Pawling, NY Homes

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  $598,500

  • 4 Beds
  • 4.5 Baths
  • 2,361 Sq Ft

  126 Old Route 55, Pawling, NY 12564

  Back on the market, the deal fell through from the buyer side. 9/17/2025 This house is owned by a church and in New York a sale has to be approved by the Attorney Generals office which can take up to six months. This can work to your benefit depending on your own timeline. This can also be set up a s a short term rental as well while waiting for the approvals WITH PORTION OF RENT GOING TOWARDS

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 576-1665

  126 Old Route 55, Pawling, NY 12564
• Explore Pawling

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  /4

  $2,650 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  215-217 Old Route 22, Pawling, NY 12564

  DUE TO UNFORESEEN WEATHER ISSUES, CURRENT TENANT NEEDED A FEW MORE DAYS TO MOVE OUT. SHOWINGS ARE DELAYED UNTIL LATER THIS WEEK. THANK YOU FOR UNDERSTANDING. Wonderful Bucolic Setting! 2 BR + den - Lovely Cottage on a private estate. Private Garden. Convenient to all.

  Celeste Pasciolla Keller Williams Realty Partner

  215-217 Old Route 22, Pawling, NY 12564
• 

  $575,000 Sold Dec 22, 2025

  7 Glen Ct, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 2,318 Sq Ft
  • Built 1997

  Last Sold Summary

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

  Current Estimated Value $571,983

  Last Listing Agent Colleen McGrath McGrath Realty Inc

  7 Glen Ct, Pawling, NY 12564
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  Est $690,000 Not Listed For Sale

  135 S Quaker Hill Rd, Pawling, NY 12564

  • 2 Beds
  • 3.5 Baths
  • 2,836 Sq Ft
  • Built 1850

  135 S Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 22% Above List Price
  • $199/SF
  • 38 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Dominick DiFilippo Keller Williams Realty Partner
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  /23

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  26 Rodina Dr, Pawling, NY 12564

  Be the first to live in this stunning four bedroom, two and a half bath home nestled on a beautiful two and a half acre lot. This home is located on the border of Putnam and Duchess counties. Step onto the full length front porch and inside to a light, bright and airy interior boasting a modern open floor plan. Spacious entrance foyer with double coat closets and sleek iron railing staircase with

  

  Douglas Servello

  Home Sweet Home Properties

  (845) 599-8285

  26 Rodina Dr, Pawling, NY 12564
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  /16

  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 911 Sq Ft
  • Apartment for Rent

  5 Spring St Unit 5E, Pawling, NY 12564

  Charming completely rebuilt carriage house with 1 BR apartment upstairs. General foyer, stairs to landing & apartment. Spacious EIK, large living room, large bedroom, full bathroom w/tub & shower. Stack able washer & dryer. The kitchen has butcher block counters, stainless appliances including fridge, stove, dishwasher & microwave. Deep sunny windows, central air & heat pump, 900 square feet of

  Gillian Stewart Gillian Stewart Real Estate

  5 Spring St Unit 5E, Pawling, NY 12564
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  $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 $831,897

  Last Listing Agent Tom Consaga RE/MAX Ace Realty

  175 Old Quaker Hill Rd, Pawling, NY 12564
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  Not Listed For Sale

  9 Ravine Rd, Pawling, NY 12564

  9 Ravine Rd, Pawling, NY 12564

  Last Sold Summary

  • 1,323 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Shannon Tully McGrath Realty Inc
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  /22

  $1,350,000

  • Land
  • 3.9 Acres
  • $346,154 per Acre

  178 Charles Colman Blvd, Pawling, NY 12564

  Exclusive Mixed-Use Property in Pawling N.Y.! Incredible Investment or Business Opportunity offering a rare blend of Residence, Greenhouse, Floral Shop, & Nursery.This beautiful Sprawling estate boasts a Commercial c & Residential component? with a 2,500 sqft greenhouse fully-equipped floral shop with retail space There is Ample parking & easy accessibility for Commercial

  

  Vince Buccieri

  Today Realty Corp.

  (845) 280-5951

  178 Charles Colman Blvd, Pawling, NY 12564
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  $2,375 per month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  134 E Main St, Pawling, NY 12564

  Fully renovated spacious apartment in the Heart of Pawling Village. Everything you see is brand new. Lives like much more than a simple 1-bedroom apartment. Just Minutes to downtown and historic Main Street, this bright and charming unit holds the perfect balance of character and convenience. Situated on the first floor of a classic 1920s Cape Cod-style home, featuring a spacious layout with

  Giancarlo Pecora eXp Realty

  134 E Main St, Pawling, NY 12564
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  $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
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  Est $352,933 Not Listed For Sale

  7 Birch Ln, Holmes, NY 12531

  7 Birch Ln, Holmes, NY 12531

  Last Sold Summary

  • 2,615% Above List Price
  • 234 Days On Market

  Last Sold Price $13,000

  Last Listing Agent Pauline Angrisani Coldwell Banker Realty
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  $1,200,000

