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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  /11

  $1,400 per month

  • 1 Bed
  • 1 Bath
  • 300 Sq Ft
  • Condo for Rent

  23 W Main St Unit 1A, Pawling, NY 12564

  Two room studio in the historical Village of Pawling. Ground floor, private entrance. Convenient parking. Walk to Metro-North, shopping, laundry. No smoking/pets Call only

  23 W Main St Unit 1A, Pawling, NY 12564
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  $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

  Last Listing Agent Colleen McGrath McGrath Realty Inc

  7 Glen Ct, Pawling, NY 12564
• 

  Est $640,000 Not Listed For Sale

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

  135 S Quaker Hill Rd, Pawling, NY 12564

  135 S Quaker Hill Rd, Pawling, NY 12564
• 

  $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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  $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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  $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

  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
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  $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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  /22

  $2,000 per month

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

  23 E Main St Unit 3B, Pawling, NY 12564

  Now leasing, a one bedroom apartment in a premier rental residence located in the heart of Pawling. Styled in the character of Pawling’s iconic Dutcher House & newly completed, it offers a unique opportunity to live in sophisticated elegance with fine finishing & details throughout. The theme is modern luxury set in a quaint upstate, bucolic 18th century village. The 3rd floor apartment boasts an

  Claudia Jiskra McGrath Realty Inc

  23 E Main St Unit 3B, 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 $344,197 Not Listed For Sale

  7 Birch Ln, Holmes, NY 12531

  7 Birch Ln, Holmes, NY 12531
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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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  $2,950 per month

  • 3 Beds
  • 1 Bath
  • 1,186 Sq Ft
  • House for Rent

  112 Charles Colman Blvd, Pawling, NY 12564

  Delightful C1900 Farmhouse Colonial located on the prettiest streets in the Village. Updated, renovated, & designed to perfection. There are period wood flrs, an updated airy kitchen w/quartz counters, open to a country dining area w/sunny bay window & back dr to patio. The large LR runs front to back w/deep windows, lots of light & sliders to the patio. The covered front porch w/vintage millwork

  Gillian Stewart Gillian Stewart Real Estate

  112 Charles Colman Blvd, 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 $638,290 Not Listed For Sale

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

  68 W Main St, Pawling, NY 12564

  68 W Main St, Pawling, NY 12564
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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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  $7,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,942 Sq Ft
  • House for Rent

  15 Kirby Hill Rd, Pawling, NY 12564

  Now for rent is one of Quaker Hill's most prestigious estate homes. The main estate at Kirby Hill Farm is available as seasonal winter, or yearly rental, impeccably furnished and equipped residential rental with an in-ground pool. Set on close to 250 acres and one of the region's finest equestrian facilities. The circa 1860 colonial farmhouse boasts 3,942 square feet. There are two separate

  Brian McGrath McGrath Realty Inc

  15 Kirby Hill Rd, Pawling, NY 12564
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  $999,000 Sold Feb 13, 2025

  37 San Souci Dr, Pawling, NY 12564

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

  Last Sold Summary

  • 2% Above List Price
  • $273/SF
  • 27 Days On Market

  Current Estimated Value $1,039,525

  Last Listing Agent Colleen McGrath McGrath Realty Inc

  37 San Souci Dr, Pawling, NY 12564
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  Est $1,888,179 Not Listed For Sale

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

  73 Cunningham Ln, Pawling, NY 12564

  73 Cunningham Ln, Pawling, NY 12564
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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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  $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 $454,380

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  103 Mohawk Trail, Pawling, NY 12564
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  Est $828,476 Not Listed For Sale

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

  34 Harmony Hill Rd, Pawling, NY 12564

  34 Harmony Hill Rd, Pawling, NY 12564
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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
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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

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  36 Elm St, Pawling, NY 12564
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  Est $827,093 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,657 Sq Ft

  30 Horseshoe Path, Pawling, NY 12564

  30 Horseshoe Path, Pawling, NY 12564
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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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  $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 $373,092

  Last Listing Agent Nick Selca Lakeshore Realty International

  37 Spruce St, Pawling, NY 12564
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  Est $877,863 Not Listed For Sale

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

  6 di Pietro Ln, Pawling, NY 12564

  6 di Pietro Ln, Pawling, NY 12564
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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
• 

  $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 $434,236

  Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

  36 Spruce St, Pawling, NY 12564
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  Est $807,626 Not Listed For Sale

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

  919 N Quaker Hill Rd, Pawling, NY 12564

  919 N Quaker Hill Rd, Pawling, NY 12564
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  $169,000

  • 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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  $746,000 Sold Feb 14, 2025

  25 Liberty Ln, Pawling, NY 12531

  • 3 Beds
  • 3 Baths
  • 2,600 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $287/SF
  • 56 Days On Market

  Current Estimated Value $787,486

  Last Listing Agent Magdalena Pawlowska Coldwell Banker Realty

  25 Liberty Ln, Pawling, NY 12531
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  Est $976,684 Not Listed For Sale

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

  809 N Quaker Hill Rd, Pawling, NY 12564

  809 N Quaker Hill Rd, Pawling, NY 12564
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  $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
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  $610,000 Sold Feb 20, 2025

  572 Quaker Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 3.5 Baths
  • 2,900 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Above List Price
  • $210/SF
  • 37 Days On Market

  Current Estimated Value $713,637

  Last Listing Agent Barbara Allen HomeSmart Homes & Estates

  572 Quaker Hill Rd, Pawling, NY 12564
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  Est $547,202 Not Listed For Sale

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

  775 N Quaker Hill Rd, Pawling, NY 12564

  775 N Quaker Hill Rd, Pawling, NY 12564
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  $399,999 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,838 Sq Ft

  2 Spruce St, Pawling, NY 12564

  Welcome home to 2 Spruce St.! 2 full floors plus a completely finished walk out basement. Home has central air and heat. Completely updated and freshly painted, all you need to do is move in. Living room features a built in flue that can be opened up for adding a wood burning fireplace. 2 full primary bedrooms, each with it's own full bathroom, plus a powder room on the first floor. One of the

  Robin Butler-Koschei Hanson Real Estate Partners

  2 Spruce St, Pawling, NY 12564
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  $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 $379,082

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

  4 Juniper Ln, Pawling, NY 12564

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