Wassaic NY Real Estate & Homes for Sale

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 primary 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 primary guest room with soaking tub and deck with views. Two bedroom suites with en-suite bathrooms, charming 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.

Nestled in the heart of Sharon, this historic 1799-built property is an incredible opportunity for those seeking a rural restoration project. Situated on 7.44 acres of picturesque land, this estate features four buildings: a main house, two barns, and a once-impressive pool house. The property exudes character and potential but is in need of extensive rehabilitation. The main house, rich in history, requires significant repairs, including a complete roof replacement. The barns, though in need of restoration, offer tremendous possibilities for storage, workshops, or equestrian use. The pool house, a remarkable structure in its prime, now awaits a visionary to bring it back to life. With its expansive acreage and deep-rooted charm, this property is a rare find for investors, renovators, or anyone looking to create a one-of-a-kind retreat in an extremely private setting.

As you approach this radiant modern homestead, a gracefully winding driveway crosses the picturesque Jack brook on a newly restored wood trestle bridge, framed by specimen trees and meticulously crafted stonework, creating a breathtaking entrance. The home's expansive design seamlessly blends indoor and outdoor living, offering a harmonious flow throughout. At its heart, a striking stone fireplace is a sculptural focal point, uniting the Living Room, Dining Room, and Kitchen. The first-floor primary suite is a private sanctuary, complete with a spa-like bathroom, a custom-built dressing room, a library with bespoke shelving, and a Sunroom that opens onto a covered porch leading to the courtyard gardens. Upstairs, two additional bedrooms each feature their own en-suite bathrooms, while a Media Room with a private balcony overlooks the landing. The main level also includes a secluded bedroom with an attached bath, ideal for guests. A breezeway connects the home to the attached four-bay garage and a Studio with a Half Bath. Additionally, a separate space, formerly a potting shed, offers versatile possibilities for the country enthusiast. Built with exceptional quality, the property boasts heated garages, an 8-zone radiant heating system across all floors, central air conditioning, and a whole-house generator, ensuring comfort and convenience year-round.

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.

Immerse yourself in the grandeur of luxury residential living at Great Elm, the unparalleled 19th century Georgian colonial that was once the home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire 8,072 sqft., roughly half of the original Buckley estate. Steeped in historical significance and architectural elegance, the living space has been extensively renovated combining old world charm with modern amenities. The impeccable design choices are thoughtfully reflected throughout from the art deco bathrooms to the William Morris wallpaper. Every room exudes sophistication and meticulous care. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplaces, 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. It's a chance to own a piece of U.S. history while enjoying care-free living. Near Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to NYC.

Immerse yourself in the grandeur of luxury residential living at Great Elm, the unparalleled 19th century Georgian colonial that was once the home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire 8,072 sqft., roughly half of the original Buckley estate. Steeped in historical significance and architectural elegance, the living space has been extensively renovated combining old world charm with modern amenities. The impeccable design choices are thoughtfully reflected throughout from the art deco bathrooms to the William Morris wallpaper. Every room exudes sophistication and meticulous care. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplaces, 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. It's a chance to own a piece of U.S. history while enjoying care-free living. Near Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to NYC.

What an opportunity! A 4 bedroom, 2 1/2 bath Colonial, a large barn with a 3 bedroom, 2 bath apartment, and a total of 12 garage bays between the two structures, all on 25 acres of peace and privacy in the Litchfield Hills. The main house is in need of significant renovation and is being offered "as is", but with a spacious, open layout and a 1st floor bedroom there is wonderful potential here. There is a deep 4 car tandem main garage with an unfinished area above. The modern 3 bedroom apartment sits above a barn/garage space with room for 8 vehicles. Both buildings are off of a winding, tree lined drive, and Joray Road itself is a very quiet dead end lane. There is so much value here. Come see for yourself!

Just outside the charming Village of Kent, this adorable Cape Cod home is ready for a new owner's vision! Since 2019, the property has seen numerous upgrades, including a new roof, a completely renovated kitchen, a revamped bathroom, and a newly installed well. As you pull into the driveway, you'll notice a wood post fence (built in 2023) featuring five gates, with two wide enough for trucks or machinery to access the land behind the barn. Inside, you'll find hardwood floors, brand new black double-hung windows, and delightful 1930s details throughout the home. The kitchen boasts vaulted ceilings with wood beams, brand new GE Cafe appliances, a white porcelain farm sink, and a charming brick backsplash. The bathroom features a custom sink vanity built from an antique desk and a spacious shower with a rainfall showerhead. The attic is bright and spacious, providing excellent storage space or space to get creative with! Hiking, restaurants, shopping, and museums are just a stone's throw away, so whether you're seeking a weekend retreat, an investment property, AirBnB, or a full-time minimalist living space, this property is the perfect opportunity for you.

