Wassaic NY Real Estate & Homes for Sale

Welcome to your dream farm retreat nestled in the picturesque foothills of the Berkshire mountains! This sprawling property spans just under 175-acres with a rich history, once serving as a prominent dairy farm and now flourishing as a horse farm. Here, you will find a stunning array of farm buildings, lush pastures, paddocks, a sprawling pond and acres of wooded mountainside. The main residence, a classic center hall colonial, offers grandness and comfort with its 5-bedrooms and 4.5-bathrooms. The charming interior is adorned with 4 fireplaces, wide plank pine flooring and a spacious layout perfect for entertaining. Admire the beauty of the landscape from the inviting wrap-around porch or take a dip in the refreshing in-ground pool. Adjacent to the main house, a large carriage house provides additional living space for possible tenants with a first floor 4-bedroom apartment and a second floor 1-bedroom apartment, accompanied by an attached 2-car garage. A quaint one-bedroom cottage tucked away on the property offers even more accommodation options. The farm itself features a vast array of well maintained barns adorned with multiple cupolas. The main barn includes ten 12'x14' horse stalls, private office space and an extensive second floor area with multiple options for its use. Outside, you'll find three paddocks, a round pen, four silos and several large and small storage sheds ensuring ample space for all your farming needs.

West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open meadow, and serene pond. Spacious rooms perfect for entertaining include a great room with a soaring peaked ceiling and a 20' stone fireplace, sun-filled formal dining room with three exposures, huge Chef's kitchen with a massive stone fireplace and adjoining catering kitchen. Beautiful reclaimed chestnut floors, exquisite detailing and banks of windows and French doors. The paneled library, office and master bedroom suite are located on the first floor in a private wing of the house. Billiard room, complete with mini-kitchen, full bath and adjoining guest bedroom. Second-floor master guest room with soaking tub and deck with views. Two bedroom suites with ensuite bathrooms, charming children's bedroom and an office complete this floor. Lower level with a media room, half-bath, wine tasting room and wine cellar with adjoining prep kitchen. Laundry room, craft room and gym. Beautiful stone steps lead to a stunning pool & pool house with full kitchen & tennis court. Two building maintenance court contains a pumping system for irrigating the lawns and gardens.

Two lots being sold together- included in the sale of 59 Fuller Mt. is 61 Fuller Mt with an additional .92 acres and additional taxes of $1489.00. Build your dream house, just 5 minutes from Macedonia State Park for hiking, biking , fishing ,etc. Minutes from Kent town center.

A truly rare opportunity to own "Dragonfly Farm", one of the most unique estates in New England which has been featured in House & Garden and many architectural books. The estate compound began in the 1700s with the construction of the mill and the millkeeper's house (which now serves as the guest house). The Federal style stone house was added to the property in the early 19th century. In the 20th century, this main house was expanded by owner and architect Heathcote Woolsey. It was then owned by the Hammerstein family (of Rogers & Hammerstein fame). The current compound includes the 5 bedroom residence, 2 bedroom guest house, antique barn, office/gym/game room complex above the 4+ car garage, caretaker's house and a stone cabana. Unique features of the main house include a gracious foyer w/ curving staircase, dining room w/ opposing fireplaces, vaulted kitchen w/ stone walls/opposing fireplaces/hand hewn beams & a stunning solarium/family room. Leisure time will find you enjoying tennis, soccer, basketball, golf chipping, archery & the gunite heated pool.

