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Hillsdale, NY Homes for Sale

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  • /5

    $225,000

    • Land
    • 6 Acres
    • $37,500 per Acre

    L135.2 Rockledge Rd, Hillsdale, NY 12529

    Escape to your own private sanctuary in the heart of Columbia County's coveted Hudson Valley. This 6 acre wooded parcel on scenic Rockledge Road offers the perfect canvas for your dream retreat, with mature trees providing natural privacy and a peaceful, secluded setting that feels worlds away from the everyday. Ideally situated in the Town of Hillsdale -- one of the region's most sought-after

    Agent Photo

    Jamie Mazuryk

    Venture Fox Realty Group LLC

    (518) 719-4612

    L135.2 Rockledge Rd, Hillsdale, NY 12529
  • /42

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 2,495 Sq Ft

    309 Pine Ridge Ln, Hillsdale, NY 12529

    Nestled on a wooded hillside on one of Hillsdale's prettiest country roads is where you will discover this exceptional 2,500 sq.ft. custom-built home. The 5.5-acre parcel sits above Pine Ridge Lane; a lightly travelled country road located just off Mitchell Street in the heart of Hillsdale. Surrounded by nature in every direction, the peaceful, park-like setting is unique and as beautiful as any

    Margaret Bower Avenia Columbia County RE Specialist

    309 Pine Ridge Ln, Hillsdale, NY 12529
  • /6

    $175,000

    $120K PRICE DROP
    • Land
    • 33.31 Acres
    • $5,254 per Acre

    50 Dugway Rd, Hillsdale, NY 12529

    Escape to 33.31 acres of untouched beauty in Columbia County, NY. This stunning parcel of wooded land offers complete privacy with no neighbors in sight, just you and the tranquility of nature. Imagine the possibilities as you explore the lush, wooded landscape teeming with wildlife. This parcel features a dynamic topography of hills that reach an elevation of over 1,000 feet. With this parcel,

    Jeffrey McKinney Beach & Bartolo Realtors

    50 Dugway Rd, Hillsdale, NY 12529
  • /33

    $389,000

    Open Sun 12PM - 2PM
    • 4 Beds
    • 1 Bath
    • 2,229 Sq Ft

    1953 County Road 11, Claverack, NY 12513

    Step into a home that feels like it has been quietly telling its story since the 1800's, where every beam and board carries the charm of a bygone era. This classic colonial residence preserves its original character with exposed beams stretching across the main floor and a layout that balances simplicity with purpose. The kitchen is modest yet functional, anchored by a traditional wood store that

    Karen Davala Davala Real Estate, LLC

    1953 County Road 11, Claverack, NY 12513
  • /23

    $305,000

    $15K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 925 Sq Ft

    9377 New York 22, Hillsdale, NY 12529

    WELCOME HOME to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard lead you to a

    Ronald Green KW Mid-Hudson

    9377 New York 22, Hillsdale, NY 12529
  • /32

    $330,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,470 Sq Ft

    9539 New York 22, Hillsdale, NY 12529

    Newly Renovated Hillsdale Gem! Welcome to this beautifully renovated 3-bedroom home in the heart of Hillsdale. Thoughtfully updated with today's buyer in mind, this residence blends modern comfort with timeless charm. Inside, you'll find a bright, welcoming kitchen featuring quartz countertops, high-end vinyl plank flooring, and a suite of updated appliances designed for both style and

    Marie Rodriguez Red Apple Realty

    9539 New York 22, Hillsdale, NY 12529
  • /50

    $999,900

    Open Sat 11AM - 1PM
    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2955 State Route 23, Hillsdale, NY 12529

    Steeped in Hillsdale’s rich history, this extraordinary property began its life as one of the area’s original grist mills, situated in the area of Hillsdale once known as Murray’s Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

    Jason Walch Coldwell Banker Advisor Realty

    2955 State Route 23, Hillsdale, NY 12529
  • /40

    $859,000

    $120K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,293 Sq Ft

    44 SW Colony Rd, Hillsdale, NY 12529

    Set on the shores of Copake Lake, this charming waterfront home blends classic lake character with thoughtful modern updates. Offering three bedrooms and 1.5 baths, the home features a bright open kitchen, living, and dining area designed for easy lake living and entertaining. Recent renovations, including HVAC, septic system, and expansion to main floor, bring fresh style and comfort while

