23

Hillsdale, NY Homes for Sale with Garage

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  • /19

    $325,000

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 SW Colony Rd, Hillsdale, NY 12529

    Welcome to THE UPSTATE RETREAT--where every day feels like a vacation on Copake Lake, the largest lake in Columbia County, spanning approximately 425 acres. Whether you're searching for the perfect weekend escape, a summer lake house, or a year-round getaway, this charming 2-bedroom, 1-bath bungalow offers the quintessential upstate lifestyle just over two hours from New York City. Beyond the

    Agent Photo

    Mark Saxby

    Berkshire Hathaway HomeService

    81 SW Colony Rd, Hillsdale, NY 12529
  • /36

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 1,977 Sq Ft

    3493 County Route 7, Hillsdale, NY 12529

    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. The 410-acre, motorboat-friendly lake is perfect for boating, waterskiing, kayaking, paddleboarding, and excellent fishing, while nearby Copake

    Agent Photo

    Sabrina Puppolo

    Corcoran Country Living

    3493 County Route 7, Hillsdale, NY 12529
  • /50

    $949,900

    $50K PRICE DROP
    • 3 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
  • /44

    $1,485,000

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    51 Taconic Creek Rd, Hillsdale, NY 12529

    This perfect modern farmhouse retreat is tucked away on one of Columbia County's most quiet and beautiful roads guaranteeing a tranquil respite from the city. Being one of just a handful of properties on the road creates a sense of peace and quiet that is unmatched. While a feeling of simplicity emanates throughout the land there is a clear level of sophistication in the design details. The

    Thomas Pawlowski Four Seasons Sotheby's Int.

    51 Taconic Creek Rd, Hillsdale, NY 12529
  • /30

    $619,000

    $30K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    416 Whippoorwill Rd, Hillsdale, NY 12529

    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 fireplace; all with hardwood floors. A 12x12 great room with hardwood floors was added to provide

    Margaret Bower Avenia Columbia County RE Specialist

    416 Whippoorwill Rd, Hillsdale, NY 12529
  • /19

    $392,500

    • 2 Beds
    • 2 Baths
    • 1,494 Sq Ft

    155 Pumpkin Hollow Rd N, Hillsdale, NY 12529

    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

    Jonathan Scarinzi Elyse Harney Real Estate

    155 Pumpkin Hollow Rd N, Hillsdale, NY 12529
  • /51

    $729,900

    • 3 Beds
    • 2.5 Baths
    • 2,210 Sq Ft

    417 Overlook Dr, Hillsdale, NY 12529

    Discover Your Dream Cape-Style Home: A Serene Escape on 2.1 Acres Nestled in a tranquil setting, this stunning Cape-style home offers the perfect blend of comfort and luxury, with 2.1 acres of nature at your doorstep. Imagine sipping your morning coffee on the spacious front porch while listening to the gentle rustle of leaves around you. Step inside to an inviting and dramatic living room, where

    Barbara Robinson Red Apple Realty

    417 Overlook Dr, Hillsdale, NY 12529
  • /36

    $749,000

    • 3 Beds
    • 2 Baths
    • 2,040 Sq Ft

    695 Wolf Hill Rd, Hillsdale, NY 12529

    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

    Kimberly Baker BHHS Hudson Valley Properties

    695 Wolf Hill Rd, Hillsdale, NY 12529
  • /21

    $339,900

    $60K 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
  • /42

    $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

    Jennifer Harvey Compass Greater NY LLC

    292 White Hill Rd, Hillsdale, NY 12529
  • /16

    $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
  • /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

    John Barbato Compass, Hillsdale

    30 Ridge Ln, Hillsdale, NY 12529
  • /58

    $949,900

    $50K PRICE DROP
    • 3 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
  • /48

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    65 Meadow Ln, Hillsdale, NY 12529

    With a view as far as the eye can see, 65 Meadow Lane, Hillsdale never fails to amaze from sunrise to sunset, as a full moon lights up your bedroom; hawks fly past wandering clouds, the fiery yellow and burnt red leaves of autumn and the pine trees dripping with snow like confectionary sugar in a winter wonderland.The only sounds you hear are woodpeckers and wild turkeys and your

    Margaret Bower Avenia Columbia County RE Specialist

    65 Meadow Ln, 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

    $649,000

    $70K 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
  • /25

    $890,000

    $105K PRICE DROP
    • 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
  • /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

    $1,195,000

    $805K 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
  • /28

    $4,750,000

    $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
  • /59

    $3,300,000

    • 4 Beds
    • 3 Baths
    • 5,760 Sq Ft

    124 Syre Ln, Hillsdale, NY 12529

    PRIVATE & QUIET ~ 124 Syre Lane, Hillsdale NY Federal Style Colonial home in Hillsdale, perched on the top of the mountain, pairing historical accuracy with state-of-the-art modern conveniences. This stately country home offers unparalleled, endless views in every direction of the valley and Catskill Mountains. Offering Immeasurable beauty, from every window and large back deck, perfect for

    Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

    124 Syre Ln, Hillsdale, NY 12529
  • /48

    $3,600,000

    $250K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,083 Sq Ft

    335 Dawson Rd, Hillsdale, NY 12529

    Presiding over 27 acres of rolling hills, meadows, and dramatic mountain views, Southview Farm is a fully reimagined country estate in the heart of Hillsdale farm country. Once part of a 300-acre dairy farm with a grand farmhouse on this site for over a century, the property has been expanded and rebuilt from the ground up to deliver modern luxury, efficiency, and comfort while honoring its

    Norah Burden Brown Harris Stevens HV LLC

    335 Dawson Rd, Hillsdale, NY 12529
  • /17

    $999,000

    $271K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,344 Sq Ft

    25 Nobletown Rd, Hillsdale, NY 12529

    Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, Stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim

    Andrew Gates HOULIHAN LAWRENCE, INC

    25 Nobletown Rd, Hillsdale, NY 12529

Home Price Trends

Median Sale Price
$725,000
Median Single Family Sale Price
$859,000
Median Townhouse Sale Price
$580,000
Median 2 Bedroom Sale Price
$532,000
Median 1 Bedroom Sale Price
$732,500
Average Price Per Sq Ft
$486
Number of Homes for Sale
31
Last 12 months Home Sales
52
Months of Supply
7.20
Median List Price
$895,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-27%
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