Taconic Hills Homes for Sale

Welcome to the Taconic Hills School District, nestled in the picturesque Columbia County of New York. This vibrant community is not just a place to live; it’s a nurturing environment where education is prioritized and students are encouraged to thrive. The Taconic Hills School District is renowned for its commitment to academic excellence, offering a diverse curriculum that caters to the varied interests and talents of its students. With dedicated educators and a plethora of extracurricular activities, children here are not only prepared for higher education but also equipped with the skills they need to succeed in life.

Families moving to this beautiful area will find a delightful array of homes for sale, each offering unique charm and character. From cozy cottages to spacious family homes, the Taconic Hills real estate market has something for everyone. Imagine waking up to the serene landscapes of the Hudson Valley, surrounded by lush greenery and the stunning backdrop of the Catskills. Many properties boast large yards, perfect for outdoor activities and family gatherings, while others feature modern amenities that blend comfort with style.

Living in the Taconic Hills School District means being part of a close-knit community that values education, recreation, and the great outdoors. With easy access to local parks, hiking trails, and charming small towns, residents enjoy a quality of life that is both peaceful and enriching. Explore the homes for sale in this enchanting area and discover the perfect place to call home, where your family can grow, learn, and create lasting memories together.

Newest Taconic Hills Homes for Sale

$1,200,000

5 Beds ⋅ 4 Baths ⋅ 1049616 MLS

Welcome to 156 Farm Road, a rare and versatile multi-residence property offering two completely renovated homes for one price. Set along a quiet country road and surrounded by mature trees, this turnkey property offers privacy, flexibility, and an array of possibilities for an owner-occupant, extended family, guests, or an investment opportunity. The lower residence is a charming two-story farmhouse offering 1,646 square feet with three bedrooms and two full bathrooms. The first floor features a bedroom and full bathroom, while upstairs are two additional bedrooms and a shared full bathroom. A wood-burning fireplace adds warmth and character to the living space. The home also features its own paved driveway, detached garage, fire pit, and partially fenced outdoor area. The upper residence is a 1,400 square-foot ranch, privately situated at the end of a gently winding, sloped driveway and nestled among the trees. Offering two bedrooms and two full bathrooms, the home includes a spacious primary suite, eat-in kitchen, and inviting living area with a wood-burning fireplace. A wraparound deck provides multiple ways to enjoy the peaceful setting, with access from both the main front entrance and the kitchen. The ranch also enjoys its own private backyard, fire pit, and partial fencing for added privacy. Both homes have been completely renovated inside and out, feature electric car chargers, and are fully electric, featuring central air in the upper house, and mini-split heating and cooling systems supplemented by electric baseboard heat in the lower house. Recent exterior improvements include reseeding of the yard, professional tree maintenance, two paved driveways, and additional gravel parking for the upper residence. With two separate residences on one tax lot, the property offers exceptional flexibility. Live in one home while using the other for guests, extended family, or potential rental income, or explore the property as an investment. The thoughtful separation of the two homes allows for privacy while still offering the convenience of a single property. Quiet, private, and completely turnkey, 156 Farm Road is a distinctive opportunity to own two beautifully renovated residences in one peaceful country setting.

156 Farm Road, Copake

$879,000

3 Beds ⋅ 3 Baths ⋅ 1048206 MLS

Located on a quiet country cul-de-sac in Hillsdale, this spacious three-bedroom home sits on 4.7 private acres. One of just three residences along the road, it enjoys an exceptionally peaceful setting, with open lawn, well-maintained woods, trails, and old stone walls. Inside, the living space provides generously proportioned rooms and abundant natural light. The living room centers around a stone fireplace, with large windows and direct access to an expansive back deck, ideal for outdoor dining, grilling, or simply enjoying the surroundings. The generously sized kitchen includes a large eat-in area, while a separate dining room offers additional space for gathering. The primary suite is notably spacious, with an en-suite bath featuring a soaking tub and separate shower. Two additional well-sized bedrooms, a second full bath, and a half bath complete the main level. A full walkout lower level spans the footprint of the house, with high ceilings, multiple windows, and French doors leading outside. Currently unfinished, it offers potential for additional living space, a studio, gym, or recreation room. The home also has an attached two-car garage. A separate two-car garage/workshop offers even more flexibility for creative pursuits, projects, or additional storage. For all its privacy, the property is exceptionally well positioned, with the village of Hillsdale, Catamount, and the Harlem Valley Rail Trail all just five minutes away. Copake is also nearby, with both Hudson and Great Barrington within easy reach.