    Austin Urban Venture Fox Realty Group

    44 SW Colony Rd, Hillsdale, NY 12529
  • /45

    $1,150,000

    • 5 Beds
    • 3 Baths
    • 1,708 Sq Ft

    1 van Bueran Dr, Hillsdale, NY 12529

    Set just off the banks of Copake Lake and privately positioned on five wooded acres, The Van Bueran House offers a rare blend of modern design, an inground pool, and deeded lake rights to one of Columbia County's most sought-after motorboat lakes. Recently renovated with forever in mind, the home pairs thoughtful design with meaningful infrastructure: white oak and radiant heated floors

    Jessica Scott Compass Greater NY, LLC

    1 van Bueran Dr, Hillsdale, NY 12529
  • /58

    $625,000

    • 2 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    534 Collins St, Hillsdale, NY 12529

    Nestled on 18+ secluded acres along one of Hillsdale's most bucolic and sought-after roads, this solidly built country home offers endless potential. Located just minutes from the Massachusetts border on the edge of the Berkshires and only 15 minutes from Great Barrington, this property provides the perfect balance of peaceful rural living and convenient access to the region's renowned cultural,

    John Barbato Compass, Hillsdale

    534 Collins St, Hillsdale, NY 12529
  • /24

    $575,000

    $40K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 864 Sq Ft

    5 Adams Dr, Hillsdale, NY 12529

    This charming 3 BR, 1.5 Bath cottage is located across the street from Copake Lake and the HOA Waterfront, Marina and Beach area. Unlike some of the other homes in the area, the house is situated on an elevated, oversized lot with a big front yard and spectacular sunset views. Inside, the house features real wood paneling and a wood burning stove in the living room, a cozy kitchen with a new gas

    Russ Stein Compass Greater NY LLC

    5 Adams Dr, Hillsdale, NY 12529
  • /41

    $2,195,000

    • 3 Beds
    • 3 Baths
    • 2,755 Sq Ft

    292 White Hill Rd, Hillsdale, NY 12529

    Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

    Tom Lynch COMPASS MASSACHUSETTS , LLC GB

    292 White Hill Rd, Hillsdale, NY 12529
  • /23

    $305,000

    $15K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 925 Sq Ft

    9377 State Route 22, Hillsdale, NY 12529

    BACK ON MARKET!! Welcome home to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard

    Scott Zobre KW MidHudson

    9377 State Route 22, Hillsdale, NY 12529
  • /28

    $1,150,000

    $125K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 1,700 Sq Ft

    401 Collins St, Hillsdale, NY 12529

    Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a

    Pamela King-Belfor Four Seasons Sothebys Intl

    401 Collins St, Hillsdale, NY 12529
  • /5

    $259,000

    • Land
    • 15.47 Acres
    • $16,742 per Acre

    191 Berkshire Rd, Hillsdale, NY 12529

    Discover the perfect opportunity to build your dream home on this expansive 15.47-acre parcel at 191 Berkshire Road, bordering Copake Country Club and just minutes from Copake Lake. This fully undeveloped property is part of the desirable Sam Hill Road community, offering shared waterfront access through the HOA. Ideally located just 25 minutes from Hudson and Great Barrington, MA, you'll enjoy

    Austin Urban Venture Fox Realty Group

    191 Berkshire Rd, Hillsdale, NY 12529
  • /7

    $257,000

    $2K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,304 Sq Ft

    9249 Route 22 Rd, Hillsdale, NY 12516

    Mixed Residential/Commercial building, with 3 rentable spaces. Current RR 30,540. One side of building has commercial reception area down and 1BR apartment above. Rental 1395/m. Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is 795 + 550. Ideal for live/work. Building in excellent condition, roof less than 5 years old.

    David Birch Barns & Farms Realty, LLC

    9249 Route 22 Rd, Hillsdale, NY 12516
  • /25

    $649,000

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft

    416 Whippoorwill Rd, Hillsdale, NY 12529

    416 Whippoorwill Rd, Hillsdale, one of the prettiest country roads Columbia County has to offer!! This one checks all of the boxes. Our newly listed two bedroom, two bath Cape Cod style home in Hillsdale has been meticulously maintained and is in excellent condition inside and out. The main level features a functional kitchen, dining area, bathroom, and living room centered around a propane

    Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

    416 Whippoorwill Rd, Hillsdale, NY 12529
  • /7

    $95,000

    • Land
    • 12.95 Acres
    • $7,336 per Acre

    00 Stone Ledge Rd, Hillsdale, NY 12529

    Quiet location next to the Berkshires. Dead end road with a 12 acre parcel. Hiking trails throughout. Glorious views off the top. Great value. More land available.

