Pawling, NY Homes

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  /29

  $575,000

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

  36 Byrds Hill Rd, Pawling, NY 12564

  Set on a quiet, scenic road in the prestigious Quaker Hill area, this home offers the perfect blend of seclusion and accessibility. You're only 3 miles from the serene waters of Quaker Lake, 2 miles from the Connecticut border, and just 20 minutes from charming CT towns like Sherman, New Milford, and Kent. From the outside, it’s a barn-like farmhouse surrounded by rolling green acreage and space

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 630-1049

  36 Byrds Hill Rd, Pawling, NY 12564
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  Explore Pawling

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  /14

  $2,100 per month

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  84 E Main St Unit 1, Pawling, NY 12564

  Available Immediately. 1 Bedroom, 1 Bath in the Village of Pawling. Upon entering, you're greeted by charming wood-built ins and freshly cleaned carpet. The large living room with a floor to ceiling, corner glass block wall, provides a ton on natural light. You'll be impressed by the large bedroom and laundry room complete with a washer and dryer. The private rental is situated on a flat,

  John DiDio Century 21 Alliance Rlty Group

  84 E Main St Unit 1, Pawling, NY 12564
• 

  $465,000 Sold Sep 15, 2025

  • 1,706 Sq Ft
  • $273/SF
  • 31 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1957

  14 Summit Ave, Pawling, NY 12564

  Tucked away on a quiet dead-end street in the serene village of Pawling, this meticulously maintained Cape Cod home offers the perfect blend of comfort, charm, and convenience. Bathed in natural light, the freshly painted interior boasts a seamless flow between living spaces, with two spacious bedrooms that live like three—ideal for guests, a home office, or flexible living. The inviting living

  Karen Gundelach Keller Williams Realty Partner

  14 Summit Ave, Pawling, NY 12564
• 

  Est $1,141,000 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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  /49

  $575,000

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

  7 Glen Ct, Pawling, NY 12564

  Welcome to this exquisitely renovated 3-bedroom, 2.5-bath Colonial home, showcasing over 2,300 square feet of elegant and comfortable living space. Perfectly situated in a serene cul-de-sac within the picturesque town of Pawling, this move-in-ready residence masterfully blends timeless charm with modern enhancements.As you step through the front door, you are greeted by a gracious

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 584-8385

  7 Glen Ct, Pawling, NY 12564
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  /25

  $3,350 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  63 River Rd Unit B, Pawling, NY 12564

  Barndominium Bliss! Captivating views and the unique opportunity to live your best life on a 39 acre working horse farm. Beautifully renovated 2nd floor of a large barn with all the rustic charm and latest amenities you need. Open living and dining areas with gleaming hardwood floors throughout. Rough hewn beams add charm and character. Niche space for sitting, reading or relaxing. Chef’s

  Judy Albert BHHS Hudson Valley Properties

  63 River Rd Unit B, Pawling, NY 12564
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  $430,000 Sold Sep 11, 2025

  • 1,835 Sq Ft
  • $234/SF
  • 64 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  19 Cushing Green S, Pawling, NY 12564

  Comfortable Townhouse Living at Squire GreenWelcome to this spacious and bright end-unit townhouse featuring 3 bedrooms, 2.5 bathrooms, and a one-car garage—all set within the highly sought-after Squire Green community. The main floor offers a welcoming layout ideal for daily living and entertaining. Enjoy an eat-in kitchen, a living room with cathedral ceilings, cozy fireplace, and a sliding

  Peggy MacLeay-Generoso McGrath Realty Inc

  19 Cushing Green S, Pawling, NY 12564
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  Est $549,000 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
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  /33

  $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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  /23

  $3,200 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
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  $1,400,000 Sold Sep 04, 2025

  • 4,683 Sq Ft
  • $299/SF
  • 139 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  21 Brady Brook Farm Rd, Pawling, NY 12564

  Nestled within the prestigious Brady Brook Falls subdivision on sought-after Quaker Hill, this exquisite colonial offers an unparalleled blend of elegance, privacy, and modern convenience. Situated at the end of a serene cul-de-sac, the home is surrounded by picturesque horse farms and country estates. A long, private driveway leads to this stunning 6.65-acre retreat, complete with a heated

  Brian McGrath McGrath Realty Inc

  21 Brady Brook Farm Rd, Pawling, NY 12564
• 

  Est $406,227 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,518 Sq Ft

  48 W Main St, Pawling, NY 12564

  48 W Main St, Pawling, NY 12564
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  /41

  $450,000

  • 2 Beds
  • 2.5 Baths
  • 2,072 Sq Ft

  27 Washington Ct, Pawling, NY 12564

  Welcome to 27 Washington Court, located in the sought-after Deerfield Ponds community!This end-unit 2-bedroom, 2.5-bath townhome offers spacious living with beautiful pond views. Step inside from the inviting front porch and you’ll be greeted by a bright, airy entryway featuring a mudroom area, half bath, and a window opening into the pass-through kitchen. The eat-in kitchen boasts stainless

