3,399

Pawling, NY Homes

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  • 14 Akindale Rd, 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 $369,820

    Last Listing Agent Kathryn McCoach Houlihan Lawrence Inc.

    14 Akindale Rd, Pawling, NY 12564
    • 206 N Quaker Hill Rd, Pawling, NY 12564

      Est $801,388 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

      • 1% Above List Price
      • $242/SF
      • 58 Days On Market

      Last Sold Price $795,000

      Last Listing Agent Shannon Tully McGrath Realty Inc

  • 0 South Rd Unit KEY853088, Pawling, NY 12531
    0 South Rd Unit KEY853088, Pawling, NY 12531
    0 South Rd Unit KEY853088, Pawling, NY 12531
    /4

    $151,000

    • Land
    • 4.21 Acres
    • $35,867 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
  • 96 Lakeview 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 $420,687

    Last Listing Agent Claudia Jiskra McGrath Realty Inc

    96 Lakeview Dr, Pawling, NY 12564
    • 77 N Quaker Hill Rd, Pawling, NY 12564

      Est $634,498 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

      • 20% Above List Price
      • $229/SF
      • 49 Days On Market

      Last Sold Price $530,000

      Last Listing Agent Shannon Tully McGrath Realty Inc

  • 0 Kirby Hill Rd, Pawling, NY 12564
    0 Kirby Hill Rd, Pawling, NY 12564
    0 Kirby Hill Rd, Pawling, NY 12564
    /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
  • Lot 18 Cox Rd, 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
    • 25 Frenchmans Ln, Pawling, NY 12564

      Est $479,409 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

      • 11% Above List Price
      • $334/SF
      • 104 Days On Market

      Last Sold Price $430,000

      Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  • 11 Cushing Green S, Pawling, NY 12564
    11 Cushing Green S, Pawling, NY 12564
    11 Cushing Green S, Pawling, NY 12564
    /34

    $375,000

    • 2 Beds
    • 2.5 Baths
    • 1,723 Sq Ft

    11 Cushing Green S, Pawling, NY 12564

    Welcome to Squire Green, a charming 2 bed, 2.5 bath townhome that’s move-in ready and full of potential. A versatile den offers the flexibility of a third bedroom, making this home a perfect fit whether you’re growing, downsizing, or simply need extra space.Enjoy the convenience of an attached garage and private driveway, plus ample guest parking. The community offers an in-ground pool,

    Taylor Cirillo Howard Hanna Rand Realty

    11 Cushing Green S, Pawling, NY 12564
  • 26 Frenchmans Ln, 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 $558,331

    Last Listing Agent Ryan Arket Compass Greater NY, LLC

    26 Frenchmans Ln, Pawling, NY 12564
    • 19 San Souci Dr, Pawling, NY 12564

      Est $475,677 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

      • 17% Above List Price
      • $257/SF
      • 40 Days On Market

      Last Sold Price $407,000

      Last Listing Agent Claudia Jiskra McGrath Realty Inc

  • 1 Cushing Green N, Pawling, NY 12564
    1 Cushing Green N, Pawling, NY 12564
    1 Cushing Green N, Pawling, NY 12564
    /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
  • 32 Gristmill 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 $706,240

    Last Listing Agent Carol Aprile

    32 Gristmill Ln, Pawling, NY 12564
    • 17 San Souci Dr, Pawling, NY 12564

      Est $562,707 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

      • 7% Above List Price
      • $226/SF
      • 39 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Celeste Pasciolla Keller Williams Realty Partner

  • 104 N Garden Dr, Pawling, NY 12564
    104 N Garden Dr, Pawling, NY 12564
    104 N Garden Dr, Pawling, NY 12564
    /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
  • 36 Byrds Hill Rd, 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 $548,252

    Last Listing Agent Regan Andrews Coldwell Banker Realty

    36 Byrds Hill Rd, Pawling, NY 12564
    • 37 San Souci Dr, Pawling, NY 12564

      Est $1,026,884 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

  • 13 Cushing Green S, Pawling, NY 12564
    13 Cushing Green S, Pawling, NY 12564
    13 Cushing Green S, Pawling, NY 12564
    /49

    $425,000 Pending

    • 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
  • 37 Baxter 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 $581,318

    Last Listing Agent Matt Rose Keller Williams Prestige Prop

    37 Baxter Rd, Pawling, NY 12564
    • 9 San Souci Dr, Pawling, NY 12564

      Est $453,908 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

      • 2% Above List Price
      • $382/SF
      • 150 Days On Market

      Last Sold Price $445,000

      Last Listing Agent Patricia Ricciuti ERA Insite Realty Services

  • 15 Kirby Hill Rd, Pawling, NY 12564
    15 Kirby Hill Rd, Pawling, NY 12564
    15 Kirby Hill Rd, Pawling, NY 12564
    /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
  • 5 Perri Ln, 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 $700,032

    Last Listing Agent Kristine Hansmann Jefferson Valley Realty

    5 Perri Ln, Pawling, NY 12564
    • 48 Poppys Ln, Pawling, NY 12564

      Est $622,457 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

      • 16% Above List Price
      • $214/SF
      • 150 Days On Market

      Last Sold Price $535,000

      Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

  • 0 Prospect St, Pawling, NY 12564
    0 Prospect St, Pawling, NY 12564
    0 Prospect St, Pawling, NY 12564
    /10

    $135,000

    • Land
    • 0.43 Acre
    • $313,953 per Acre

    0 Prospect St, Pawling, NY 12564

    First time on market! BOHA not required - Town Water and Sewer!! Majority of the property is cleared. Great location! Short drive to Metro-North, Pawling schools, Lakeside Park, Dutcher Golf Course, grocery stores, great restaurants and shops.