Discover a fantastic opportunity to own a rare ground floor two-bedroom condo in the vibrant heart of Kent's village center. This beautifully renovated, move-in ready unit boasts a modern kitchen and a spacious living and dining area that opens onto an oversized screened-in porch. The two bright bedrooms share a completely updated bathroom featuring premium Kohler fixtures. Recent upgrades enhance the home with new recessed lighting, sound insulation, and refinished/expanded hardwood flooring throughout, in addition to the stunning kitchen and bathroom renovations. Don't miss out on this incredible offering in an ideal location with easy access to shopping and dining!

Amazing privacy atop one of the highest points in Sharon, CT. This 33 acre property is a wildlife paradise. Set amidst this property is a lovely 3 bedroom country cottage on 33 acres of large oaks, maples, brook and lots of stone walls. The home has a stunning wood beamed living room anchored by a fireplace. Sliding doors open to a porch and the level grassed yard. The spacious kitchen flooded with natural light. Upgrades to house and mechanicals have recently been made making this a comfortable weekend retreat. Selective clearing could open up views to the south, west and east. Privacy is assured as abutting neighboring land has development restrictions. Substantial woods replete with hardwoods, mountain laurel and amazing rock outcroppings. There is a small brook and historic remnants of the iron industry with charcoal circles and stone huts. Should one wish there are additional building sites for a larger home development. Across from the Sharon Audubon Center with interactive programs, hiking trails and raptor rehabilitation program, the property is minutes from the village of Sharon and Metro North Trains to NYC. This is an outdoorsman's paradise!

"The Falls." Prominent Modernist Architect, Charles Gwathmey of Guggenheim Museum renovation fame, designed this masterpiece in one of the most beautiful locations, offering dramatic views, cascading waterfall, nestled on 40+ acres of beautifully landscaped grounds with serene stream and extensive stonework. The property boasts a breathtaking western view of the Litchfield Hills. Just minutes to Kent Center with Swyft, Wilson's and great shopping, this exceptional offering provides tranquil escape while remaining close to vibrant shops and renowned award winning restaurants and just 90 minutes from NYC. Step inside and discover a light filled haven with soaring ceilings and curved walls and a stunning view of the waterfall from the Living room, which opens on to a picturesque stone terrace overlooking the babbling brook. A Michael Arad-designed addition of a full bedroom suite complete with office and captivating vistas. A tennis court, gorgeously designed pool and spa, acres of meadows and rolling landscape make this the perfect estate. A natural planted roof, and Deborah Nevins-designed park, gardens, perennial paths. The Stephen Sills designed interior spaces complement the curved walls, glass-covered corridor

Utterly Magical Kent Compound with Pool. c1850 2-3 Bedroom, 3 Bath Main House with High Ceilings, 3 Fireplaces & Wonderful Period Details. Separate Grand Antique Party Barn/Guest House with 1 Bedroom & 2 Full Baths; High Ceilings; Beams & Views. Central Gunite Pool with Cabana & 2-Car Garage. Less than 5 Min to the Center of Kent CT & 20 Min to Metro North Train.

Welcome to this charming historic eyebrow colonial home in the heart of Sharon, Connecticut. This property perfectly combines country charm with modern comfort, offering a peaceful retreat with easy access to the beauty of the Litchfield Hills. The home features a spacious living room with hardwood floors and natural light, creating an inviting atmosphere. The spacious eat-in kitchen also offers hardwood floors and abundant natural light, while the extra room could be used as an office space or formal dining room for family meals. With four spacious bedrooms and well-kept bathrooms, this home offers ample room for comfort and convenience. Located just minutes from Sharon's village center, you'll enjoy easy access to local shops, restaurants, and outdoor recreation, including hiking the Appalachian Trail and exploring nearby lakes. This home offers the perfect balance of tranquility and convenience.

