Recently Sold Homes in 12529

/14
$104,000

Sold May 27, 2026

10021 New York 22, Hillsdale, NY 12529
- 4 Beds
- 1 Bath
- 2,116 Sq Ft
- Built 1856
Last Sold Summary
- 31% Below List Price
- $49/SF
- 91 Days On Market
Last Listing Agent Paul Crayton Coldwell Banker Advisor Realty

10021 New York 22, Hillsdale, NY 12529
/30
$650,000

Sold Dec 22, 2025

63 Cherokee Dr, Hillsdale, NY 12529
- 3 Beds
- 2.5 Baths
- 2,256 Sq Ft
- Built 1985
Last Sold Summary
- 2% Below List Price
- $288/SF
- 33 Days On Market
Current Estimated Value $663,088

Last Listing Agent Blanche Mackey Copake Lake Realty Corp.

63 Cherokee Dr, Hillsdale, NY 12529
/18
$500,000

Sold Jan 23, 2026

2253 County Route 21, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 1,493 Sq Ft
- Built 2021
Last Sold Summary
- 7% Below List Price
- $335/SF
- 124 Days On Market
Last Listing Agent Jeffries Blackerby Houlihan Lawrence Inc.

2253 County Route 21, Hillsdale, NY 12529
/9
$675,000

Sold Jun 09, 2026

3244 Cr 7, Hillsdale, NY 12529
- Land
- 56.9 Acres
- $11,863 per Acre
Last Sold Summary
- 20% Below List Price
- 809 Days On Market
Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

3244 Cr 7, Hillsdale, NY 12529
/20
$605,000

Sold Sep 17, 2025

15 Roosevelt Dr, Hillsdale, NY 12529
- 1,080 Sq Ft
- Built 1958
Last Sold Summary
- 34% Below List Price
- $560/SF
- 742 Days On Market
Current Estimated Value $642,748

Last Listing Agent Donna Peck Past Member

15 Roosevelt Dr, Hillsdale, NY 12529
/77
$1,625,000

Sold May 18, 2026

46 Collins St, Hillsdale, NY 12529
- 4 Beds
- 3 Baths
- 2,608 Sq Ft
- Built 1850
Last Sold Summary
- 4% Below List Price
- $623/SF
- 62 Days On Market
Current Estimated Value $1,579,708

Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc.

46 Collins St, Hillsdale, NY 12529
$3,700,000

Sold Jul 17, 2026

54 Far View Ln, Hillsdale, NY 12529
- 4 Beds
- 3 Baths
- 3,666 Sq Ft
- Built 1971
Last Sold Summary
- 7% Below List Price
- $1,009/SF
- 20 Days On Market
Current Estimated Value $3,926,762

Last Listing Agent Anthony D'Argenzio Houlihan Lawrence, Inc

54 Far View Ln, Hillsdale, NY 12529
/20
$295,000

Sold Dec 30, 2025

376 Approx Whippoorwill Rd, Hillsdale, NY 12529
- Land
- 12 Acres
- $24,583 per Acre
Last Sold Summary
- 39 Days On Market
Last Listing Agent John Avenia Columbia County RE Specialist

376 Approx Whippoorwill Rd, Hillsdale, NY 12529
/44
$725,000

Sold Dec 09, 2025

15 Tory Hill Rd, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,592 Sq Ft
- Built 2007
Last Sold Summary
- $280/SF
- 45 Days On Market
Current Estimated Value $766,107

Last Listing Agent John Avenia Columbia County RE Specialist

15 Tory Hill Rd, Hillsdale, NY 12529
/45
$1,150,000

Sold Jul 31, 2026

1 van Bueran Dr, Hillsdale, NY 12529
- 5 Beds
- 3 Baths
- 1,708 Sq Ft
- Built 1988
Last Sold Summary
- $673/SF
- 40 Days On Market
Current Estimated Value $1,126,613

