Pawling


Nestled in the rolling hills of Dutchess County, Pawling offers a perfect blend of historic charm and modern convenience. This picturesque community features stunning country landscapes and distinctive architecture while providing exceptional accessibility with two Metro-North train stations and proximity to interstate transportation.

Rich in heritage, Pawling proudly preserves landmarks like the historic Quaker Meeting House, listed on the National Register of Historic Places. History enthusiasts can explore the John Kane House, which served as George Washington’s headquarters for two months in 1778. Golf lovers will appreciate the historic Dutcher Golf Course, recognized as the oldest public golf course in the United States and still welcoming players today.

Outdoor recreation abounds with tennis courts, two lakes, and more than 300 acres of parkland. Nature enthusiasts can explore the Great Swamp, traverse sections of the Appalachian Trail, or discover protected areas within the Nature Conservancy. The community spirit thrives through numerous volunteer organizations that contribute to Pawling’s distinctive character.

The area offers excellent educational opportunities through various learning institutions, along with diverse cultural experiences at local theaters. The community’s economic vitality is supported by businesses including the Pawling Corporation, a manufacturer of industrial products.

With its perfect combination of natural beauty, historic significance, and modern amenities, Pawling provides an exceptional lifestyle for those seeking a welcoming community in a picturesque setting.

Nestled in the rolling hills of Dutchess County, Pawling offers a perfect blend of historic charm and modern convenience. This picturesque community features stunning country landscapes and distinctive architecture while providing exceptional accessibility with two Metro-North train stations and proximity to interstate transportation.

Rich in heritage, Pawling proudly preserves landmarks like the historic Quaker Meeting House, listed on the National Register of Historic Places. History enthusiasts can explore the John Kane House, which served as George Washington’s headquarters for two months in 1778. Golf lovers will appreciate the historic Dutcher Golf Course, recognized as the oldest public golf course in the United States and still welcoming players today.

Outdoor recreation abounds with tennis courts, two lakes, and more than 300 acres of parkland. Nature enthusiasts can explore the Great Swamp, traverse sections of the Appalachian Trail, or discover protected areas within the Nature Conservancy. The community spirit thrives through numerous volunteer organizations that contribute to Pawling’s distinctive character.

The area offers excellent educational opportunities through various learning institutions, along with diverse cultural experiences at local theaters. The community’s economic vitality is supported by businesses including the Pawling Corporation, a manufacturer of industrial products.

With its perfect combination of natural beauty, historic significance, and modern amenities, Pawling provides an exceptional lifestyle for those seeking a welcoming community in a picturesque setting.

Nestled in the rolling hills of Dutchess County, Pawling offers a perfect blend of historic charm and modern convenience. This picturesque community features stunning country landscapes and distinctive architecture while providing exceptional accessibility with two Metro-North train stations and proximity to interstate transportation.

Rich in heritage, Pawling proudly preserves landmarks like the historic Quaker Meeting House, listed on the National Register of Historic Places. History enthusiasts can explore the John Kane House, which served as George Washington’s headquarters for two months in 1778. Golf lovers will appreciate the historic Dutcher Golf Course, recognized as the oldest public golf course in the United States and still welcoming players today.

Outdoor recreation abounds with tennis courts, two lakes, and more than 300 acres of parkland. Nature enthusiasts can explore the Great Swamp, traverse sections of the Appalachian Trail, or discover protected areas within the Nature Conservancy. The community spirit thrives through numerous volunteer organizations that contribute to Pawling’s distinctive character.

The area offers excellent educational opportunities through various learning institutions, along with diverse cultural experiences at local theaters. The community’s economic vitality is supported by businesses including the Pawling Corporation, a manufacturer of industrial products.

With its perfect combination of natural beauty, historic significance, and modern amenities, Pawling provides an exceptional lifestyle for those seeking a welcoming community in a picturesque setting.

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Featured Listings

6 Byrds Hill Road
Pawling, NY $1,350,000

6 Byrds Hill Road

Pawling, NY

$1,350,000
  • 3 Beds
  • 2/1 Baths
  • 3,035 Sqft
15 Kirby Hill Road
Pawling, NY $14,995,000

15 Kirby Hill Road

Pawling, NY

$14,995,000
  • 4 Beds
  • 3/1 Baths
  • 3,942 Sqft
225 Route 22
Pawling, NY $9,750,000

225 Route 22

Pawling, NY

$9,750,000
  • 500.00 Acres
225 Route 22
Pawling, NY $9,750,000

225 Route 22

Pawling, NY

$9,750,000
  • 4,800 Sqft
618 Quaker Hill Road
Pawling, NY $5,500,000

618 Quaker Hill Road

Pawling, NY

$5,500,000
  • 17 Beds
  • 9/4 Baths
  • 15,000 Sqft
955 Old Quaker Hill Road
Pawling, NY $5,450,000

955 Old Quaker Hill Road

Pawling, NY

$5,450,000
  • 8 Beds
  • 7/4 Baths
  • 11,301 Sqft
57 Quaker Hill Road
Pawling, NY $3,900,000

57 Quaker Hill Road

Pawling, NY

$3,900,000
  • 108.00 Acres
125A Valley View Farms Road
Pawling, NY $2,347,621

125A Valley View Farms Road

Pawling, NY

$2,347,621
  • 6 Beds
  • 7/1 Baths
  • 6,511 Sqft

Pawling

Area Map

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Pawling

Market Snapshot

Units Sold

May 2025

9 TOTAL UNITS

image description +0.0% image description +50.0% vs

Median Sales Price

May 2025 - Single Family Homes

$641K
image description +8.4% image description +34.2% vs

Percentage of Asking Price

May 2025 Single Family Homes

98%
image description +4.4% image description -2.5% vs
98%
image description +4.4% image description -2.5% vs
98%
image description +4.4% image description -2.5% vs
98%
image description +4.4% image description -2.5% vs