  • 5 Beds
  • 4 Baths
  • 4,248 Sq Ft

  64 S Quaker Hill Rd, Pawling, NY 12564

  Welcome to Country Living at Its Finest!Nestled on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential for those looking to restore a piece of history. A long, tree-lined driveway leads to this charming 4-bedroom, 4-bath home surrounded by open fields, mature trees, and peaceful country views. The property features a spacious 4-car garage with finished living space with

  

  Shannon Tully

  McGrath Realty Inc

  (845) 415-7723

  64 S Quaker Hill Rd, Pawling, NY 12564
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  /40

  $5,000 per month

  • 4 Beds
  • 3 Baths
  • 3,664 Sq Ft
  • House for Rent

  159 Old Quaker Hill Rd, Pawling, NY 12564

  Stunning views to the west can't be beat, this 10.83 acre Ranch style home with 4 bedrooms, 3 full bathrooms (2 en suite) has been completely renovated from top to bottom. There is a stunning chef's kitchen with Silestone counters, stainless appliances & views for days outside the picture window. There is a spectacular great room with wall to ceiling wraparound windows which absorb the view & the

  Gillian Stewart Gillian Stewart Real Estate

  159 Old Quaker Hill Rd, Pawling, NY 12564
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  $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
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  Est $620,029 Not Listed For Sale

  68 W Main St, Pawling, NY 12564

  • 7 Beds
  • 3 Baths
  • 3,400 Sq Ft
  • Built 1920

  68 W Main St, Pawling, NY 12564

  Last Sold Summary

  • 68% Above List Price
  • $109/SF
  • 20 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Ronald Green KW MidHudson
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  $9,750,000

  • Land
  • 558.35 Acres
  • $17,462 per Acre

  225 Route 22, Pawling, NY 12564

  Unparalleled Opportunity Awaits! Discover this breathtaking 558+ acre parcel, just 90 minutes from Manhattan, offering a canvas of endless possibilities for personal and commercial endeavors. Whether you envision a sprawling family compound or a premier commercial facility, this land is primed for your dreams. Featuring level terrain, extensive trails, and vibrant pastures, this property is

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (845) 377-2512

  225 Route 22, Pawling, NY 12564
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  $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 $395,079

  Last Listing Agent Robin Butler-Koschei Hanson Real Estate Partners

  2 Spruce St, Pawling, NY 12564
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  Est $1,970,557 Not Listed For Sale

  73 Cunningham Ln, Pawling, NY 12564

  • 5 Beds
  • 5 Baths
  • 8,331 Sq Ft
  • Built 2009

  73 Cunningham Ln, Pawling, NY 12564

  Last Sold Summary

  • 23% Above List Price
  • $192/SF
  • 121 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Helen Murray William Pitt Sothebys Int Rlty
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  $199,000 Pending

  • Land
  • 16.67 Acres
  • $11,938 per Acre

  1D Margherita Ln, Pawling, NY 12564

  Discover an incredible opportunity to build on a rare 16+ acre parcel in the town of Pawling! Located just five minutes from the charming village, which is filled with lively shops and restaurants, this property offers a peaceful retreat in the woods. The parcel is approved by the board of health and is ready for you to construct a home with up to four bedrooms. New York City is conveniently

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 470-5610

  1D Margherita Ln, 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 $453,902

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  103 Mohawk Trail, Pawling, NY 12564
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  Est $816,795 Not Listed For Sale

  34 Harmony Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 4.5 Baths
  • 3,340 Sq Ft
  • Built 2007

  34 Harmony Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 32% Above List Price
  • $185/SF
  • 88 Days On Market

  Last Sold Price $619,500

  Last Listing Agent Lawrence Zacks Keller Williams Realty Partner
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  $229,000

  • Land
  • 5.57 Acres
  • $41,113 per Acre

  Lot 21 Cox Rd, Pawling, NY 12564

  Come build your dream home on this 5.6-acre Board of Health–approved lot in the highly desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom residence, this property offers both privacy and convenience—just minutes from Route 22, the Village of Pawling, shopping, Metro-North, Route 55, and even the Appalachian Trail. Nestled within the Oblong Trails, residents of Brady Brook

  

  Shannon Tully

  McGrath Realty Inc

  (845) 328-6866

  Lot 21 Cox Rd, Pawling, NY 12564
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  $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 $444,269

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  36 Elm St, Pawling, NY 12564
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  Est $882,637 Not Listed For Sale

  6 di Pietro Ln, Pawling, NY 12564

  • 4 Beds
  • 4.5 Baths
  • 6,042 Sq Ft
  • Built 2002

  6 di Pietro Ln, Pawling, NY 12564

  Last Sold Summary

  • 18% Above List Price
  • $124/SF
  • 46 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Tony Zaccardo Coldwell Banker Realty
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  $1,450,000 Pending

  • 5 Beds
  • 7.5 Baths
  • 5,470 Sq Ft

  604 N Quaker Hill Rd, Pawling, NY 12564

  Exceptional living awaits in this stately Georgian manor house sitting on 7 acres at the top of prestigious North Quaker Hill Road. This mostly original home offers 9’ ceilings, radiant heating and ownership that has changed hands only once. A Belgian cobblestone driveway has a center focal point awaiting your personal touch.The Living room opens to an elegant wraparound terrace, perfect for the

