Pawling, NY Homes

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  $599,900

  • 2 Beds
  • 2.5 Baths
  • 1,820 Sq Ft

  36 Byrds Hill Rd, Pawling, NY 12564

  The Perfect Weekend Escape or Full-Time Country Home, just 90 minutes from NYC. Set on a quiet, scenic road in the prestigious Quaker Hill area, you’re a short drive to the Village of Pawling with shopping, restaurants, highways, and Metro-North access. From the outside, it’s a classic farmhouse with rolling green acreage and space to breathe. Step inside, and you’re met with modern, yet cozy

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 630-1049

  36 Byrds Hill Rd, Pawling, NY 12564
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  $3,500 per month

  • 3 Beds
  • 2 Baths
  • 1,936 Sq Ft
  • House for Rent

  11 Glen Arden Dr, Pawling, NY 12564

  Welcome to a rare opportunity to live on the prestigious Quaker Hill in Pawling, NY. Set on a stunning farm estate, this beautifully preserved single-family home offers timeless charm, privacy, and peaceful countryside living — all just minutes from town conveniences.Steeped in history, the home showcases original wood floors, hand-hewn wooden beams, and detailed woodwork throughout. The first

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 640-5503

  11 Glen Arden Dr, Pawling, NY 12564
• 

  $360,000 Sold Jun 20, 2025

  • 1,115 Sq Ft
  • $323/SF
  • 27 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  53 Mohawk Trail, Pawling, NY 12564

  Welcome to beautiful Deerfield Ponds. Just across from a picturesque horse farm, you'll find this community of single family and townhouse dwellings. Unit 53 is a single-level, end unit townhome. It offers 2 Bedrooms, 2 Full Bathrooms, an open Eat-in-Kitchen, Dining Area and Spacious Living Room w/wood-burning Fireplace. Just off the living room is access to the rear Trex-like deck and lots

  Pamela Blecker Keller Williams Realty Partner

  53 Mohawk Trail, Pawling, NY 12564
• 

  Est $1,143,000 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,150 Sq Ft

  711 Old Quaker Hill Rd, Pawling, NY 12564

  711 Old Quaker Hill Rd, Pawling, NY 12564
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  /48

  $799,999

  • 4 Beds
  • 3 Baths
  • 3,360 Sq Ft

  94 S Quaker Hill Rd, Pawling, NY 12564

  Welcome to Sunset View! Nestled on 3.24 acres of picturesque private land, this sprawling 4-bedroom split-level home offers a perfect blend of spacious living and expansive outdoor amenities including a 20 x 50 salt water inground pool. As you approach along the freshly paved driveway, you'll be welcomed into your very own private oasis. Upon entering through the front door, you’ll step into a

  

  Shannon Tully

  McGrath Realty Inc

  (845) 622-7595

  94 S Quaker Hill Rd, Pawling, NY 12564
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  /8

  $1,285 per month

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

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

  Two room studio Ground floor, private entrance. Convenient parking. Walk to shopping, laundry. No smoking/pets Call only

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

  $376,500 Sold Jun 18, 2025

  • 1,427 Sq Ft
  • $264/SF
  • 13 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1997

  18 Evergreen Way, Pawling, NY 12564

  Welcome to this well maintained end unit in the desirable Cedar Valley. This home features two spacious bedrooms including a large first floor primary with en suite bath and walk in closet. The second bedroom is located upstairs and also includes a full bath along with plenty of closet space and storage. The main living area boasts a cozy fireplace with large windows that flood the space with

  Vicki Reinach BHHS Hudson Valley Properties

  18 Evergreen Way, Pawling, NY 12564
• 

  Est $425,142 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,190 Sq Ft

  37 Old Route 55, Pawling, NY 12564

  37 Old Route 55, Pawling, NY 12564
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  /8

  $185,000

  • Land
  • 6 Acres
  • $30,629 per Acre

  8 Ravine Rd, Pawling, NY 12564

  Location Location Location in the prestigious Quaker Hill area in Pawling! Come build your private Estate on 6.04 acres. This lot is BOHA for a 5 bedroom home and already have a beautiful stone entry to greet you. Well is drilled and other amenities listed. Close to Everything, horse trails, Metro-North, Route 22, I684 and more.