Just steps from Sharon's village center on a farm-like one acre setting, this charming 4 BDR home has the best of both worlds. The classic New England one level design seen from the road belies the amazing space, size and comfort that this country home offers. The property features 2666SF of living space, including a 480SF finished den on the lower level.There are 10 rooms offering ample space for personal and private enjoyment. The kitchen is a chef and sous-chef's dream with generous counter space. A large deck off the kitchen is available for al fresco dining. Or open the dining room's French doors for both inside/outside dining. Natural sunlight floods the LR through the huge window and also revealing colorful sunsets. An antique book-cased lined office is tucked quietly off the LR. There are 4 BDR and 2 Full Baths on the main floor. The lower level is adorned with a native stone fireplace, a wall of windows, and direct access to the side yard. This level offers a large workout area, laundry room, a shop, and an expansive storage room, significantly enhancing the home's surprising spaciousness. This house is more than a great space and location. The oak flooring, curved arch doorways and Ipe Wood deck reveal thoughtful style and quality material choices. The level one acre open parcel offers mature native trees, simple gardens and privacy. Minutes from Sharon's shops. Visit nearby Lakeville and Millerton. 15 minutes to train station to NYC. Come & enjoy this special gem.

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.

Enjoy rest and relaxation in this spacious 1 bedroom cottage situated on an oversized lot in the desirable Silver Lake Shores Association! Features a nice open layout with a large living room and slider access to the deck overlooking the beautiful grounds and rolling hills of Sharon. There is an eat-in kitchen with a breakfast bar, a good sized bedroom, plus a full bathroom with tub & shower. The living room is setup for a wood stove and laundry is conveniently located on the main level. Located just minutes to the boat launch and Sharon Beach on picturesque Mudge Pond where you can enjoy fishing, swimming and kayaking, plus easy access to Lime Rock Park, Hotchkiss, Salisbury, & Indian Mountain School, skiing, hiking, antiquing, restaurants, and more. The Wassaic Metro North train station is just 15 mins away and NYC is just a 2 hour commute by car!

Nestled on 8 private acres with a pond, on a private road, this house is in the picturesque town of Kent, CT. The home has 10 rooms including 4 bedrooms, 3 full bathrooms and 2 half baths. A large guest wing with a separate entrance includes a sitting/living room, 1 bedroom and a full bathroom. There are 3 beautiful stone fireplaces that provide warmth and ambiance to the living room, kitchen and primary bedroom. There is also a library with custom-built mahogany shelves and a stunning stained glass skylight. The lower level includes a large room with a pool table, built in bar and a half bath. The home's screened porch on the main level is a serene retreat and the open deck on the upper level is a tranquil space to enjoy the natural beauty surrounding the home. A true Kent treasure, this home is waiting to become the backdrop for your family's cherished memories. Kent has a variety of great eateries, galleries, library, private schools, hiking trails, and Metro North just a few miles away.

Chic & Private Single Level Living. Totally Private Brick 4 Bedroom, 3.5 Bath Home Nestled Up Long Driveway on 9+ acres. Beautifully Scaled, Elegant Rooms with High Ceilings. 4 Fireplaces. 2-Car In House Garage. Finished Walk-Up Attic Space with 3 Rooms. Wonderful Stone Terrace. Abuts Land Trust in Area of Fine Homes. Owners Ready, Was $1.795.000 now $1.150.000!

Perfectly positioned off a country road close to Sharon's historic town green, this quintessential 1959 ranch style home offers 1,170 sq ft of sunlit living space on a park-like 1.90-acre village lot. This well-preserved residence combines period charm with thoughtful updates, including original hardwood floors throughout the main level and a versatile third bedroom/office and a fireplace in the partially finished basement. The inviting interior welcomes with a distinctive bay-windowed living room featuring a Glacier woodstove insert in the original brick fireplace, providing efficient supplemental heating during Connecticut winters. An air conditioning split system was added for the summer months enjoyment. The light-filled Galley kitchen showcases custom cabinetry and a convenient wall oven, flowing naturally to the dining area and the screened porch-an ideal setting for morning coffee or tea overlooking established perennial gardens. Outdoor spaces distinguish this property from typical village homes. It offers an expansive private backyard with a natural stone patio, mature specimen trees, and meticulously tended garden beds showcasing heirloom plantings. The property is close to Sharon's village core, with the Sharon Pharmacy, Sharon Package Store, and JP Gifford Market & Cafe. Enjoy convenient access to Mudge Pond beach, Sharon Audubon.

