Pawling, NY Homes

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  $580,000 Pending

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

  10 Rebecca Dr, Pawling, NY 12564

  Nestled in the charming village of Pawling, this delightful house offers new owners the opportunity to create their dream home with a touch of personal flair. Situated on just over 2 acres, the property boasts 3 spacious bedrooms, 2 full bathrooms, and a convenient powder room.The large eat-in kitchen, illuminated by a skylight, provides abundant natural light and features sliders that open

  Maria Justo Howard Hanna Rand Realty

  10 Rebecca Dr, Pawling, NY 12564
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  $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 $346,593

  Last Listing Agent Martha Woodhouse Howard Hanna Rand Realty

  88 Lakeview Dr, Pawling, NY 12564
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  Est $649,134 Not Listed For Sale

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

  77 N Quaker Hill Rd, Pawling, NY 12564

  77 N Quaker Hill Rd, Pawling, NY 12564
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  $154,900

  • Land
  • 0.73 Acre
  • $212,192 per Acre

  0 Walnut St, Pawling, NY 12564

  Great lot in the Village of Pawling! *Board of Health Approval is NOT required because the house will be hooked up to municipal water and sewer! This .73-acre lot offers a lovely western view. Walk to the picturesque Village center with its quaint shops, bakeries, restaurants, library, post office, health care, so much more! Metro-North Train Station (Harlem Line) is located in the Village as

  Lisa Liffland McGrath Realty Inc

  0 Walnut St, Pawling, NY 12564
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  $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
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  Est $470,747 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,286 Sq Ft

  25 Frenchmans Ln, Pawling, NY 12564

  25 Frenchmans Ln, Pawling, NY 12564
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  $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
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  $485,000 Sold Jan 23, 2025

  94 David Ln, Pawling, NY 12564

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Above List Price
  • $415/SF
  • 42 Days On Market

  Current Estimated Value $520,239

  Last Listing Agent Shannon Tully McGrath Realty Inc

  94 David Ln, Pawling, NY 12564
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  Est $486,494 Not Listed For Sale

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

  19 San Souci Dr, Pawling, NY 12564

  19 San Souci Dr, Pawling, NY 12564
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  $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
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  $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
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  Est $560,874 Not Listed For Sale

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

  17 San Souci Dr, Pawling, NY 12564

  17 San Souci Dr, Pawling, NY 12564
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  $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
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  $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

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  30 Dewey Ln, Pawling, NY 12564
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  Est $462,917 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,166 Sq Ft

  9 San Souci Dr, Pawling, NY 12564

  9 San Souci Dr, Pawling, NY 12564
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  $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
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  $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 $1,421,912

  Last Listing Agent Brian McGrath McGrath Realty Inc

  21 Brady Brook Farm Rd, Pawling, NY 12564
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  Est $651,654 Not Listed For Sale

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

  48 Poppys Ln, Pawling, NY 12564

  48 Poppys Ln, Pawling, NY 12564
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  $479,900 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,467 Sq Ft

  2 Bridle Way, Pawling, NY 12564

  Welcome to 2 Bridle Way, a rare opportunity to own a spacious 3-bedroom, 3.5-bath Colonial in one of Pawling’s most desirable and well-kept communities. Built in 1992, this young home offers an impressive layout with generous room sizes, abundant natural light, and endless potential for the next owner to bring their vision to life. Located in a sought-after HOA neighborhood, residents enjoy the

  Arafat Ibrahim AI Realty Brokerage LLC

  2 Bridle Way, Pawling, NY 12564
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  $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 $430,214

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  39 Nathan Pierce Ct, Pawling, NY 12564
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  Est $345,189 Not Listed For Sale

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

  24 Spruce St, Pawling, NY 12564

  24 Spruce St, Pawling, NY 12564
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  $425,000 Open Sun 12AM - 2PM

  • 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
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  $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 $336,850

  Last Listing Agent Vincent Reda Keller Williams Realty

  24 Timberline Trail, Pawling, NY 12564
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  Est $386,110 Not Listed For Sale

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

  13 Juniper Ln, Pawling, NY 12564

  13 Juniper Ln, Pawling, NY 12564
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  $419,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  23 Union St, Pawling, NY 12564

  3 Bed | 2 Bath | Fully Electric | Walkable Village LocationTurnkey, updated, freshly painted, and full of charm—this 3-bedroom, 2-bath home is perfectly situated in the heart of Pawling Village. Whether you're a first-time buyer using FHA or VA financing, a downsizer, or simply seeking a low-maintenance, energy-efficient home, this property offers a flexible layout, thoughtful upgrades, and

  Brett David Miller K Fortuna Lighthouse Realty

  23 Union St, Pawling, NY 12564
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  $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

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  96 Lakeview Dr, Pawling, NY 12564
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  Est $402,508 Not Listed For Sale

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

  14 Spruce St, Pawling, NY 12564

  14 Spruce St, Pawling, NY 12564
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  /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
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  $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
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  Est $402,473 Not Listed For Sale

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

  9 Juniper Ln, Pawling, NY 12564

  9 Juniper Ln, Pawling, NY 12564
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  $650,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,640 Sq Ft

  85 Harmony Hill Rd, Pawling, NY 12564

  This charming fully remodeled, bright, and sunny ranch—featuring 3 bedrooms, 3 full bathrooms, and 2.90 acres of land. Prepare meals in the beautiful new kitchen, complete with custom cabinets, LG appliances, and quartz countertops. Relax in the family room beside the gorgeous stone fireplace. From there, step out onto the lovely wood deck and savor your morning coffee surrounded by

  Mary Craig Coldwell Banker Realty

  85 Harmony Hill Rd, Pawling, NY 12564
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  $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

  Last Listing Agent Ryan Arket Compass Greater NY, LLC

  26 Frenchmans Ln, Pawling, NY 12564
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  Est $395,036 Not Listed For Sale

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

  5 Hemlock Cir, Pawling, NY 12564

  5 Hemlock Cir, Pawling, NY 12564
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  $699,900 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,766 Sq Ft

  48 W Main St, Pawling, NY 12564

  The PERFECT location for a Weekend/Vacation home or Extended/Large Family. 19th Century Colonial/Farmhouse completely remodeled in 2025. Located in the highly desirable Hudson Valley village of Pawling, NY. The photos tell the story of the updates, but it is the LOCATION that is unbeatable! Imagine a brisk autumn morning, waking up in your oversized Primary Bedroom to the warm glow of the morning

  Christopher Filangeri BHHS Hudson Valley Properties

  48 W Main St, Pawling, NY 12564
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  $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 $655,791

  Last Listing Agent Carol Aprile

  32 Gristmill Ln, Pawling, NY 12564
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  Est $403,544 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,030 Sq Ft

  4 Aspen Ct, Pawling, NY 12564

  4 Aspen Ct, Pawling, NY 12564
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  $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 $578,920

  Last Listing Agent Matt Rose Keller Williams Prestige Prop

  37 Baxter Rd, Pawling, NY 12564
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  Est $385,967 Not Listed For Sale

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

  28 Evergreen Way, Pawling, NY 12564

  28 Evergreen Way, Pawling, NY 12564
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  $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 $460,871

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  38 Old Route 55, Pawling, NY 12564
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  Est $380,426 Not Listed For Sale

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

  7 Evergreen Way, Pawling, NY 12564

  7 Evergreen Way, Pawling, NY 12564

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