84 properties for sale in Green River, Hillsdale town Columbia County New York

Architecture meets nature in Hillsdale. A fully secluded getaway at the end of a private dead-end road on 7.3 pristine acres. This sunny 3-bedroom, 2-1/2 bath house is inspired by Scandinavian design and features 3 outdoor decks, with views of a spring-fed stream, a crystal clear pond, and deep green woodlands. Central AC for summer days and a wood stove for snowy nights. An ideal layout for working from home and for guests, this well-maintained house includes a ground-level walkout room which would be ideal for a studio or for entertaining. Reimagined by a fashion editor and creative director, 10 minutes from Great Barrington and 7 minutes to the Catamount Ski Resort, this property is situated between the Berkshires and the City of Hudson, with endless shopping, food and cultural destinations

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility

Completely renovated New England farmhouse offering the perfect blend of historic charm and modern convenience. Thoughtfully remodeled throughout with updated kitchen, baths, systems, and finishes while preserving the character and warmth of a classic Berkshire home. Bright, inviting living spaces, abundant natural light, and quality craftsmanship create a move-in-ready residence with potentially two primary suites, one up and one down. Conveniently located near Gt Barrington's shops, restaurants, Berkshire County cultural attractions and ski/outdoor recreation. A rare opportunity to enjoy modern living in a beautifully restored farmhouse with lush private setting and fenced yard. A garden level pergola with seating area invites conversation with family and friends in complete privacy

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility

This is a two-family structure with a lower level unit for renting with 884 SF, 2 beds 1 bath. Seller is a not for profit entity constructing work force housing. Four units in two structures. Rental income is intended to make the primary residence more affordable. Full time residency will be required. Buyers and renters must be qualified by seller. For showings and offers, contact owner directly or via email

Completely renovated New England farmhouse offering the perfect blend of historic charm and modern convenience. Thoughtfully remodeled throughout with updated kitchen, baths, systems, and finishes while preserving the character and warmth of a classic Berkshire home. Bright, inviting living spaces, abundant natural light, and quality craftsmanship create a move-in-ready residence with potentially two primary suites, one up and one down. Conveniently located near Gt Barrington's shops, restaurants, Berkshire County cultural attractions and ski/outdoor recreation. A rare opportunity to enjoy modern living in a beautifully restored farmhouse with lush private setting and fenced yard. A garden level pergola with seating area invites conversation with family and friends in complete privacy

This is a two-family structure with a lower level unit for renting with 884 SF, 2 beds 1 bath that is not included in the square footage. Seller is a not for profit entity constructing work force housing. Four units in two structures. Rental income is intended to make the primary residence more affordable. Full time residency will be required. Buyers and renters must be qualified by seller. For showings and offers, contact owner directly via email

Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front courtyard, edged with stately Bradford pear trees and arbor vitae and anchored by the 2716sf, single-level residence and a matched pair of outbuildings-a two-car garage and a garden house. (See MORE) The front entry of architect-designed residence leads to a luminous interior with tall ceilings, reflective white walls, generous windows and 19 screened French doors that welcome sunlight and breezes and provide for ideal interior-exterior living. To the left of the entry are a living room with a wood-burning Rumford fireplace and hallway to the primary suite with an airy, comfortable bedroom, refined,

This is being constructed by Community Development Corporation of South Berkshire, a local non-profit, as work force housing. Four units in two structures. Each structure is sold as a two family. Rental income is intended to make the primary residence more affordable. Full time residency will be required. Contact CDCSB directly or via email for qualification and showing. No showings until fall as it is under construction

Beautifully appointed four-bedroom, one-and-a-half-bath contemporary New England farmhouse, perfectly situated in Egremont's most desirable location, Baldwin Hill. This thoughtfully designed residence blends timeless farmhouse charm with light filled rooms, delivering a serene retreat with Iconic Westerly Berkshire views. Protected land (APR Land) both front and rear ensure these views are protected for generations to come