    Tracy Tassinari Gabel Real Estate

    00 Stone Ledge Rd, Hillsdale, NY 12529
  • /13

    $595,000

    • Land
    • 30 Acres
    • $19,833 per Acre

    0 Labranch Unit 20252234, Hillsdale, NY 12529

    Wonderful southern exposure on one of the most scenic byways in Columbia County. Large parcels and restrictive covenants on abutting land. High fields and ancient tree lines dotted with maples and old stone walls. Nice mix of open and wooded to tuck your home into the hedge row without another home in site. Distant views of Catamount Mountain. Close to Hawthorne Valley School and the Berkshires.

    Tracy Tassinari Gabel Real Estate

    0 Labranch Unit 20252234, Hillsdale, NY 12529
  • /21

    $346,900

    $53K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,381 Sq Ft

    9659 New York 22, Hillsdale, NY 12529

    Come see the new me!. I've had a face lift and you are sure to enjoy the gleaming hardwood floors and the updated kitchen with granite counters and new appliances. It's one level of easy living, and offers many wonderful features. Enjoy the spacious living room framed by a fireplace, or the cozy den which has one as well..The middle bedroom features sliders that open onto a deck, great to enjoy

    Tammy Molinski Coldwell Banker Advisor Realty

    9659 New York 22, Hillsdale, NY 12529
  • /19

    $850,000

    • Land
    • 150 Acres
    • $5,667 per Acre

    400 Overlook Dr, Hillsdale, NY 12529

    Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

    MATTHEW CAREY Rouse + Co Real Estate

    400 Overlook Dr, Hillsdale, NY 12529
  • /7

    $39,900

    • Land
    • 26,571 Sq Ft
    • $65,410 per Acre

    0 Prach Road Extension Unit 20263433, Claverack, NY 12513

    Take advantage of this opportunity to build your dream home on this cleared, flat, .61 acre parcel (with well on property). Conveniently located just minutes to Hudson's restaurants, shops, and Amtrak station, or if you prefer outdoor activities e.g. hiking, kayaking, skiing, and ariel adventure, it's all within a short drive to Bash Bish Falls State Park, Copake Lake, and Catamount Mountain

    Wendy Kenney Davala Real Estate, LLC

    0 Prach Road Extension Unit 20263433, Claverack, NY 12513
  • /10

    $3,600,000

    • 4 Beds
    • 2 Baths
    • 3,200 Sq Ft

    90 W End Rd, Hillsdale, NY 12529

    For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is

    Parker Meyer Four Seasons Sotheby's Int.

    90 W End Rd, Hillsdale, NY 12529
  • /19

    $850,000

    • Land
    • 150 Acres
    • $5,667 per Acre

    0 Overlook Dr, Hillsdale, NY 12529

    Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

    MATTHEW CAREY Rouse + Co Real Estate

    0 Overlook Dr, Hillsdale, NY 12529
  • /13

    $299,000

    $96K PRICE DROP
    • Land
    • 49.91 Acres
    • $5,991 per Acre

    61 Dugway Rd, Hillsdale, NY 12529

    Discover Your Dream Retreat: 49+ Acres of Serenity and Potential!Nestled between the charming towns of Chatham, NY, and Great Barrington, MA, this stunning parcel of over 49 acres offers a unique blend of privacy and accessibility. With impressive road frontage on two roads, this property is easily accessible while still providing a tranquil escape.Imagine waking up to the soothing sounds of the

    Jeffrey McKinney Beach & Bartolo Realtors

    61 Dugway Rd, Hillsdale, NY 12529
  • /20

    $325,000

    • Land
    • 22.84 Acres
    • $14,229 per Acre

    0 County Route 21, Hillsdale, NY 12529

    Welcome to DREAMLAND.Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow--perfectly oriented for southern

    Pamela King-Belfor Four Seasons Sotheby's Int.

    0 County Route 21, Hillsdale, NY 12529
  • /37

    $695,000

    New Construction
    • 3 Beds
    • 3 Baths
    • 1,824 Sq Ft

    30 Ridge Ln, Hillsdale, NY 12529

    Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town. Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in mind.

    John Barbato Compass, Hillsdale

    30 Ridge Ln, Hillsdale, NY 12529
  • /58

    $999,900

    Open Sat 11AM - 1PM
    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2955 New York 23, Hillsdale, NY 12529

    Steeped in Hillsdale's rich history, this extraordinary property began its life as one of the area's original grist mills, situated in the area of Hillsdale once known as Murray's Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

    Jason Walch Coldwell Banker Advisor Realty

    2955 New York 23, Hillsdale, NY 12529
  • /23

    $495,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,375 Sq Ft

    217 Anthony St, Hillsdale, NY 12529

    A newly built home ideally located on the edge of the charming hamlet of Hillsdale, NY, this home offers the convenience of true walkability--just steps to everyday essentials including the local hardware store, grocery market, wine shop, post office, town hall, coffee shops, restaurants, and boutique shops. With 3-bedrooms and 2-bathrooms, the home spans approximately 1,350 square feet of modern