Charming Cape in Ideal Location - This lovely Cape Cod home located on an amazing lot in idyllic Sharon CT is now available for sale. Cross the threshold of the extra deep wrap-around porch and enter the home with hardwood floors and generous proportions. The light-filled kitchen has a dining area with a large bay of bowed windows overlooking the side yard. A laundry room/mudroom is adjacent. The living room features an extra large double-height stone fireplace that has doors to a heated sunroom with wrap-around windows and access to the back patio with gorgeous views. The main floor primary bedroom has its own stone fireplace, a private sunroom, an en-suite bath, and ample closet space. Ascend to the second floor to discover two guest bedrooms and a full bath, providing comfortable accommodations for family or visitors. A detached two-car garage with loft storage space accompanies the property, featuring an attached room housing an exercise pool, perfect for relaxation and fitness. Enjoy the peaceful ambiance of country living, with convenient proximity to local amenities including in-town shopping, the Sharon Playhouse, Indian Mountain School, Hotchkiss School, and easy access to NYC train transportation. Don't miss the opportunity to make this tranquil retreat your own.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of William F. Buckley Jr., author and influential political commentator. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,872 sq ft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplace, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of William F. Buckley Jr., author and influential political commentator. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,872 sq ft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplace, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.

A remarkable opportunity to own and renovate a home across from Sharon Hospital in the Village of Sharon, Ct. This home is in the center of Sharon and all that offers, such as the restaurants, library, hospital and all the associated doctor's offices. This home is served with both Town water and sewer and is minutes away from the train station to NYC.

Welcome to 1 Jackson Hill Road. With its refinished wood floors and rustic ceiling beams this home blends modern comfort with historic details. The spacious living room with its cozy fireplace, flows naturally into the well-appointed kitchen and formal dining room. Natural light pours into this delightful cottage from the dining room bay window and the sky lights in the renovated bathrooms. Set off the main living area is the first floor primary en suite with ample closet space and soaring ceiling height. Upstairs the second bedroom boasts sturdy built-ins. The enchanting curb appeal is created by mature landscaping and flourishing perennials. A detached garage provides additional storage.

Welcome to 34 Jackson Hill Road, a recently remodeled retreat just a mile from the quintessential Sharon center. This ultra-chic haven is surrounded by apple trees and boasts captivating views of the CT/NY mountain range. Nestled into the rolling hillside, the black/white facade home features 3 full bedrooms, offering the sleeping capacity of 4. This residence is designed for sophisticated living, with an array of inviting spaces spread across both floors. Each floor presents real wood-burning fireplaces, access to balconies or patios, and full baths. The renovation includes new doors, trim, floors, plumbing, electrical, heating, and cooling systems. The main level seamlessly integrates the living, kitchen, and dining areas into an open floor plan. The kitchen is a culinary delight with white shaker cabinets adorned with brush gold hardware, stainless steel appliances, and a substantial 7-foot island. Recent upgrades encompass brand new hardwood floors with a rich dark chestnut stain, slate foyer tile, a new garage door, front walkway, and an architectural shingle roof. Conveniently situated just minutes away from shopping, restaurants, Route 4, and the metro north station, this property is accessible and commuter friendly. With its unparalleled combination of modern elegance and thoughtful updates, 34 Jackson Hill Road stands out as a distinctive and unmatched home in the current market. Welcome home to 34 Jackson Hill Road, where luxury meets tranquility.

Originally constructed in 1739, this delightful Antique is nestled in Kent's picturesque Flanders Historic District, right along scenic Cobble Road. Steeped in history, the home boasts many original features, from its wide board floors to the central chimney that serves two fireplaces in the living and dining rooms, not to mention the charming hand-hewn beams overhead. Meticulously maintained, the original house has undergone a thoughtful expansion, creating a generous open-concept space that seamlessly blends a modern kitchen with high-end stainless steel appliances and butcher block counters, flowing into a sun-drenched dining area and seating area adorned with custom built-in bookcases. Venture upstairs to discover the primary bedroom with its luxurious en suite bathroom, flanked by two additional bedrooms sharing a bath. The walk-out lower level offers a versatile large room that could easily serve as an overflow bedroom, accompanied by a full bath. The property also features a grand party barn and a separate studio, adding an extra living space ideal for a home office or a future guest home. Outside, the 2.4-acre property borders Cobble Brook and showcases a serene pond, enchanting vegetable and flower gardens, a charming grape arbor, and a fruitful orchard, creating an absolutely idyllic setting.