310 Pine Ridge Lane, Hillsdale

$299,000

1 Beds ⋅ 1 Baths ⋅ 1048427 MLS

Built in 1807, this charming one-bedroom, one-bath cottage feels like a little piece of history. Recent thoughtful updates have brought comfort and ease to the home while keeping the details and character that make it so special. The main level is open and light filled, with original wide plank floors and exposed beams running through the living and dining space, a nod to the home’s early origins. Just beyond is a home office with French doors that open directly onto the patio, bringing fresh air and garden views into the workday. Upstairs, the lofted bedroom is tucked beneath the roofline, a cozy space with a character all its own. Outside, the partially fenced yard offers plenty of reasons to spend time outdoors, with a fire pit for evenings under the stars. A separate studio is perhaps the property’s most unexpected feature. With its own wood-burning stove, it’s a space for painting, writing, making, or whatever creative pursuit takes hold. With the Hudson Valley and Berkshires both at your fingertips, there’s plenty to do in every direction. Hudson is 20 minutes away, Great Barrington 10 minutes, Millerton 20 minutes and Copake just 5. Ski at Catamount, bike the Harlem Valley Rail Trail, wander through Roeliff Jansen Park and stop by the farmers market, enjoy every season at Bash Bish Falls, or pick up a stretch of the Appalachian Trail. Restaurants, markets, antique shops and local favorites fill the surrounding towns, making it easy to head out without much of a plan and still end up somewhere wonderful.

2779 State Route 23, Hillsdale

$799,900

3 Beds ⋅ 3 Baths ⋅ 1048408 MLS

Tucked into the woods on a quiet country road, just a mile from Route 22, 224 Under Mountain Road is the kind of home that makes you slow down, take a breath, and settle in. Surrounded by nature yet wonderfully convenient, this warm and inviting 3-bedroom, 2.5-bath home on 4 acres offers a relaxed country lifestyle with thoughtful updates and spaces designed for everyday living and entertaining. Step inside and you are immediately welcomed by gorgeous wood floors, natural light and a sense of warmth that continues throughout the home. The living room centers around a wood insert fireplace, creating the perfect gathering place on cool evenings. The heart of the house is the incredible chef's kitchen, complete with a generous island and high-BTU gas range--just right for unleashing your inner professional chef. From casual breakfasts to elaborate dinners with friends, this is a kitchen meant to be enjoyed. A proper mudroom provides a practical transition from the outdoors and leads into the inviting family room, where wooden ceiling beams and a wood stove add character and warmth. When the weather cooperates, life naturally moves outdoors to the rear covered, screened-in porch. It is an ideal spot for morning coffee, dinner al fresco, or lingering with friends while listening to the sounds of nature. Here, the distinction between inside and outside seems to disappear. Upstairs, the private primary en-suite bedroom offers a comfortable retreat with its own walk-in shower, while two additional bedrooms and a full hall bath provide plenty of room for family and guests. Recent improvements make this country retreat as comfortable as it is charming, including a new HVAC system (central AC too!), new windows, durable cement siding, and a new rear deck and fire pit area. High-speed internet is on site, making it possible to enjoy the tranquility of the woods without giving up modern connectivity. A full basement provides abundant storage and offers potential for additional finished living space, studio, recreation room or workshop. The attached two-car garage keeps vehicles protected and provides easy access to the house, while a smaller detached garage is perfectly suited for lawn equipment, bicycles and all the tools needed to maintain your country surroundings. The whole house generator will rise above any storm and keep the electric on. And then there is the location. The Harlem Valley Rail Trail and Alander mountain trail heads are just steps away, offering miles of scenic terrain for walking, running and cycling. Under Mountain Golf Course is practically at your doorstep, just yards up the road. Spend Saturday mornings at the Copake Farmers' Market, explore the nearby lakes, villages and restaurants, or head out for a day of skiing at Butternut or Catamount, both approximately 30-45 minutes away. Hudson and Amtrak are about 25 minutes away, while New York City is approximately 2.25 hours. A peaceful woodland setting, wonderful character, exceptional kitchen, inviting outdoor spaces and significant recent improvements come together beautifully here. This is more than a house in the country--it is a place where nature becomes part of everyday life.