  

  Shannon Tully

  McGrath Realty Inc

  (845) 444-3725

  27 Washington Ct, 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
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  $555,000 Sold Aug 22, 2025

  • 3,322 Sq Ft
  • $167/SF
  • 20 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2002

  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

  7 Watchhill Rd, Pawling, NY 12564
• 

  Est $435,726 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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  /48

  $749,000

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

  94 S Quaker Hill Rd, Pawling, NY 12564

  Set on 3.62 acres of picturesque and private land, this expansive 4-bedroom split-level home offers the perfect balance of spacious living and resort-style outdoor amenities, highlighted by a 20’ x 50’ saltwater in-ground pool. As you arrive along the freshly paved driveway, you’ll feel instantly at home in your own private oasis. Inside, a bright foyer with gleaming hardwood floors leads to the

  

  Shannon Tully

  McGrath Realty Inc

  (845) 253-5932

  94 S Quaker Hill Rd, Pawling, NY 12564
• 

  $415,000 Sold Aug 19, 2025

  • 1,152 Sq Ft
  • $360/SF
  • 33 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  42 Harmony Rd, Pawling, NY 12564

  Located on one of Pawling's most charming country roads, while still within a five-minute drive from the quaint and lively village center, this salt-box style home is awaiting your creativity and love. With a cozy and convenient fireplace in the living room, and a front-porch that overlooks an idyllic forest and beaver-pond across the street, the property feels isolated and quiet while still

  Reid McGrath McGrath Realty Inc

  42 Harmony 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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  /49

  $1,299,000

  • 4 Beds
  • 2.5 Baths
  • 4,880 Sq Ft

  53 Dugway Dr, Pawling, NY 12564

  Tucked away on 4.5 acres with hundreds of Acres of landlocked State land behind us in the iconic rolling hills of Pawling Lake Estates, 53 Dugway Drive is more than a house—it's a lifestyle. Just a bit over an hour to NYC by Metro North.... Pull into Our gated fully blacktopped driveway, Nestled in the mountains of Dutchess County. Built in 2025 boasting lifestyle with 10’

  

  Jeannie Shipman

  NextGen Real Estate LLC

  (845) 415-7093

  53 Dugway Dr, Pawling, NY 12564
• 

  $175,000 Sold Aug 15, 2025

  • Land
  • 6.04 Acres
  • $28,974 per Acre

  • 278 Days On Market

  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

  8 Ravine Rd, Pawling, NY 12564
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  Est $1,634,822 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

  • 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

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 576-1665

  126 Old Route 55, Pawling, NY 12564
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  $361,000 Sold Aug 13, 2025

  • 1,413 Sq Ft
  • $255/SF
  • 51 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1993

  37 Spruce St, Pawling, NY 12564

  Discover comfort and convenience in this beautifully maintained 2-bedroom, 2.5-bath townhouse nestled in the sought-after Cedar Valley Complex in Pawling, NY. The sun-drenched, open-concept living and dining area features a charming fireplace, offering the perfect setting for cozy nights in or easy entertaining. The kitchen is generously sized for a townhouse, offering ample cabinet space and

  Nick Selca Lakeshore Realty International

  37 Spruce St, Pawling, NY 12564
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  Est $462,470 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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  /34

  $699,000

  • 4 Beds
  • 5 Baths
  • 4,199 Sq Ft

  29 Cunningham Ln, Pawling, NY 12564

  Harmony Woods, an enclave of beautiful homes on the outskirts of the Village. This contemporary home has so much living space. Meticulously & continuously maintained by the current owners, there is nothing to be done! The 2 story foyer w/tile floors leads to the sunken LR which has high ceilings, a 2 sided fireplace, large windows & w/w carpet. There is formal DR, 2 powder rooms, then on to the

  Gillian Stewart Gillian Stewart Real Estate

  29 Cunningham Ln, Pawling, NY 12564
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  $315,000 Sold Aug 05, 2025

  • 2,130 Sq Ft
  • $148/SF
  • 51 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1997

  24 Timberline Trail, Pawling, NY 12564

  Welcome to 24 Timberline Trail—Located in a peaceful, sought-after neighborhood in Pawling, NY. This residence offers the perfect blend of comfort, functionality, and modern updates. Featuring 3 spacious bedrooms and 2.5 bathrooms, the home boasts an open and versatile layout ideal for everyday living and entertaining.Step outside to a generous first-floor deck that seamlessly extends your

