Homes in ZIP Code 12529

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  /27

  $1,290,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,474 Sq Ft

  120 Pumpkin Hollow Rd N, Hillsdale, NY 12529

  A WORK OF ART IN HILLSDALETucked into the quiet beauty of Hillsdale, this stunning new build is anything but ordinary. Designed by award-winning architecture firm FORMA, this is their debut in the Hudson Valley. The home feels like a modern sculpture in nature—bold, thoughtful, and completely at ease in its surroundings.From the moment you arrive, there's a sense of calm and

  

  Steven Gray

  Compass Greater NY, LLC

  (518) 808-2502

  120 Pumpkin Hollow Rd N, Hillsdale, NY 12529
• 

  

  

  /4

  $895 per month

  • 1 Bed
  • 1.5 Baths
  • 500 Sq Ft
  • Apartment for Rent

  9249 New York 22, Hillsdale, NY 12529

  Great studio apt on 2nd floor on Route 22 near intersection with Route 23. opposite Stewarts Convenience/Gas. Building has mixed commerical/residential zoning. 6 month lease, pay own utilities. Walk to convenience store, restaurant, supermarket, other stores. 1 mile to Ski Catamount.

  David Birch Barns & Farms Realty, LLC

  9249 New York 22, Hillsdale, NY 12529
• 

  $426,500 Sold Sep 11, 2025

  • 1,012 Sq Ft
  • $421/SF
  • 358 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2021

  69 SW Colony Rd, Hillsdale, NY 12529

  A Lake house in the country is perfect for those seeking a simple way of life. You'll feel like you're living in a storybook. Watch your story unfold before your eyes. Leona's Country Cottage is not your average cottage. It was architecturally designed and built to last many years to come. A new rebuild from the foundation up between 2020-2021 With all new requirements for efficiency and new code

  Michelle Ayala BHHS Hudson Valley Properties

  69 SW Colony Rd, Hillsdale, NY 12529
• 

  

  

  /41

  Est $1,053,435 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,538 Sq Ft

  27 Maple St, Hillsdale, NY 12529

  27 Maple St, Hillsdale, NY 12529
• 

  

  

  /38

  $795,000

  • 3 Beds
  • 3 Baths
  • 1,876 Sq Ft

  441 Overlook Dr, Hillsdale, NY 12529

  1940's stone cottage sited on 10 acres along the Green River. Main house has a lovely kitchen, with center island and soapstone counters, open to the dining area with French doors to screened porch. Stone fireplace in the living room with recent gas insert for ease of use. There is also a small den, full bath and laundry on this level. Upstairs there are two bedrooms, a hall bath and landing

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  441 Overlook Dr, Hillsdale, NY 12529
• 

  

  /21

  $8,000 per month

  • 3 Beds
  • 3 Baths
  • 3,425 Sq Ft
  • House for Rent

  101 Overlook Dr, Hillsdale, NY 12529

  Style and CharmA beautifully sited, handsomely designed, light filled, 3 bedroom plus, 3 bathroom house with a handsome screen porch, inviting terrace and a stunning deck off the principal suite. There is a lovely private walking trail, a fabulous pool, a delightful garden movie screen and one of the best sledding hill's in the county. Extremely well located; 10 minutes to Hawthorne Valley,

  Nicole Vidor Nicole Vidor Real Estate Inc.

  101 Overlook Dr, Hillsdale, NY 12529
• 

  $1,100,000 Sold Sep 05, 2025

  • 2,128 Sq Ft
  • $517/SF
  • 78 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1942

  228 County Road 21, Hillsdale, NY 12529

  Set amongst the rolling hills of southern Columbia County, this c1942 antique farmhouse sits on seven acres with beautiful, pastoral views down the valley to the east. There is a separate studio, a three car garage and a potting shed on the property. Renovated top-to-bottom, the main house has both old world charm with its original hardwood floors, and modern comforts like new windows and roof,

  Annabel Taylor Four Seasons Sothebys Intl

  228 County Road 21, Hillsdale, NY 12529
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  /32

  Not Listed For Sale

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

  2653 New York 23, Hillsdale, NY 12529

  2653 New York 23, Hillsdale, NY 12529
• 

  

  /38

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  2955 New York 23, Hillsdale, NY 12529

  Historic Upstate NY Sanctuary - 8.7 Magical Acres in Hillsdale, NY - known for its scenic beauty and small-town charmEscape to your own private paradise on this enchanting 8.7-acre property featuring a charming 1820's cottage, pristine swimming pond with waterfall, and endless outdoor adventures. This secluded sanctuary offers the perfect blend of historic character and natural beauty, just

  Chris Getman Houlihan Lawrence Inc.

