54

Hillsdale, NY Homes for Sale

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  • /19

    $299,888

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 SW Colony Rd, Hillsdale, NY 12529

    PRICE REDUCTION - Under 300,000 dollars on Copake Lake! Welcome to 81 SW Colony Road, a charming 2-bedroom, 1-bath bungalow now offered at a newly adjusted price point that makes owning a piece of Columbia County paradise more accessible than ever. Experience the quintessential upstate lifestyle just over two hours from New York City and 30 minutes from both the Hudson and Wassaic train

    Agent Photo

    Mark Saxby

    Berkshire Hathaway HomeService

    81 SW Colony Rd, Hillsdale, NY 12529
  • /35

    $620,000

    • 3 Beds
    • 2 Baths
    • 2,932 Sq Ft

    33 Twin Bridges Rd, Copake, NY 12516

    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

    Agent Photo

    Brad Rebillard

    DUTCHESS COUNTRY REALTY INC. M

    33 Twin Bridges Rd, Copake, NY 12516
  • /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

    L135.2 Rockledge 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
  • /75

    $290,000

    • Land
    • 40.25 Acres
    • $7,205 per Acre

    0 Anthony St Unit LotWP001, Copake, NY 12529

    Located within the Town of Hillsdale itself, this unique 40.25 acre offering presents a rare opportunity to own a sizable tract of land in one of Columbia County's most desirable communities. While the property enjoys immediate access to the restaurants, shops, services, and amenities that make Hillsdale such a sought-after destination, its layout and surrounding landscape create a surprisingly

    Mitchell Serlin Whitetail Properties Real Estate

    0 Anthony St Unit LotWP001, Copake, NY 12529
  • /42

    $900,000

    $200K PRICE DROP
    • 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
  • /66

    $1,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,115 Sq Ft

    351 Dugway Rd, Austerlitz, NY 12017

    Welcome to Bons Reves House, a beautifully designed escape tucked away on nearly seven acres in the most desirable part of the Austerlitz hills. Built in 1985 and meticulously renovated and expanded by a top builder in 2012 and again in 2025, this 4-bedroom, 3.5-bath contemporary home feels like a luxury treehouse hidden among mature hardwoods and surrounded by large estates and high-end

    Anthony D'Argenzio Houlihan Lawrence Inc.

    351 Dugway Rd, Austerlitz, NY 12017
  • /68

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    261 Yonderview Rd, Hillsdale, NY 12529

    Nestled on 3.36 serene acres near the New York-Massachusetts line, this completely renovated ranch-style home is a stunning blend of modern elegance and rural charm. Spanning 1,600 square feet, the open floor plan invites you into a sleek kitchen that boasts contemporary cabinetry, a spacious center island, stainless steel appliances, and luxurious quartz countertops, making it a dream for any

    Barbara Robinson Red Apple Realty

    261 Yonderview Rd, 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
  • /50

    $849,900

    $150K 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

    Jason Walch Coldwell Banker Advisor Realty

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

    $799,000

    $180K 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
  • /52

    $21,000,000

    • 5 Beds
    • 5.5 Baths
    • 5,203 Sq Ft

    21 Schoolhouse Rd, Hillsdale, NY 12529

    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

    Nikki Carchedi STONE HOUSE PROPERTIES, LLC

    21 Schoolhouse Rd, 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
  • /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
  • /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

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    292 White Hill Rd, Hillsdale, NY 12529
  • /43

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    261 Yonderview Rd, Copake, NY 12516

    Nestled on 3.36 serene acres near the New York-Massachusetts line, this completely renovated ranch-style home is a stunning blend of modern elegance and rural charm. Spanning 1,600 square feet, the open floor plan invites you into a sleek kitchen that boasts contemporary cabinetry, a spacious center island, stainless steel appliances, and luxurious quartz countertops, making it a dream for any

    Barbara Robinson Red Apple Realty Inc

    261 Yonderview Rd, Copake, NY 12516
  • /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
  • /25

    $575,000

    $74K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft

    416 Whippoorwill Rd, Hillsdale, NY 12529

    416 Whippoorwill Rd, Hillsdale, NY ~ PRIVATE SETTING!! Cape Cod style home, built in 2000, 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 additional living space.

    Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

    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
  • /20

    $795,000

    • Land
    • 50.5 Acres
    • $15,743 per Acre

    0 Rd Unit 20264993, Hillsdale, NY 12529

    A short 5 minute drive from the Taconic State Parkway, tucked up on a mountainside with incredible far-reaching panoramic views of the Catskills and the Hudson Valley. Untouched and unencumbered, this former farmland has no archaeological issues or no endangered species. Stone walls and gentle slopes. Ready for building. Divided into 5 lots of varying sizes. Sell off the lots one by one, or keep

    John Barbato Compass, Hillsdale

    0 Rd Unit 20264993, Hillsdale, NY 12529
  • /7

    $75,000

    $20K PRICE DROP
    • Land
    • 12.95 Acres
    • $5,792 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
  • /36

    $698,000

    $51K PRICE DROP
    • 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
  • /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

    $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
  • /33

    $1,398,000

    • 3 Beds
    • 3 Baths
    • 2,366 Sq Ft

    63 Knapp Hollow Ln, Hillsdale, NY 12529

    Where Nature and Serenity Take Center Stage!At the end of a private road, a magical country retreat awaits. Offered with two lots totaling over 10 acres, this secluded sanctuary brings together tranquility, natural beauty, and privacy.A winding gravel drive leads to the home, framed by colorful gardens and two picturesque ponds. A stone pathway meanders through vibrant flowers and

    Martin Salerno The Kinderhook Group, Inc.

    63 Knapp Hollow Ln, 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
  • /22

    $365,000

    • 1 Bed
    • 1 Bath
    • 684 Sq Ft

    251 Overlook Dr, Hillsdale, NY 12529

    Are you dreaming of times spent tucked away in a rustic cabin, preferably wrapped in a cozy blanket in front of a roaring fireplace? Or maybe you're dreaming of barefoot in the stream that feds into the Green River and sunbathing with rays of sunshine beaming through the trees? Welcome to 251 Overlook, Hillsdale NY! Cira 1900 Cottage in the woods, built on the side of a mountain, on 4.5 Acres. A

    Margaret Bower Avenia Columbia County RE Specialist

    251 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
  • /30

    $575,000

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

    416 Whippoorwill Rd, Hillsdale, NY 12529

    PRIVATE SETTING!! Cape Cod style home, built in 2000, 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 additional living space.Ideally located on one of Hillsdale's

    Margaret Bower Avenia Columbia County RE Specialist

    416 Whippoorwill 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
  • /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
  • /20

    $275,000

    $50K PRICE DROP
    • Land
    • 22.84 Acres
    • $12,040 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
  • /58

    $849,900

    $150K 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

    Jason Walch Coldwell Banker Advisor Realty

    2955 New York 23, Hillsdale, NY 12529
  • /48

    $725,000

    $70K PRICE DROP
    • 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
  • /9

    $85,000

    • Land
    • 11.09 Acres
    • $7,665 per Acre

    0 Ny 22 Unit 20264890, Hillsdale, NY 12529

    So many possibilities for this 11 acre parcel on Route 22. Approximately 240 feet of road frontage provides options for a driveway up hill to flat land and eastern views The property is currently wooded. The upper land had been cleared over 30 years ago. Use this property to build your home or for hunting. Close to The Berkshires, Great Barrington

    Peter Newman Beach & Bartolo Realtors

    0 Ny 22 Unit 20264890, Hillsdale, NY 12529
  • /30

    $995,000

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft

    2227 New York 23, Hillsdale, NY 12529

    COUNTRY CONTEMPORARY RANCH ON 9.5 ACRES WITH FOREVER WILD VIEWSA truly special country getaway, this distinctive 3-bedroom, 2-bath contemporary home is set on 9.5 beautiful acres with sweeping views of protected farmland and forever-wild Audubon sanctuary lands. Designed to embrace its natural surroundings, the home enjoys southern exposure and passive solar orientation, creating a warm

    Theresa Westlake Copake Lake Realty Corp.

    2227 New York 23, 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 AcresStep 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

    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
  • /66

    $290,000

    • Land
    • 40.25 Acres
    • $7,205 per Acre

    00WTP Anthony St, Hillsdale, NY 12529

    Located within the Town of Hillsdale itself, this unique 40.25± acre offering presents a rare opportunity to own a sizable tract of land in one of Columbia County's most desirable communities. While the property enjoys immediate access to the restaurants, shops, services, and amenities that make Hillsdale such a sought-after destination, its layout and surrounding landscape create a surprisingly

    Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

    00WTP 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:

    Margaret Bower Avenia Columbia County RE Specialist

    2666 New York 23, Hillsdale, NY 12529

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.

Hillsdale, NY Home Prices

Hillsdale, NY
Median Home Price
$879,000
Median Sale Price
$725,000
-34% YoY
Avg. Price per Square Foot
$587
Median Single Family Price
$849,950
Median Townhouse Price
$580,000
Total Active Listings
54 listings
Market Conditions
8 Months of Supply
Buyer's Market

Frequently Asked Questions

What is the average home price in Hillsdale, NY?
Homes for sale in Hillsdale, NY have an average home price of $1,797,552.
Are home prices dropping in Hillsdale?
Yes, home prices in Hillsdale are down 4% in the last 12 months.
How many homes have sold over the last 12 months in Hillsdale, NY?
49 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, 12075, 12516, 01230 and 01266.
How much do you need to make to afford a house in Hillsdale?
The median home price in Hillsdale is $879,000. If you put a 20% down payment of $175,800 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $4,360 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $187K 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.
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