224 Under Mountain Road, Ancram

$21,000,000

5 Beds ⋅ 7 Baths ⋅ 1040841 MLS

There are beautiful homes in the Hudson Valley, and then there are properties that seem to occupy a world entirely their own. Set at one of the most extraordinary vantage points in the region, this exceptional contemporary estate presides over 135 private acres with sweeping, unobstructed views across the Hudson Valley to the Catskill Mountains. The sense of scale is remarkable: open sky, rolling land, distant mountains, and complete privacy in every direction—yet Hudson and Great Barrington are each only 25 minutes away. The residence was designed around this landscape; dramatic walls of glass frame the Catskills throughout the house, while soaring ceilings and expansive, open living spaces give the interiors a sense of volume without sacrificing warmth. Living, dining, and kitchen spaces unfold effortlessly toward the terrace and infinity pool, where the water appears to disappear into the mountains beyond. The entire home lives on a single level, an increasingly rare luxury at this scale. Two primary suites and three additional ensuite bedrooms create five beautifully private bedroom suites, equally suited to intimate everyday living or a house full of family and friends. Throughout, the architecture is sophisticated but restrained, allowing the extraordinary setting to remain the focus. And the house is only the beginning. The estate encompasses 135 acres of lawns, fields, woods, and private trails, creating a property that can be experienced as much as admired. A large, crystal-clear swimming pond offers an idyllic counterpoint to the infinity pool. Miles of trails wind through the acreage for riding, hiking, and exploring, while a barn and riding arena establish the property as a true equestrian retreat. A separate two-bedroom cottage provides charming guest accommodations, while a carriage house with its own apartment creates additional flexibility for guests, staff, an office, or studio. What ultimately distinguishes this property, however, is something photographs and specifications can only begin to convey: the feeling of being here. Morning light moving across 135 private acres. Long afternoons by the pond. Horses on the trails. Dinner overlooking the mountains. And, each evening, the sun setting behind the Catskills from an infinity pool seemingly suspended above the Hudson Valley. It is extraordinarily private without being isolated, grand without being ostentatious, and remarkably complete without feeling overdone. Properties of this caliber are exceedingly difficult to create—and even harder to find. Just 25 minutes from the restaurants, galleries, shops, and cultural life, this is not simply a country house. It is one of those rare places that makes leaving the city feel like arriving somewhere else entirely.

21 Schoolhouse Road, Hillsdale

$620,000

3 Beds ⋅ 2 Baths ⋅ 1044728 MLS

Welcome to this charming country home set along a quiet rural road in Copake. Bright, comfortable living spaces and a peaceful setting surrounded by mature trees and open lawn create an atmosphere that feels instantly relaxing. The open living area brings together the updated kitchen, dining room, and living room anchored by a brick fireplace—perfect for cozy evenings. French doors open to a warm, sun filled room, with additional French doors from both the dining room and sunroom leading out to a private deck for effortless indoor-outdoor living. The home offers a good-sized primary bedroom with its own bath, plus 2 bedrooms, a common bath, and a family room for flexible use. A built-in garage adds convenience, while the detached 2 car garage features a workshop and a finished studio above ideal for creative space, guests, or a home office. The home has an automatic whole-house generator installed just incase of a power outage. Enjoy privacy, nature, and easy access to Copake Lake, Bash Bish Falls, Catamount, Hudson, and Great Barrington. An ideal choice for full time living or a welcoming weekend retreat in the Hudson Valley.

33 Twin Bridges Road, Copake

$615,000

3 Beds ⋅ 2 Baths ⋅ 1042091 MLS

Set on 3.28 acres amid the open farmland of Copake, this inviting 1960s farmhouse has the relaxed character of a country house that immediately makes you feel at home. A generous covered porch stretches across the front of the house, overlooking its own open field and the agricultural landscape beyond. Inside, wide-plank pine floors, abundant windows, and natural wood details give the house its easy country character. The living room is centered around a wood-burning stove, with built-in bookshelves and cabinetry adding both charm and function. The adjoining kitchen is bright and thoughtfully laid out, with generous workspace and views onto the surrounding greenery. From there, the house opens into an inviting dining room with wraparound windows that bring the landscape into the room, while doors lead directly outside to an outdoor dining area. Two generously sized bedrooms and a full bath are located on the first floor. Upstairs, the primary bedroom sits beneath vaulted, pine-clad ceilings and includes an en-suite bath and spacious walk-in closet. A large additional room on this level offers plenty of flexibility for a library, studio, office, den, or guest space. Outside, the property unfolds from lawn and established plantings into an open field, with room to garden, play, gather with friends, or simply enjoy the landscape. The front porch is an especially lovely perch for taking it all in, while a rear deck offers a more tucked-away place outdoors. A two-car garage, basement, laundry area, and additional storage round out the property. The location puts some of the best of Columbia County and the Berkshires within easy reach. Copake and Hillsdale are close at hand, with Egremont and Great Barrington just across the Massachusetts border. Catamount, nearby lakes and hiking trails, farm stands, and local markets offer plenty to explore throughout the year, with Hudson an easy drive to the west. Unfussy, comfortable, and surrounded by farmland, this is a house that captures much of what makes this corner of the Hudson Valley so appealing. It offers space to spread out, a close connection to the landscape, and the pleasures of country life.