  2955 New York 23, Hillsdale, NY 12529
• 

  

  /28

  $400,000 Sold Sep 02, 2025

  • 1,728 Sq Ft
  • $231/SF
  • 27 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529

  FINAL AND BEST OFFERS DUE 7/22/25 AT 12:00 NOON. As the original farmhouse on this road, this is the epitome of a charming south-facing Upstate home with an abundance of natural light and privacy. Cool in the summer and cozy in the winter, this home is a peaceful retreat all year long.Seated between the Hudson Valley and the Berkshires, the home is just two short miles from Copake Lake. A

  Theresa Westlake Copake Lake Realty Corp.

  840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529
• 

  Not Listed For Sale

  0 Route 71 Unit 170123471, Unknown Ny City, NY 12529

  0 Route 71 Unit 170123471, Unknown Ny City, NY 12529
• 

  

  /44

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 3,282 Sq Ft

  9960 New York 22, Hillsdale, NY 12529

  Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat.The grand

  Pamela King-Belfor Four Seasons Sotheby's Int.

  9960 New York 22, Hillsdale, NY 12529
• 

  

  /68

  $3,700,000 Sold Aug 18, 2025

  • 3,604 Sq Ft
  • $1,027/SF
  • 39 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  149 Tory Hill Farm Rd, Hillsdale, NY 12529

  Perched high on a quiet mountainside in one of Hillsdale's most coveted locations, Willow Pond is a modern farmhouse sanctuary blending timeless Hudson Valley romance with the ease of updated, contemporary living. Accessed via a private road and tucked discreetly into the hillside, this calming and zen-like retreat offers complete privacy—just minutes from the center of town. Reminiscent of the

  John Barbato Compass, Hillsdale

  149 Tory Hill Farm Rd, Hillsdale, NY 12529
• 

  

  /53

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,382 Sq Ft

  1090 Route 217, Philmont, NY 12513

  1090 Route 217, Philmont, NY 12513
• 

  

  /25

  $1,525,000

  • 4 Beds
  • 4.5 Baths
  • 3,024 Sq Ft

  83 Schmeichel Rd, Hillsdale, NY 12529

  A Home of Distinction -- there are two distinct sections of this 4+ BR, 4.5 BA, 2 office spaces, 3,666 sf home that is sited on 18.5 private acres. Wood-burning fireplace, 2 gas wood stoves. Pond with gazebo. The main section has 3 BR's, living room, family room, eat-in kitchen, access to the deck with Catamount views and an attached 2-car garage. The addition has a welcoming entrance, 1 BR.

  Lindsay Lebrecht Copake Lake Realty Corp.

  83 Schmeichel Rd, Hillsdale, NY 12529
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  /35

  $410,000 Sold Aug 15, 2025

  • 1,920 Sq Ft
  • $214/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  51 Taconic Creek Rd, Hillsdale, NY 12529

  Tucked away on one of Hillsdale's most beautiful and quiet country roads, this three-bedroom, two-bathroom home offers a rare blend of privacy, potential, and charm. Set on a serene one-acre lot, the property features an inviting open-concept living, dining, and kitchen area with vaulted ceilings--perfect for gathering and entertaining. Step outside to enjoy the peaceful screened porch, a

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  51 Taconic Creek Rd, Hillsdale, NY 12529
• 

  

  /22

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,896 Sq Ft

  39 - stop 26 Justice Rd, Hillsdale, NY 12529

  39 - stop 26 Justice Rd, Hillsdale, NY 12529
• 

  

  /25

  $1,290,000

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

  161 Stagecoach Rd, Hillsdale, NY 12529

  Architecture meets nature in Hillsdale. A fully secluded getaway at the end of a private dead-end road on 7.3 pristine acres. This sunny 3-bedroom, 2-1/2 bath house is inspired by Scandinavian design and features 3 outdoor decks, with views of a spring-fed stream, a crystal clear pond, and deep green woodlands. Central AC for summer days and a wood stove for snowy nights. An ideal layout

  Owen Davidson Brown Harris Stevens HV LLC

  161 Stagecoach Rd, Hillsdale, NY 12529
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  /42

  $1,500,000 Sold Aug 01, 2025

  • 7,656 Sq Ft
  • $196/SF
  • 59 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1928

  57 Cold Water St, Hillsdale, NY 12529

  Dating back to 1928, this stately brick building originally a Masonic Temple is a stunning blend of historic charm and modern functionality. Meticulously restored and reimagined as an artist live/work space, it offers a unique opportunity to enjoy both a stately residence and/or a thriving business location.Set on a private, gated 0.54-acre lot in the charming Hamlet of Hillsdale, this property

  Annabel Taylor Four Seasons Sotheby's Int.

