combination dining room/living room has a fireplace and wood floors. Central air on the first level and a split system/AC on the 2nd floor. Plus there's a full basement, detached two-car garage and whole house generator. New roof in 2025. Importantly, it's a town maintained road. The property offers the ultimate privacy, a true sanctuary, in a peaceful setting surrounded by endless nature and the occasional wildlife.

30 Graham Rd, Sharon

$1,025,000

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.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211887 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

$650,000

Enchanting circa-1850 cedar-shingled cottage tucked into a lush, beautifully landscaped setting along one of Sharon's picturesque country roads. Surrounded by mature specimen trees, layered perennial gardens, stone walls and pathways, and a meandering brook, the property offers a wonderful sense of privacy and the feeling of a secluded garden retreat. Inside, the home is warm and inviting, with original exposed beams that speak to its 19th-century character. A spacious eat-in country kitchen offers an inviting gathering place. The generously proportioned living room features 10-foot ceilings and a fireplace. The home offers three bedrooms and two-and-a-half baths, including a main-floor primary bedroom with an ensuite bath. Two porches, including a screened in porch, are a highlight of the property, extending the living spaces outdoors and creating idyllic settings for seasonal dining, entertaining, morning coffee, or quiet evenings overlooking the gardens. A separate barn currently serves as a two-car garage and offers additional possibilities for studio, workshop, or other creative use. The house also has a newly installed generator. Rich in character and beautifully connected to its natural surroundings, this charming country cottage captures the essence of relaxed Litchfield County living, all just minutes from the center of Sharon. Bring your vision and make it your own.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24208108 MLS

Enchanting circa-1850 cedar-shingled cottage tucked into a lush, beautifully landscaped setting along one of Sharon's picturesque country roads. Surrounded by mature specimen trees, layered perennial gardens, stone walls and pathways, and a meandering brook, the property offers a wonderful sense of privacy and the feeling of a secluded garden retreat. Inside, the home is warm and inviting, with original exposed beams that speak to its 19th-century character. A spacious eat-in country kitchen offers an inviting gathering place. The generously proportioned living room features 10-foot ceilings and a fireplace. The home offers three bedrooms and two-and-a-half baths, including a main-floor primary bedroom with an ensuite bath. Two porches, including a screened in porch, are a highlight of the property, extending the living spaces outdoors and creating idyllic settings for seasonal dining, entertaining, morning coffee, or quiet evenings overlooking the gardens. A separate barn currently serves as a two-car garage and offers additional possibilities for studio, workshop, or other creative use. The house also has a newly installed generator. Rich in character and beautifully connected to its natural surroundings, this charming country cottage captures the essence of relaxed Litchfield County living, all just minutes from the center of Sharon. Bring your vision and make it your own.

32 Calkinstown Rd, Sharon

$749,000

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.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$694,999

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!

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$509,000

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.

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$555,000

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!

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

$725,000

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. Owner is an agent.

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. Owner is an agent.

40 Calkinstown Rd, Sharon

$950,000

Welcome to this beautifully maintained custom-built home tucked away in a peaceful, private setting surrounded by mature trees and wide open lawn space in Litchfield County. This charming Cape Cod-style home features striking blue-gray siding, crisp white trim, dormer windows and a 3 bay garage, offering a possible in-law apartment above. The interior offers nicely kept hardwood floors flowing through-out the main floor, natural light through large windows, a main level laundry room, half bath, an office, a large eat-in kitchen, a formal dining room, and a spacious living room with a brick fireplace insert. The upper level features a large master bedroom with the choice to put your personal touch on the flooring, a large walk-in closet, 9ft+ ceilings and a beautiful master bath leading through french doors. On the second floor you will also find two well sized bedrooms, and a full bath. Newly installed in the basement, you will find meticulously kept mechanicals and ample room for storage with a walkout. Don't miss the chance to own this wonderful home in the most sought after area in the Northwest corner, only two hours from the city, multiple private schools, skiing, golfing, equestrian stables, airports and train stations in close proximity.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24177954 MLS

Welcome to this beautifully maintained custom-built home tucked away in a peaceful, private setting surrounded by mature trees and wide open lawn space in Litchfield County. This charming Cape Cod-style home features striking blue-gray siding, crisp white trim, dormer windows and a 3 bay garage, offering a possible in-law apartment above. The interior offers nicely kept hardwood floors flowing through-out the main floor, natural light through large windows, a main level laundry room, half bath, an office, a large eat-in kitchen, a formal dining room, and a spacious living room with a brick fireplace insert. The upper level features a large master bedroom with the choice to put your personal touch on the flooring, a large walk-in closet, 9ft+ ceilings and a beautiful master bath leading through french doors. On the second floor you will also find two well sized bedrooms, and a full bath. Newly installed in the basement, you will find meticulously kept mechanicals and ample room for storage with a walkout. Don't miss the chance to own this wonderful home in the most sought after area in the Northwest corner, only two hours from the city, multiple private schools, skiing, golfing, equestrian stables, airports and train stations in close proximity.

104 Lambert Rd, Sharon

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