Refine Search
Sort by
$937,000
6 Beds 6 Baths 202621701 MLS
Spacious 3-Story Berkshire Mountain Retreat Sleeps 16 Fully Furnished Family Home/Turnkey Airbnb Investment. Panoramic views and exceptional space for large families, group getaways, or a turnkey short-term rental investment. Move-in ready. The light-filled main living area features a dramatic wall of windows showcasing the mountain views, a soaring stone fireplace, an open-concept floor plan perfect for entertaining. The kitchen is equipped with granite countertops, custom cherry cabinetry, newer appliances, & a large dining area where everyone can gather. The first-floor primary suite offers comfort and privacy with an oversized bathroom featuring a soaking tub, walk-in shower, bidet, and walk-in closets. An additional first-floor bedroom/office includes a closet, full bath, and sleeper couch. Upstairs you'll find two generous bedrooms with a shared bath, along with an open balcony overlooking the living and dining area below. The finished lower level boasts impressive 12-foot ceilings, two additional bedrooms, two full bathrooms, a large family room, and a recreation area-ideal for guests or extended family. Step outside onto the expansive trex deck and enjoy stunning Berkshire sunsets, entertain around the outdoor fire pit, or take advantage of the large cleared backyard with plenty of room for a future tennis court or in-ground pool. This home is being sold fully furnished and includes numerous extras: Backup generator Two game rooms with handcrafted checkers table, and backgammon, for the adults. And a second room for the kids with basketball shooting and a foosball table among other games. All with a private bathroom. Garage with extra refrigerator, mini refrigerator, air comp portable power tools, radial arm saw, and more. 220-volt outlet for convenient EV. Located just minutes from Queechy Lake, with lake access, excellent restaurants, Tanglewood, Lenox, Stockbridge, Chatham, Williamstown, Hudson & TSP, I90

35 Whitetail Trace

$650,000
3 Beds 3 Baths 202621523 MLS
Escape to your own private retreat where lake living, outdoor adventure, and timeless country charm come together! Just steps from scenic Copake Lake, this property offers access to one of Columbia County's premier recreational destinations. Copake Country Club features an 18-hole championship golf course and year-round dining. Conveniently located between Hudson and Great Barrington, and just a short drive to Catamount Mountain Resort, the area offers four-season recreation, with the tranquility of your own beautifully landscaped 4.66 acre setting. Inside, this home is rich with warmth and timeless character. The inviting eat-in kitchen features a breakfast bar, abundant cabinetry, and a pantry, creating a functional space that will delight any home chef. Just beyond, the dining area flows seamlessly into the spacious living room where a cozy wood-burning stove, custom built-in bookcases, and decorative wood trim create a welcoming atmosphere for everyday living and entertaining. The bright, glass enclosed sunroom provides the perfect spot for morning coffee, reading, or simply relaxing, while a handily located half bath completes the main level. Upstairs, you'll find three comfortable bedrooms and two full bathrooms. Gleaming hardwood floors span throughout both levels, and an abundance of natural light fills the home, enhancing the attractive appeal. Outside, the detached two-car garage includes ample room for a workshop, lawn equipment and recreational storage. The second floor of the garage offers endless possibilities as an artist's studio, home office, fitness room, or hobby space. . Unwind beneath the covered patio and enjoy the serenity of your surroundings. Whether you're searching for a full-time residence or the perfect weekend getaway, this exceptional property offers the ideal balance of privacy, recreation, and convenience--just minutes from the Taconic State Parkway and only 2.5 hours from New York City.