New Home proposed to be custom built to the wants and needs of the contract purchaser on this beautiful lot in St. John's Peak. Pricing is based on a 2 story 3300 square foot house size. Final price, house plan and specifications to be agreed upon between buyer and builder. Home to be built by Multi Award Winning Litchfield county builders Ground Breakers. Builder has built several homes in the subdivision as well as many other homes in CT. Lot has been cleared and all engineering data has been updated to move forward as soon as plans and specs are finalized. Financing if necessary to be a construction to perm mortgage. Photos are an example of homes built by Ground Breakers and are not necessarily what is proposed in this home listing. Taxes based on land only.

Converted Barn In Ideal Location - Set on 2 beautiful parcels totaling over 14 acres, sits this beautifully converted chestnut post and beam barn with meadow views on Sharon Mountain. The design and conversion of this barn was done by noted architect Einar Lindholm. As you enter from the ground floor, a staircase leads you to a grand great room with vaulted ceilings, seamlessly connecting to both a dining area and a kitchen. The panoramic meadow views serve as a picturesque backdrop, complemented by a striking large brick fireplace that adds a touch of drama and warmth. The main level features two bedrooms, a full bath, and an oversized library with a private stair leading to the primary suite. The second-floor primary bedroom features a spacious en-suite bath with a tub, shower, and water closet. Additionally, three more bedrooms, a laundry room, an office, and another full bath complete the sleeping quarters. The "crows nest" and gallery area suspended over the great room offer unique vantage points to enjoy the surrounding beauty, making them ideal for stargazing or simply taking in breathtaking views. The lower level adds another dimension to this remarkable home, featuring an additional bedroom, sauna, and a den with a fireplace and greenhouse-style windows. Step outside to discover a beautifully gated garden with a dining pavilion and sculpture garden, providing the perfect setting for al fresco meals. The property is also equipped with a solar-powered electric system.

Welcome to this wonderful post & beam tobacco barn origingal built in 1900's and renovated in 2001. Open floor plan provides easy living for all ages. Many upgrades include new floors in primary bedroom and adjacent bedroom. New shower installed in master bath with transferrable warranty. Rebuilt outdoor deck and whole house generator installed in 2001. Sit, enjoy a glass a wine by the brook on North side of property giving peace & serentity.

Introducing a unique country estate now available for sale in the picturesque Sharon, CT. This distinctive property offers a blend of historic charm and modern amenities, comprising a captivating main house, a cozy one-bedroom guest house, a versatile studio/gym, and a plethora of outdoor amenities including a heated pool with a charming cabana, a detached three-car garage, and a well-maintained tennis court. The main house, a tastefully converted and renovated antique schoolhouse, features a spacious and finely appointed kitchen that opens to a light-bathed dining area, a cozy living room complete with a charming fireplace, a luxurious primary ensuite bedroom boasting paneled walls and another fireplace, a den with a sunroom and a separate guest bedroom wing. Enjoy alfresco dining experiences on the inviting bluestone porch, offering idyllic pond views. Next to the main house, discover the enchanting guest house, offering a rustic ambiance accentuated by a warming wood stove and a second-floor sleeping area, perfect for accommodating visitors in comfort and style. For those seeking recreation and fitness, there is a newly constructed studio/gym, offering radiant heating and a versatile loft space. Outdoors, indulge in leisure and entertainment by the heated pool, complemented by a charming cabana, barrel sauna, and tennis court. Experience the epitome of country living and luxury at this remarkable compound in Sharon, CT.

Very Special & Architecturally Significant Home just off Cobble Road in Kent and featured in the NY Times: 4 bedrooms, 4.5 baths, room to spread out, and full of natural light. With just over 2 acres and open views, this wonderfully maintained Frank Lloyd Wright-inspired home sits on Cobble Heights Road about 5 minutes from downtown Kent. Built for entertaining and a floor plan that creates privacy and separation within the home. Terrific location, with convenience to NYC via Metro North (20 minutes to Harlem Valley Wingdale). If hiking is your thing, trails abound including Kent Falls State Park, and the town of Kent is one of the more sought-after in Litchfield County, with many highly rated restaurants and shopping options. Less than two hours to NYC but a world away in bucolic Litchfield County.