    John Barbato Compass, Hillsdale

    217 Anthony St, Hillsdale, NY 12529
  • /25

    $770,000

    New Construction $30K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    801 Rodman Rd, Hillsdale, NY 12529

    New listing in Hillsdale, set high on a quiet dirt road where privacy, peace, and panoramic views define your backdrop. Why wait a year and a half for a new house to be built? This brand-new construction is being sold as it stands today, as a blank unfinished canvas ready for you to make it your own. The structure is in place with a brand-new drilled well, septic system, and 200-amp electrical

    Michael Castellano Gilcrest Properties

    801 Rodman Rd, Hillsdale, NY 12529
  • /31

    $725,000

    • 4 Beds
    • 2.5 Baths
    • 2,225 Sq Ft

    2999 New York 23, Hillsdale, NY 12529

    2999 Route 23, Hillsdale, New York - Historic Country Estate on 12.5 Acres Step into a piece of living history with this beautifully preserved 1915 home, perfectly situated on a private 12.5-acre parcel in the heart of the Berkshires. Offering four generous bedrooms and three baths (2 full, 1 Half), this classic residence blends timeless charm with everyday comfort, creating an ideal setting for

    Tyler Bervy Stone House Properties, LLC

    2999 New York 23, Hillsdale, NY 12529
  • /34

    $695,000

    $24K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,475 Sq Ft

    81 Black Grocery Rd, Hillsdale, NY 12529

    On a quiet country road, sit's the prettiest sunshine yellow house you've ever seen.Welcome to a property where outdoor splendor and indoor comfort merge seamlessly, where everything has been taken care of, and all you need to do is arrive and exhale. Rolling hills and open farmland stretch out before you, and they're all yours to enjoy.Inside, the dining room flows into an open kitchen

    Shaina Marron Houlihan Lawrence Inc.

    81 Black Grocery Rd, Hillsdale, NY 12529
  • /31

    $995,000

    • 2 Beds
    • 2 Baths
    • 2,060 Sq Ft

    17 Memory Ln, Hillsdale, NY 12529

    Lakefront living in one of the most peaceful and serene locations on Copake Lake. An expansive 75 feet of private waterfront with an existing dock, this charming home offers beautiful eastern views across the lake, where sunrises and tranquil water vistas become part of everyday life.The home's inviting open-concept layout has a spacious kitchen, dining, and living area. A first-floor primary

    John Barbato Compass, Hillsdale

    17 Memory Ln, Hillsdale, NY 12529
  • /28

    $1,150,000

    $125K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 1,700 Sq Ft

    401 Collins St Unit Stop 11, Hillsdale, NY 12529

    Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County's most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Plans are available for a one or two bedroom

    Pamela King-Belfor Four Seasons Sotheby's Int.

    401 Collins St Unit Stop 11, Hillsdale, NY 12529
  • /28

    $795,000

    $787K PRICE INCREASE
    • 6 Beds
    • 2 Baths
    • 2,998 Sq Ft

    60 Anthony St, Hillsdale, NY 12529

    1800s farm house. Just waiting for some TLC. This property consists of the main farm house. one very large barn. Addtional 3 out building. One of the back building contains an attractive apartment.The property butts up to the Harlem Valley Rail Trail. Walking distant to the Hamlet of Hillsdale. Including the Roe Jan Brewing Co. IGA, The Hillsdale House, The town park. Less then 5 min ride to

    Gerard Meenagh The Meenagh Group Realty

    60 Anthony St, Hillsdale, NY 12529
  • /54

    $1,100,000

    • 3 Beds
    • 4 Baths
    • 2,880 Sq Ft

    2666 New York 23, Hillsdale, NY 12529

    Unique investment opportunity in the hamlet of Hillsdale. This new-to-the-market commercial/residential property has been meticulously renovated by the current owner, a commercial builder, who over-engineered the project with high-end features throughout. The property consists of four distinct rental units:2666 Route 23, Main (Blue) Building- First-Floor Commercial Unit Right Side: 360

    Margaret Bower Avenia Columbia County RE Specialist

    2666 New York 23, Hillsdale, NY 12529
  • /55

    $1,525,000

    • 4 Beds
    • 4.5 Baths
    • 3,666 Sq Ft

    83 Schmeichel Rd, Hillsdale, NY 12529

    Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with a vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a

    Jennifer Harvey Compass Greater NY LLC

    83 Schmeichel Rd, Hillsdale, NY 12529
  • /30

    $1,495,000

    $505K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,419 Sq Ft

    75 Upper Hollow Rd, Hillsdale, NY 12529

    A rare 193-acre estate in Austerlitz/Hillsdale, very close to the Berkshire border. The charming 3-bed cottage overlooks a pristine pond with a bordering creek. The wooded land has clearly marked and maintained hiking trails. Recently renovated, the cottage features an updated bathroom and an expanded living room, blending modern comfort with rustic charm. Geothermal heating and air conditioning

    Janet Kain The Kinderhook Group, Inc.