3493 County Road 7

$799,000
3 Beds 1 Baths 202620821 MLS
Discover the perfect blend of privacy, space, and versatility with this custom-built 2,400 sq. ft. home nestled on 5.5 scenic acres. Featuring 3 bedrooms, 1 bath, and soaring cathedral ceilings, this one-of-a-kind property offers comfortable living with exceptional indoor and outdoor amenities. Step outside to your own private retreat, complete with an inground pool, pool house, greenhouse with a newer metal roof, basketball court, and beautifully landscaped grounds. Enjoy the beauty of mature plum, apple, pear, and mimosa trees, stunning Japanese maples, and a charming grape arbor that creates a peaceful setting for relaxing or entertaining. Ideal for car enthusiasts, hobbyists, or small business owners, the property includes an attached 4-car garage plus a separate insulated building with electric that accommodates up to three additional vehicles. The upper level offers a dedicated home office and a second finished room perfect for a gym, art studio, guest space, hobby room, or private retreat. Whether you're dreaming of a hobby farm, home-based business, workshop, studio, or simply a peaceful country escape with room to grow, this exceptional property offers endless possibilities. The combination of acreage, multiple outbuildings, abundant storage, recreation, and mature landscaping makes this a rare opportunity. Conveniently located while offering the privacy and tranquility of country living, this is more than a home--it's a lifestyle. Schedule your private showing today and experience everything this remarkable property has to offer. Virtual tour https://walkthruphoto.info/Public/25-Hawthorne-Hill-Rd-6-29-26/25-Hawthorne-Hill-Rd-6-29-26.mp4 3D tour https://youriguide.com/25-Hawthorne-Hill-Rd-6-29-26/

25 Hawthorne Hill Road

$525,000
3 Beds 2 Baths 202620781 MLS
Sweet, cozy, well maintained home on 4.5 acres of manicured rolling lawn. Three bedrooms, and an office/sitting room on the second floor. Walk in closet in main bedroom. Laundry on the second floor. Cozy living room fireplace on cold winter nights. Castle windows with a transferrable lifetime warranty. New roof with Helmut gutter system. Quaint country kitchen that is open to the living and dining rooms and looks out over the backyard. Sit on the back deck and be one with nature in your own Oasis with a creek to cool down in at the back of the yard. Easy access to The Berkshires, Chatham, Hudson, Albany. Move in ready. And a huge bonus, a giant size 2 car garage with a storage building/small business space/ retail shop attached, approx 65'x35' comes with this property. Endless opportunities here. Close to The Berkshires, Hudson, Chatham, TSP, I90, I87, Albany. Come experience it.

1188 U.S. 20

$694,000
3 Beds 2 Baths 202620622 MLS
Escape to your own private retreat! Nestled on 22.2 scenic acres and backing directly to Hand Hollow State Forest, this unique property offers the perfect blend of country living, recreation, and convenience.The charming 2,000-square-foot Cape features 3 bedrooms, 2 full baths, a dedicated home office, and a sun-filled sunroom where you can relax and enjoy peaceful Mountain views and surrounding landscape. A standout feature of the property is the impressive 28' x 36' heated garage and workshop, complete with abundant storage space for vehicles, equipment, and all your recreational toys. Above the garage, you'll find a separate 960-square-foot apartment with its own septic system--ideal for guests, extended family, rental income, or a private home office. Outdoor enthusiasts will love the direct access to nature and the property's prime location. Enjoy hiking &, snowmobiling and exploring right from your backyard. Conveniently located just 20 minutes from Jiminy Peak, 30 minutes from Albany, 5 minutes from Lebanon Valley Speedway, and a short drive to both Chatham and the Berkshires, you'll have easy access to year-round recreation, dining, shopping, and entertainment.Whether you're looking for a full-time residence, multi-generational living opportunity, hobby farm potential, or the ultimate weekend getaway, this one-of-a-kind property offers endless possibilities.

2439 County Route 5

$499,999
3 Beds 1 Baths 202620533 MLS
Welcome to your own private Hudson Valley retreat with breathtaking Hudson River and Catskill Mountain views. Exceptionally clean, well-maintained, and move-in ready, this home offers the perfect balance of comfort, scenery, and lifestyle. Enjoy peaceful mornings overlooking the river and relaxing evenings from the deck and hot tub surrounded by nature. Inside, the home features thoughtful updates, sun filled living spaces, and a warm, inviting layout designed for everyday living or weekend escapes. The walk-out basement is already plumbed and offers outstanding potential for additional finished living space, guest quarters, a home office, gym, recreation area, or possible in-law setup. A detached garage provides added storage, workshop possibilities, or future expansion opportunities. Perfectly positioned near the Stuyvesant Boat Launch, this property offers convenient access to kayaking, boating, fishing, and everything the Hudson Valley lifestyle has to offer. Whether you're searching for a full-time residence or a peaceful getaway, this property delivers privacy, views, and lasting value in one exceptional setting.

