Hillsdale, NY Homes

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  /18

  $335,000 Sold Jul 24, 2025

  118 Yonderview Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,536 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Below List Price
  • $218/SF
  • 58 Days On Market

  Current Estimated Value $349,546

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

  118 Yonderview Rd, Hillsdale, NY 12529
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  Est $702,735 Not Listed For Sale

  62 Bucky Rd, Hillsdale, NY 12529

  • 4 Beds
  • 3 Baths
  • 3,034 Sq Ft
  • Built 1960

  62 Bucky Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 1% Above List Price
  • $228/SF
  • 110 Days On Market

  • Last Sold Price $693,000
  • Jan 03, 2024

  Last Listing Agent Ronald Green KW MidHudson
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  /39

  $5,950,000

  • 5 Beds
  • 4.5 Baths
  • 6,438 Sq Ft

  890 Bald Mountain Rd, Austerlitz, NY 12017

  Welcome to Bald Mountain Estate, an extraordinary private compound spanning 85 breathtaking acres overlooking the Hudson Valley and the Berkshire Hills. This four-building, ultra-contemporary estate epitomizes modern country luxury, featuring floor-to-ceiling glass walls and a steel infrastructure that creates a distinctive blend of rustic elegance and architectural sophistication. The

  Janet Kain The Kinderhook Group, Inc.

  890 Bald Mountain Rd, Austerlitz, NY 12017
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  /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
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  /25

  Est $559,286 Not Listed For Sale

  15 Henich Ln, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1990

  15 Henich Ln, Hillsdale, NY 12529

  Last Sold Summary

  • 6% Above List Price
  • $320/SF
  • 46 Days On Market

  • Last Sold Price $528,000
  • Jun 24, 2024

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
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  /6

  $175,000

  • Land
  • 33.31 Acres
  • $5,254 per Acre

  50 Dugway Rd, Hillsdale, NY 12529

  Create Your Own Vision.Escape to 33.31 acres of untouched beauty in Columbia County, NY, and close to Great Barrington, MA. 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. Over 1,677 feet of road frontage, and an old roadway that

  Jeffrey McKinney Beach & Bartolo Realtors

  50 Dugway Rd, Hillsdale, NY 12529
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  /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 $249,087

  Last Listing Agent Sarah Lipsky William Pitt Sothebys Intn'l

  49 Stonehill Dr, Hillsdale, NY 12529
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  /37

  Est $616,096 Not Listed For Sale

  68 Cherokee Dr, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft
  • Built 1994

  68 Cherokee Dr, Hillsdale, NY 12529

  Last Sold Summary

  • 8% Above List Price
  • $338/SF
  • 61 Days On Market

  • Last Sold Price $570,000
  • Jan 09, 2025

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
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  /23

  $290,000 Pending

  • 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
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  /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
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  Est $1,419,887 Not Listed For Sale

  656 Breezy Hill Rd, Hillsdale, NY 12529

  • 4 Beds
  • 3.5 Baths
  • 2,272 Sq Ft
  • Built 1850

  656 Breezy Hill Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 1% Below List Price
  • $632/SF
  • 57 Days On Market

  • Last Sold Price $1,435,000
  • Feb 07, 2025

  Last Listing Agent John Panzer Elyse Harney Real Estate
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  /32

  $339,000

  • 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
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  /68

  $3,700,000 Sold Aug 18, 2025

  149 Tory Hill Farm Rd, Hillsdale, NY 12529

  • 4 Beds
  • 2.5 Baths
  • 3,604 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Above List Price
  • $1,027/SF
  • 39 Days On Market

  Current Estimated Value $3,356,646

  Last Listing Agent John Barbato Compass, Hillsdale

  149 Tory Hill Farm Rd, Hillsdale, NY 12529
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  /28

  Est $376,234 Not Listed For Sale

  119 Black Grocery Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1971

  119 Black Grocery Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 7% Above List Price
  • $286/SF
  • 211 Days On Market

  • Last Sold Price $352,000
  • Jun 28, 2024

  Last Listing Agent Wendy Kenney Davala Real Estate, LLC
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  /24

  $615,000

  • 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
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  /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
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  /14

  Est $494,484 Not Listed For Sale

  52 Connelly Rd, Hillsdale, NY 12529

  • 4 Beds
  • 2 Baths
  • 2,343 Sq Ft
  • Built 1952

  52 Connelly Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 77% Above List Price
  • $120/SF
  • 142 Days On Market

  • Last Sold Price $280,000
  • Nov 19, 2024

  Last Listing Agent Amjad Mughal M J J Realty
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  /46

  $3,350,000 Pending

  • 4 Beds
  • 4 Baths
  • 4,000 Sq Ft

  411 Texas Hill Rd, Hillsdale, NY 12529

  411 Texas Hill Road is an exemplary portrait of a Mid-Century home, set on 40 private acres. The home is positioned on one of the highest points in Columbia County, with views of both the Taconic and the Helderberg ranges. Located just 20 minutes from Hudson and surrounded by all the wonderful amenities of the Hudson Valley. Set on a quiet one-lane, town-maintained road, this private sanctuary is

  Marina Tatistcheff Compass Greater NY LLC

  411 Texas Hill Rd, Hillsdale, NY 12529
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  /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
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  /27

  Est $899,682 Not Listed For Sale

  66 Fado Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • Built 1850

  66 Fado Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 28% Above List Price
  • $496/SF
  • 368 Days On Market

  • Last Sold Price $705,000
  • Apr 22, 2024

  Last Listing Agent John Avenia Columbia County RE Specialist
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  /23

  $290,000 Pending

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  9377 State Route 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

  Scott Zobre KW MidHudson

  9377 State Route 22, Hillsdale, NY 12529
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  $1,100,000 Sold Aug 18, 2025

