Pawling, NY Homes

• 

  $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 $361,856

  Last Listing Agent Vincent Reda Keller Williams Realty

  24 Timberline Trail, Pawling, NY 12564
• 

  Est $493,959

  Not Listed For Sale

  2 Mallow Ct, Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1984

  2 Mallow Ct, Pawling, NY 12564

  Last Sold Summary

  • 19 Days On Market
• 

  

  

  /38

  $385,000

  $10K PRICE INCREASE Pending

  • 2 Beds
  • 2 Baths
  • 1,639 Sq Ft

  16 Juniper Ln, Pawling, NY 12564

  Welcome to Cedar Valley! This bright corner unit offers the perfect blend of comfort and convenience, with potential for easy one-floor living. The main level features both bedrooms, while a spacious loft upstairs provides flexible bonus space—ideal for a home office, gym, guest area, or additional living space.Enjoy the ease of just two steps from the parking lot to your front door, with two

  Vanessa Longo Briante Realty Group, LLC

  16 Juniper Ln, 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 $439,964

  Last Listing Agent Kathryn McCoach Houlihan Lawrence Inc.

  14 Akindale Rd, Pawling, NY 12564
• 

  Est $956,556

  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

  • 71 Days On Market
• 

  

  /22

  $599,900

  Pending

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

  85 Harmony Hill Rd, Pawling, NY 12564

  **Highest & Best 7pm Monday 4/27.** Set on nearly three private acres just minutes from Metro-North, this fully renovated country retreat delivers the space, privacy, and lifestyle buyers are searching for right now. Bright, open, and thoughtfully updated, the home is designed for both everyday living and easy entertaining. The kitchen features custom cabinetry, quartz countertops, and stainless

  Anna Proctor Compass Greater NY, LLC

  85 Harmony Hill 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 $425,147

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  96 Lakeview Dr, Pawling, NY 12564
• 

  Est $785,369

  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

  • 58 Days On Market
• 

  

  /33

  $495,000

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  17 Townsend Blvd, Pawling, NY 12564

  Fall in Love with this Charming Mediterranean Style Garden Home. A Private Oasis Hidden Away and Nestled among a Grove of Mature Trees. Follow meandering paths that lead to Splashes of Color from the Cultivated Perennial Gardens of a Lifetime and a Gentle Woodland Stream. This Home is Sparkling Clean, Freshly Polished, Newly Painted, Move-In Ready and awaits your Arrival. Tucked in at the end of

  Martha Woodhouse Howard Hanna Rand Realty

  17 Townsend Blvd, 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 $677,758

  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

  • 49 Days On Market
• 

  

  /10

  $999,000

  • Land
  • 68.39 Acres
  • $14,607 per Acre

  0 Old Quaker Hill Rd Unit KEY986977, Pawling, NY 12564

  You can stop looking now because this is the piece of land you've been dreaming of. Over 68 acres atop Pawling's prestigious Quaker Hill. Approximately 20 acres clear and level with the remainder old woods crisscrossed by multiple streams and revolutionary era or older trails. In the heart of Quaker Hill's equestrian enclave, your views are the neighboring mountains and large estates. The short

  Brian McGrath McGrath Realty Inc

  0 Old Quaker Hill Rd Unit KEY986977, Pawling, NY 12564
• 

  $350,000

  Sold May 18, 2026

  21 Kings Way, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,960 Sq Ft
  • Built 2000

  Last Sold Summary

  • 14% Below List Price
  • $179/SF
  • 71 Days On Market

  Current Estimated Value $372,951

  Last Listing Agent Bopaul Sookdeo YourHomeSold Guaranteed Realty

  21 Kings Way, Pawling, NY 12564
• 

  Est $487,713

  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

  • 104 Days On Market
• 

  

  /7

  $135,000

  • Land
  • 31,798 Sq Ft
  • $184,932 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
• 