  

  Shannon Tully

  McGrath Realty Inc

  (845) 385-1182

  8 Ravine Rd, Pawling, NY 12564
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  /21

  $3,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  39 Nathan Pierce Ct, Pawling, NY 12564

  Welcome to 39 Nathan Pierce Court – a beautifully updated 3-Bedroom, 2.5 Bath townhouse located in the desirable Deerfield Ponds Community. Offering 1,600 sq ft of thoughtfully designed living space, this home combines modern upgrades with everyday comfort and convenience! The kitchen features stainless steel appliances, generous cabinet space, and a bright eat-in area perfect for casual meals or

  LAUREL MASCIA BHHS Hudson Valley Properties

  39 Nathan Pierce Ct, Pawling, NY 12564
• 

  $645,000 Sold Jun 13, 2025

  • 1,900 Sq Ft
  • $339/SF
  • 20 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1880

  32 Elm St, Pawling, NY 12564

  Welcome to 32 Elm Street – a stunning blend of historic charm and modern convenience! This beautifully renovated 1880s home, reimagined in 2025, offers 3 spacious bedrooms, 2.5 bathrooms, and 1,900 sq ft of stylish living space. Nestled on a .27-acre lot with easy access from both Elm and Walnut Streets, this home is perfectly located just a 4-minute walk to the Metro North train station and a

  Patrycja Warda

  32 Elm St, 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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  /33

  $9,750,000

  • Land
  • 558 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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  /31

  $2,500 per month

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

  71 E Main St Unit 303, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 303, Pawling, NY 12564
• 

  $435,000 Sold Jun 06, 2025

  • 1,917 Sq Ft
  • $227/SF
  • 13 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2001

  103 Mohawk Trail, Pawling, NY 12564

  Welcome to your dream home nestled in the heart of Pawling's coveted Deerfield Ponds community! This rarely available and most sought-after 3-bedroom, 2 1/2-bathroom townhome features the primary bedroom conveniently located on the first floor. Spanning 1,917 square feet across two floors, with an additional 1,104 square foot unfinished basement, this home offers unlimited potential, complete

  Claudia Jiskra McGrath Realty Inc

  103 Mohawk Trail, Pawling, NY 12564
• 

  Est $1,545,903 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,347 Sq Ft

  82 S Quaker Hill Rd, Pawling, NY 12564

  82 S Quaker Hill Rd, Pawling, NY 12564
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  /42

  $599,000 Pending

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

  126 Old Route 55, Pawling, NY 12564

  This charming, expansive ranch home is thoughtfully designed to suit a variety of living arrangements, whether for a large family, extended family, or a mother-daughter setup. With 4-5 bedrooms and 4 full bathrooms (3 of which are en suite), this home offers both space and privacy for everyone.The kitchen is a chef's dream, featuring elegant soapstone countertops, a copper sink, and distressed

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 576-1665

  126 Old Route 55, Pawling, NY 12564
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  /43

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 302, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 302, Pawling, NY 12564
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  $412,500 Sold May 27, 2025

  • 1,564 Sq Ft
  • $264/SF
  • 43 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  10 John Kane Ct, Pawling, NY 12564

  Welcome to your dream home in the heart of Pawling's Deerfield Ponds community! This beautiful 2-bedroom, 2-bathroom townhouse features an open floor plan that flows between the dining room and the spacious living room, which has a wood-burning fireplace. It also includes a bonus room and a full unfinished basement. The basement could become a playroom, multimedia room, or a storage area. This

  Jessica Diaz Coldwell Banker Realty

  10 John Kane Ct, Pawling, NY 12564
• 

  Est $447,586 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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  /49

  $569,000

  • 4 Beds
  • 2.5 Baths
  • 3,322 Sq Ft

  7 Watchhill Rd, Pawling, NY 12564

  Step into comfort and elegance in this spacious 4-bedroom, 2.5-bath Colonial nestled in the sought-after Deerfield Ponds neighborhood. From the moment you enter the grand foyer, you'll feel right at home. The heart of the house is the expansive kitchen featuring a large center island, light wood cabinetry, and tiled flooring, seamlessly flowing into both the formal dining room and the cozy living

  

  Shannon Tully

  McGrath Realty Inc

  (845) 524-1380

  7 Watchhill Rd, Pawling, NY 12564
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  /43

  $3,350 per month

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 301, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 301, Pawling, NY 12564
• 

  $540,000 Sold May 23, 2025

  • 2,341 Sq Ft
  • $231/SF
  • 23 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2001

  85 W Deer Trail, Pawling, NY 12564

  Nestled just minutes from the charming Village of Pawling, this stunning 4-bedroom, 2.5-bath home offers the perfect blend of comfort, elegance, and breathtaking views of a neighboring horse farm. Step onto the inviting front porch and enter through a formal entryway that sets the tone for the warmth and beauty found throughout. Hardwood floors guide you past the traditional living room and into

  Shannon Tully McGrath Realty Inc

  85 W Deer Trail, Pawling, NY 12564
• 

  Est $1,641,019 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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  /3

  $175,000

  • Land
  • 4.21 Acres
  • $41,568 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

  