    75 Upper Hollow Rd, Hillsdale, NY 12529
  • /13

    $1,080,000

    $5K PRICE INCREASE
    • Land
    • 72 Acres
    • $15,000 per Acre

    0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529

    Picturesque farmland located close to the Village of Hillsdale, only 1.8 to Catamount Ski Area, and 9.5 miles to Great Barrington. Extensive road frontage, totaling 3979 feet on Yonderview Road and Route 23. Barn complex. This parcel is zoned RU in the Town of Hillsdale. Property currently enjoys an agricultural exemption. Survey available. Inspect Now!

    Robert D Ferris R. Ferris Real Estate, LLC

    0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529
  • /28

    $4,950,000

    $2M PRICE DROP
    • 6 Beds
    • 6 Baths
    • 6,309 Sq Ft

    890 Bald Mountain Rd, Austerlitz, NY 12017

    Located in a private gated community of large acreage land holders, this exquisite enclave of 3 homes, on 84 acres, hasbeen listed in Interior Design magazine. The main house is a stunning post and beam contemporary home, combining steel, glass, wood and stone panels. It overlooks the gunite pool, surrounded by stone walls and the two additional designed and inviting cottages. Continuing past

    Janet Kain The Kinderhook Group, Inc.

    890 Bald Mountain Rd, Austerlitz, NY 12017

Showing Results 1 - 40, Page 1 of 2

Why Live in Hillsdale

Hillsdale is a rural Columbia County town set against the Berkshire Mountains, appealing to buyers who want a quieter lifestyle surrounded by nature. With Catamount Mountain Resort nearby, residents have easy access to skiing, snowboarding and year-round hiking, along with quick trips to nearby Great Barrington. The town feels less busy than Copake or Chatham and offers more open, gently rolling land than neighboring Austerlitz, creating wide farmland views and a sense of space. Many buyers are drawn to Hillsdale for second homes or vacation properties, though there is also a core group of year-round residents. Living here means embracing rural infrastructure, including private wells and septic systems, occasional spotty cell service and winter maintenance responsibilities on private roads. At the same time, strong fiber internet coverage makes remote work realistic for many households. The hamlet itself is small but provides essential amenities, including a grocery store, library, farmers market and a handful of well-loved restaurants. Families have access to the Taconic Hills Central School District for public education and a highly rated private Hawthorne Valley Waldorf School. While daily errands usually require a car, Hillsdale is within easy driving distance of Hudson and New York City is two to three hours away.

Frequently Asked Questions

What is the average home price in Hillsdale, NY?
Homes for sale in Hillsdale, NY have an average home price of $1,175,981.
Are home prices dropping in Hillsdale?
Yes, home prices in Hillsdale are down 6% in the last 12 months.
How many homes have sold over the last 12 months in Hillsdale, NY?
57 homes have sold in Hillsdale, NY over the last 12 months.
What is the average household income in Hillsdale, NY?
The average household income in Hillsdale, NY is $114K.
What are the most popular zip codes in Hillsdale, NY?
The most popular zip codes in Hillsdale, NY include 12529, 12516, 01230, 12075 and 12017.
How much do you need to make to afford a house in Hillsdale?
The median home price in Hillsdale is $995,000. If you put a 20% down payment of $199,000 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $5,020 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $215K a year to afford the median home price in Hillsdale. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Hillsdale is $114K.
How are the schools in Hillsdale, NY?
Hillsdale, NY has highly rated public and private schools. Some of the best schools in Hillsdale based on Niche Grades are Hawthorne Valley School, Chatham High School and Mt. Everett High School. Browse all the schools in Hillsdale, NY to learn more.

Home Prices in Hillsdale, NY

Home Price Trends

Median Sale Price
$820,000
Median Single Family Sale Price
$995,000
Median Townhouse Sale Price
$580,000
Median 2 Bedroom Sale Price
$640,000
Median 1 Bedroom Sale Price
$1,150,000
Average Price Per Sq Ft
$484
Number of Homes for Sale
32
Last 12 months Home Sales
57
Months of Supply
6.70
Median List Price
$995,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
21%
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