Step into tranquility with this fully renovated Mid-Century gem tucked away on a private drive. Nestled on 5 acres of wooded bliss, this home offers the perfect blend of privacy and nature. Enjoy the serene surroundings from your brand new deck and porch, where every sunset feels like a moment of pure magic. With a finished basement offering additional space for entertainment or relaxation, this home is a true sanctuary for those seeking tranquility and style. Welcome home to your peaceful retreat.

Escape to a serene fishing cottage in Sharon, Ct nestled on a tranquil trout stream. This cozy retreat features a charming living room with a fireplace and a great room, three inviting bedrooms, with the primary on the first floor. Also included is a detached garage, extensive landscaping, and an enclosed garden. Embrace the beauty of nature and enjoy a peaceful fishing experience right at your doorstep. This property also offers for the outdoor enthusiast the close proximity to both the Housatonic River and the Appalachian Trail.

GRANDVIEW FARM ~ one of Sharon's most Iconic barns with legendary views and sunsets! Recently renovated, the interior showcases a unique blend of the original 1920s barn with wood beams and gorgeous refinished floors, new appliances, upgraded utilities, new roof and so much more! Situated on 28+ pastoral acres with scenic pond and pastures, the large picture windows from the barn-house capture the most magnificent western views rivalling a movie set. The residential portion of the barn features cathedral ceilings and an impressive open floor plan including the kitchen, living room and dining area with access to deck. Fabulous Great Room with wood stove and loft area, serving as an exercise room or study. 3 comfortably-sized bedrooms (primary en suite) and 2 full baths complete the main level. The Piece de Resistance is the 2022 installation of an 18' x 42' Saltwater Pool and spectacular 850 sqft Pool House. The tastefully built pool house possesses gorgeous European imported cobblestones with radiant floors, wood stove, kitchen by Devol, full bath and laundry. Large basement ~ great for storage. Enjoy this one-of-a kind property and its fantastical features that are simply unforgettable. Minutes to the villages of Sharon and Lakeville, and area private schools (Hotchkiss, Salisbury, Indian Mountain School and Berkshire School). Across from 181 acres and 2.5 miles of hiking trails at the Mary Moore Preserve (Sharon Land Trust). Once seen, the Grand View will not be forgotten.

Welcome to 333 Kent Rd. This is a beautiful opportunity to own a mixed-use property in Kent featuring two fully rented units and a 120-seat restaurant with an updated kitchen and full bar on the main level. The possibilities are endless. Bring your imagination. This property has been wonderfully maintained by the current owner. Located across the street from Bulls Bridge, a well-known covered bridge, as well the Appalachian Trail. Hiking, biking, and nature are just across the street! Located in the picturesque town of Kent Ct, just south of the center of town, boasting high-end stores, restaurants, and boutiques. Let your imagination run wild with all the possibilities!

Totally Private Top of the World Setting with Monster Catskill Views. 10-Min to the Center of Millerton NY/Sharon CT & 15-Min to Metro North Train. Graciously Scaled Rooms Throughout. 4 Fireplaces. The Ultimate Swimming Pool & Pool Area Complete with: Hot Tub; Outdoor Kitchen; Fireplace & Large Stone Terrace. Tennis Court. 3-Car+ Attached Garaging. 6 Paddocks with Run-In Sheds + Riding Ring & Barn. BIG Value for the Dollar!

Nestled in the serene rural town of Sharon, this charming cape-style home offers a tranquil retreat with direct river frontage. Built in 1940, this property exudes character and potential, situated on a generous 2-acre lot. Upon entering, you are greeted by the warmth of hardwood floors that flow throughout the home. The living room features a welcoming fireplace, creating a cozy atmosphere for gatherings or quiet evenings. One of the highlights of this property is the covered side porch, where you can unwind and take in the picturesque views of the river. The 2-acre lot offers endless possibilities for outdoor activities, whether it's gardening, creating outdoor living spaces, or simply enjoying the expansive greenery. While the property needs updating, it presents a wonderful opportunity to personalize and make it your own. With its desirable location, river frontage, and classic cape-style charm, this home in rural Sharon is well worth the investment.

