Pawling, NY Homes

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  $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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  $1,275 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. Call only

  23 W Main St Unit 1A, Pawling, NY 12564
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  $949,900 Sold May 02, 2025

  • 3,798 Sq Ft
  • $250/SF
  • 6 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2000

  14 Little Pond Rd, Pawling, NY 12564

  This Colonial home is absolutely lovely and is situated in a serene and beautiful setting. With 7.88 acres of land on a quiet country road, it offers both privacy and convenience. The design and features are perfect for comfortable living, whether you're looking for a year-round residence or a weekend retreat. The home welcomes you through a charming rocking chair front porch, leading into a

  Teddie Leonaggeo McGrath Realty Inc

  14 Little Pond Rd, Pawling, NY 12564
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  Est $1,089,712 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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  $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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  $2,850 per month

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

  71 E Main St Unit 202, 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 202, Pawling, NY 12564
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  $200,000 Sold Apr 30, 2025

  • Land
  • 11 Acres
  • $17,953 per Acre

  • 47 Days On Market

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

  Very nice size building lot 11.14 Acres. Builders take a look. 869 feet road frontage on S Quaker Hill Road Zoned CD-R5 residential. directions look for mail box # 40 property located right across the street. long road frontage. four real estate signs along the frontage. new listing. you know some one once said .drive up for the week end stay a life time. this is a keeper will not last long

  John Melchior Howard Hanna Rand Realty

  0 S Quaker Hill Rd Unit KEY822354, Pawling, NY 12564
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  Est $451,290 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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  $540,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,341 Sq Ft

  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

  (845) 250-3483

  85 W Deer Trail, 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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  $499,850 Sold Apr 28, 2025

  • 1,876 Sq Ft
  • $266/SF
  • 14 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  56 Gristmill Ln, Pawling, NY 12564

  Escape to your own private sanctuary in the heart of Pawling! This unique and multi-functional split ranch is situated on over an acre of meticulously maintained lawns, offering exceptional privacy and breathtaking natural beauty. Just minutes away from nature reserves and the historic Dutcher Golf Course, this home provides the perfect blend of serenity and recreation. Inside, discover a

  Gino Bello Howard Hanna Rand Realty

  56 Gristmill Ln, 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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  $499,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft

  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

  (845) 493-3423

  17 Fenwood Dr, Pawling, NY 12564
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  /31

  $2,400 per month

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

  71 E Main St Unit 203, 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 203, Pawling, NY 12564
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  $840,000 Sold Apr 28, 2025

  • 2,768 Sq Ft
  • $303/SF
  • 103 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1967

  9 Strawberry Hill Rd, Pawling, NY 12564

  Nestled on 7 serene acres, this exceptional property offers complete privacy and tranquility. Designed by renowned local architect William Berkley, known for his mid-century modern and contemporary designs on Quaker Hill, this 2,768 SF home, built in 1967, is bathed in natural light and surrounded by stunning landscapes. The property’s design integrates walls of windows and sliding glass doors,

  Brian McGrath McGrath Realty Inc

  9 Strawberry Hill Rd, Pawling, NY 12564
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  Est $1,474,593 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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  $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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  $3,250 per month

  • 2 Beds
  • 2 Baths
  • 1,089 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 205, 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 205, Pawling, NY 12564
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  $355,000 Sold Apr 21, 2025

  • 1,639 Sq Ft
  • $217/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  34 Spruce St, Pawling, NY 12564

  End unit townhome in Cedar Valley. Living room has cathedral ceilings, fireplace and french doors to patio. Primary bedroom/bath suite on first floor. Second floor bedroom/bath guest suite. Only one step from curb to entrance. Easy access to Route 22 and Route 55. Close to the Village of Pawling, shopping, schools and services.

  James Bergstraser RE/MAX Classic Realty

  34 Spruce St, Pawling, NY 12564
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  Est $1,200,961 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,745 Sq Ft

  47 Lola Ln, Pawling, NY 12564

  47 Lola Ln, Pawling, NY 12564
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  $799,999 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 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. 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 bright foyer with hardwood floors, leading to a

  

  Shannon Tully

  McGrath Realty Inc

  (845) 622-7595

  94 S Quaker Hill Rd, Pawling, NY 12564
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  /43

  $3,400 per month

  • 2 Beds
  • 2 Baths
  • 1,089 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 305, 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 305, Pawling, NY 12564
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  $365,000 Sold Apr 10, 2025

  • 2,100 Sq Ft
  • $174/SF
  • 20 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  4 Juniper Ln, Pawling, NY 12564

  Welcome to this cozy and well-maintained 2-bedroom, 2.5-bathroom townhouse with finished basement, offering a perfect blend of comfort, functionality, and extra living space. The open-concept living area with fire place is filled with natural light, creating a warm, inviting atmosphere that’s perfect for relaxing or entertaining. The kitchen is thoughtfully designed with efficient storage and

  Josephine Diego K. Fortuna Realty, Inc.