  515 Turnpike, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Built 1983

  Last Sold Summary

  • 8% Below List Price
  • $515/SF
  • 50 Days On Market

  Last Listing Agent Joseph Briggs William Pitt Sothebys Int Rlty

  515 Turnpike, Hillsdale, NY 12529
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  /2

  Est $384,849 Not Listed For Sale

  189 Prach Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • Built 1964

  189 Prach Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 54% Above List Price
  • $283/SF
  • 24 Days On Market

  • Last Sold Price $250,000
  • Jun 12, 2023

  Last Listing Agent Daniel Mahar Coldwell Banker Advisor Realty
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  /7

  $259,000

  • 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
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  $1,150,000 Sold Nov 17, 2025

  306 County Route 21c, Ghent, NY 12075

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • Built 1890

  Last Sold Summary

  • 8% Below List Price
  • $460/SF
  • 48 Days On Market

  Current Estimated Value $1,182,142

  Last Listing Agent Nancy Felcetto Brown Harris Stevens HV LLC

  306 County Route 21c, Ghent, NY 12075
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  /20

  Est $313,691 Not Listed For Sale

  10977 New York 22, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,841 Sq Ft
  • Built 1950

  10977 New York 22, Hillsdale, NY 12529

  Last Sold Summary

  • 49% Above List Price
  • $115/SF
  • 34 Days On Market

  • Last Sold Price $211,000
  • Sep 13, 2024

  Last Listing Agent Scott Varley KW Platform
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  /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!! Private and quiet on 5 acres, home is in immaculate condition. First floor offers an open floor plan, kitchen, dining room, propane fireplace in living-room, sunroom & bathroom. Second floor offers two bedrooms with walk-in closets and full bathroom. Lower level offers full dry basement with laundry

  Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

  416 Whippoorwill Rd, Hillsdale, NY 12529
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  /18

  $586,000 Sold Jun 30, 2025

  676 County Route 21, Ghent, NY 12075

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Above List Price
  • $452/SF
  • 38 Days On Market

  Last Listing Agent Terry Cozzolino Cozzolino Real Estate Inc

  676 County Route 21, Ghent, NY 12075
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  /13

  Est $373,201 Not Listed For Sale

  4 Texas Hill Rd, Hillsdale, NY 12529

  • 4 Beds
  • 2 Baths
  • 1,076 Sq Ft
  • Built 1952

  4 Texas Hill Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 13% Above List Price
  • $307/SF
  • 38 Days On Market

  • Last Sold Price $330,000
  • Aug 29, 2024

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
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  /28

  $535,000 Pending

  • 4 Beds
  • 5 Baths
  • 3,425 Sq Ft

  364 Yonderview Rd, Hillsdale, NY 12529

  Reduced Price! Close to skiing and the Berkshires. Once the Flood farmhouse, circa 1850. Over 3400 sf sited on 5 acres. Beautiful perennial gardens. Farmland views of the Taconic Range. Attached 2-car garage. The main floor has an office, that connects the home to the garage. Formal living room and formal dining room. The primary suite includes both his and hers full bathrooms, and a changing

  Lindsay Lebrecht Copake Lake Realty Corp.

  364 Yonderview Rd, Hillsdale, NY 12529
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  /32

  $1,175,000 Sold Jul 03, 2025

  17 White Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,194 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $536/SF
  • 38 Days On Market

  Current Estimated Value $1,208,813

  Last Listing Agent PATRICIA HINKEIN Patricia A. Hinkein Realty

  17 White Hill Rd, Hillsdale, NY 12529
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  /44

  Est $1,140,092 Not Listed For Sale

  2367 County Road 11, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1887

  2367 County Road 11, Hillsdale, NY 12529

  Last Sold Summary

  • 23% Below List Price
  • $567/SF
  • 27 Days On Market

  • Last Sold Price $1,475,000
  • Jul 31, 2024

  Last Listing Agent Raj Kumar Four Seasons Sotheby's Int.
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  /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
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  $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 $776,103

  Last Listing Agent Tom Lynch Compass Greater NY LLC

  470 N Mountain Rd, Copake Falls, NY 12517
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  /20

  Est $351,658 Not Listed For Sale

  1337 County Route 21, Ghent, NY 12075

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1910

  1337 County Route 21, Ghent, NY 12075

  Last Sold Summary

  • 43% Above List Price
  • $134/SF
  • 35 Days On Market

  • Last Sold Price $246,000
  • Sep 05, 2024

  Last Listing Agent April Seney Core Real Estate Team
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  /21

  $349,900

  • 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
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  /42

  $1,500,000 Sold Aug 01, 2025

  57 Cold Water St, Hillsdale, NY 12529

  • 2 Beds
  • 3 Baths
  • 7,656 Sq Ft
  • Built 1928

  Last Sold Summary

  • 5% Below List Price
  • $196/SF
  • 59 Days On Market

  Current Estimated Value $1,491,830

  Last Listing Agent Annabel Taylor Four Seasons Sotheby's Int.

  57 Cold Water St, Hillsdale, NY 12529
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  /17

  Not Listed For Sale

  9398 New York 22, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1951

  9398 New York 22, Hillsdale, NY 12529

  Last Sold Summary

  • $157/SF
  • 32 Days On Market

  • Last Sold Price $143,100
  • Jul 12, 2024

  Last Listing Agent Barbara Robinson Red Apple Realty
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  /15

  $2,999,000

  • Land
  • 242 Acres
  • $12,393 per Acre

  00 Dugway Rd, Austerlitz, NY 12017

  242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

  Michael Tellerday Houlihan Lawrence Inc.

  00 Dugway Rd, Austerlitz, NY 12017
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  /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 $427,050

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

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

Showing Results 41 - 80, Page 2 of 18