Rare and sought-after, this exquisite property in prestigious Spectacle Ridge offers a unique opportunity to own a piece of paradise with shared access to pristine South Spectacle Lake. Nestled on a private 8+ scenic acres of natural beauty, this home provides access to a shared waterfront with private beach, tennis courts, and clubhouse, making it a coveted retreat for those seeking tranquility and luxury. The beautifully-decorated Cape exudes charm and cheerfulness boasting hardwood floors, two fireplaces, and 9' ceilings, adding warmth and elegance to the space. The well-equipped kitchen with a propane cooktop and walk-in pantry flows seamlessly into a cozy family room with a wood stove and French doors opening to a private rear patio, perfect for outdoor entertaining. The main level features a living room, dining room, and private office, providing ample space for relaxation and work. Additionally, the lower level offers a ping pong table for added enjoyment. Ownership of this property includes private lake rights, boating equipment, and access to community clubhouse amenities, ensuring a lifestyle of leisure and recreation. Situated just over 90 minutes from Manhattan in the charming town of Kent, this home offers a rare opportunity to experience a year-round country/lake lifestyle that is truly unparalleled.

Welcome to this charming Farmhouse nestled on over 19 acres of picturesque landscape, boasting breathtaking sunrises and sunsets along a serene scenic route. Embracing classic elegance, this tastefully renovated home seamlessly blends timeless allure with modern comforts. The heart of this residence is its epic chef's kitchen, featuring soaring vaulted ceilings, carrara marble counters, deVOL fixtures and hardware, a spacious pantry, and a grand oversized window offering panoramic western views of Indian Mountain. Entertain effortlessly in the inviting living and dining areas, enhanced by Dutch doors, exposed beams, and cozy fireplaces, all showcasing both eastern and western vistas. The main level also presents a convenient bedroom and full bath, along with a generous den boasting its own fireplace -- an entertainer's dream. Ascend to the upper level to discover a luxurious master suite with a sumptuous private bath and custom walk-in closet, accompanied by three additional bedrooms, two additional full baths, and a separate laundry room, ensuring practicality and comfort. A versatile landing that serves as a media room completes the upper level. Step outside to discover the in-ground heated pool, thoughtfully positioned to capture the surrounding scenery and breathtaking sunsets. Adjacent, the pool house beckons with a built-in stone outdoor kitchen, a half bath, and a western-facing patio, perfect for alfresco dining and relaxation.

Get away from it all and come to a place where you can live, work and play in beautiful Litchfield County. The perfect residential compound with a stunning historic main house, charming guest house and beautiful barn on 5 scenic acres, this incredible property also has pre-existing approvals for a bed and breakfast and other commercial uses. The property begins with one of Warren's most significant and historic homes, the Buell Carter House, an exquisite 3244 sq ft 4-bedroom, 4.5-bathroom home, built circa 1779, lovingly updated and expanded over the years, while preserving the integrity of the historic details including wide board chestnut and heart pine floors, 4 fireplaces, crown moldings, a split center chimney and more. Extensive updates include new roof on home, guest house & barn, Marvin windows, Hardie board siding, ensuite bathrooms in each bedroom, radiant heat, steam shower, sauna, outdoor shower, stone patio, stone wall bench & fire pit, second floor deck, screened in porch, full house generator and much more. Plenty of room for a pool or tennis court & horse paddocks. Perfectly located, just minutes from Kent, Washington, New Preston and many other charming towns, 15 minutes to Mohawk Mountain Ski Area and 2 hours to NYC. Warren residents enjoy a private beach on Lake Waramaug. Close to thousands of acres of hiking trails, lakes and rivers for fishing, kayaking, boating and ice skating throughout the area. An incredible value for a property with so much to offer.