Recently Sold Pawling, NY Homes

• 

  $637,500 Sold Dec 31, 2025

  175 Old Quaker Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 5 Baths
  • 4,018 Sq Ft
  • Built 1952

  Last Sold Summary

  • 9% Below List Price
  • $159/SF
  • 114 Days On Market

  Current Estimated Value $800,674

  Last Listing Agent Tom Consaga RE/MAX Ace Realty

  175 Old Quaker Hill Rd, Pawling, NY 12564
• Explore Pawling

• 

  $115,000 Sold Nov 14, 2025

  0 Overlook Rd, Pawling, NY 12564

  • Land
  • 1.4 Acres
  • $82,143 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 249 Days On Market

  Last Listing Agent Judith 'Judy' Albert BHHS Hudson Valley Properties

  0 Overlook Rd, Pawling, NY 12564
• 

  $200,000 Sold Oct 21, 2025

  Lot #2 Dodge Rd, Pawling, NY 12564

  • Land
  • 9.73 Acres
  • $20,555 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 312 Days On Market

  Last Listing Agent Brian McGrath McGrath Realty Inc

  Lot #2 Dodge Rd, Pawling, NY 12564
• 

  $400,000 Sold Jan 28, 2026

  2 Spruce St, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 1,838 Sq Ft
  • Built 1993

  Last Sold Summary

  • $218/SF
  • 37 Days On Market

  Current Estimated Value $399,905

  Last Listing Agent Robin Butler-Koschei Hanson Real Estate Partners

  2 Spruce St, Pawling, NY 12564
• 

  $435,000 Sold Jun 06, 2025

  103 Mohawk Trail, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,917 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Above List Price
  • $227/SF
  • 13 Days On Market

  Current Estimated Value $449,435

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  103 Mohawk Trail, Pawling, NY 12564
• 

  $436,000 Sold Dec 18, 2025

  36 Elm St, Pawling, NY 12564

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft
  • Built 1900

  Last Sold Summary

  • 17% Below List Price
  • $260/SF
  • 133 Days On Market

  Current Estimated Value $448,822

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  36 Elm St, Pawling, NY 12564
• 

  $361,000 Sold Aug 13, 2025

  37 Spruce St, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 1,413 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $255/SF
  • 51 Days On Market

  Current Estimated Value $363,761

  Last Listing Agent Nick Selca Lakeshore Realty International

  37 Spruce St, Pawling, NY 12564
• 

  $330,000 Sold Oct 02, 2025

  36 Spruce St, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 1,414 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $233/SF
  • 41 Days On Market

  Current Estimated Value $441,909

  Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

  36 Spruce St, Pawling, NY 12564
• 

  $365,000 Sold Apr 10, 2025

  4 Juniper Ln, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $174/SF
  • 20 Days On Market

  Current Estimated Value $378,471

  Last Listing Agent Josephine Diego K. Fortuna Realty, Inc.

  4 Juniper Ln, Pawling, NY 12564
• 

  $725,000 Sold Dec 17, 2025

  27 Millstream Ct, Pawling, NY 12564

  • 4 Beds
  • 2.5 Baths
  • 3,283 Sq Ft
  • Built 2000

  Last Sold Summary

  • $221/SF
  • 162 Days On Market

  Current Estimated Value $726,434

  Last Listing Agent Christopher Filangeri BHHS Hudson Valley Properties

  27 Millstream Ct, Pawling, NY 12564
• 

  $540,000 Sold May 23, 2025

  85 W Deer Trail, Pawling, NY 12564

  • 4 Beds
  • 2.5 Baths
  • 2,341 Sq Ft
  • Built 2001

  Last Sold Summary

  • $231/SF
  • 23 Days On Market

  Current Estimated Value $561,096

  Last Listing Agent Shannon Tully McGrath Realty Inc

  85 W Deer Trail, Pawling, NY 12564
• 

  $430,000 Sold Sep 11, 2025

  19 Cushing Green S, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $234/SF
  • 64 Days On Market

  Current Estimated Value $434,364

  Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

  19 Cushing Green S, Pawling, NY 12564
• 

  $410,000 Sold Jul 24, 2025

  11 Birch Terrace, Pawling, NY 12564

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $293/SF
  • 34 Days On Market

  Current Estimated Value $402,964

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  11 Birch Terrace, Pawling, NY 12564
• 

  $350,000 Sold Dec 18, 2025

  33 Spruce St, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 1,413 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $248/SF
  • 51 Days On Market

