Pawling, NY Homes

• 

  

  

  /29

  $699,000

  • 4 Beds
  • 3 Baths
  • 3,888 Sq Ft

  12 Rebecca Dr, Pawling, NY 12564

  Surrounded by the natural beauty of the Hudson Valley region, this Multi-Family home benefits from a private environment that outdoor enthusiasts will find irresistible. This property's location offers convenient access to the Lakeside Park Disc Golf Course, the nearby Appalachian Trail which provides endless hiking opportunities for nature lovers and the Metro-North Railroad being about a 5

  Kevin Sanabria eRealty Advisors, Inc

  12 Rebecca Dr, Pawling, NY 12564
• 

  $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
• 

  Est $649,491 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,314 Sq Ft

  77 N Quaker Hill Rd, Pawling, NY 12564

  77 N Quaker Hill Rd, Pawling, NY 12564
• 

  

  

  /10

  $159,000

  • Land
  • 0.73 Acre
  • $217,808 per Acre

  0 Walnut St, Pawling, NY 12564

  Great lot in the Village of Pawling! *Board of Health Approval is NOT required because the house will be hooked up to municipal water and sewer! This .73-acre lot offers a lovely western view. Walk to the picturesque Village center with its quaint shops, bakeries, restaurants, library, post office, health care, so much more! Metro-North Train Station (Harlem Line) is located in the Village as

  Lisa Liffland McGrath Realty Inc

  0 Walnut St, 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 $471,308 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  19 San Souci Dr, Pawling, NY 12564

  19 San Souci Dr, Pawling, NY 12564
• 

  

  /28

  $419,900

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  23 Union St, Pawling, NY 12564

  3 Bed | 2 Bath | Fully Electric | Walkable Village LocationTurnkey, updated, freshly painted, and full of charm—this 3-bedroom, 2-bath home is perfectly situated in the heart of Pawling Village. Whether you're a first-time buyer using FHA or VA financing, a downsizer, or simply seeking a low-maintenance, energy-efficient home, this property offers a flexible layout, thoughtful upgrades, and

  Brett David Miller K Fortuna Lighthouse Realty

  23 Union St, Pawling, NY 12564
• 

  $376,500 Sold Jun 18, 2025

  • 1,427 Sq Ft
  • $264/SF
  • 13 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1997

  18 Evergreen Way, Pawling, NY 12564

  Welcome to this well maintained end unit in the desirable Cedar Valley. This home features two spacious bedrooms including a large first floor primary with en suite bath and walk in closet. The second bedroom is located upstairs and also includes a full bath along with plenty of closet space and storage. The main living area boasts a cozy fireplace with large windows that flood the space with

  Vicki Reinach BHHS Hudson Valley Properties

  18 Evergreen Way, Pawling, NY 12564
• 

  Est $535,371 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,324 Sq Ft

  17 San Souci Dr, Pawling, NY 12564

  17 San Souci Dr, 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
• 

  $645,000 Sold Jun 13, 2025

  • 1,900 Sq Ft
  • $339/SF
  • 20 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1880

  32 Elm St, Pawling, NY 12564

  Welcome to 32 Elm Street – a stunning blend of historic charm and modern convenience! This beautifully renovated 1880s home, reimagined in 2025, offers 3 spacious bedrooms, 2.5 bathrooms, and 1,900 sq ft of stylish living space. Nestled on a .27-acre lot with easy access from both Elm and Walnut Streets, this home is perfectly located just a 4-minute walk to the Metro North train station and a

  Patrycja Warda

  32 Elm St, Pawling, NY 12564
• 

  Est $454,106 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,166 Sq Ft

  9 San Souci Dr, Pawling, NY 12564

  9 San Souci Dr, Pawling, NY 12564
• 

  

  /47

  $574,900

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft

  28 Gobblers Knob Rd, Pawling, NY 12564

  Welcome to 28 Gobblers Knob Road – A Hudson Valley Retreat! Nestled in the heart of the rolling hills of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on over 20 acres, offering peace, privacy, and natural beauty in every direction. Just over 3 miles from the Metro-North line to Manhattan, you can enjoy the quiet of a country escape without sacrificing

  Mark Snyder eXp Realty

  28 Gobblers Knob Rd, Pawling, NY 12564
• 

  $435,000 Sold Jun 06, 2025

  • 1,917 Sq Ft
  • $227/SF
  • 13 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2001

  103 Mohawk Trail, Pawling, NY 12564

  Welcome to your dream home nestled in the heart of Pawling's coveted Deerfield Ponds community! This rarely available and most sought-after 3-bedroom, 2 1/2-bathroom townhome features the primary bedroom conveniently located on the first floor. Spanning 1,917 square feet across two floors, with an additional 1,104 square foot unfinished basement, this home offers unlimited potential, complete

  Claudia Jiskra McGrath Realty Inc

  103 Mohawk Trail, Pawling, NY 12564
• 

  Est $618,843 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,500 Sq Ft

  48 Poppys Ln, Pawling, NY 12564

  48 Poppys Ln, Pawling, NY 12564
• 

  

  /24

  $399,000

  • 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
• 

  $412,500 Sold May 27, 2025

  • 1,564 Sq Ft
  • $264/SF
  • 43 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  10 John Kane Ct, Pawling, NY 12564

  Welcome to your dream home in the heart of Pawling's Deerfield Ponds community! This beautiful 2-bedroom, 2-bathroom townhouse features an open floor plan that flows between the dining room and the spacious living room, which has a wood-burning fireplace. It also includes a bonus room and a full unfinished basement. The basement could become a playroom, multimedia room, or a storage area. This