Last Listing Agent Jessica Scott Compass Greater NY LLC

1 van Bueran Dr, Hillsdale, NY 12529
/29
$965,000

Sold Dec 22, 2025

271 Texas Hill Rd, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,279 Sq Ft
- Built 1930
Last Sold Summary
- $423/SF
- 21 Days On Market
Current Estimated Value $966,958

Last Listing Agent Kelcey Otten Compass Greater NY, LLC d/b/a

271 Texas Hill Rd, Hillsdale, NY 12529
/58
$686,000

Sold Jul 30, 2026

534 Collins St, Hillsdale, NY 12529
- 2 Beds
- 2.5 Baths
- 2,060 Sq Ft
- Built 1975
Last Sold Summary
- 10% Above List Price
- $333/SF
- 17 Days On Market
Current Estimated Value $621,452

Last Listing Agent John Barbato Compass, Hillsdale

534 Collins St, Hillsdale, NY 12529
$850,000

Sold Feb 24, 2026

9254 New York 22, Hillsdale, NY 12529
- 4 Beds
- 3 Baths
- 2,500 Sq Ft
- Built 1980
Last Sold Summary
- 8% Above List Price
- $340/SF
- 16 Days On Market
Last Listing Agent David Birch Barns and Farms Realty LLC

9254 New York 22, Hillsdale, NY 12529
/23
$360,000

Sold Aug 20, 2026

16 Robin Rd, Craryville, NY 12521
- 3 Beds
- 1 Bath
- 1,303 Sq Ft
- Built 1955
Last Sold Summary
- 14% Below List Price
- $276/SF
- 95 Days On Market
Last Listing Agent Blanche Mackey Copake Lake Realty Corp.

16 Robin Rd, Craryville, NY 12521
/4
$81,000

Sold Jan 27, 2026

0 Rodman Rd, Hillsdale, NY 12529
- Land
- 4.4 Acres
- $18,409 per Acre
Last Sold Summary
- 2% Above List Price
- 14 Days On Market
Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

0 Rodman Rd, Hillsdale, NY 12529
/4
$199,999

Sold Dec 31, 2025

2605 New York 23, Hillsdale, NY 12529
- 5 Beds
- 3 Baths
- 2,578 Sq Ft
- Built 1890
Last Sold Summary
- $78/SF
- 40 Days On Market
Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

2605 New York 23, Hillsdale, NY 12529
/46
$3,245,000

Sold Jun 08, 2026

411 Texas Hill Rd, Hillsdale, NY 12529
- 4 Beds
- 4 Baths
- 4,000 Sq Ft
- Built 1967
Last Sold Summary
- 3% Below List Price
- $811/SF
- 32 Days On Market
Current Estimated Value $3,307,101

Last Listing Agent Marina Tatistcheff Compass Greater NY LLC

411 Texas Hill Rd, Hillsdale, NY 12529
$515,000

Sold Jun 16, 2026

180 Collins St, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
- Built 1906
Last Sold Summary
- 14% Above List Price
- $418/SF
- 9 Days On Market
Current Estimated Value $498,006

Last Listing Agent Joseph Shirk The Kinderhook Group, Inc.

180 Collins St, Hillsdale, NY 12529
/26
$510,000

Sold Dec 15, 2025

25 Catamount Rd, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 820 Sq Ft
- Built 2024
Last Sold Summary
- 7% Below List Price
- $622/SF
- 33 Days On Market
Last Listing Agent Paige Backhaus William Raveis Real Estate

25 Catamount Rd, Hillsdale, NY 12529
/28
$450,000

Sold Jun 18, 2026

364 Yonderview Rd, Hillsdale, NY 12529
- 4 Beds
- 5 Baths
- 3,425 Sq Ft
- Built 1850
Last Sold Summary
- 16% Below List Price
- $131/SF
- 7 Days On Market
Current Estimated Value $557,163

Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

364 Yonderview Rd, Hillsdale, NY 12529
/14
$255,000

Sold Feb 13, 2026

49 Stonehill Dr, Hillsdale, NY 12529
- 1 Bed
- 1 Bath
- 525 Sq Ft
- Built 1963
Last Sold Summary
- 9% Above List Price
- $486/SF
- 78 Days On Market
Current Estimated Value $253,806

Last Listing Agent Sarah Lipsky William Pitt Sothebys Intn'l

49 Stonehill Dr, Hillsdale, NY 12529
/26
$1,037,500

Sold Apr 28, 2026

9715 New York 22, Hillsdale, NY 12529
- 5 Beds
- 2.5 Baths
- 3,350 Sq Ft
- Built 1788
Last Sold Summary
- 6% Below List Price
- $310/SF
- 160 Days On Market
Last Listing Agent Annabel Taylor Four Seasons Sotheby's Int.

9715 New York 22, Hillsdale, NY 12529
/4
$150,000

Sold Jan 29, 2026

0 Knapp Hollow Ln, Hillsdale, NY 12529
- Land
- 6.25 Acres
- $24,000 per Acre
Last Sold Summary
- 12% Below List Price
- 39 Days On Market
Last Listing Agent marylou Kersten Copake Lake Realty Corp.

0 Knapp Hollow Ln, Hillsdale, NY 12529
/36
$580,000

Sold Jun 12, 2026

2657 State Route 23, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,057 Sq Ft
- Built 1780
Last Sold Summary
- 11% Below List Price
- $282/SF
- 244 Days On Market
Current Estimated Value $587,474

Last Listing Agent John Barbato Compass, Hillsdale

2657 State Route 23, Hillsdale, NY 12529
/39
$912,500

Sold Nov 07, 2025

11 Cold Water St, Hillsdale, NY 12529
- 5 Beds
- 3.5 Baths
- 2,834 Sq Ft
- Built 1848
Last Sold Summary
- 2% Above List Price
- $322/SF
- 29 Days On Market
Last Listing Agent MATTHEW CAREY Rouse + Co Real Estate

11 Cold Water St, Hillsdale, NY 12529
/29
$450,000

Sold Jul 08, 2026

44 Collins St, Hillsdale, NY 12529
- 2 Beds
- 1.5 Baths
- 1,630 Sq Ft
- Built 1933
Last Sold Summary
- 6% Above List Price
- $276/SF
- 64 Days On Market
Current Estimated Value $431,843

Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist

44 Collins St, Hillsdale, NY 12529
/34
$580,000

Sold Jun 05, 2026

66 Anthony St, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,300 Sq Ft
- Built 1971
Last Sold Summary
- 2% Below List Price
- $252/SF
- 112 Days On Market
Last Listing Agent Susan Calkins STONE HOUSE PROPERTIES, LLC

66 Anthony St, Hillsdale, NY 12529
/23
$460,000

Sold Aug 13, 2026

217 Anthony St, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 1,375 Sq Ft
- Built 2026
Last Sold Summary
- 7% Below List Price
- $335/SF
- 101 Days On Market
Last Listing Agent John Barbato Compass, Hillsdale

217 Anthony St, Hillsdale, NY 12529
$805,000

Sold Nov 14, 2025

470 N Mountain Rd, Copake Falls, NY 12517
- 3 Beds
- 3 Baths
- 1,636 Sq Ft
- Built 1840
Last Sold Summary
- 1% Above List Price
- $492/SF
- 8 Days On Market
Current Estimated Value $803,906

Last Listing Agent Tom Lynch Compass Greater NY LLC

470 N Mountain Rd, Copake Falls, NY 12517
/64
$4,450,000

Sold Dec 17, 2025

27 Lake Ridge Ln, Copake Lake, NY 12521
- 4 Beds
- 4.5 Baths
- 6,400 Sq Ft
- Built 2025
Last Sold Summary
- $695/SF
- 27 Days On Market
Last Listing Agent John Barbato Compass, Hillsdale