  Current Estimated Value $356,762

  Last Listing Agent Edmond Albano Keller Williams NY Realty

  33 Spruce St, Pawling, NY 12564
• 

  $490,000 Sold May 16, 2025

  17 Fenwood Dr, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $286/SF
  • 85 Days On Market

  Current Estimated Value $515,714

  Last Listing Agent Shannon Tully McGrath Realty Inc

  17 Fenwood Dr, Pawling, NY 12564
• 

  $645,000 Sold Jun 13, 2025

  32 Elm St, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1880

  Last Sold Summary

  • 3% Above List Price
  • $339/SF
  • 20 Days On Market

  Current Estimated Value $565,763

  Last Listing Agent Patrycja Warda Corcoran Country Living

  32 Elm St, Pawling, NY 12564
• 

  $975,000 Sold Apr 07, 2025

  11 Birch Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 3.5 Baths
  • 4,615 Sq Ft
  • Built 2000

  Last Sold Summary

  • $211/SF
  • 21 Days On Market

  Current Estimated Value $1,004,933

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  11 Birch Hill Rd, Pawling, NY 12564
• 

  $376,500 Sold Jun 18, 2025

  18 Evergreen Way, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 1,427 Sq Ft
  • Built 1997

  Last Sold Summary

  • 2% Above List Price
  • $264/SF
  • 13 Days On Market

  Current Estimated Value $383,147

  Last Listing Agent Vicki Reinach BHHS Hudson Valley Properties

  18 Evergreen Way, Pawling, NY 12564
• 

  $949,900 Sold May 02, 2025

  14 Little Pond Rd, Pawling, NY 12564

  • 4 Beds
  • 4.5 Baths
  • 3,798 Sq Ft
  • Built 2000

  Last Sold Summary

  • $250/SF
  • 6 Days On Market

  Current Estimated Value $959,156

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  14 Little Pond Rd, Pawling, NY 12564
• 

  $355,000 Sold Apr 08, 2025

  26 Taber Knolls Dr, Pawling, NY 12564

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Below List Price
  • $493/SF
  • 82 Days On Market

  Current Estimated Value $346,556

  Last Listing Agent Reid McGrath McGrath Realty Inc

  26 Taber Knolls Dr, Pawling, NY 12564
• 

  $345,000 Sold Jul 09, 2025

  88 Lakeview Dr, Pawling, NY 12564

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Above List Price
  • $383/SF
  • 26 Days On Market

  Current Estimated Value $340,556

  Last Listing Agent Martha Woodhouse Howard Hanna Rand Realty

  88 Lakeview Dr, Pawling, NY 12564
• 

  $674,900 Sold May 21, 2025

  24 Sheridan Dr, Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 2,876 Sq Ft
  • Built 1930

  Last Sold Summary

  • $235/SF
  • 134 Days On Market

  Last Listing Agent John Gabriel Jr KW MidHudson

  24 Sheridan Dr, Pawling, NY 12564
• 

  $240,000 Sold Nov 12, 2025

  51 Kirby Hill Rd, Pawling, NY 12564

  • Land
  • 5.36 Acres
  • $44,776 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 80 Days On Market

  Last Listing Agent Donna Kennedy Compass Greater NY, LLC

  51 Kirby Hill Rd, Pawling, NY 12564
• 

  $2,700,000 Sold Jan 10, 2026

  30 Dewey Ln, Pawling, NY 12564

  • 6 Beds
  • 6 Baths
  • 6,460 Sq Ft
  • Built 1860

  Last Sold Summary

  • 28% Below List Price
  • $418/SF
  • 146 Days On Market

  Current Estimated Value $1,957,057

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  30 Dewey Ln, Pawling, NY 12564
• 

  $660,000 Sold Jan 16, 2026

  29 Cunningham Ln, Pawling, NY 12564

  • 4 Beds
  • 5 Baths
  • 4,199 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $157/SF
  • 72 Days On Market

  Current Estimated Value $690,071

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  29 Cunningham Ln, Pawling, NY 12564
• 

  $1,400,000 Sold Sep 04, 2025

  21 Brady Brook Farm Rd, Pawling, NY 12564

  • 4 Beds
  • 3.5 Baths
  • 4,683 Sq Ft
  • Built 2003

  Last Sold Summary

  • 17% Below List Price
  • $299/SF
  • 139 Days On Market

  Current Estimated Value $1,398,539

  Last Listing Agent Brian McGrath McGrath Realty Inc

  21 Brady Brook Farm Rd, Pawling, NY 12564
• 

  $422,000 Sold Apr 07, 2025

  39 Nathan Pierce Ct, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Above List Price
  • $264/SF
  • 30 Days On Market

  Current Estimated Value $433,333

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  39 Nathan Pierce Ct, Pawling, NY 12564
• 