This beautiful home was built in 2006, and updated in 2022. The house is situated on just shy of 5 Acres in the town of Egremont. The home is flooded with sun all day, rarely needing a light on in the house. Direct access to the Green River at the edge of property to cool off on those hot summer days. A new central AC system was installed throughout home and apt A New backup generator, rain gutters, new lighting inside and out, full painting inside and out in 2025. First floor primary suite with jet tub and separate shower. The oversized rear screened in porch is divine, you will never want to leave. A Giant lawn for entertaining and a separate in law apartment for your guests. The garage with radiant heat is perfect for your classic cars or boat. Low Taxes and 5 minutes to GB town

Charming Cape on desirable Baldwin Hill, minutes from the village of South Egremont. This inviting home blends classic New England character with comfortable living, beautiful oak floors, natural light and spacious living room centered around a fireplace with insert. The kitchen flows into the dining area, creating a welcoming space for everyday living and entertaining. A large three-season porch provides the perfect place to relax and enjoy the surrounding landscape throughout much of the year. Outside, you'll find two covered porches, attractive mature landscaping, two-car garage with a dedicated workshop and separate garden shed, offering ample space for hobbies, storage and gardening. With two bedrooms, two full baths and warm, welcoming feel, this delightful home is move-in ready and easy to show

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main floor for year round comfort. The first-floor primary suite offers a private retreat with a spacious spa-like bath, featuring a large shower, soaking tub, and generous walk-in closet. An impressive entry fo

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main

Beautifully maintained 1922 Sears Arts & Crafts bungalow where timeless craftsmanship meets thoughtful modern updates. Rich in original character and move-in ready, this exceptional home features beautiful woodwork, inviting living spaces, an updated kitchen and baths, and a charming enclosed front porch perfect for morning coffee or peaceful evenings. The true hidden gem is the quiet, private backyard sanctuary surrounded by mature landscaping, offering the perfect setting for entertaining, gardening, or simply relaxing in nature. A rare three-car garage provides outstanding space for vehicles, hobbies, storage, or a workshop. Ideally located in the heart of Columbia County, just minutes from Chatham, Hudson, and the Berkshires, with easy access to hiking, skiing, farm markets, restaurants, shopping, and year-round cultural attractions. A perfect full-time home or weekend retreat offering charm, privacy, and a lifestyle that's increasingly hard to find

Beautifully maintained 1922 Sears Arts & Crafts bungalow where timeless craftsmanship meets thoughtful modern updates. Rich in original character and move-in ready, this exceptional home features beautiful woodwork, inviting living spaces, an updated kitchen and baths, and a charming enclosed front porch perfect for morning coffee or peaceful evenings. The true hidden gem is the quiet, private backyard sanctuary surrounded by mature landscaping, offering the perfect setting for entertaining, gardening, or simply relaxing in nature. A rare three-car garage provides outstanding space for vehicles, hobbies, storage, or a workshop. Ideally located in the heart of Columbia County, just minutes from Chatham, Hudson, and the Berkshires, with easy access to hiking, skiing, farm markets, restaurants, shopping, and year-round cultural attractions. A perfect full-time home or weekend retreat offering charm, privacy, and a lifestyle that's increasingly hard to find

Refined and classic elegance abounds in this historic and prominent Spencertown hamlet home. Built in 1810 as a fashionable Federal Style home, it featured magnificent details and craftsmanship throughout. Step back in time in this glorious and updated property. The abundance of 19th century luxury features have been lovingly restored and enhanced from the polished original flooring, window trims, the grand staircase, 3 fireplaces with original mantles and so much more. Step outside to view the pristine landscaping, which continues to evoke the home's historic character. The sun filled property and home are both formal and casual and is designed for grand entertaining and/or a quiet retreat. You will feel the warmth immediately upon entering the home. Its 3200 sq ft. Offers a spacious living room and a magnificent dining room, both anchored with original fireplaces, a glorious sun porch, a large kitchen with a full pantry, and a den with a wood burning stove. A powder room and laundry

