Pawling, NY Homes

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  $1,300,000

  • 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
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  $3,200 per month

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft
  • House for Rent

  40 Cedar Ln, Pawling, NY 12564

  A charming Cape Cod rental, 3 bedroom, 2.5 bathrooms privately located on 5.5 acres & a long private driveway. This home has been renovated with wood floors throughout the downstairs, pergo flooring upstairs, all carpeting has been removed. A new roof has been installed. There is a private patio behind the home & a 12 x 20 shed for storage. The primary bedroom has a laundry chute for your

  Gillian Stewart Gillian Stewart Real Estate

  40 Cedar Ln, Pawling, NY 12564
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  $1,375,000 Sold May 13, 2025

  • 2,910 Sq Ft
  • $473/SF
  • 60 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1926

  54 Burgess Rd, Pawling, NY 12564

  Nestled in the prestigious Quaker Hill Hamlet of Pawling, NY, Burgess House is a distinguished estate where historic charm meets modern refinement. Perched atop a scenic hillside, this exceptional residence offers breathtaking panoramic views of the protected landscapes of Connecticut Audubon’s Deer Pond Farm, ensuring a serene and private retreat. Steeped in history, the 3-bedroom, 3.1-bathroom

  Jake Garay Serhant LLC

  54 Burgess Rd, Pawling, NY 12564
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  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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  $720,000

  • 4 Beds
  • 4.5 Baths
  • 2,920 Sq Ft

  12 W Wind Rd, Pawling, NY 12564

  Nestled on over two serene acres and backing to a tranquil nature preserve, this beautifully maintained home offers the perfect blend of peace, privacy, and natural beauty. With breathtaking seasonal views of the surrounding woodlands, the setting is ideal for quiet reflection or lively gatherings.Though the tax card shows four-bedrooms, this spacious home lives like a five-bedroom, offering

  Doris Jean William Raveis Real Estate

  12 W Wind Rd, Pawling, NY 12564
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  $25,000 per month

  • 4 Beds
  • 3.5 Baths
  • 4,233 Sq Ft
  • House for Rent

  121 N Quaker Hill Rd, Pawling, NY 12564

  $20k June, July $25k, August $30k Summer 2025. 4 bedroom 3.5 designer inspired home intended to complement the splendor of its natural surroundings. Fully furnished for comfortable luxury. 3 fireplaces and awe inspiring panoramic views. Soak in a breathtaking scene spanning the great meadow, rolling hills and mountains beyond. Long driveway with mature landscape, this hideaway provides pure

  Joseph Lorino Brown Harris Stevens HV LLC

  121 N Quaker Hill Rd, Pawling, NY 12564
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  $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
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  Est $536,177 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,262 Sq Ft

  775 N Quaker Hill Rd, Pawling, NY 12564

  775 N Quaker Hill Rd, Pawling, NY 12564
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  $799,900 Open Sat 2:30PM - 4:30PM

  • 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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  $3,800 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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  $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 $524,961 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,884 Sq Ft

  18 Anderson Rd, Pawling, NY 12564

  18 Anderson Rd, Pawling, NY 12564
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  $699,000

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  5 Red Tail Ct, Pawling, NY 12564

  Tucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tail Court is a beautifully maintained 5-bedroom, 2.5-bathroom Colonial offering space, style, and convenience. With 2,924 sq ft of living space, this home features an inviting floor plan, perfect for both everyday living and entertaining.Step inside to find a sun-filled living room with a cozy fireplace, a

  Julius Cooper eXp Realty

  5 Red Tail Ct, 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 $1,361,579 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,234 Sq Ft

  535 N Quaker Hill Rd, Pawling, NY 12564

  535 N Quaker Hill Rd, Pawling, NY 12564
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  $1,250,000

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

  120 Harmony Rd, Pawling, NY 12564

  New construction 4 bedroom, 4.5 bathroom home on 5 acres. Don't miss this opportunity to customize your dream home. This home features a open floor plan with large kitchen, perfect for entertaining. The main living area has exposed beams and high ceilings. The primary bedroom has large walk in closet and ensuite. There is also a junior suite with ensuite. See attached floor plans for full detail.

  Bliss Voutsinas

  120 Harmony Rd, 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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  Est $1,042,820 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,407 Sq Ft

  50 Meeting House Rd, Pawling, NY 12564

  50 Meeting House Rd, Pawling, NY 12564
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  $1,100,000

  • 5 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  51 Estate Dr, Pawling, NY 12564

  Don't miss this opportunity to have your dream home built and custom designed to your finishes. As you step inside, you're greeted by a grand foyer entrance with high ceilings open to the second floor. Discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, quartz countertops, and center island. The oversized open floor plan seamlessly

  Tony Zaccardo Coldwell Banker Realty

  51 Estate Dr, 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 $1,188,555 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft

  908 Old Quaker Hill Rd, Pawling, NY 12564

  908 Old Quaker Hill Rd, Pawling, NY 12564
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  $845,000 Pending

  • 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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  $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
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  Est $693,048 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft

  270 N Quaker Hill Rd, Pawling, NY 12564

  270 N Quaker Hill Rd, Pawling, NY 12564
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  $1,300,000 Pending

  • 3 Beds
  • 3 Baths
  • 3,038 Sq Ft

  7 Tower Hill Rd, Pawling, NY 12564

  Nestled among the towering trees, this spacious 5-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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  $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 $690,051 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,209 Sq Ft

  64 Game Farm Rd, Pawling, NY 12564

  64 Game Farm Rd, Pawling, NY 12564
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  $650,000

  • 3 Beds
  • 3 Baths
  • 1,450 Sq Ft

  54 Nanny Hill Rd, Pawling, NY 12564

  This stunning home is brand new from Westchester modular, built with top-of-the-line finishes and quality materials. As soon as you step inside, you'll be greeted by a bright and airy open floor plan that creates a spacious and inviting atmosphere. The chef's kitchen is a standout feature, featuring an oversized island with a prep sink and high-end appliances that are sure to appeal to the

  Kaye Saglibene

  54 Nanny Hill Rd, 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 $1,155,892 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 6,052 Sq Ft

  382 Old Quaker Hill Rd, Pawling, NY 12564

  382 Old Quaker Hill Rd, Pawling, NY 12564
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  $425,000

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  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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  $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 $369,208 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  62 S Quaker Hill Rd, Pawling, NY 12564

  62 S Quaker Hill Rd, Pawling, NY 12564
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  $456,600

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  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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  $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 $613,960 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,220 Sq Ft

  42 Sumner Ln, Pawling, NY 12564

  42 Sumner Ln, Pawling, NY 12564
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  $499,000

  • 5 Beds
  • 1,062 Sq Ft

  215 Little Pond Rd, Pawling, NY 12564

  Private Lake House on a Private Lake!Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and peaceful environment.

  Jillian Pajer Douglas Elliman Real Estate

  215 Little Pond Rd, Pawling, NY 12564
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  $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
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  Est $673,951 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,944 Sq Ft

  1104 Route 22, Pawling, NY 12564

  1104 Route 22, Pawling, NY 12564
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  $495,000

  • 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

Showing Results 41 - 80, Page 2 of 18