  4 Juniper Ln, Pawling, NY 12564
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  Est $463,198 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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  $1,500,000 Open Sat 1PM - 5PM

  • 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

  604 N Quaker Hill Rd, Pawling, NY 12564
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  $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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  $355,000 Sold Apr 08, 2025

  • 720 Sq Ft
  • $493/SF
  • 82 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  26 Taber Knolls Dr, Pawling, NY 12564

  Nestled in a serene country setting just a few miles from the charming village of Pawling, this delightful bungalow offers the perfect blend of tranquility and convenience. Located close to the Metro North Train Station, local shops, restaurants, and parks, this home makes both commuting and leisure readily accessible. With the ease of one level living and charming details like hardwood floors, a

  Reid McGrath McGrath Realty Inc

  26 Taber Knolls Dr, Pawling, NY 12564
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  Est $1,632,732 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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  $799,900 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,350 Sq Ft

  134 Old Pawling Rd, Pawling, NY 12564

  Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

  Drita Shala Howard Hanna Rand Realty

  134 Old Pawling Rd, Pawling, NY 12564
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  $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
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  $422,000 Sold Apr 07, 2025

  • 1,600 Sq Ft
  • $264/SF
  • 30 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2000

  39 Nathan Pierce Ct, Pawling, NY 12564

  Welcome to your dream townhome in the heart of Pawling's sought-after Deerfield Ponds community! This rarely available 3-bedroom, 2.5-bathroom home offers 1,600 square feet of living space across its main floors, complemented by a basement that provides abundant storage. From the moment you step onto the charming front porch and through the inviting foyer, you’ll feel right at home. The large,

  Claudia Jiskra McGrath Realty Inc

  39 Nathan Pierce Ct, Pawling, NY 12564
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  Est $769,229 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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  $1,495,000

  • 3 Beds
  • 2.5 Baths
  • 3,035 Sq Ft

  6 Byrds Hill Rd, Pawling, NY 12564

  Modern Pawling Farmhouse - This beautifully renovated Colonial home near Scenic Quaker Hill offers a perfect blend of charm and modern amenities. The spacious kitchen, complete with a center island with seating, flows seamlessly into an open dining and living area, where a cozy fireplace awaits. A separate light-filled den provides a peaceful retreat for relaxation. The main floor features a

  Stephen Pener William Pitt Sothebys Int Rlty

  6 Byrds Hill Rd, Pawling, NY 12564
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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
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  $975,000 Sold Apr 07, 2025

  • 4,615 Sq Ft
  • $211/SF
  • 21 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2000

  11 Birch Hill Rd, Pawling, NY 12564

  An incredible opportunity awaits atop Quaker Hill. Set on a park-like 1.34-acre parcel framed by picturesque stone walls, this custom-built colonial spans 4,615 SF over three floors. The home is complemented by a stunning 24 x 36 two-story post-and-beam barn, a serene pond, raised garden beds, and expansive outdoor spaces. The home's design is incredibly functional, with a flexible floor plan

  Claudia Jiskra McGrath Realty Inc

  11 Birch Hill Rd, Pawling, NY 12564
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  Est $784,720 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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  $845,000

  • 4 Beds
  • 3 Baths
  • 3,304 Sq Ft

  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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  /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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  $100,000 Sold Mar 11, 2025

  • Land
  • 0.36 Acre
  • $277,778 per Acre

  • 129 Days On Market

  1074 W Dover Rd, Pawling, NY 12564

  Come build your Dream Home and experience the Good Life at this Wonderful Parcel of Land for Sale in Dutchess County! This is the ideal location to come home to for some peace and relaxation, underneath your lush, Crimson Maple Tree! You'll have a head start with your preparation plans. Not only is this a BOE approved property, but it boasts a 1250 foot drilled well (Pump is located 600 ft down &

  Robert Pape Keller Williams NY Realty

  1074 W Dover Rd, Pawling, NY 12564
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  Est $931,538 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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