Old Chatham NY Real Estate & Homes for Sale

Straight up the Taconic Parkway, just 2.5 hours from Midtown, your driveway is barely noticeable -- but you know what lies beyond - safety, serenity, and seclusion. Unlock the gate, drive through the woods, and prepare to experience a different kind of rush hour - tracking big buck or flushing wild pheasants or raucous turkeys. Better still, just rest and relax on your ultra-private 223+ ac retreat on the hillsides of the Hudson River. Your driveway reveals nothing to the rest of the world about the lovely accommodations that await in the custom-built, true-log home. Outdoor enthusiasts or those just looking for a unique family or group retreat in the Hudson River highlands will find it here. The grounds of the home are well-maintained with landscaping around 2 ponds, and ample parking, plus a 500 sq ft double-door equipment barn. Enter the home and take in the cathedral-like lodge with an open living-dining-kitchen space anchored by a massive 25 foot floor-to-ceiling fieldstone wood burning fireplace. True log walls and rich pinewood floors throughout the home add strength and character in every room. The kitchen, where everyone gathers, is open to this lovely space, with a great seating peninsula, ideal for travelers and wilderness voyagers to sit while the feast is prepared. 2 bdrms on main floor, off kitchen w a shared full bath. Upstairs, a master suite w private bdrm ( massive closets ), full ba, & loft overlooking fireplace. Full basement nicely finished w bonus room ideal for a pull-out couch / guest room, laundry and work area, + .5 bath. Don (or shed) camo, boots, and parkas while still in the comfort of the lower level. There is ample storage, with drive-out doors! Whole house AC. The property is tax-advantaged with ag AND NYS Section 480-a Forest protections. The main driveway covers more than a mile as it curves through the property. Miles more off-road trails provide further access to the parcels, including the 5 high-mounted blinds. Actively managed farm fields, also within the property boundaries, mean ready-made access is waiting for your next ATV adventure.Enjoy this masterpiece along the hills of the Hudson!

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 27 bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the region's premier full-service equestrian facility. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. Equestrian enthusiasts will revel in the compound's state-of-the-art amenities including a 6000 square foot heated arena with a luxurious owner's apartment and viewing area, an outdoor arena, a jump field, and 3 barns housing 26 stalls and 2 tack rooms. Five paddocks grace the property, offering ample space for horses to roam.

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 11+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility (see related listing for $2.25m and ask for pictures). The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations.

Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim all summer in your own pond. Pull a trophy buck in the fall. Hike to the peak and back country ski down in the wintertime. Be the first to catch a trout in your own private trout stream.

Welcome to Meadow Wood. This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lilypond, terraces, pastoral views, and wonderful privacy. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours & has received a Garden Club of America award for its ethos & thoughtful use of building materials. The house was constructed using sustainable & recycled low maintenance building materials designed to last a lifetime. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays. A barn, cutting gardens, and a separate private drive complete this part of the estate. Hidden from the road, the main house is approached by a long drive lined with mature Scarlet Oaks & daffodils. A courtyard filled with specimen crabapple trees, stone walls & walkways creates the welcome entry to this one level home.The exterior walls are planted w/ climbing hydrangea that blur the

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of the future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+-year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by.

Welcome to 53 Bellevale-a charming 3-bedroom raised ranch nestled in one of Monroe's most desirable neighborhoods. Situated on a level one-acre lot, this home offers both comfort and functionality, with plenty of space to relax and entertain. Step inside to find a bright and inviting living area that flows effortlessly into the dining space and kitchen. Just off the kitchen, you'll fall in love with the beautiful enclosed porch-perfect for morning coffee or evening dinners-while enjoying serene views of the backyard. This home features 3 Bedrooms, 1.5 bathrooms, a spacious 2-car garage, and plenty of storage throughout. The lower level offers additional living space ideal for a family room, home office or an additional 4th bedroom. Enjoy the best of suburban living with nearby parks, top-rated schools, and easy access to local amenities. Don't miss the opportunity to make this well-maintained home your own!

GRACIOUS IN-TOWN LIVING IN THE SOUTHERN BERKSHIRES This gracious vintage home has been thoughtfully renovated and lovingly maintained by the current owners for over 20 years. High ceilings, wonderful light, spacious rooms, a ''walk to everything'' in town location, and residential/commercial zoning provide comfort and unlimited possibilities. A 1,000 sq. ft. outbuilding with water & electric service adds more potential. Beautiful period detail combines with with modern updates-crown molding, soapstone counters, farmer's sink, cherry cabinets, a built in hutch, wood & tile flooring, a South facing bay window, French doors, a large 1st floor Laundry Room, new water heater, and new septic are just the beginning. The large, private room above the Garage is an ideal Studio or Office. There is so much to enjoy here-come see for yourself!

MOTIVATED SELLERS! Charming and cozy two-bedroom, one-bath cottage situated in the picturesque Catskills region, ideal for those seeking a simple life or a weekend getaway. Spanning 750 sq ft, this well-maintained home offers single-floor living, making it accessible and convenient, The cottage features two comfortable bedrooms, providing ample space for family or guests. This home has seen numerous enhancements, ensuring both comfort and efficiency, including: Upgraded electrical system, including electric baseboard heat for the entire house; improved insulation for improved efficiency; brand new kitchen appliances; new pellet stove; new plumbing for kitchen and bathroom, including a new, on-demand water heater; and a new and improved laundry room with new laundry appliances. Nestled in the scenic Catskills, this property is ideally located near ski resorts and various tourist attractions, making it a perfect escape for both winter sports enthusiasts and summer adventurers. The cottage promotes a simple, peaceful lifestyle, ideal for those looking to unwind from the hustle and bustle of city life. The single-floor layout enhances livability, perfect for individuals of all ages. 231 Stone Bridge Rd is a delightful cottage that combines modern comforts with the beauty of nature. With its strategic location near recreational activities and recent updates that enhance functionality, this property is a fantastic opportunity for anyone looking to embrace the charm of Catskill living.

