Pawling, NY Homes

• 

  $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
• 

  Est $953,846 Not Listed For Sale

  235 N Quaker Hill Rd, Pawling, NY 12564

  • 5 Beds
  • 2.5 Baths
  • 3,216 Sq Ft
  • Built 1928

  235 N Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 6% Above List Price
  • $280/SF
  • 71 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Regan Andrews Coldwell Banker Realty
• 

  

  

  /11

  $125,000

  • Land
  • 0.31 Acre
  • $403,226 per Acre

  3 Pine Dr, Pawling, NY 12564

  This property offers endless possibilities, whether for development, investment, or creating a personalized mobile home environment. Key features include: Expansive Lot: 13,500 sq ft for development, investment, or personal use.Prime Location: Close to town with shops, dining, and community events.Transportation Access: Near major routes and public transit (Dover Plains Metro North

  Brandon Doswell-Stephens Silverside Realty LLC

  3 Pine Dr, 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 $710,808

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  29 Cunningham Ln, Pawling, NY 12564
• 

  Est $826,375 Not Listed For Sale

  206 N Quaker Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 3.5 Baths
  • 3,287 Sq Ft
  • Built 1979

  206 N Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 4% Above List Price
  • $242/SF
  • 58 Days On Market

  Last Sold Price $795,000

  Last Listing Agent Shannon Tully McGrath Realty Inc
• 

  

  /3

  $149,900

  • Land
  • 4.21 Acres
  • $35,606 per Acre

  0 South Rd Unit KEY853088, Pawling, NY 12531

  Beautiful 4.21-acre lot in Pawling, NY presents a unique opportunity to build your dream home. This secluded property offers the ideal blend of privacy and convenience, situated just minutes from the charming Village of Pawling, Metro-North train station, restaurants, shopping, and all the amenities the historic Hudson Valley has to offer. Only three miles off I-84. Perfect for a year-round

  Michael Knecht Howard Hanna Rand Realty

  0 South Rd Unit KEY853088, Pawling, NY 12531
• 

  $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 $1,381,804

  Last Listing Agent Brian McGrath McGrath Realty Inc

  21 Brady Brook Farm Rd, Pawling, NY 12564
• 

  Est $672,003 Not Listed For Sale

  77 N Quaker Hill Rd, Pawling, NY 12564

  • 5 Beds
  • 2.5 Baths
  • 2,314 Sq Ft
  • Built 1920

  77 N Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 27% Above List Price
  • $229/SF
  • 49 Days On Market

  Last Sold Price $530,000

  Last Listing Agent Shannon Tully McGrath Realty Inc
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  /3

  $189,000

  • Land
  • 11.4 Acres
  • $16,579 per Acre

  0 Kirby Hill Rd, Pawling, NY 12564

  Great 11 acre BOHA property in Quaker Hill area of Pawling. Great views. Located quiet area next to historic library (not active. Shown as museum in warmer weather). Fantastic getaway area or permanent dream house.

  Richard Castro Howard Hanna Rand Realty

  0 Kirby Hill 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 $431,947

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  39 Nathan Pierce Ct, Pawling, NY 12564
• 

  Est $487,880 Not Listed For Sale

  25 Frenchmans Ln, Pawling, NY 12564

  • 3 Beds
  • 1 Bath
  • 1,286 Sq Ft
  • Built 1971

  25 Frenchmans Ln, Pawling, NY 12564

  Last Sold Summary

  • 13% Above List Price
  • $334/SF
  • 104 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate
• 

  

  /14

  $345,000

  • 2 Beds
  • 2.5 Baths
  • 1,567 Sq Ft

  1 Cushing Green N, Pawling, NY 12564

  This great 2 bedroom 2.5 bath townhome is a must see. Many great amenities including attached garage, formal dining room, fireplace, rear deck and more. This is a Fannie Mae HomePath property.