  

  Leigh Tripathi

  Ellis Sotheby's Intl Realty

  (845) 606-4026

  604 N Quaker Hill Rd, Pawling, NY 12564
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  $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 $364,778

  Last Listing Agent Nick Selca Lakeshore Realty International

  37 Spruce St, Pawling, NY 12564
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  Est $862,547 Not Listed For Sale

  919 N Quaker Hill Rd, Pawling, NY 12564

  • 3 Beds
  • 3 Baths
  • 2,435 Sq Ft
  • Built 1987

  919 N Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 24% Above List Price
  • $285/SF
  • 22 Days On Market

  Last Sold Price $695,000

  Last Listing Agent Lori Rheingold
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  /4

  $169,000 Pending

  • Land
  • 4.87 Acres
  • $34,702 per Acre

  51 Estate Dr, Pawling, NY 12564

  Discover your dream sanctuary at lot #21, now cherished as 51 Estate Drive, nestled within the serene Cushman Farms subdivision in picturesque Pawling, NY. This enchanting property offers nearly 5 acres of secluded, buildable land, beckoning you to design the home you've always envisioned OR take advantage of the current plans in place. Picture waking up surrounded by nature's beauty, while still

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 622-7384

  51 Estate Dr, Pawling, NY 12564
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  $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 $435,939

  Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

  36 Spruce St, Pawling, NY 12564
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  Est $941,741 Not Listed For Sale

  809 N Quaker Hill Rd, Pawling, NY 12564

  • 3 Beds
  • 3 Baths
  • 3,600 Sq Ft
  • Built 1759

  809 N Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 59% Below List Price
  • $639/SF
  • 20 Days On Market

  Last Sold Price $2,300,000

  Last Listing Agent Raj Kumar Four Seasons Sothebys Intl
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  /3

  $199,000 Pending

  • Land
  • 17.63 Acres
  • $11,288 per Acre

  1C Margherita Ln, Pawling, NY 12564

  Over 17.6 acres to build your hillside oasis! This private lot is approved by the Board of Health for a four-bedroom home, and is located less than two miles from the charming village of Pawling, which offers shops, restaurants, a train station, and parks! Commute to NYC in under two hours (by car OR train), or explore nearby hiking trails, including the infamous Appalachian Trail.

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 552-2709

  1C Margherita Ln, 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 $378,157

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

  4 Juniper Ln, Pawling, NY 12564
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  Est $576,991 Not Listed For Sale

  775 N Quaker Hill Rd, Pawling, NY 12564

  • 5 Beds
  • 2 Baths
  • 2,262 Sq Ft
  • Built 1960

  775 N Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 14% Above List Price
  • $223/SF
  • 13 Days On Market

  Last Sold Price $505,000

  Last Listing Agent ALEXIS MALSBURY Coldwell Banker Realty
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  /11

  $229,000

  • Land
  • 6.63 Acres
  • $34,540 per Acre

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564

  Come build your dream home on this 6.63-acre Board of Health–approved lot in the desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom home, this property offers the perfect setting for those seeking privacy while remaining just minutes from all the conveniences the Town of Pawling has to offer. Enjoy easy access to Route 22, Route 55, Metro-North, shopping, the charming

  

  Shannon Tully

  McGrath Realty Inc

  (845) 378-9417

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
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  $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 $728,746

  Last Listing Agent Christopher Filangeri BHHS Hudson Valley Properties

  27 Millstream Ct, Pawling, NY 12564
• 

  Est $906,824 Not Listed For Sale

  16 Anderson Rd, Pawling, NY 12564

  • 2 Beds
  • 3 Baths
  • 2,008 Sq Ft
  • Built 2023

  16 Anderson Rd, Pawling, NY 12564

  Last Sold Summary

  • 59% Above List Price
  • $284/SF
  • 100 Days On Market

  Last Sold Price $570,000

  Last Listing Agent Brian McGrath McGrath Realty Inc
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  /50

  $599,000

  • 2 Beds
  • 2 Baths
  • 1,428 Sq Ft

  168 Old Route 55, Pawling, NY 12564

  Step into the very year our nation was born and own a piece of American history! Originally constructed in 1776, this iconic stone residence later became the "Pawling Toll Gate and Toll House," serving as a vital gateway for travelers, a general store, a post office, and a legendary tavern. It is even whispered that George Washington himself once proved his strength within these walls, winning a

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 932-0435

  168 Old Route 55, 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 $577,006

  Last Listing Agent Shannon Tully McGrath Realty Inc

  85 W Deer Trail, Pawling, NY 12564
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  Est $565,510 Not Listed For Sale

  8 Brady Ln, Pawling, NY 12564

  • 3 Beds
  • 1.5 Baths
  • 1,972 Sq Ft
  • Built 1966

  8 Brady Ln, Pawling, NY 12564

  Last Sold Summary

  • 97% Above List Price
  • $146/SF
  • 45 Days On Market

  Last Sold Price $287,000

  Last Listing Agent Ernie Acampora River Realty Services, Inc.

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