Charming 1923 Sears Arts & Crafts Bungalow. A rare and beautifully preserved home that radiates character, craftsmanship, and warmth. Nestled in the peaceful Spencertown hamlet this sears and roebuck home holds historic charm with thoughtful updates for today's lifestyle. Step inside through the inviting front porch(enclosed for year-round enjoyment) and experience the glow of original woodwork, and an abundance of natural light. The home showcases hallmark Craftsman details: a spacious dormer, original trim, and a handsome brick chimney with a new wood stove insert. Open living and dining spaces are perfect for cozy evenings or entertaining, anchored by rich hardwood floors. The kitchen offers both style and function, maintaining a sense of heritage while being ready for everyday cooking and gatherings. Outside a 1900s 3 car brick garage ready to be a studio & beautiful oversized raised bed garden, partially fenced private back yard oasis and much more

OPEN HOUSE Sunday June 21 st 11AM-1PM In the desirable Spencertown hamlet, this'top to bottom' quality renovated Cape is move-in ready for summer enjoyment. Everything is new. Roof, heating and AC, windows, doors, hardware, fully equipped kitchen with stainless appliances and granite countertops, flooring, lighting, bathrooms, fencing, washer and dryer and more. A fantastic location, close to Chatham, Hudson, The Berkshires and The Taconic Parkway. There are 3 bedrooms, 2 large bedrooms on the upper floor and a smaller bedroom/office on the main level. The 2 full bathrooms are beautifully appointed with distinctive tiling and vanities. A large screened porch adds to the comfort of the property. The sun filled 1.3 acres, (2 lots) with a babbling brook is ready for your gardening expertise. There is a large barn/garage at the far end of the property, which needs some love to create a studio, guest space or workshop. This is a home you will want to see! Whether you seek a full time reside

OPEN HOUSE SUNDAY JULY 26TH 11AM-1PM In the desirable Spencertown hamlet, this'top to bottom' quality renovated Cape is move-in ready for summer enjoyment. Everything is new. Roof, heating and AC, windows, doors, hardware, fully equipped kitchen with stainless appliances and granite countertops, flooring, lighting, bathrooms, fencing, washer and dryer and more. A fantastic location, close to Chatham, Hudson, The Berkshires and The Taconic Parkway. There are 3 bedrooms, 2 large bedrooms on the upper floor and a smaller bedroomu002Foffice on the main level. The 2 full bathrooms are beautifully appointed with distinctive tiling and vanities. A large screened porch adds to the comfort of the property. The sun filled 1.3 acres, (2 lots) with a babbling brook is ready for your gardening expertise. There is a large barnu002Fgarage at the far end of the property, which needs some love to create a studio, guest space or workshop. This is a home you will want to see! Whether you seek a full time

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Located on a quiet street in Housatonic, this charming cottage offers easy single-level living in a peaceful neighborhood setting. Set on a sunny double lot, the property provides extra outdoor space and flexibility with room to garden, entertain, play, or simply enjoy the surroundings. Inside, the home features an efficient layout filled with natural light, creating a bright and comfortable feeling. An oversized garage adds valuable storage and space for hobbies, tools, or workshop use. One of the highlights of this location is being within walking distance to Old Maids Park, where you can enjoy fishing, swimming, and a picnic area along the river. This sweet cottage offers a wonderful opportunity for those seeking a manageable home with everyday simplicity and nearby recreation. Minutes to downtown GB, and local amenities!

Experience a rare Zen-inspired retreat in the heart of the Berkshires, designed in harmony with its natural surroundings. Set on nearly 120 acres of protected land with striking rock outcroppings, sweeping mountain views, and ~1,000 feet along the Williams River, this architecturally significant Contemporary offers exceptional privacy just minutes from Great Barrington. Designed by Steven Haas, the home blends steel, glass, concrete, and wood, with soaring interiors and Sorpetaler sliding glass walls that open seamlessly to nature. Expansive decks overlook a 25-meter heated saltwater lap pool, hot tub, and fire pit. The open chef's kitchen with oversized wood-burning fireplace anchors the home, while the living room offers a second fireplace and serene views. A glass and stone courtyard enhances the tranquil design. The primary suite is a private sanctuary with spa-like bath, dressing room, office/lounge, and its own deck. Guest accommodations throughout offer comfort and privacy. The

Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Walk to Berkshire Mountain Bakery; minutes to Great Barrington and Tanglewood. A rare, turnkey find!