  57 Cold Water St, Hillsdale, NY 12529
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  /4

  Not Listed For Sale

  0 Mitchell St Unit 132496, Hillsdale, NY 12529

  0 Mitchell St Unit 132496, Hillsdale, NY 12529
• 

  

  /38

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  110 Meadow Ln, Hillsdale, NY 12529

  Ultra-private dead-end lot overlooking Hillsdale, this extraordinary home offers some of the most breathtaking panoramic views in the entire Hudson Valley. Set on 11.9 totally private acres, the property is a rare combination of refined living and natural serenity, with a gentle stream meandering below and a charming footbridge crossing over—straight out of a storybook. There is even a pond with

  Michael Castellano Gilcrest Properties

  110 Meadow Ln, Hillsdale, NY 12529
• 

  

  /18

  $335,000 Sold Jul 24, 2025

  • 1,536 Sq Ft
  • $218/SF
  • 58 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1963

  118 Yonderview Rd, Hillsdale, NY 12529

  Mid-century ranch that was (is) more than just a house -- it was (is) a home. Many family gatherings were held here. Now it's time for the next generation to carry on.Barely 10 minutes to Catamount Adventure Park/Ski Area and the Berkshires just on the other side of Molasses Hill. Should be less than 2.25 hours from Manhattan.Three + bedrooms +and over 1500 sf of living space.

  Lindsay Lebrecht Copake Lake Realty Corp.

  118 Yonderview Rd, Hillsdale, NY 12529
• 

  

  /45

  Est $964,475 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft

  445 Lakeview Rd, Craryville, NY 12521

  445 Lakeview Rd, Craryville, NY 12521
• 

  

  /24

  $845,000

  • 6 Beds
  • 2 Baths
  • 2,998 Sq Ft

  60 Anthony St, Hillsdale, NY 12529

  Price reduction.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

  Gerard Meenagh The Meenagh Group Realty

  60 Anthony St, Hillsdale, NY 12529
• 

  

  /57

  $1,168,500 Sold Jul 11, 2025

  • 1,931 Sq Ft
  • $605/SF
  • 44 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  523 Breezy Hill Rd, Hillsdale, NY 12529

  Well maintained ranch set on 8.3 open acres with beautiful views of the Taconic Range. The home with 3 bedrooms and 2.5 baths is lovely as is, and offers excellent possibilities for future additions. Enjoy expansive mountain views from both the open living space and the primary bedroom. A large deck provides great outdoor living/dining space, mature gardens and landscaping finish the property

  Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  523 Breezy Hill Rd, Hillsdale, NY 12529
• 

  /2

  Est $1,493,834 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,263 Sq Ft

  172 W End Rd, Hillsdale, NY 12529

  172 W End Rd, Hillsdale, NY 12529
• 

  

  /24

  $799,900 New Construction

  • 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 build when you could be in by Christmas? This brand-new construction is underway and 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 service already set.

  Michael Castellano Gilcrest Properties

  801 Rodman Rd, Hillsdale, NY 12529
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  /32

  $1,175,000 Sold Jul 03, 2025

  • 2,194 Sq Ft
  • $536/SF
  • 38 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1970

  17 White Hill Rd, Hillsdale, NY 12529

  Secluded Hillsdale Contemporary on 27.7 acres with incredible far reaching views. Located off a scenic country road, the long private driveway leads to this 2200 square foot home. Originally built in 1970, the house has been upgraded with new windows and sliding doors which create walls of glass for enjoying the natural beauty of the surrounding landscape. The house features 3 bedrooms, 2.5

  PATRICIA HINKEIN Patricia A. Hinkein Realty

  17 White Hill Rd, Hillsdale, NY 12529
• 

  

  /11

  Est $541,210 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft

  40 Marsten Ln, Hillsdale, NY 12529

  40 Marsten Ln, Hillsdale, NY 12529
• 

  

  /39

  $895,000 Under Contract

  • 5 Beds
  • 3.5 Baths
  • 2,834 Sq Ft

  11 Cold Water St, Hillsdale, NY 12529

  This handsome Greek Revival sits on a quiet street occupying a generous village lot in the historic Hamlet of Hillsdale. Built around 1848, the home feels historic and fresh with plenty of room to spread out. A wide front porch with Doric columns welcomes you inside to a central foyer. To one side, a front parlor opens to a spacious dining room with elegant moldings. The kitchen is a highlight,

  MATTHEW CAREY Rouse + Co Real Estate, LLC

  11 Cold Water St, Hillsdale, NY 12529
• 

  

  /42

  $1,350,000 Sold Jun 27, 2025

  • 3,540 Sq Ft
  • $381/SF
  • 15 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  864 W End Rd, Hillsdale, NY 12529