  $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 $565,668

  Last Listing Agent Ryan Arket Compass Greater NY, LLC

  26 Frenchmans Ln, Pawling, NY 12564
• 

  Est $495,416

  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

  • 40 Days On Market
• 

  

  /49

  $460,000

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  12 John Kane Ct, Pawling, NY 12564

  It’s the townhome in Deerfield Ponds you have been waiting for. The most sought-after layout is finally available, featuring a primary bedroom on the first floor along with the added bonus of a detached garage. Offering 3 levels, 3 bedrooms, 2.5 baths, and 1,920 finished square feet across the first and second floors, plus an additional 1,080 square feet of unfinished basement space, this home

  Claudia Jiskra McGrath Realty Inc

  12 John Kane Ct, 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 $559,837

  Last Listing Agent Regan Andrews Coldwell Banker Realty

  36 Byrds Hill Rd, Pawling, NY 12564
• 

  Est $575,644

  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

  • 39 Days On Market
• 

  

  /3

  $189,000

  Pending

  • 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
• 

  $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 $610,034

  Last Listing Agent Matt Rose Keller Williams Prestige Prop

  37 Baxter Rd, Pawling, NY 12564
• 

  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

  • 27 Days On Market
• 

  

  /34

  $375,000

  Pending

  • 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
• 

  $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 $708,988

  Last Listing Agent Kristine Hansmann Jefferson Valley Realty

  5 Perri Ln, Pawling, NY 12564
• 

  Est $479,015

  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

  • 150 Days On Market
• 

  

  /48

  $1,799,000

  Open Sun 1PM - 4PM

  • 5 Beds
  • 5.5 Baths
  • 5,390 Sq Ft

  41 and 43 Meeting House Rd, Pawling, NY 12564

  Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious

  Richard Esman Douglas Elliman Real Estate

  41 and 43 Meeting House Rd, 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 $529,476

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  38 Old Route 55, Pawling, NY 12564
• 

  Est $652,653

  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

  • 150 Days On Market
• 

  

  /56

  $3,100,000

  • 3 Beds
  • 3 Baths
  • 3,600 Sq Ft

  809 N Quaker Hill Rd, Pawling, NY 12564

  Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property's idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling

  Raj Kumar Four Seasons Sotheby's Int.

  809 N Quaker Hill 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 $711,275

  Last Listing Agent Doris Jean William Raveis Real Estate

  12 W Wind Rd, Pawling, NY 12564
• 

  Est $347,004

  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

  • 264 Days On Market
• 

  

  /13

  $335,000

  $10K PRICE DROP

  • 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
• 

  $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 $792,000

  Last Listing Agent Claudia Dizenzo Hudson River Line Realty

  48 David Ln, Pawling, NY 12564
• 

  Est $370,993

  Not Listed For Sale

  34 Spruce St, Pawling, NY 12564

  • 2 Beds
  • 2 Baths
  • 1,639 Sq Ft
  • Built 1987

  34 Spruce St, Pawling, NY 12564

  Last Sold Summary

  • 14 Days On Market
• 

  

  /9

  $249,000

  • Land
  • 5.5 Acres
  • $45,273 per Acre

  0 Marble Ln, Pawling, NY 12564

  Nestled in the scenic Hudson Valley and just 75 minutes from New York City, this exceptional residential parcel offers a rare blend of luxury, privacy, and convenience. Ideally located minutes from the charming village of Pawling and Sherman, the property provides easy access to the Metro-North Railroad, boutique shopping, fine dining, farmers markets, hiking trails, historic landmarks, major

  Stacey Cronin Houlihan Lawrence Inc.

  0 Marble 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 $445,312

  Last Listing Agent Shannon Tully McGrath Realty Inc

  27 Washington Ct, Pawling, NY 12564
• 

  Est $368,188

  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

  • 65 Days On Market
• 

  

  /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
• 

  $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 $551,733

  Last Listing Agent Maria Justo Howard Hanna Rand Realty

  10 Rebecca Dr, Pawling, NY 12564

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