  $315,000 Sold Aug 05, 2025

  24 Timberline Trail, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 1997

  Last Sold Summary

  • 10% Below List Price
  • $148/SF
  • 51 Days On Market

  Current Estimated Value $344,828

  Last Listing Agent Vincent Reda Keller Williams Realty

  24 Timberline Trail, Pawling, NY 12564
• 

  $155,000 Sold Feb 12, 2026

  14 Akindale Rd, Pawling, NY 12564

  • Land
  • 8.44 Acres
  • $18,365 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 290 Days On Market

  Current Estimated Value $945,000

  Last Listing Agent Kathryn McCoach Houlihan Lawrence Inc.

  14 Akindale Rd, Pawling, NY 12564
• 

  $400,000 Sold Nov 21, 2025

  96 Lakeview Dr, Pawling, NY 12564

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Below List Price
  • $247/SF
  • 41 Days On Market

  Current Estimated Value $416,282

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  96 Lakeview Dr, Pawling, NY 12564
• 

  $229,000 Sold Jan 06, 2026

  Lot 18 Cox Rd, Pawling, NY 12564

  • Land
  • 7.02 Acres
  • $32,621 per Acre

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Shannon Tully McGrath Realty Inc

  Lot 18 Cox Rd, Pawling, NY 12564
• 

  $575,000 Sold Nov 24, 2025

  26 Frenchmans Ln, Pawling, NY 12564

  • 3 Beds
  • 1.5 Baths
  • 1,518 Sq Ft
  • Built 1970

  Last Sold Summary

  • 21% Above List Price
  • $379/SF
  • 53 Days On Market

  Current Estimated Value $550,608

  Last Listing Agent Ryan Arket Compass Greater NY, LLC

  26 Frenchmans Ln, Pawling, NY 12564
• 

  $607,000 Sold May 16, 2025

  32 Gristmill Ln, Pawling, NY 12564

  • 5 Beds
  • 4 Baths
  • 3,732 Sq Ft
  • Built 1967

  Last Sold Summary

  • 12% Below List Price
  • $163/SF
  • 235 Days On Market

  Current Estimated Value $655,086

  Last Listing Agent Carol Aprile

  32 Gristmill Ln, Pawling, NY 12564
• 

  $545,000 Sold Feb 03, 2026

  36 Byrds Hill Rd, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 1,820 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Below List Price
  • $299/SF
  • 28 Days On Market

  Current Estimated Value $551,451

  Last Listing Agent Regan Andrews Coldwell Banker Realty

  36 Byrds Hill Rd, Pawling, NY 12564
• 

  $560,000 Sold Oct 06, 2025

  37 Baxter Rd, Pawling, NY 12564

  • 3 Beds
  • 3.5 Baths
  • 2,616 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $214/SF
  • 50 Days On Market

  Current Estimated Value $575,257

  Last Listing Agent Matt Rose Keller Williams Prestige Prop

  37 Baxter Rd, Pawling, NY 12564
• 

  $697,500 Sold Jan 24, 2026

  5 Perri Ln, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 2,796 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $249/SF
  • 68 Days On Market

  Current Estimated Value $709,133

  Last Listing Agent Kristine Hansmann Jefferson Valley Realty

  5 Perri Ln, Pawling, NY 12564
• 

  $430,000 Sold Aug 01, 2025

  38 Old Route 55, Pawling, NY 12564

  • 4 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Below List Price
  • $267/SF
  • 126 Days On Market

  Current Estimated Value $470,157

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  38 Old Route 55, Pawling, NY 12564
• 

  $688,000 Sold Nov 24, 2025

  12 W Wind Rd, Pawling, NY 12564

  • 4 Beds
  • 4.5 Baths
  • 2,920 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $236/SF
  • 146 Days On Market

  Current Estimated Value $689,626

  Last Listing Agent Doris Jean William Raveis Real Estate

  12 W Wind Rd, Pawling, NY 12564
• 

  $810,000 Sold Dec 29, 2025

  48 David Ln, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Built 1987

  Last Sold Summary

  • 17% Above List Price
  • $453/SF
  • 23 Days On Market

  Current Estimated Value $716,000

  Last Listing Agent Claudia Dizenzo Hudson River Line Realty

  48 David Ln, Pawling, NY 12564
• 

  $444,000 Sold Dec 09, 2025

  27 Washington Ct, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 2,072 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $214/SF
  • 33 Days On Market

  Current Estimated Value $445,611

  Last Listing Agent Shannon Tully McGrath Realty Inc

  27 Washington Ct, Pawling, NY 12564

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