  Tucked away on one of Hillsdale's most picturesque and coveted country roads, this extraordinary property is a celebration of nature, craftsmanship, and connection—blending serene seclusion with easy access to the vibrant Hudson Valley lifestyle.Set on a park-like expanse of rolling lawns, mature woodlands, and a dreamy lilypad-covered pond, this one-of-a-kind home offers the welcome sense of

  John Barbato Compass, Hillsdale

  864 W End Rd, Hillsdale, NY 12529
• 

  /2

  Est $849,698 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,322 Sq Ft

  137 Whippoorwill Rd, Hillsdale, NY 12529

  137 Whippoorwill Rd, Hillsdale, NY 12529
• 

  

  /24

  $850,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,574 Sq Ft

  407 Lakeview Rd, Craryville, NY 12521

  Copake Lake, New YorkA Lifetime of MemoriesNow is the time for the next generation. There is no shortage of views from this 2 BR + sleeping loft, 2 BA, 1574 sf log home. Be it the rocking chair porch or the 46' deck on the water this is the place to be for those famous ''Copake Lake Sunsets''. Copake Lake is ~425 acre motorboat lake strategically located equal-distance

  Lindsay Lebrecht Copake Lake Realty Corp.

  407 Lakeview Rd, Craryville, NY 12521
• 

  

  /29

  $1,220,000 Sold Jun 24, 2025

  • 2,100 Sq Ft
  • $581/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2014

  90 Overlook Dr, Hillsdale, NY 12529

  The Upside Down House, designed by Adam Rolston of INC Architecture and Design. Set on 3 acres along one of Columbia County's most desirable roads, just minutes to downtown Great Barrington and the City of Hudson, NY. Surrounded by hayfields with distant views, this super-energy efficient home features a 40-foot saltwater lap pool, outdoor shower, spring-fed pond, heated tile

  Jennifer Harvey Compass Greater NY LLC

  90 Overlook Dr, Hillsdale, NY 12529
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  /37

  Est $860,229 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,234 Sq Ft

  111 Hunt Rd, Hillsdale, NY 12529

  111 Hunt Rd, Hillsdale, NY 12529
• 

  

  /44

  $725,000

  • 3 Beds
  • 2 Baths
  • 2,268 Sq Ft

  15 Tory Hill Rd, Hillsdale, NY 12529

  Nestled on a hillside just outside the vibrant hamlet of Hillsdale sits this exceptional 2007 Cape Cod cedar sided home. The views are simply one-of-a-kind, directly overlooking the Rheinstrom Hill Audubon Sanctuary and offering distant views reaching from the Taconic Range to the Catskill peaks. Energy saving features include a geo-thermal heating and cooling system, fully conditioned

  John Avenia Columbia County RE Specialist

  15 Tory Hill Rd, Hillsdale, NY 12529
• 

  

  /114

  $3,000,000 Sold Jun 10, 2025

  • 4,130 Sq Ft
  • $726/SF
  • 35 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2021

  184A Cambridge Rd, Hillsdale, NY 12529

  Up a winding country drive in a beautifully rural part of southern Columbia County, a modern house is notched into the hillside. West facing toward the sunset, the home was built to frame a magnificent view of the Catskill Mountains. The interior has wonderfully high 12ft ceilings and wideboard white oak flooring. The large Great Room features a striking wall of glass looking out over the

  Annabel Taylor Four Seasons Sotheby's International Realty

  184A Cambridge Rd, Hillsdale, NY 12529
• 

  

  /25

  Est $710,822 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,272 Sq Ft

  274 Texas Hill Rd, Hillsdale, NY 12529

  274 Texas Hill Rd, Hillsdale, NY 12529
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  /8

  $375,000

  • Land
  • 90 Acres
  • $4,167 per Acre

  0 Harlemville Rd Unit 20254229, Hillsdale, NY 12529

  On a bucolic country by-way you will find this very private wooded hilltop parcel with Catskill Mountain views. Gorgeous mature timber and beautiful rocky outcrops dot this parcel. Access is via a brief right-of-way and along a pretty private lane. Note reduced taxes due to a power line easement to the rear of the property. Suitable for a single main residence.

  James Male HOUSE Hudson Valley Realty

  0 Harlemville Rd Unit 20254229, Hillsdale, NY 12529
• 

  

  /3

  $25,000 Sold May 28, 2025

  • Land
  • 0.96 Acre
  • $26,042 per Acre

  • 13 Days On Market

  0 Stonehill Dr, Hillsdale, NY 12529

  Very private location at end of dead end road. Access to Route 22 and the Taconic Parkway. Easy drive to Hudson, Hillsdale, Catamount Ski Area and Great Barrington.

  David Birch Barns & Farms Realty, LLC

  0 Stonehill Dr, Hillsdale, NY 12529

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