1169 NY-9J

$694,000
4 Beds 3 Baths 202620368 MLS
Escape to your own private retreat! Nestled on 22.2 scenic acres and backing directly to Hand Hollow State Forest, this unique property offers the perfect blend of country living, recreation, and convenience.The charming 2,000-square-foot Cape features 3 bedrooms, 2 full baths, a dedicated home office, and a sun-filled sunroom where you can relax and enjoy peaceful Mountain views and surrounding landscape. A standout feature of the property is the impressive 28' x 36' heated garage and workshop, complete with abundant storage space for vehicles, equipment, and all your recreational toys. Above the garage, you'll find a separate 960-square-foot apartment with its own septic system--ideal for guests, extended family, rental income, or a private home office. Outdoor enthusiasts will love the direct access to nature and the property's prime location. Enjoy hiking &, snowmobiling and exploring right from your backyard. Conveniently located just 20 minutes from Jiminy Peak, 30 minutes from Albany, 5 minutes from Lebanon Valley Speedway, and a short drive to both Chatham and the Berkshires, you'll have easy access to year-round recreation, dining, shopping, and entertainment.Whether you're looking for a full-time residence, multi-generational living opportunity, hobby farm potential, or the ultimate weekend getaway, this one-of-a-kind property offers endless possibilities.

2439 County Route 5

$859,000
3 Beds 3 Baths 202620356 MLS
''The Lodge at Blue Hill'' Nestled on 2.88 private acres along scenic Blue Hill Road, this exceptional 3-bedroom, 3-bath log home offers breathtaking, unobstructed Catskill Mountain views, spectacular sunsets, and a peaceful Hudson Valley setting. Providing the perfect balance of privacy, natural beauty, and accessibility.Built in 2005 and meticulously maintained, the home showcases soaring cathedral ceilings, cherry hardwood floors, and a warm propane fireplace framed by custom 8-foot built-in bookcases. Large windows throughout capture stunning mountain vistas, while thoughtfully selected finishes--including Rejuvenation lighting, Casablanca ceiling fans, custom wood blinds, quartz countertops, a farmhouse sink, and clay tile flooring--add timeless character and comfort.The open-concept kitchen, dining, and living areas create an inviting atmosphere for entertaining or everyday living. Each bedroom features its own en-suite bath, including a luxurious upstairs primary suite complete with a California Closet dressing room, blackout shades, and a private deck overlooking the Catskills.Outdoor living is equally impressive with a 42-foot covered front porch perfect for sunset views and a 16x16 screened porch surrounded by nature. The finished lower level adds approximately 1,000 square feet of living space, featuring a 7-seat home theater with Bose surround sound, a large utility/laundry room, and a soundproof guest suite with private bath.Modern amenities include a Navien on-demand furnace, central air conditioning, whole-house generator, and owner-owned propane tanks. Additional improvements include an oversized heated 2-car garage and a powered 16x16 workshop shed.This turnkey Hudson Valley retreat combines quality craftsmanship, modern convenience, and stunning natural surroundings, all within easy reach of Hudson, Germantown, Olana, the Rip Van Winkle Bridge, the Skywalk, and just two hours from New York City.

1374 Blue Hill Road

$475,000
4 Beds 3 Baths 202620014 MLS
Welcome to your private retreat at 28 Covenant Circle in East Nassau. Nestled on 5 peaceful acres, this beautifully updated 4-bedroom, 2.5-bath home offers the perfect blend of modern comfort and country tranquility. The inside features many updates including: the entire home has been freshly painted, the gorgeous farmhouse wood floors have just been redone, the bathrooms have modern vanities and fixtures, and at the center of it all is the showstopping gourmet kitchen. Designed for both everyday living and entertaining, the expansive wraparound porch offers the perfect space to host gatherings, enjoy your morning coffee, or simply relax while taking in the privacy and natural surroundings. During the warmer months, the above-ground pool is the ideal place to cool off and enjoy the outdoors. The spacious basement offers abundant storage and the opportunity to create additional finished living space, whether you envision a recreation room, home gym, office, or guest suite. If you're looking for modern updates, generous space, and a quiet, private setting just a short drive from everyday conveniences, this exceptional property is one you won't want to miss. This home is USDA Loan Eligible, and the sellers are offering negotiable closing costs.