  Matthew Cave Hudson Property Services, LLC

  1 Cushing Green N, 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 $353,188

  Last Listing Agent Vincent Reda Keller Williams Realty

  24 Timberline Trail, Pawling, NY 12564
• 

  Est $500,213 Not Listed For Sale

  19 San Souci Dr, Pawling, NY 12564

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft
  • Built 1958

  19 San Souci Dr, Pawling, NY 12564

  Last Sold Summary

  • 23% Above List Price
  • $257/SF
  • 40 Days On Market

  Last Sold Price $407,000

  Last Listing Agent Claudia Jiskra McGrath Realty Inc
• 

  

  /29

  $705,000

  • 4 Beds
  • 3 Baths
  • 3,888 Sq Ft

  12 Rebecca Dr, Pawling, NY 12564

  Surrounded by the natural beauty of the Hudson Valley region, this Multi-Family home benefits from a private environment that outdoor enthusiasts will find irresistible. This property's location offers convenient access to the Lakeside Park Disc Golf Course, the nearby Appalachian Trail which provides endless hiking opportunities for nature lovers and the Metro-North Railroad being about a 5

  Kevin Sanabria eRealty Advisors, Inc

  12 Rebecca Dr, 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 $950,333

  Last Listing Agent Kathryn McCoach Houlihan Lawrence Inc.

  14 Akindale Rd, Pawling, NY 12564
• 

  Est $545,404 Not Listed For Sale

  17 San Souci Dr, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 2,324 Sq Ft
  • Built 1960

  17 San Souci Dr, Pawling, NY 12564

  Last Sold Summary

  • 4% Above List Price
  • $226/SF
  • 39 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Celeste Pasciolla Keller Williams Realty Partner
• 

  

  /46

  $39,000,000

  • 9 Beds
  • 15 Baths
  • 55,000 Sq Ft

  104 N Garden Dr, Pawling, NY 12564

  Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it

  Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

  104 N Garden Dr, 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
• 

  Est $1,029,077 Not Listed For Sale

  37 San Souci Dr, Pawling, NY 12564

  • 6 Beds
  • 4 Baths
  • 3,660 Sq Ft
  • Built 1981

  37 San Souci Dr, Pawling, NY 12564

  Last Sold Summary

  • 3% Above List Price
  • $273/SF
  • 27 Days On Market

  Last Sold Price $999,000

  Last Listing Agent Colleen McGrath McGrath Realty Inc
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  /49

  $425,000

  • 2 Beds
  • 2.5 Baths
  • 1,567 Sq Ft

  13 Cushing Green S, Pawling, NY 12564

  A rare find and an incredible opportunity awaits in Squire Green with this two-story end-unit townhome featuring the highly sought-after attached garage. Townhomes are seldom available in the Squire Green section of the Deerfield Ponds community, and end units are even more uncommon, making this offering especially desirable. Steps inside reveal a spacious entry foyer leading to an updated

  Claudia Jiskra McGrath Realty Inc

  13 Cushing Green S, 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
• 

  Est $466,438 Not Listed For Sale

  9 San Souci Dr, Pawling, NY 12564

  • 3 Beds
  • 1 Bath
  • 1,166 Sq Ft
  • Built 1960

  9 San Souci Dr, Pawling, NY 12564

  Last Sold Summary

  • 5% Above List Price
  • $382/SF
  • 150 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Patricia Ricciuti ERA Insite Realty Services
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  /41

  $595,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,254 Sq Ft

  79 W Main St, Pawling, NY 12564

  One of the prettiest homes you will see! Lovingly maintained home has all the original character and charm yet offers desired modern updates. Truly park-like property features a babbling brook, stone walls and perennial gardens. Special interior features throughout the home include solid hardwood floors, vintage doors with glass doorknobs, original trim work, all new windows, central air. A

  Lisa Liffland McGrath Realty Inc

  79 W Main St, 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
• 

  Est $635,367 Not Listed For Sale

  48 Poppys Ln, Pawling, NY 12564

  • 3 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • Built 1986

  48 Poppys Ln, Pawling, NY 12564

  Last Sold Summary

  • 19% Above List Price
  • $214/SF
  • 150 Days On Market

  Last Sold Price $535,000

  Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc
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  /37

