Pawling, NY Homes

• 

  $900,000 Sold May 09, 2025

  • 2,538 Sq Ft
  • $355/SF
  • 197 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  139 Old Quaker Hill Rd, Pawling, NY 12564

  First time on market in 44 years, this 4.08 acre magical property on Quaker Hill has been fully renovated. One won't believe the charm, character, interest & detail that has been added. Wall to wall bookshelves in the primary suite, w/a large wic, a bathroom w/shower & pocket doors, floor to ceiling windows to absorb the outdoors & guest cottage w/deck & patio nestled in a Birch grove. The LR has

  Gillian Stewart Gillian Stewart Real Estate

  139 Old Quaker Hill Rd, Pawling, NY 12564
• 

  Est $1,208,140 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,500 Sq Ft

  10 Cox Rd, Pawling, NY 12564

  10 Cox Rd, Pawling, NY 12564
• 

  

  

  /40

  $550,000 Pending

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

  36 Byrds Hill Rd, Pawling, NY 12564

  Welcome to 36 Byrds Hill Rd, Pawling, NY—a serene 3.95-acre country retreat that feels like home from the moment you arrive. This charming property features a well-designed country house that offers all the comforts of modern living, with the warmth and character of a classic country setting. Step inside and you’re immediately welcomed by a spacious mudroom—perfect for keeping shoes, boots,

  Regan Andrews Houlihan Lawrence Inc.

  36 Byrds Hill Rd, Pawling, NY 12564
• 

  $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
• 

  Est $627,431 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,152 Sq Ft

  55 Akindale Rd, Pawling, NY 12564

  55 Akindale Rd, Pawling, NY 12564
• 

  

  /36

  $359,999 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,413 Sq Ft

  33 Spruce St, Pawling, NY 12564

  Welcome to 33 Spruce Lane, a charming 2-bedroom, 2.5-bath home located in the sought-after Cedar Valley community in Pawling. This inviting townhome lives like a single-family home and offers the perfect balance of comfort, convenience, and amenities.Step inside to find a bright and open living space designed for easy living. The home features a spacious living room, a functional kitchen with

  Edmond Albano Keller Williams NY Realty

  33 Spruce St, Pawling, NY 12564
• 

  $200,000 Sold Apr 30, 2025

  • Land
  • 11.14 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
• 

  Est $527,223 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,749 Sq Ft

  30 W Wind Rd, Pawling, NY 12564

  30 W Wind Rd, Pawling, NY 12564
• 

  

  /29

  $399,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft

  12 Anderson Way, Pawling, NY 12564

  This charming cottage is within walking distance of the picturesque village of Pawling and on the market for the first time in over 35 years. Lovingly maintained and enhanced by its owner, this home boasts the ease and convenience of one level living. The renovated front porch welcomes you to the house while the beautiful sundrenched addition features heating, hardwood floor, oversized windows,

  Stacey Cronin Houlihan Lawrence Inc.

  12 Anderson Way, Pawling, NY 12564
• 

  $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
• 

  Est $1,476,016 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,480 Sq Ft

  49 S Quaker Hill Rd, Pawling, NY 12564

  49 S Quaker Hill Rd, Pawling, NY 12564
• 

  

  /37

  $449,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  36 Elm St, Pawling, NY 12564

  A historic Village Colonial on a quiet street, is a delight to show. Immaculate, well maintained & updated. Downstairs, a formal living room with a gas stove fireplace & bay windows, a formal dining room with built ins for storage, an office with closets & shelves for storage, a foyer, hardwood floors, a stunning eat in chef's kitchen with stone counters, stainless appliances, a big closet &

  Gillian Stewart Gillian Stewart Real Estate

  36 Elm St, Pawling, NY 12564
• 

  $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
• 

  Est $512,989 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,889 Sq Ft

  36 S Quaker Hill Rd, Pawling, NY 12564

  36 S Quaker Hill Rd, Pawling, NY 12564
• 

  

  /42

  $504,900

  • 3 Beds
  • 3.5 Baths
  • 3,467 Sq Ft

  2 Bridle Way, Pawling, NY 12564

  Wonderful investment opportunity awaits with this spacious home. The inviting library-style living room showcases nicely finished built-ins, while the expansive kitchen with a dining area seamlessly flows into the family room, highlighted by a cozy fireplace. The primary suite includes a private bathroom, ensuring comfort and convenience. A finished walkout lower level expands the living space

  Jonathan Gineo Jonathan D. Gineo

  2 Bridle Way, Pawling, NY 12564
• 

  $335,000 Sold Apr 21, 2025

  • 1,639 Sq Ft
  • $204/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
• 

  Est $546,847 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,992 Sq Ft

  92 W Deer Trail, Pawling, NY 12564

  92 W Deer Trail, Pawling, NY 12564
• 

  $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
• 

  Est $416,740 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  15 Washington Ct, Pawling, NY 12564

  15 Washington Ct, Pawling, NY 12564
• 

  $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
• 

  Est $557,120 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,550 Sq Ft

  86 W Deer Trail, Pawling, NY 12564

  86 W Deer Trail, Pawling, NY 12564
• 

  $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
• 

  Est $578,196 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,901 Sq Ft

  71 W Deer Trail, Pawling, NY 12564

  71 W Deer Trail, Pawling, NY 12564
• 

  $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
• 

  Est $555,067 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,898 Sq Ft

  48 W Deer Trail, Pawling, NY 12564

  48 W Deer Trail, Pawling, NY 12564
• 

  $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
• 

  Est $701,804 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,898 Sq Ft

  69 W Deer Trail, Pawling, NY 12564

  69 W Deer Trail, Pawling, NY 12564
• 

  $367,500 Sold Mar 04, 2025

  • 1,572 Sq Ft
  • $234/SF
  • 68 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1945