  Kimberly Cardona-Smith

  Howard Hanna Rand Realty

  (845) 606-0417

  0 South Rd Unit KEY853088, Pawling, NY 12531
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  $2,900 per month

  • 2 Beds
  • 2 Baths
  • 997 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 204, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 204, Pawling, NY 12564
• 

  $674,900 Sold May 21, 2025

  • 2,876 Sq Ft
  • $235/SF
  • 134 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1930

  24 Sheridan Dr, Pawling, NY 12564

  Check out this Charming Country Cottage in the Village of Pawling! Nestled on almost 7 acres of serene land, this delightful country cottage offers the perfect blend of comfort and tranquility. Hardwood floors flow throughout the home, enhancing the warm, rustic charm. The sun-soaked living room, complete with a wood-burning fireplace, invites relaxation, while the eat-in kitchen is perfect for

  John Gabriel Jr KW MidHudson

  24 Sheridan Dr, Pawling, NY 12564
• 

  Est $812,185 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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  /47

  $749,900

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft

  28 Gobblers Knob Rd, Pawling, NY 12564

  Welcome to 28 Gobblers Knob Road – A Hudson Valley Equestrian Retreat! Nestled in the heart of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on a breathtaking 20+ acre property offering peace, privacy, and natural beauty in every direction. Whether you're looking for a serene country getaway or a horse property, this one-of-a-kind home is the perfect match. The

  Mark Snyder eXp Realty

  28 Gobblers Knob Rd, Pawling, NY 12564
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  /43

  $3,200 per month

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 201, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 201, Pawling, NY 12564
• 

  $560,000 Sold May 20, 2025

  • 2,552 Sq Ft
  • $219/SF
  • 132 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1975

  130 Old Route 55, Pawling, NY 12564

  Single family 5 bedroom, 3 bath country home. Secluded in the woods, but close to town. 10.39 acres with pool and 2 paddock barn offering a unique experience for those desiring privacy and a connection to nature. Small bungalow in back perfect for an office or recreational area.

  Derek Eisenberg Continental Real Estate Group

  130 Old Route 55, Pawling, NY 12564
• 

  Est $788,877 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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  /29

  $889,000 Open Sun 2PM - 4PM

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

  26 Rodina Dr, Pawling, NY 12564

  Welcome to your brand new dream home! Nestled on a beautiful and peaceful two and half acres. Be the first to live in this stunning four bedroom, two and a half bath home. 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 with motion sensor lighting on

  Douglas Servello Home Sweet Home Properties

  26 Rodina Dr, Pawling, NY 12564
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  /43

  $2,850 per month

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 102, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 102, Pawling, NY 12564
• 

  $490,000 Sold May 16, 2025

  • 1,716 Sq Ft
  • $286/SF
  • 85 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  17 Fenwood Dr, Pawling, NY 12564

  This charming, tucked-away Raised Ranch offers 3 bedrooms and 2 bathrooms, providing a cozy and modern living space. As you step through the front door and ascend the stairs, you're greeted by a bright and airy living room featuring a bay window and hardwood floors, which seamlessly flow into the dining area and open kitchen. The updated kitchen is equipped with stainless steel appliances,

  Shannon Tully McGrath Realty Inc

  17 Fenwood Dr, Pawling, NY 12564
• 

  Est $879,752 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
• 

  

  /43

  $724,900

  • 4 Beds
  • 2.5 Baths
  • 2,773 Sq Ft

  27 Millstream Ct, Pawling, NY 12564

  Welcome to your new home in the neighborhood you want and with all the amenities you want. Imagine waking in your Oversized Primary bedroom to the sounds of birds chirping and the sun warming your face. Get the day going in your Primary Bath Suite with Double Vanity, Heated Floors, Heated Towel Rack and Jacuzzi Tub. Smell the coffee brewing in your Chef's kitchen where you can prepare meals that

  CHRISTOPHER FILANGERI BHHS Hudson Valley Properties

  27 Millstream Ct, Pawling, NY 12564
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  /43

  $3,100 per month

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 101, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 101, Pawling, NY 12564
• 

  $607,000 Sold May 16, 2025

  • 3,732 Sq Ft
  • $163/SF
  • 235 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1967

  32 Gristmill Ln, Pawling, NY 12564

  Enjoy the village lifestyle in historic Pawling. This private, 1.4-acre, treelined property is less than a mile to the Village with shops, restaurants, library, Metro North station, Dutcher Golf Course, and the Village Green with Farmer's Market (June-October). Close proximity to Lakeside & Morrow parks and the Appalachian & Oblong Trails. This sprawling, mother/ daughter style home includes an

  Carol Aprile

  32 Gristmill Ln, Pawling, NY 12564
• 

  Est $818,568 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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