  $14,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,942 Sq Ft

  15 Kirby Hill Rd, Pawling, NY 12564

  Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct

  Brian McGrath McGrath Realty Inc

  15 Kirby Hill Rd, 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 $651,101

  Last Listing Agent Carol Aprile

  32 Gristmill Ln, Pawling, NY 12564
• 

  Est $338,290 Not Listed For Sale

  24 Spruce St, Pawling, NY 12564

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

  24 Spruce St, Pawling, NY 12564

  Last Sold Summary

  • 30% Above List Price
  • $184/SF
  • 264 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Joann Perna Guardian Realty Center, LLC
• 

  

  /27

  $509,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft

  66 Fairway Dr, Pawling, NY 12564

  Experience the charm of village living in historic, picturesque Pawling. This convenient .37-acre corner lot offers sidewalk access to local shops, restaurants, the Metro-North Harlem Line station, the library, The Dutcher Golf Course, and Lakeside Park. Enjoy year-round community activities on the Village Green, including the popular, seasonal Farmer’s Market.This well-maintained 3-bedroom,

  Carol Aprile

  66 Fairway Dr, 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 $545,112

  Last Listing Agent Regan Andrews Coldwell Banker Realty

  36 Byrds Hill Rd, Pawling, NY 12564
• 

  Est $378,497 Not Listed For Sale

  13 Juniper Ln, Pawling, NY 12564

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

  13 Juniper Ln, Pawling, NY 12564

  Last Sold Summary

  • 5% Above List Price
  • $255/SF
  • 65 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Nanci Kubik Houlihan Lawrence Inc.
• 

  

  /35

  $399,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  16 Townsend Blvd, Pawling, NY 12564

  Welcome to 16 Townsend Blvd, a lovely brick home set in the heart of picturesque Pawling, NY. On the end of a quiet, dead-end road, within walking distance of the historic Village of Pawling, this charming domicile will not last long. The Village of Pawling is home to the oldest public-golf course in the United States, George Washington's headquarters during the Revolutionary War, ample eateries

  Reid McGrath McGrath Realty Inc

  16 Townsend Blvd, 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 $572,857

  Last Listing Agent Matt Rose Keller Williams Prestige Prop

  37 Baxter Rd, Pawling, NY 12564
• 

  Est $412,598 Not Listed For Sale

  14 Spruce St, Pawling, NY 12564

  • 2 Beds
  • 3.5 Baths
  • 2,109 Sq Ft
  • Built 1993

  14 Spruce St, Pawling, NY 12564

  Last Sold Summary

  • 16% Above List Price
  • $168/SF
  • 27 Days On Market

  Last Sold Price $355,000

  Last Listing Agent Joseph Polewaski Houlihan Lawrence Inc.
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  /26

  $299,500

  • 3 Beds
  • 1 Bath
  • 1,653 Sq Ft

  14 Old Route 55, Pawling, NY 12564

  Welcome HOME to this charming and historic 3-bedroom, 1-bath residence located in the heart of Pawling in the Pawling School District. This beautifully updated antique home offers the perfect blend of timeless character and modern convenience. Recent updates include brand-new carpeting, refinished hardwood floors, fresh paint, updated fixtures, an updated bathroom, and a renovated kitchen with

  Ronald Green KW MidHudson

  14 Old Route 55, 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 $724,953

  Last Listing Agent Kristine Hansmann Jefferson Valley Realty

  5 Perri Ln, Pawling, NY 12564
• 

  Est $391,184 Not Listed For Sale

  9 Juniper Ln, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 1988

  9 Juniper Ln, Pawling, NY 12564

  Last Sold Summary

  • 13% Above List Price
  • $163/SF
  • 9 Days On Market

  Last Sold Price $347,000

  Last Listing Agent Regan Andrews Coldwell Banker Realty
• 

  $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 $461,255

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  38 Old Route 55, Pawling, NY 12564
• 

  Est $413,901 Not Listed For Sale

  5 Hemlock Cir, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 2,113 Sq Ft
  • Built 1988

  5 Hemlock Cir, Pawling, NY 12564

  Last Sold Summary

  • 13% Above List Price
  • $173/SF
  • 15 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Christine Ricci Keller Williams NY Realty

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