    Lisa Liffland McGrath Realty Inc

    0 Prospect St, Pawling, NY 12564
  • 38 Old Route 55, 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 $467,086

    Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

    38 Old Route 55, Pawling, NY 12564
    • 24 Spruce St, Pawling, NY 12564

      Est $335,610 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

      • 29% Above List Price
      • $184/SF
      • 264 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Joann Perna Guardian Realty Center, LLC

  • 12 W Wind Rd, 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 $696,225

    Last Listing Agent Doris Jean William Raveis Real Estate

    12 W Wind Rd, Pawling, NY 12564
    • 13 Juniper Ln, Pawling, NY 12564

      Est $378,713 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.

  • 48 David Ln, 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 $739,000

    Last Listing Agent Claudia Dizenzo Hudson River Line Realty

    48 David Ln, Pawling, NY 12564
    • 14 Spruce St, Pawling, NY 12564

      Est $402,735 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

      • 13% Above List Price
      • $168/SF
      • 27 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Joseph Polewaski Houlihan Lawrence Inc.

  • 27 Washington Ct, 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 $444,198

    Last Listing Agent Shannon Tully McGrath Realty Inc

    27 Washington Ct, Pawling, NY 12564
    • 4 Juniper Ln, Pawling, NY 12564

      Est $387,908 Not Listed For Sale

      4 Juniper Ln, Pawling, NY 12564

      • 2 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 1988
      4 Juniper Ln, Pawling, NY 12564

      Last Sold Summary

      • 6% Above List Price
      • $174/SF
      • 20 Days On Market

      Last Sold Price $365,000

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

  • 10 Rebecca Dr, Pawling, NY 12564

    $540,000 Sold Jan 31, 2026

    10 Rebecca Dr, Pawling, NY 12564

    • 3 Beds
    • 2.5 Baths
    • 1,893 Sq Ft
    • Built 1984

    Last Sold Summary

    • 7% Below List Price
    • $285/SF
    • 64 Days On Market

    Current Estimated Value $549,073

    Last Listing Agent Maria Justo Howard Hanna Rand Realty

    10 Rebecca Dr, Pawling, NY 12564
    • 5 Hemlock Cir, Pawling, NY 12564

      Est $396,982 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

      • 9% Above List Price
      • $173/SF
      • 15 Days On Market

      Last Sold Price $365,000

      Last Listing Agent Christine Ricci Keller Williams NY Realty

  • 12 Berry Ln, Pawling, NY 12564

    $820,000 Sold Jul 28, 2025

    12 Berry Ln, Pawling, NY 12564

    • 4 Beds
    • 3 Baths
    • 3,304 Sq Ft
    • Built 1965

    Last Sold Summary

    • 6% Below List Price
    • $248/SF
    • 52 Days On Market

    Current Estimated Value $823,774

    Last Listing Agent Brian McGrath McGrath Realty Inc

    12 Berry Ln, Pawling, NY 12564
    • 4 Aspen Ct, Pawling, NY 12564

      Est $394,662 Not Listed For Sale

      4 Aspen Ct, Pawling, NY 12564

      • 2 Beds
      • 2.5 Baths
      • 2,030 Sq Ft
      • Built 1995
      4 Aspen Ct, Pawling, NY 12564

      Last Sold Summary

      • 13% Above List Price
      • $172/SF
      • 58 Days On Market

      Last Sold Price $349,000

      Last Listing Agent Jeffrey Green Compass Greater NY, LLC

  • 54 Burgess Rd, Pawling, NY 12564

    $1,375,000 Sold May 13, 2025

    54 Burgess Rd, Pawling, NY 12564

    • 4 Beds
    • 3.5 Baths
    • 2,910 Sq Ft
    • Built 1926

    Last Sold Summary

    • 1% Below List Price
    • $473/SF
    • 60 Days On Market

    Current Estimated Value $1,396,603

    Last Listing Agent Jake Garay Serhant LLC

    54 Burgess Rd, Pawling, NY 12564
    • 28 Evergreen Way, Pawling, NY 12564

      Est $378,662 Not Listed For Sale

      28 Evergreen Way, Pawling, NY 12564

      • 2 Beds
      • 2.5 Baths
      • 1,413 Sq Ft
      • Built 1997
      28 Evergreen Way, Pawling, NY 12564

      Last Sold Summary

      • 15% Above List Price
      • $234/SF
      • 67 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Monica Marsich Progeny Realty Inc

  • 26 Fenwood Dr, Pawling, NY 12564

    $430,000 Sold Jul 22, 2025

    26 Fenwood Dr, Pawling, NY 12564

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • Built 1963

    Last Sold Summary

    • 7% Below List Price
    • $287/SF
    • 177 Days On Market

    Current Estimated Value $438,947

    Last Listing Agent Vicki Reinach BHHS Hudson Valley Properties

    26 Fenwood Dr, Pawling, NY 12564
    • 7 Evergreen Way, Pawling, NY 12564

      Est $370,632 Not Listed For Sale

      7 Evergreen Way, Pawling, NY 12564

      • 2 Beds
      • 2.5 Baths
      • 1,413 Sq Ft
      • Built 1998
      7 Evergreen Way, Pawling, NY 12564

      Last Sold Summary

      • 14% Above List Price
      • $230/SF
      • 37 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Colleen McGrath McGrath Realty Inc

Showing Results 81 - 120, Page 3 of 18

New York Dutchess County Pawling

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