Pawling, NY Homes

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  /50

  $775,000

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,729 Sq Ft

  103 S Harmony Hill Rd, Pawling, NY 12564

  Properties like this don't come along often! As you turn off the road, the world quiets. The driveway pulls you back through a canopy of mature trees, and by the time the house appears, you already feel the privacy with over five acres, buffered on all sides, thoughtfully expanded and upgraded far beyond its 1975 origins. Step inside to a living room anchored by a stone fireplace, original

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 720-4119

  103 S Harmony Hill Rd, Pawling, NY 12564
• Explore Pawling

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  /24

  $1,950 Per Month

  • 2 Beds
  • 1 Bath
  • 818 Sq Ft
  • Apartment for Rent

  129 Charles Colman Blvd Unit A2, Pawling, NY 12564

  At your fingertips! Everything the Village of Pawling has to offer - Metro North, Lakeside Park, shopping, restaurants and services. Clean, affordable, two bedroom second floor apartment with newer windows and lots of extra storage. Good sized Living Room with plenty of sunshine. Eat in Kitchen with maple cabinets, recessed lighting and tile floor makes this fully functional for your cooking

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  (845) 668-4575

  129 Charles Colman Blvd Unit A2, Pawling, NY 12564
• 

  $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 $843,300

  Last Listing Agent Tom Consaga RE/MAX Ace Realty

  175 Old Quaker Hill Rd, Pawling, NY 12564
• 

  Est $539,000

  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

  • 38 Days On Market
• 

  

  

  /28

  $530,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,706 Sq Ft

  58 Pine Dr, Pawling, NY 12564

  Tucked away at the end of a quiet cul-de-sac, this beautifully maintained home sits on 2.87 acres of mostly level, private property—offering the perfect blend of peaceful surroundings and everyday convenience. Step into a bright and welcoming main living area featuring a sun-filled living room with an oversized picture window framing peaceful views of the front lawn, and a dining room with

  

  Teddie Leonaggeo

  McGrath Realty Inc

  (845) 299-0848

  58 Pine Dr, Pawling, NY 12564
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  /24

  $1,800 Per Month

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft
  • Apartment for Rent

  25 Fairway Dr Unit 2, Pawling, NY 12564

  Rare Village of Pawling 2 bedroom, second floor apartment. Open concept Living Room allows you to use the space to fit your needs. Remodeled kitchen with luxury vinyl flooring, stainless steel appliances, granite counter tops and white shaker cabinets for lots of storage. Beautiful, weathered wood backsplash adds a designer touch. Updated bathroom with tub/shower enclosure, white vanity and

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  (845) 202-4082

  25 Fairway Dr Unit 2, Pawling, NY 12564
• 

  $415,000

  Sold May 22, 2026

  7 Juniper Ln, Pawling, NY 12564

  • 2 Beds
  • 2 Baths
  • 2,596 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $160/SF
  • 48 Days On Market

  Current Estimated Value $415,785

  Last Listing Agent Elizabeth Poggiogalle Real Broker NY LLC

  7 Juniper Ln, 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
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  $2,500,000

  • 3 Beds
  • 3.5 Baths
  • 2,292 Sq Ft

  34 Meeting House Rd, Pawling, NY 12564

  Nestled in the heart of historic Quaker Hill, this bucolic property offers timeless charm just a stone’s throw from the iconic Meeting House. Originally built in 1983, the home underwent a meticulous, top-to-bottom renovation in 2016, thoughtfully upgrading all major systems, finishes, and living spaces to modern standards while preserving its serene setting. The residence is exceptionally

  

  Mark Friedman

  McGrath Realty Inc

  (845) 723-3249

  34 Meeting House Rd, Pawling, NY 12564
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  $30,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 4,233 Sq Ft
  • House for Rent

  121 N Quaker Hill Rd, Pawling, NY 12564

  $30k/month summer. Inquire for other terms. 4 bedroom 3.5 designer inspired home intended to complement the splendor of its natural surroundings. Fully furnished for comfortable luxury. 3 fireplaces and awe inspiring panoramic views. Soak in a breathtaking scene spanning the great meadow, rolling hills and mountains beyond. Long driveway with mature landscape, this hideaway provides pure

  Joseph Lorino Brown Harris Stevens HV LLC

  121 N Quaker Hill Rd, Pawling, NY 12564
• 

  $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 $160,238

  Not Listed For Sale

  7 Birch Ln, Holmes, NY 12531

  7 Birch Ln, Holmes, NY 12531

  Last Sold Summary

  • 234 Days On Market
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  /22

  $1,350,000

  $50K PRICE INCREASE

  • 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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  /10

  $1,425

  Total Monthly Price

  • 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
• 

  $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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  Not Listed For Sale

  0 S Quaker Hill Rd Unit KEY822354, Pawling, NY 12564

  0 S Quaker Hill Rd Unit KEY822354, Pawling, NY 12564

  Last Sold Summary

  • 47 Days On Market
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  /8

  $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) 412-9125

  Lot 21 Cox Rd, Pawling, NY 12564
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  /23

  $2,900 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,413 Sq Ft
  • House for Rent

  12 Evergreen Way, Pawling, NY 12564

  Welcome to Cedar Valley! Two-story Townhouse features a spacious Living Rm with fireplace and doors to a brick patio. There is also an open Dining Rm Area. The kitchen has a good amount of cabinets and counter-space, and a small dining area. Also on the first floor is a half bath. The second floor offers a Primary Bedroom with walk-in closet and primary bath. The second bedroom also has an