27 Lake Ridge Ln, Copake Lake, NY 12521
$1,183,000

Sold Aug 10, 2026

161 Stagecoach Rd, Hillsdale, NY 12529
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
- Built 1968
Last Sold Summary
- 21% Below List Price
- $538/SF
- 338 Days On Market
Current Estimated Value $1,101,203

Last Listing Agent Owen Davidson Brown Harris Stevens HV LLC

161 Stagecoach Rd, Hillsdale, NY 12529
/28
$400,000

Sold Sep 02, 2025

840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529
- 4 Beds
- 2 Baths
- 1,728 Sq Ft
- Built 1900
Last Sold Summary
- 11% Above List Price
- $231/SF
- 27 Days On Market
Current Estimated Value $508,871

Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529
/43
$675,000

Sold Mar 23, 2026

7 Birch Hill Rd, Craryville, NY 12521
- 3 Beds
- 2.5 Baths
- 2,296 Sq Ft
- Built 2003
Last Sold Summary
- 8% Below List Price
- $294/SF
- 136 Days On Market
Current Estimated Value $682,445

Last Listing Agent Michael Castellano Gilcrest Properties

7 Birch Hill Rd, Craryville, NY 12521
/19
$190,000

Sold Jun 05, 2026

2227 County Route 21, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 794 Sq Ft
- Built 1950
Last Sold Summary
- 37% Below List Price
- $239/SF
- 362 Days On Market
Last Listing Agent Michael Castellano Gilcrest Properties

2227 County Route 21, Hillsdale, NY 12529
/41
$786,000

Sold Nov 20, 2025

441 Overlook Dr, Hillsdale, NY 12529
- 3 Beds
- 3 Baths
- 1,875 Sq Ft
- Built 1940
Last Sold Summary
- 1% Below List Price
- $419/SF
- 50 Days On Market
Current Estimated Value $775,583

Last Listing Agent Jennifer Harvey Compass Greater NY LLC

441 Overlook Dr, Hillsdale, NY 12529
/57
$957,000

Sold Jul 24, 2026

1 Breezy Hill Rd, Copake Falls, NY 12517
- 3 Beds
- 2 Baths
- 1,376 Sq Ft
- Built 1887
Last Sold Summary
- 20% Above List Price
- $695/SF
- 24 Days On Market
Current Estimated Value $601,596

Last Listing Agent Eva Reece Houlihan Lawrence Inc.

1 Breezy Hill Rd, Copake Falls, NY 12517
/13
$725,000

Sold Jan 20, 2026

2318 County Road 11, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 1,569 Sq Ft
- Built 2025
Last Sold Summary
- 3% Below List Price
- $462/SF
- 24 Days On Market
Last Listing Agent Emma French Gabel Real Estate

2318 County Road 11, Hillsdale, NY 12529
$426,500

Sold Sep 11, 2025

69 SW Colony Rd, Hillsdale, NY 12529
- 2 Beds
- 1 Bath
- 1,012 Sq Ft
- Built 2021
Last Sold Summary
- 10% Below List Price
- $421/SF
- 358 Days On Market
Current Estimated Value $444,434

Last Listing Agent Michelle Ayala BHHS Hudson Valley Properties

69 SW Colony Rd, Hillsdale, NY 12529
/40
$2,180,000

Sold Mar 02, 2026

35 Harlemville Rd, Hillsdale, NY 12529
- 5 Beds
- 5.5 Baths
- 7,200 Sq Ft
- Built 1980
Last Sold Summary
- 34% Below List Price
- $303/SF
- 441 Days On Market
Current Estimated Value $1,882,841

Last Listing Agent Non MLS HVCR MLS HV Catskill Region MLS

35 Harlemville Rd, Hillsdale, NY 12529
/9
$215,000

Sold Nov 13, 2025

10011 New York 22, Hillsdale, NY 12529
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
- Built 1975
Last Sold Summary
- 17% Below List Price
- $207/SF
Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

10011 New York 22, Hillsdale, NY 12529

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