1492 County Route 7A, Copake

$349,500

2 Beds ⋅ 1 Baths ⋅ 1039149 MLS

Experience the benefits of luxury living without the luxury price tag. Nestled in the northern Hudson Valley just minutes from the Taconic State Parkway, 80 Lakeshore Acres offers a rare opportunity to embrace a slower, more beautiful way of life. Set in the charming community of Craryville. Inside, 2 bedrooms, one bathroom and the open-concept layout creates a warm and welcoming space for gathering, while the beautiful bonus room offers the flexibility to become a home office, guest retreat, studio, or simply a quiet place to escape. Thoughtful details include rich cherry wood cabinetry, granite countertops, generous closets, and well-maintained mechanical systems. A two-car garage and plenty of additional parking is available on the property. It also includes three heating options such as electric hot air, a pellet stove, and a Toyotomi kerosene fireplace. You can enjoy the home comfortably throughout the seasons. Step outside and let the beauty unfold. The fenced-in-ground pool, with its inviting pool house, creates a private setting for relaxing, entertaining, and enjoying long summer days. Just a short walk from Copake Lake, the property offers deeded lake access rights coupled with a dock, inviting you to spend your days on the water and take in the surrounding natural beauty. And beyond the property, there is so much to enjoy. Start your morning with a peaceful walk or hike, spend the afternoon by the lake, listen to live music at the marina, or wander through the local farmers market. Golf, playgrounds, a dog park, local dining, and Roe Jan Brewing Company are all nearby. When winter arrives, trade the lake for the slopes at Catamount Mountain Ski Resort. Whether you're looking for a weekend getaway, a full-time residence, or a place to enjoy the beauty of the Hudson Valley, this property offers comfort, outdoor enjoyment, and an ideal setting. This is more than a home. It is a place to create the lifestyle you've been dreaming about.

80 Lake Shore Acres, Craryville

$389,000

3 Beds ⋅ 1 Baths ⋅ 1035127 MLS

Welcome to your dream country escape! This charming, fully renovated Cape Cod home has been meticulously rebuilt down to the studs, offering brand-new modern finishes while preserving its classic character.Step inside to discover a bright, airy open floor plan designed for effortless entertaining and comfortable daily living. Owner in process of finishes which will include, electric fireplace, front porch and new kitchen. Still time to pick cabinetry colors for kitchen once under contract. Situated just a 2-hour drive via the Taconic State Parkway, this property is the ideal second home or weekend retreat. Enjoy the tranquility of Columbia County with the ultimate convenience: you are within walking distance to Copake Lake, local dining, marina access, golf course and outdoor recreation. Move right in and start enjoying Hudson Valley living from day one!

235 Birch Hill Road, Copake

$392,500

2 Beds ⋅ 2 Baths ⋅ 1030579 MLS

Colonial Home on a Beautiful Country Parcel with New Garage Nestled on a peaceful country road, this charming two-bedroom Colonial offers the perfect blend of privacy, comfort, and convenience. Set back from the road on a beautiful parcel, the home welcomes you into a bright, open-concept living and dining area filled with natural light and complemented by attractive hardwood floors. The galley-style kitchen features stainless steel appliances, making meal preparation and entertaining effortless. Enjoy dinner in the adjoining dining area, relax in the inviting three-season sunroom, or step outside to the spacious rear deck to soak in the surrounding countryside. The first floor also offers the convenience of a full bathroom and laundry area. Upstairs, you'll find two generously sized bedrooms, including a spacious primary suite complete with a walk-in closet and private full bath. A standout feature of the property is the newly constructed two-bay garage, already equipped with electricity and plumbing, making it ideal for a workshop, hobby space, or future expansion. The unfinished second level provides a blank canvas for a studio, home office, guest space, or whatever the next owner envisions. A large rear patio offers the perfect place to enjoy your morning coffee while overlooking the expansive fenced backyard, ideal outdoor gatherings. While offering the tranquility of country living, this home is conveniently located just two hours from New York City. Enjoy easy access to the charming towns of Hudson, Rhinebeck, and Catskill, where you'll find exceptional shopping, dining, entertainment, and cultural attractions. Outdoor enthusiasts will appreciate the nearby hiking trails at Stissing Mountain, boating and fishing on Copake Lake, and skiing at Catamount Mountain Resort or Hunter Mountain during the winter months. Whether you're looking for a full-time residence or a weekend retreat, this inviting property offers the best of the Hudson Valley lifestyle.