  Vincent Reda Keller Williams Realty

  24 Timberline Trail, Pawling, NY 12564
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  Est $2,101,618 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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  /46

  $650,000

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

  85 Harmony Hill Rd, Pawling, NY 12564

  This charming fully remodeled, bright, and sunny ranch—featuring 3 bedrooms, 3 full bathrooms, and 2.90 acres of land. Prepare meals in the beautiful new kitchen, complete with custom cabinets, LG appliances, and quartz countertops. Relax in the family room beside the gorgeous stone fireplace. From there, step out onto the lovely wood deck and savor your morning coffee surrounded by

  Mary Craig Coldwell Banker Realty

  85 Harmony Hill Rd, Pawling, NY 12564
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  $420,000 Sold Aug 01, 2025

  • 1,056 Sq Ft
  • $398/SF
  • 29 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  7 Holiday St, Pawling, NY 12564

  Wonderful mid-century ranch enjoys beautiful, park-like property in the scenic town of Pawling! Nearby Lakeside Park is open for the summer! 36 acre lake with beach, pickle ball courts, Snack Shack, more. Now, back to the house! Large, sun-filled living rm features a bay window and hardwood floor. The spacious kitchen and dining area are lovely! Beautiful cabinetry, quartz-like countertops,

  Lisa Liffland McGrath Realty Inc

  7 Holiday St, Pawling, NY 12564
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  Est $811,558 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
• 

  

  /15

  $975,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  14 Akindale Rd, Pawling, NY 12564

  TO BE BUILT Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. Enter onto freshly paved road and stone wall entrance. This beautiful lot is on 8.44 pastoral acres with amazing views of open sky and grassy meadows. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better

  Kathryn McCoach Houlihan Lawrence Inc.

  14 Akindale Rd, Pawling, NY 12564
• 

  $430,000 Sold Aug 01, 2025

  • 1,608 Sq Ft
  • $267/SF
  • 126 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1900

  38 Old Route 55, Pawling, NY 12564

  Turn back the hands of time with this beautiful home built in 1798 reminiscent of the deep south! It's 3 stories, two of which have gorgeous wrap around newly redone porches, that you can envision with rocking chairs, sipping mint juleps or enjoying a summer meal. The 3-story farmhouse has a newly refurbished kitchen, two living rooms, 3 bedrooms, two and a half bathrooms, a cozy fireplace and

  Teddie Leonaggeo McGrath Realty Inc

  38 Old Route 55, Pawling, NY 12564
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  Est $803,131 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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  /37

  $699,000

  • 4 Beds
  • 5 Baths
  • 4,018 Sq Ft

  175 Old Quaker Hill Rd, Pawling, NY 12564

  A Stately Cape Cod Estate with exceptional Potential awaits. Set on an expansive, flat parcel of land surrounded by farms, rolling hills, and mountain views, this once grand and elegant residence offers a rare opportunity to restore and reimagine a home of timeless distinction. A property of this caliber, featuring grand proportions, architectural charm, and breathtaking grounds, is a true gem

  Tom Consaga RE/MAX Ace Realty

  175 Old Quaker Hill Rd, Pawling, NY 12564
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  $820,000 Sold Jul 28, 2025

  • 3,304 Sq Ft
  • $248/SF
  • 52 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1965

  12 Berry Ln, Pawling, NY 12564

  Nestled high atop Quaker Hill, this enchanting property offers 8.5 acres of privacy on a serene lane, just two homes away from the 4th hole of the prestigious Quaker Hill Country Club. A mid-century ranch-style home, with its distinct architectural charm and details, awaits a new owner to bring it into its next chapter. Boasting 2,704 square feet on the main floor and an additional 600 square

  Brian McGrath McGrath Realty Inc

  12 Berry Ln, Pawling, NY 12564
• 

  Est $834,843 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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  /29

  $859,000

  • 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
• 

  $510,000 Sold Jul 24, 2025

  • 1,736 Sq Ft
  • $294/SF
  • 20 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1971

  74 Harmony Hill Rd, Pawling, NY 12564

  Charming Ranch with Scenic Views and Prime Location!Nestled on a quiet street just minutes from the heart of town, this well-maintained 4-bedroom, 2-bath home offers a rare opportunity to own a piece of classic suburban charm on a sprawling 1.86-acre flat lot. Built in 1971 and on the market for the first time, this bright and sunny home combines timeless character with an unbeatable

  Patrycja Warda

  74 Harmony Hill Rd, Pawling, NY 12564
• 

  Est $823,518 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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