Dutchess, NY Homes

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  /49

  $595,000 Open Sun 12PM - 2PM

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

  7 Glen Ct, Pawling, NY 12564

  Welcome to this beautifully renovated 3-bedroom, 2.5-bath Colonial home offering over 2,300 sq ft of stylish and comfortable living space. Nestled in a quiet cul-de-sac and private setting in Pawling, this move-in-ready residence blends classic charm with modern upgrades. Step into the heart entryway where you can hang your coat, kick your shoes off, and feel right where you need to be. Make your

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 584-8385

  7 Glen Ct, Pawling, NY 12564
• 

  Explore Pawling

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  /23

  $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
• 

  $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
• 

  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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  /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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  /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
• 

  $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 $420,456 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

  $785,000

  • 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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  /43

  $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
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  $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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  Not Listed For Sale

  9 Ravine Rd, Pawling, NY 12564

  9 Ravine 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

  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. This charming, expansive ranch home is thoughtfully designed to suit a variety of living

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 576-1665

  126 Old Route 55, 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
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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
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  Est $1,591,521 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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  /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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  /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
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  $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
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  Est $459,834 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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  /8

  $185,000 Pending

  • 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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  /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
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  $410,000 Sold Jul 24, 2025

  • 1,400 Sq Ft
  • $293/SF
  • 34 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1960

  11 Birch Terrace, Pawling, NY 12564

  Welcome to Pawling Lake Estates - a private lake community about 10 minutes outside the Village of Pawling. This adorable cozy Cape is located on a dead-end road. Has 2 bedrooms but can easily live like a 3-bedroom home. Main level has eat in kitchen with breakfast nook, cozy living room with big bay window. 2 Bedrooms and a main bath. Doors in kitchen that lead out to a nice size deck

  Teddie Leonaggeo McGrath Realty Inc

  11 Birch Terrace, Pawling, NY 12564
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  Est $2,315,149 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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  /49

  $569,000 Pending

  • 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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  /24

  $3,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,229 Sq Ft
  • Apartment for Rent

  921 W Dover Rd, Pawling, NY 12564

  ALL INCLUSIVE RENTAL! All utilities and services are included. This 3-bedroom, 2.5 bathroom no-step main floor apartment is now available. Consisting of the whole main level of a beautiful, custom quality built ranch home and nestled on 8+ private acres, this apartment is 2200+ square feet! This modern house boasts a beautiful and open floor plan. A chef's kitchen has extensive granite counters,

  Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  921 W Dover Rd, Pawling, NY 12564
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  $1,405,000 Sold Jul 24, 2025

  • 3,038 Sq Ft
  • $462/SF
  • 49 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  7 Tower Hill Rd, Pawling, NY 12564

  Nestled among the towering trees, this spacious 4-bedroom, 3-bath custom-designed home offers the perfect blend of privacy, comfort, and modern amenities. Sit back and enjoy the captivating views from the three expansive decks, overlooking the waterfall, ponds, and large yard below. The home's distinctive architecture is shown in its thoughtful design, encompassing the natural setting, while

  Ryan Arket Compass Greater NY, LLC

  7 Tower Hill Rd, Pawling, NY 12564
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  Est $774,598 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
• 

  

  /17

  $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
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  $430,000 Sold Jul 22, 2025

  • 1,500 Sq Ft
  • $287/SF
  • 177 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1963

  26 Fenwood Dr, Pawling, NY 12564

  Welcome to this delightful sunlit Ranch style home nestled on a beautiful and quiet corner lot. This home features 3 nice size bedrooms, a full bath and convenient half bath off the dining/family room. The eat in kitchen offers upscale stainless steel appliances along with ample counter and cabinet space for all your culinary needs. The full size attic can be used for storage or even transformed

  Vicki Reinach BHHS Hudson Valley Properties

  26 Fenwood Dr, Pawling, NY 12564
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  Est $797,963 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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  $532,000 Sold Jul 18, 2025

  • 2,175 Sq Ft
  • $245/SF
  • 23 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1999

  104 Mohawk Trail, Pawling, NY 12564

  Charming 3-Bedroom Home in Pawling’s Desirable Deerfield Ponds Community.Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom single-family home nestled in the sought-after Deerfield Ponds Community in Pawling, NY. Offering 2,175 sq. ft. of living space, this home boasts both comfort and convenience.Step inside to find a thoughtfully designed floor plan with renovated bathrooms

  Pete Rodriguez William Raveis Real Estate

  104 Mohawk Trail, Pawling, NY 12564
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  Est $844,409 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

  $879,000

  • 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
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  $345,000 Sold Jul 09, 2025

  • 900 Sq Ft
  • $383/SF
  • 26 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1990

  88 Lakeview Dr, Pawling, NY 12564

  Charming Cottage in Private Community of Pawling Lake Estates. Adjacent to the Appalachian Trail and the Great Swamp of Putnam and Dutchess County, sitting atop the West Mountain State Park you will find our Community, a Hidden Gem. Privacy, Peace and Tranquility abound in this Natural Setting. This Home has been lovingly cared for and updated with Replacement Windows, Vinyl Siding, Gutter Guards

  Martha Woodhouse Howard Hanna Rand Realty

  88 Lakeview Dr, Pawling, NY 12564
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  Est $822,450 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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  /47

  $1,250,000

  • 4 Beds
  • 6 Baths
  • 3,012 Sq Ft

  16 Anderson Rd, Pawling, NY 12564

  Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping

  Ryan Arket Compass Greater NY, LLC

  16 Anderson Rd, 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 $1,125,016 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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