Constructed in 2012, this charming four-bedroom Cape is nestled on over 3 acres of complete privacy. The main floor boasts an open-concept kitchen and living area, accompanied by two bedrooms with a shared bathroom. Upstairs, you'll find two more bright and airy bedrooms that share a second full bathroom. The property also includes a roomy two-car garage and a backup generator. This is a fantastic opportunity located on a picturesque road in the heart of the Litchfield Hills.

Secluded Country Estate with Modern Amenities Nestled on over 11 acres in the charming town of Kent, CT, this beautifully renovated country home, built in 2002, offers the perfect blend of rustic charm and contemporary elegance. The spacious interior boasts a newly renovated country kitchen, ideal for entertaining, and extensive renovations throughout, including new floors, fresh paint inside and out, and a whole home generator. Step outside to the expansive front porch, where you can enjoy breathtaking mountain sunset views and sip your favorite beverage. The lovely deck off the kitchen and family room provides another outdoor retreat for relaxation and al fresco dining. The master suite, complete with ample space and private amenities, is complemented by two nearby family bedrooms. At the other end of the hall, you'll find two additional bedrooms sharing a convenient Jack-and-Jill bathroom. Whether you have a big family, or need separate space for visiting guests, this home is truly ready for everyone. One of the estate's standout features is the modern barn, offering endless possibilities. Whether you dream of keeping a horse or other animals, or simply updating it into a separate workshop, private studio, or office retreat, the barn provides a versatile and adaptable space to suit your needs.

1st Time on Market in 40+ Years. Wonderful 4 Bedroom, 4.5 Bath Period Home with Additions. Property is 12+ Acres & Encompasses Both Sides of a Lesser-Known Coveted Town Road. Less than 1-Minute to Mudge Pond Lake & the Town Beach. The Famous "Twin Oaks" Sharon Land Trust Field is Just Down the Street. Lots to be Discovered here including a Jaw-Dropping Great Room with Fireplace & 20' Ceilings. Main Level Primary Suite includes: Dressing Room, Office, Closeting & Screened Porch. Inviting Library with Fireplace & Antique Beams. Large Dining Room with Fireplace Speaks to an Eat-in Kitchen bathed in Light. Separate 600 Square Foot 1-bedroom Guest Quarters Above 2-Car Garage.

Great opportunity to own this expansive New England farm/horse property situated on 70+ acres with great views of the CT Litchfield Hills! This is an estate sized parcel adjacent to National Audubon Society owned land and features multiple homes, barns/garages and paddock. The main farmhouse was built in 1780 and has been added to over the years including a post and beam addition with first floor primary bedroom/suite and family room. There is a separate detached 807 sq ft two bedroom one bath cottage with full basement built in 1967 that could be used as a possible accessory unit or studio. There might be the possibility of subdividing and the buyer is responsible for doing their own due diligence with the town. The property is being sold "As Is".

Country Home In Private Location - This home is located on a private road in Lakeville and features a first-floor primary, a large living room with wood wood-burning fireplace, and a screened-in porch overlooking the grounds. The eat-in kitchen has a separate laundry room, wood cabinets with granite countertops, and sliding glass doors that open to the back deck perfect for outdoor dining or relaxing. The gunite swimming pool has plenty of room for seating and includes an outdoor dining area under a wisteria-covered pergola. Conveniently located near the local private schools, shopping, restaurants, the Sharon Playhouse, and Wassaic train station. Enjoy country living at its best!

"Best In Class" Lake Property just 10 minutes from the vibrant center of Kent, CT. Rare opportunity to purchase a property with access to South Spectacle Lake which is a pristine Crystal Clear 85-acre, spring-fed lake perfect for fishing, swimming and boating. This property is located within an enclave of approximately 20 homes that have use of a community private beach, recreation area, clubhouse, tennis & boating equipment. At the heart of this 3-bedroom, 2.5 bath Cape-style home is a large, sunny, open-floor plan country kitchen/family room with wood-burning stove. Living room with wood-burning fireplace, formal dining room, study, powder room & 2-car attached garage are located on the 1st floor. Upstairs is the primary en-suite plus two additional bedrooms with a shared bath. Located on 8+/- private acres in excellent condition located across the street from the lake. Quiet. Private. 85-miles to NYC. No Motorboats. Must See.