28 Covenant Circle

$785,000
3 Beds 3 Baths 202618692 MLS
Welcome to Hastings House, a circa 1880s residence set high on the eastern hill of Worth Avenue in the heart of Hudson. This sophisticated 3-bedroom, 2.5-bath home features wide plank original hardwood floors, abundant natural light, and well-proportioned interiors that combine warmth with understated elegance. The galley kitchen opens both to the dining room and to a bright sunroom, creating an inviting flow for everyday living and entertaining. Updated Anderson windows bring light deep into the principal rooms, and mini split systems provide heating and cooling throughout. Mature trees and established plantings surround the property, offering privacy and a serene setting just steps from Hudson's vibrant center. The fully refurbished two-story carriage house adds 750 square feet of flexible living space, complete with a newly installed wood burning stove and air conditioning. Whether used as a studio, guest retreat, office, or creative workspace, it is among the property's most distinctive and versatile features, carrying its own history as a former schoolhouse. A covered front porch frames rooftop views of Hudson and the Catskill Mountains beyond, and a private fenced backyard with patio and fire pit offers a quiet outdoor retreat. Private off-street parking for two vehicles is accessed via the rear alley, with additional parking available out front. Located just steps from Warren Street, Hastings House offers the best of Hudson living, with easy access to Rivertown Lodge, Hudson Roastery, Union Street Brewing, Lil' Debs Oasis, and Cafe Mutton. Amtrak service to New York City is within easy walking distance.

16 Worth Avenue

$1,599,000
6 Beds 5 Baths 202617663 MLS
Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6 spacious bedrooms and 5 bathrooms, including an ideal in-law suite or private apartment setup for extended family, guests, or potential additional living space. The heart of the home is the incredible chef's kitchen--thoughtfully designed with generous work space, high-end finishes, and the kind of layout any chef or aspiring cook would absolutely love. Step outside to enjoy the wrap around deck overlooking the built-in saltwater pool and serene grounds, creating the perfect setting for entertaining or simply relaxing into total privacy. A 3-car garage plus an additional garage beneath the residence provide plenty of room for tractor, hobbies, and storage. This one-of-a-kind Chatham retreat combines elegant country living with modern convenience, all just a short drive to the charming villages, restaurants, and culture the Hudson Valley is known for.

20 Stony Knoll

$2,285,000
3 Beds 3 Baths 202616466 MLS
Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the beautiful Catskills. Stepping through the front door of a wide covered front porch, you'll find an open plan kitchen, dining & living room - the heart of the home, made cozy in winter by an efficient wood stove. The first floor also includes a mud room, office, powder room, laundry room and den. However, it is the 600 sq ft ''Great Room'', with windows on 3 sides that immerse you in the ever-shifting displays of nature and the Catskill range. Upstairs you'll find 3 generous sized bedrooms and 2 full baths including a primary suite with walk-in closet room. The pond, designed by famed UK pool master Anthony Archer-Wills, provides an unparalleled natural swimming experience, set among a chorus of frogs and dragonfly's dancing across the water. A variety of colorful waterlilies and other pond plantings keep to keep the water fresh and inviting. Renovated throughout in 2024-2025, this solar powered home offers you privacy, comfort and jaw dropping sunsets. Conveniently located 10 minutes from Chatham, 30 minutes to the train in Hudson, 40 minutes to the Albany Airport and 25 minutes to Great Barrington & all the culture and fun that our neighboring Berkshires offer. Broker Owned.

