View 104 North Garden Drive Pawling, NY MLS# 936279
$39,000,000
9

Beds

9.6

Baths

55,000

Sq.Ft.

104 North Garden Drive

Pawling, NY

Courtesy of JULIA B FEE SOTHEBYS INT. RLTY
View 225 Route 22 Pawling, NY MLS# H6215066
  • Virtual Tour
1 of 33
$9,750,000
Studio

Beds

0.0

Baths

24,321,726

Sq.Ft.

225 Route 22

Pawling, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 225 Route 22 Pawling, NY MLS# H6215756
  • Virtual Tour
1 of 33
$9,750,000
4,800

Sq.Ft.

225 Route 22

Pawling, NY

Courtesy of HOULIHAN LAWRENCE INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 225 Route 22 Pawling, NY MLS# 170530107
  • Virtual Tour
1 of 33
$9,750,000
Studio

Beds

0.0

Baths

225 Route 22

Pawling, NY

View 225 Route 22 Pawling, NY MLS# 170530136
  • Virtual Tour
1 of 33
$9,750,000
4,800

Sq.Ft.

225 Route 22

Pawling, NY

View 57 Quaker Hill Road Pawling, NY MLS# H6328765
  • Virtual Tour
1 of 20
$3,900,000
Studio

Beds

0.0

Baths

4,704,480

Sq.Ft.

57 Quaker Hill Road

Pawling, NY

Courtesy of MCGRATH REALTY INC
View 604 N Quaker Hill Road Pawling, NY MLS# 855450
  • Virtual Tour
1 of 47
$1,450,000
5

Beds

7.1

Baths

5,470

Sq.Ft.

604 N Quaker Hill Road

Pawling, NY

Courtesy of ELLIS SOTHEBY'S INTL REALTY
View 178 Charles Colman Boulevard Pawling, NY MLS# H6329957
$1,350,000
Studio

Beds

0.0

Baths

169,884

Sq.Ft.

178 Charles Colman Boulevard

Pawling, NY

Courtesy of TODAY REALTY CORP.
View 120 Harmony Road Pawling, NY MLS# 811617
$1,250,000
4

Beds

4.1

Baths

3,200

Sq.Ft.

120 Harmony Road

Pawling, NY

Courtesy of HILLSIDE REALTY & DEVELOPMENT
View 64 S Quaker Hill Road Pawling, NY MLS# 930472
$1,200,000
5

Beds

4.0

Baths

4,248

Sq.Ft.

64 S Quaker Hill Road

Pawling, NY

Courtesy of MCGRATH REALTY INC
View 16 Anderson Road Pawling, NY MLS# 853078
$1,175,000
4

Beds

6.0

Baths

3,012

Sq.Ft.

16 Anderson Road

Pawling, NY

Courtesy of COMPASS GREATER NY, LLC
View 128 Old Pawling Road Pawling, NY MLS# 952512
  • Recently Listed
1 of 24
$950,000
4

Beds

3.1

Baths

3,434

Sq.Ft.

128 Old Pawling Road

Pawling, NY

Courtesy of COMPASS GREATER NY, LLC
View 1125 Old Quaker Hill Road Pawling, NY MLS# 952611
  • Recently Listed with Virtual Tour
1 of 33
$889,900
3

Beds

2.0

Baths

2,048

Sq.Ft.

1125 Old Quaker Hill Road

Pawling, NY

Courtesy of HOMESMART HOMES & ESTATES
View 26 Rodina Drive Pawling, NY MLS# 951810
  • Recently Listed with Virtual Tour
1 of 23
$799,000
4

Beds

2.1

Baths

3,200

Sq.Ft.

26 Rodina Drive

Pawling, NY

Courtesy of HOME SWEET HOME PROPERTIES
View 85 Harmony Hill Road Pawling, NY MLS# 891094
$650,000
3

Beds

3.0

Baths

1,640

Sq.Ft.

85 Harmony Hill Road

Pawling, NY

Courtesy of COLDWELL BANKER REALTY
View 10 E Main Street Pawling, NY MLS# 888846
  • Virtual Tour
1 of 34
$640,000
2,185

Sq.Ft.

10 E Main Street

Pawling, NY

Courtesy of MCGRATH PREMIER REAL ESTATE
View 322 Old Route 22 Pawling, NY MLS# 927208
  • Virtual Tour
1 of 50
$619,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

322 Old Route 22

Pawling, NY

Courtesy of BHHS HUDSON VALLEY PROPERTIES
View 126 Old Route 55 Pawling, NY MLS# 811537
  • Virtual Tour
1 of 42
$598,500
4

Beds

4.1

Baths

2,361

Sq.Ft.

126 Old Route 55

Pawling, NY

Courtesy of HOMESMART HOMES & ESTATES
View 10 Rebecca Drive Pawling, NY MLS# 916805
  • Virtual Tour
1 of 46
$580,000
3

Beds

2.1

Baths

1,893

Sq.Ft.

10 Rebecca Drive

Pawling, NY

Courtesy of HOWARD HANNA RAND REALTY
View 36 Byrds Hill Road Pawling, NY MLS# 925623
$550,000
2

Beds

2.1

Baths

1,820

Sq.Ft.

36 Byrds Hill Road

Pawling, NY

Courtesy of HOULIHAN LAWRENCE INC.

About Pawling

Set in a naturally beautiful terrain of wooded hillsides just a few miles from the Connecticut state border, the Pawling area offers a classic small-town environment for those who desire to escape the bustle of the “big city.”  In addition to respected public schools that have earned a reputation for academic excellence, Pawling is also home to a private high school.  Although some businesses operate in Pawling, the town is primarily residential in nature and claims a significant commuter population.  The area’s scattered retail activity meets many of the needs for daily goods and services, although expanded shopping facilities are available just a few miles away in Danbury Mall or Poughkeepsie shopping centers.  Sports and recreational amenities include local parks,  sports courts and fields, athletic leagues, tennis courts, golf courses, multi-purpose trails, lakes with swimming areas, winter sports areas, and country clubs.

Listings in Pawling, NY

44

Estimated median home price

$492,000
Pawling NY Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Pawling, New York real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Pawling, NY.

Homes for Sale by Price in Pawling, NY

Price Count
$0 - 100K 2
$100K - 200K 9
$200K - 300K 3
$300K - 400K 4
$400K - 500K 5
$500K - 600K 4
$600K - 700K 3
$700K - 800K 1
$800K - 900K 1
$900K - 1M 1
$1M - Max 11

Homes for Sale by Type in Pawling, NY

Property Type Count
Single Family 23
Townhouse 0
Condo 0
Commercial 5
Rental 9
Lots and Land 15
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 1/28/2026)

Information deemed reliable but not guaranteed.

Listing information has been assembled from various sources of varying degrees of reliability. Any information critical to a buying decision should be independently verified.

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