155 Pumpkin Hollow Road N, Hillsdale

$1,850,000

3 Beds ⋅ 3 Baths ⋅ 1028112 MLS

Beaver Mountain Farms is an exceptional 41-acre Hudson Valley estate in the picturesque town of Ancram, Columbia County, offering an extraordinary opportunity for agriculture, equestrian pursuits, or a private country retreat. At the heart of this remarkable property is an impressive collection of farm buildings, including a classic dairy barn, an expansive 80' x 200' steel barn ideally suited for an indoor riding arena, equipment storage, agricultural production, or event space, along with workshops, office space, and a detached artist studio. Rolling pastures, open fields, and a tranquil pond create an idyllic landscape that embodies the timeless beauty of the Hudson Valley while providing endless possibilities for farming, livestock, horses, or creative ventures. Complementing the exceptional farmstead is a beautifully updated three-bedroom, two-and-a-half-bath farmhouse featuring a gourmet kitchen, inviting propane fireplaces, a spacious primary suite with an ensuite bath, and expansive windows that frame breathtaking views of the surrounding countryside and in-ground pool. A partially finished basement offers additional flexible living or workspace. Ideally located near Hudson, Copake, Hillsdale, Millerton, and Great Barrington, Massachusetts, Beaver Mountain Farms offers the perfect balance of rural privacy and convenient access to the Hudson Valley's renowned restaurants, cultural attractions, farmers' markets, and outdoor recreation. This is a rare legacy property where agricultural heritage, modern comfort, and boundless opportunity come together in one of Columbia County's most desirable locations.

1030 County Route 27A, Ancram

$749,000

3 Beds ⋅ 2 Baths ⋅ 1005033 MLS

This country home is nestled on 8.7 private acres just five miles from the center of Hillsdale, this charming retreat offers the perfect blend of comfort, character, and natural beauty. A meandering driveway winds through the woods, leading to a welcoming cottage-style home surrounded by perennial gardens filled with native ferns and plantings. The inviting covered front porch opens to a spacious bluestone patio, creating an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Offering approximately 2,040 square feet, the home features three bedrooms and two full bathrooms, with natural woodwork and wide-board Pine floors throughout. At the heart of the home is a beautifully renovated chef's kitchen with a six-burner propane Bertazzoni range, Marble like tile countertops, a porcelain farm sink, wood cabinetry with abundant storage. The kitchen flows seamlessly into the dining area, where a cast-iron wood stove creates a warm and inviting atmosphere for gatherings around a large farmhouse table. The dramatic great room showcases soaring cathedral ceilings with exposed beams and a natural stone wood burning fireplace as its centerpiece, providing a wonderful space for relaxing and entertaining. The light-filled first-floor primary suite offers a peaceful retreat with an ensuite full bathroom. The additional two spacious bedrooms, feature cathedral ceilings, wide-board Pine floors, warm wood walls, and walls of windows that bring the views of the outdoors in. A welcoming front foyer serves as a practical mudroom with built-in bench seating, a coat closet and laundry/storage closet. The attached one-car garage offers ample space for storage and the utility room. The home includes many updates such as the kitchen, bathrooms, electrical service (200 amp), septic system (2020), paved driveway, a high-efficiency on-demand heating and hot water system (2025). Conveniently located near the villages of Hillsdale, Great Barrington, Chatham, and Hudson, and just minutes from Catamount Ski Area, local farms, hiking trails, state parks, and schools, this exceptional property is equally suited as a full-time residence or a peaceful weekend getaway. A must see to fully appreciate this special home. Please see 3D Interactive Floor Plan & Property Tour.

695 Wolf Hill Road, Hillsdale

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