53 May Lane

$599,000
4 Beds 3 Baths 202615994 MLS
Move right in! Enjoy the best of both worlds at 22 Van Winkle Road -- a sophisticated retreat tucked away in the serene ''Silent Zone'' of Hudson's sought-after Academy Hill community. This spacious 4-bedroom plus den, 3 full bath townhome offers stunning Hudson River and mountain views, blending peaceful suburban privacy with convenient access to the vibrant energy of nearby Warren Street's acclaimed dining, breweries, art galleries, and boutiques. Bring your own vision and personal touches to this generously sized home featuring two fireplaces, a relaxing jet bath, finished basement and two private balconies and deck overlooking the Catskill and Berkshire mountains. A scenic walking path with breathtaking views adds to the tranquil setting. Whether you are seeking a stylish primary residence, weekend escape, or investment opportunity, the low-maintenance lifestyle allows more time to enjoy the nearby Greenport Conservation area or hop on Amtrak for an easy trip to NYC. Discover modern convenience, natural beauty, and Hudson Valley charm in a community that truly offers it all.

22 Van Winkle Road

$12,750,000
4 Beds 6 Baths 202614668 MLS
DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling hayfields with formal gardens, offering unobstructed vistas to the Catskill Mountains, dramatic sunsets and a lifestyle rooted in beauty, craftmanship and serenity. A tree lined drive leads to the stately 4,900 SF Greek Revival manor home where classic architecture meets stately elegance. Adjacent sits a heated three-car garage complete with a 1.200 SF second floor office apartment and a spacious parking court. Entering the home, you will experience some of the finest craftmanship, curated lighting and architectural detailing. The entrance foyer, with a grand staircase to the second floor, is flanked by a Mahogany paneled library and a sunlit breakfast room. Further, is the formal salon and dining room which extend onto a deep ''southern-style'' covered sitting porch with views of the far-reaching meadows and Catskill range beyond. The chef's kitchen is designed for effortless entertaining while remaining intimate enough for everyday living. Just beyond the kitchen is a service entrance with access to a private one-bedroom apartment above. Upstairs, the primary en-suite is joined by two additional en-suite bedrooms and a richly paneled home office which connects to a third-floor studio with panoramic views. The finished lower level includes a gym, a fully appointed laundry, a second pantry, a cedar lined walk-in closet and the home's mechanical systems. Every floor is serviced by an in-home elevator.

199 Eichybush Road

$3,595,000
6 Beds 5 Baths 202528709 MLS
A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, a fully equipped eat-in kitchen, and a gracious formal dining room—an exceptional blend of timeless architecture and modern luxury. The grounds are equally compelling, featuring a spacious in-ground pool, a tranquil pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, amenities rival those of a private resort, with a full gym, game and entertainment room, home theater, and a refined library creating an environment of comfort, recreation, and retreat. A finished attic and an impressive 4,500-square-foot barn with foosball and ping pong provide additional flexible space for leisure and gathering. Fiber-optic internet and a full-house generator ensure seamless modern living, while the estate's thoughtful infrastructure and meticulous maintenance support effortless year-round ownership. Bellavista stands as a premier private estate, offering a rare combination of total privacy, exceptional amenities, and enduring quality. Just minutes from Chatham, Hudson, and Kinderhook—and a short drive to Lenox, Stockbridge, and Great Barrington—the property is surrounded by acclaimed farm-to-table dining, art galleries, organic markets, and the historic Crandell Theater. Easily accessible via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, and Albany International Airport, Bellavista is as convenient as it is extraordinary.

147 Rock City Road

$109,888
3 Beds 2 Baths 202526860 MLS
Step back in time with this historic colonial home built in 1857, a rare opportunity to own a true piece of American history predating the Civil War. Rich with character and original charm, this property offers the perfect canvas for someone who appreciates historic homes and their timeless craftsmanship With thoughtful rehabilitation, this property presents significant upside potential, with an estimated after-repair value much, much higher. Conveniently located just minutes from the rail station, it combines historic charm with modern accessibility for commuters. Inside, you'll find three bedrooms and two baths, along with beautiful wood floors and two classic fireplaces that evoke the warmth and elegance of another era. The home also features a traditional summer kitchen, a charming reminder of 19th-century living that adds both historical significance and unique character.

45 County Route 26A

©2019 Global Multiple Listing Service, Inc. The data relating to real estate on this website comes in part from the Internet Data Exchange program of the GMLS. All information is deemed reliable but not guaranteed and should be independently verified. All properties subject to prior sale, change, or withdrawal. Neither listing broker(s), GMLS shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties they may be interested in purchasing. Data last updated