Idyllic cabin in the woods set on 14 acres amongst long pines, a large barn w/horse stalls. 2 hours from NYC, 6 miles to NY State hiking trails, 15 minutes to the Windham Mountain Ski slopes, and less than 30 minutes to HunterMountain ski slopes, The property is bordered by a beautiful mountain stream & the Agroforestry Model Forest, which includes 147 acres of marked hiking trails. The cabin provides cozy charm with modern comfort--including a cook's kitchen with Thermador appliances, 2 renovated baths, 3 bedrooms and a separate office space (possible 4 th bedroom), living room with barn doors, family room w/soapstone wood stove, three covered porches and an open deck, 4 zone hw ht. They have put in new basement windows and door to the backyard, restored the front and rear deck support systems, installed a security system. system and smart home devices, barn doors on the living room, a new washer and dryer, a French drain in front of the house and just re-stained the exterior and decks along with landscaping around the home. This is no ordinary cabin in the woods''

The post-and-beam residence showcases soaring ceilings and expansive windows that frame the spectacular landscape while highlighting the architectural character throughout. Natural materials-including local woods, native stone, and artisanal steel elements-create a sophisticated dialogue between interior spaces and the surrounding countryside. The heart of the main level features a grand Great Room anchored by a floor-to-ceiling stone fireplace, flowing seamlessly into a gourmet Chef's Kitchen with double islands and custom cabinetry. An elegant staircase serves as a natural divider between living areas, while French doors open to a spacious patio overlooking the pastoral grounds, historic barns, and mountain vistas beyond. The thoughtful floor plan includes a main-level with 3 en suite bedrooms, a library, and formal sitting room accessible from the gracious entry hall. A classic New England mudroom provides practical transition space for all seasons. The second level offers 2 primary bedroom suites plus two charming office spaces with northwestern mountain views. A custom steel staircase ascends to a serene meditation loft, creating a private retreat. The finished lower level opens directly to the landscaped side yard, featuring fieldstone walls that echo the property's agricultural roots. Several outbuildings, including a substantial barn, await their next chapter and offer a blank slate for the country hobbiest.

Clarion Farm is an iconic French Country Estate & Horse Property in Salisbury, CT. It is a serenely private retreat with a 4-bedroom main house, a Studio on 16.25 acres, and a Horse Property on 30.72 acres for a total of 47 acres only a few minutes from the village of Salisbury and 15 minutes into Great Barrington. This exquisite property seamlessly blends tranquility with sophistication, creating an unparalleled living experience. Every aspect has been thoughtfully crafted to ensure maximum comfort and well-being, making it a true haven of peace and French Country Casual Luxury. All rooms are generously sized and flow beautifully into one another. The stunning private stone-walled pool courtyard is perfectly situated on the professionally landscaped property. Clarion Farm has a 12 Stall Horse Barn, a 6 Stall Barn, an Indoor 80 x180 Indoor Riding Ring, a 100 x 200 Outdoor Riding Ring, 6 Paddocks, and a 2 Bedroom Barn Apartment. Ideally situated near the many private & public schools, Catamount Ski Area and Aerial Park, and the villages of Salisbury, CT, Millerton, NY, Great Barrington, MA, and Wassaic Train Station. This listing includes two parcels: 10 N. Beaver Dam Road (Parcel ID: 2408134) and 471 Undermountain Road (Parcel ID: 2769378), with acreage and taxes reflective of both properties.

It's no wonder why this property is the home of Berkshire county's oldest elm tree! The abundant sunshine, quietude and peace would make anybody want to set down roots and stay a while. This light filled home has refinished wood floors throughout the main level. Kitchen has granite counters, ample cabinet space, pantry and large island. As part of the open floor plan there is a bright dining room and living room area that opens to an expansive composite deck. The great room has endless mountain views, river views and a welcoming fireplace. The lower level also has a main floor bedroom, laundry, office and lots of closet space. Upstairs is the spacious primary bedroom with private bathroom and exterior balcony overlooking horse pastures. There is a third full bath, two additional bedrooms and bonus room. This property really comes alive outside! The two stall barn is in excellent condition. Stalls are 12x12 with electric and frost free hydrant, tack/feed room. Exterior access to two private paddocks that open into a lush pasture. Barn also includes equipment area, workshop and RV parking space or use this space as a run in for livestock. The home is surrounded by mature gardens and hardscapes. Walkout basement has slider to a stone patio area and a fireplace. Could be spectacular extra living space. Home is complete with an invisible fence system for your pups and whole house generator. Horse property, waterfront and views this property is it!

Nestled on a peaceful 1-acre lot, this 2 bedroom, 2 bath Cape provides warmth, character, and opportunity! A spacious kitchen, with adjoining pantry, and dining area provides plenty of room for gathering. The inviting living room features exposed beams and a brick hearth, perfect for a wood or pellet stove. The first floor includes a bedroom, laundry and full bath, while upstairs boasts a large bedroom, another full bath and a versatile landing area. Outside you will find an oversized shed with ample storage, perfect for tools, equipment or hobby space. With major updates already done by the owners of 23 years, this home is ready for your personal touch. A little vision and TLC can transform it into the perfect starter home, cozy getaway or AirBnB! A short drive to Great Barrington. Don't miss out! Newly adjusted price.