  27 Gobblers Knob Rd, Pawling, NY 12564

  Welcome home to this light and airy 4 Bedroom, 2 Bath Cape located on over 1 acre of level property. House sits on an expansive lot with mature plantings in a quiet and peaceful setting. Spend relaxing days on the deck or serene evenings on the rear enclosed screened in porch. Enter into an amazing living room with stone fireplace that is perfect for family gatherings. The kitchen opens into a

  Douglas McGowan Coldwell Banker Realty

  27 Gobblers Knob Rd, Pawling, NY 12564
• 

  Est $444,215 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  29 Old Route 55, Pawling, NY 12564

  29 Old Route 55, Pawling, NY 12564
• 

  $750,000 Sold Feb 27, 2025

  • 2,719 Sq Ft
  • $276/SF
  • 104 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2004

  197 Highlands Dr, Pawling, NY 12564

  Stunning Sun-Drenched Postmodern Home with Elegant Features and Curb Appeal Nestled on a lush, private lot, this beautifully maintained postmodern home offers striking curb appeal with its classic facade, landscaped gardens, and welcoming front porch-perfect for morning coffee or evening relaxation. Step inside to a bright, open-concept floor plan filled with natural light. The cathedral

  Mary Capria Shawn Michael Realty

  197 Highlands Dr, Pawling, NY 12564
• 

  Est $703,119 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,599 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  $692,500 Sold Feb 26, 2025

  • 3,078 Sq Ft
  • $225/SF
  • 144 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  31 Millstream Ct, Pawling, NY 12564

  Discover this charming 4-bedroom 2 1/2 bath, 3078 Sq Ft home on 1.57 acres minutes from the quaint Village of Pawling. At entry, step onto a beautiful wrap-around front porch, perfect for enjoying your morning coffee or unwinding in the evening. The inside foyer leads you to this bright first level, where a spacious double-sized family room awaits. Abundant natural light floods the space,

  Mary Craig Coldwell Banker Realty

  31 Millstream Ct, Pawling, NY 12564
• 

  Est $620,329 Not Listed For Sale

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

  57 Millstream Ct, Pawling, NY 12564

  57 Millstream Ct, Pawling, NY 12564
• 

  $610,000 Sold Feb 20, 2025

  • 2,900 Sq Ft
  • $210/SF
  • 37 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1999

  572 Quaker Hill Rd, Pawling, NY 12564

  Set on over 3 acres in Quaker Hill, this beautiful Colonial offers flexibility, privacy, and endless potential. The open floor plan includes a formal dining room, inviting family room with a gas fireplace, and a kitchen with granite countertops and stainless steel appliances.A mudroom accessed from the 2 gar garage helps keep messy shoes and coats organized and out of sight. Upstairs, the primary

  Barbara Allen HomeSmart Homes & Estates

  572 Quaker Hill Rd, Pawling, NY 12564
• 

  Est $404,847 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,394 Sq Ft

  6 Harmony Hill Rd, Pawling, NY 12564

  6 Harmony Hill Rd, Pawling, NY 12564
• 

  $150,000 Sold Feb 20, 2025

  • Land
  • 4.43 Acres
  • $33,860 per Acre

  • 151 Days On Market

  Unlisted Address

  Explore this exceptional 4+ acre level lot on Estate Drive, nestled further into the peaceful Cushman Road subdivision in Pawling, NY. Enjoy the privacy of this serene setting while benefiting from shared access with two other similar properties via a common driveway. This lot is equipped with underground utilities and a well, offering a smooth building process. Located just 6 minutes from the

  Colleen McGrath McGrath Realty Inc

  Unlisted Address
• 

  Est $463,534 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,021 Sq Ft

  34 Mohawk Trail, Pawling, NY 12564

  34 Mohawk Trail, Pawling, NY 12564
• 

  $746,000 Sold Feb 14, 2025

  • 2,600 Sq Ft
  • $287/SF
  • 56 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2021

  25 Liberty Ln, Pawling, NY 12531

  EXQUISITE Bi-level Colonial custom-built in 2021. This ENERGY EFFICIENT & ECO friendly home is an ideal blend of country design with modern characteristics. Situated on 2 ACRES of private level all fenced-in land w/a long driveway, lush lawns and beautiful gardens with patios & decks, a swimming pool, and breathtaking views of the countryside. Enter through a mahogany door to the 2-story foyer

  Magdalena Pawlowska Coldwell Banker Realty

  25 Liberty Ln, Pawling, NY 12531
• 

  /2

  Est $385,573 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,115 Sq Ft

  45 Mohawk Trail, Pawling, NY 12564

  45 Mohawk Trail, Pawling, NY 12564
• 

  $999,000 Sold Feb 13, 2025

  • 3,660 Sq Ft
  • $273/SF
  • 27 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1981

  37 San Souci Dr, Pawling, NY 12564

  This unique and beautifully designed 5-bedroom mother-daughter property offers the perfect blend of togetherness and independence surrounded by peace and nature. Nestled in a tranquil, picturesque setting, both homes are separate yet conveniently close, ideal for multi-generational living. As you approach, you’ll be greeted by a beautiful entrance lined with flowering trees and gorgeous

  Colleen McGrath McGrath Realty Inc

  37 San Souci Dr, Pawling, NY 12564

Showing Results 121 - 160, Page 4 of 18