  Lisa Liffland McGrath Realty Inc

  12 Evergreen Way, 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 $403,739

  Last Listing Agent Robin Butler-Koschei Hanson Real Estate Partners

  2 Spruce St, Pawling, NY 12564
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  Est $612,311

  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

  • 20 Days On Market
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  /6

  $79,000

  $9K PRICE DROP

  • Land
  • 20,037 Sq Ft
  • $171,739 per Acre

  0 Lakeview Dr Unit KEY962482, Pawling, NY 12531

  Build your ideal home on this prime .46-acre lot perfectly situated within the sought-after Pawling Lake Estates community. Offering a rare blend of beauty and value, this property boasts picturesque views of Jones Pond and benefits from the lower property taxes of the Dover Union Free School District. Nature enthusiasts will love being surrounded by the sprawling West Mountain State Forest,

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 385-2808

  0 Lakeview Dr Unit KEY962482, Pawling, NY 12531
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  /17

  $3,250 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft
  • Apartment for Rent

  10 Fenwood Dr Unit B, Pawling, NY 12564

  Bright & Spacious 3-Bedroom Apartment in Private Setting – Close to Train, Shopping & Schools Enjoy privacy and convenience in this light-filled 3-bedroom, 2.5-bath apartment located in a well-maintained three-family home on a quiet, secluded road just off the main thoroughfare. This spacious apartment offers the perfect balance of peaceful living while being minutes from shopping centers,

  Clayton Livingston McGrath Premier Real Estate

  10 Fenwood Dr Unit B, 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 $465,149

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  103 Mohawk Trail, Pawling, NY 12564
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  Not Listed For Sale

  24 Sheridan Dr, Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 2,876 Sq Ft
  • Built 1930

  24 Sheridan Dr, Pawling, NY 12564

  Last Sold Summary

  • 134 Days On Market
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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) 684-9806

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
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  /8

  $2,000 Per Month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Apartment for Rent

  10 Fenwood Dr Unit C, Pawling, NY 12564

  Charming and spacious 2-bedroom, 1-bath apartment featuring high ceilings, skylights, and ceramic tile floors throughout, creating a bright and open living environment. This inviting home offers a private entry, providing added privacy and convenience. The apartment is filled with natural light thanks to the skylights and generous ceiling height, giving the living spaces an airy and comfortable

  Clayton Livingston McGrath Premier Real Estate

  10 Fenwood Dr Unit C, Pawling, NY 12564
• 

  $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 $435,761

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  36 Elm St, Pawling, NY 12564
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  Est $2,408,570

  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

  • 121 Days On Market
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  /46

  $725,000

  Open Sun 11AM - 1PM $25K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,687 Sq Ft

  6 Martingale Way, Pawling, NY 12564

  Welcome to 6 Martingale Way, an impressive 4-bedroom, 3.5-bathroom colonial offering nearly 4,700 square feet of living space in the highly sought-after Highlands community of Pawling, NY. From the moment you step inside, you'll be greeted by beautifully refinished hardwood floors that flow throughout the entire first floor, setting the tone for the quality and care found throughout this

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 209-0713

  6 Martingale Way, Pawling, NY 12564
• 

  $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 $374,796

  Last Listing Agent Nick Selca Lakeshore Realty International

  37 Spruce St, Pawling, NY 12564
• 

  Est $860,948

  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

  • 46 Days On Market
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  /6

  $215,000

  $10K PRICE DROP

  • Land
  • 33,105 Sq Ft
  • $282,895 per Acre

  15 Dykeman St, Pawling, NY 12564

  Rare opportunity to build in the heart of the Village of Pawling! Cleared and ready for development, this residential lot at 15 Dykeman Street offers municipal water and sewer available at the street — a major advantage for new construction. The property features a defined driveway lined with item four stone, providing immediate access and a head start on site work. Level and open, the lot offers

  

  Joanne Debellis

  Debellis Real Estate LLC

  (845) 660-6758

  15 Dykeman St, 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 $459,988

  Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

  36 Spruce St, Pawling, NY 12564
• 

  Est $558,865

  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

  • 13 Days On Market
• 

  

  /43

  $565,000

  • 2 Beds
  • 2 Baths
  • 2,194 Sq Ft

  168 Old Route 55, Pawling, NY 12564

  Set on 2.7 private acres, this historic 1776 stone Toll Gate House at 168 Old Route 55 offers a rare blend of Hudson Valley history and modern comfort. Built in the year America declared independence—and meticulously renovated/restored in 1981—this remarkable property is more than a home; it’s a living piece of local history with timeless character, thoughtful updates, and an unbeatable location

  Alea Vorillas RE/MAX Classic Realty

  168 Old Route 55, Pawling, NY 12564
• 

  $580,000

  Sold May 28, 2026

  322 Old Route 22, Pawling, NY 12564

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • Built 1929

  Last Sold Summary

  • 6% Below List Price
  • $297/SF
  • 151 Days On Market

  Current Estimated Value $590,860

  Last Listing Agent Susan Stevens BHHS Hudson Valley Properties

  322 Old Route 22, Pawling, NY 12564
• 

  Est $851,406

  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

  • 100 Days On Market
• 

  

  /31

  $900,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,434 Sq Ft

  128 Old Pawling Rd, Pawling, NY 12564

  You finally have the opportunity to own a home with year-round mountain views set on an expansive property. A place where you can bring your vision to life and transform the space into a true masterpiece. 128 Old Pawling Road is a beautifully positioned property in Pawling, NY, offering a rare combination of scenic views, generous land, and the potential to create a truly special home. Set back

  Juliska Martino Compass Greater NY, LLC

  128 Old Pawling Rd, Pawling, NY 12564
• 

  $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 $727,373

  Last Listing Agent Christopher Filangeri BHHS Hudson Valley Properties

  27 Millstream Ct, Pawling, NY 12564
• 

  Est $474,577

  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

  • 45 Days On Market

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