  Jessica Diaz Coldwell Banker Realty

  10 John Kane Ct, Pawling, NY 12564
• 

  Est $391,663 Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 1,943 Sq Ft

  2 Timberline Trail, Pawling, NY 12564

  2 Timberline Trail, Pawling, NY 12564
• 

  

  /47

  $1,175,000

  • 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
• 

  $540,000 Sold May 23, 2025

  • 2,341 Sq Ft
  • $231/SF
  • 23 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2001

  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

  85 W Deer Trail, Pawling, NY 12564
• 

  Est $323,623 Not Listed For Sale

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

  24 Spruce St, Pawling, NY 12564

  24 Spruce St, Pawling, NY 12564
• 

  

  /3

  $149,900

  • Land
  • 4.21 Acres
  • $35,606 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

  Michael Knecht Howard Hanna Rand Realty

  0 South Rd Unit KEY853088, Pawling, NY 12531
• 

  $674,900 Sold May 21, 2025

  • 2,876 Sq Ft
  • $235/SF
  • 134 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1930

  24 Sheridan Dr, Pawling, NY 12564

  Check out this Charming Country Cottage in the Village of Pawling! Nestled on almost 7 acres of serene land, this delightful country cottage offers the perfect blend of comfort and tranquility. Hardwood floors flow throughout the home, enhancing the warm, rustic charm. The sun-soaked living room, complete with a wood-burning fireplace, invites relaxation, while the eat-in kitchen is perfect for

  John Gabriel Jr KW MidHudson

  24 Sheridan Dr, Pawling, NY 12564
• 

  Est $386,710 Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 2,109 Sq Ft

  14 Spruce St, Pawling, NY 12564

  14 Spruce St, Pawling, NY 12564
• 

  

  /47

  $1,450,000

  • 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
• 

  $560,000 Sold May 20, 2025

  • 2,552 Sq Ft
  • $219/SF
  • 132 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1975

  130 Old Route 55, Pawling, NY 12564

  Single family 5 bedroom, 3 bath country home. Secluded in the woods, but close to town. 10.39 acres with pool and 2 paddock barn offering a unique experience for those desiring privacy and a connection to nature. Small bungalow in back perfect for an office or recreational area.

  Derek Eisenberg Continental Real Estate Group

  130 Old Route 55, Pawling, NY 12564
• 

  Est $381,668 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  9 Juniper Ln, Pawling, NY 12564

  9 Juniper Ln, Pawling, NY 12564
• 

  

  /33

  $1,250,000

  • 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
• 

  $490,000 Sold May 16, 2025

  • 1,716 Sq Ft
  • $286/SF
  • 85 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  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

  17 Fenwood Dr, Pawling, NY 12564
• 

  Est $381,813 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,113 Sq Ft

  5 Hemlock Cir, Pawling, NY 12564

  5 Hemlock Cir, Pawling, NY 12564
• 

  

  /15

  $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 Hillside Realty & Development

  120 Harmony Rd, Pawling, NY 12564
• 

  $607,000 Sold May 16, 2025

  • 3,732 Sq Ft
  • $163/SF
  • 235 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1967

  32 Gristmill Ln, Pawling, NY 12564

  Enjoy the village lifestyle in historic Pawling. This private, 1.4-acre, treelined property is less than a mile to the Village with shops, restaurants, library, Metro North station, Dutcher Golf Course, and the Village Green with Farmer's Market (June-October). Close proximity to Lakeside & Morrow parks and the Appalachian & Oblong Trails. This sprawling, mother/ daughter style home includes an

  Carol Aprile

  32 Gristmill Ln, Pawling, NY 12564
• 

  Est $387,699 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,030 Sq Ft

  4 Aspen Ct, Pawling, NY 12564

  4 Aspen Ct, Pawling, NY 12564
• 

  

  /20

  $3,900,000

  • Land
  • 108 Acres
  • $36,111 per Acre

  57 S Quaker Hill Rd, Pawling, NY 12564

  Seldom does a property like this become available. Two parcels totaling 108 acres create the most idyllic setting on Quaker Hill. Imagine a pastoral retreat blanketed by farmed fields, well-maintained trails, and productive land. With approximately 56 cleared acres, the possibilities are endless. Build your dream country estate, an extended family compound, or an equestrian paradise with ample

  Brian McGrath McGrath Realty Inc

  57 S Quaker Hill Rd, Pawling, NY 12564
• 

  $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
• 

  Est $369,512 Not Listed For Sale

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

  28 Evergreen Way, Pawling, NY 12564

  28 Evergreen Way, Pawling, NY 12564
• 

  

  /3

  $189,000

  • Land
  • 11.4 Acres
  • $16,579 per Acre

  0 Kirby Hill Rd, Pawling, NY 12564

  Great 11 acre BOHA property in Quaker Hill area of Pawling. Great views. Located quiet area next to historic library (not active. Shown as museum in warmer weather). Fantastic getaway area or permanent dream house.

  Richard Castro Howard Hanna Rand Realty

  0 Kirby Hill Rd, Pawling, NY 12564
• 

  $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 $366,300 Not Listed For Sale

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

  7 Evergreen Way, Pawling, NY 12564

  7 Evergreen Way, Pawling, NY 12564
• 

  

  /36

  $5,500,000

  • 17 Beds
  • 13 Baths
  • 15,000 Sq Ft

  618 Quaker Hill Rd, Pawling, NY 12564

  25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4

  Harriet Norris Douglas Elliman Real Estate

  618 Quaker Hill Rd, Pawling, NY 12564

Showing Results 81 - 120, Page 3 of 18