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

Beds

9.6

Baths

55,000

Sq.Ft.

104 N Garden Drive

Pawling, NY

Courtesy of JULIA B FEE SOTHEBYS INT. RLTY
View 15 Kirby Hill Road Pawling, NY MLS# 965662
  • Virtual Tour
1 of 37
$14,995,000
4

Beds

3.1

Baths

3,942

Sq.Ft.

15 Kirby Hill Road

Pawling, NY

Courtesy of MCGRATH REALTY INC
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.
The time to sell is now! THE TIME TO SELL IS NOW!
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.
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 618 Quaker Hill Road Pawling, NY MLS# 968589
$5,000,000
8

Beds

9.4

Baths

15,000

Sq.Ft.

618 Quaker Hill Road

Pawling, NY

Courtesy of SERHANT LLC
View 809 N Quaker Hill Road Pawling, NY MLS# 20262841
  • Recently Listed
1 of 56
$3,100,000
3

Beds

3.0

Baths

3,600

Sq.Ft.

809 N Quaker Hill Road

Pawling, NY

UlsterCountyNY
Courtesy of FOUR SEASONS SOTHEBY'S INT.
View 809 QUAKER HILL Road Pawling, NY MLS# 1005064
  • Recently Listed
1 of 50
$3,100,000
3

Beds

3.0

Baths

3,600

Sq.Ft.

809 QUAKER HILL Road

Pawling, NY

Courtesy of FOUR SEASONS SOTHEBYS INTL
View 3302 Route 55 Pawling, NY MLS# 956656
$2,500,000
6

Beds

6.1

Baths

6,625

Sq.Ft.

3302 Route 55

Pawling, NY

Courtesy of DIXON SMITH REALTY
View 34 Meeting House Road Pawling, NY MLS# 965224
  • Virtual Tour
1 of 44
$2,500,000
3

Beds

3.1

Baths

2,292

Sq.Ft.

34 Meeting House Road

Pawling, NY

Courtesy of MCGRATH REALTY INC
View 527 Route 22 Pawling, NY MLS# 1005925
  • Recently Listed
1 of 32
$2,450,000
11,989

Sq.Ft.

527 Route 22

Pawling, NY

Courtesy of MCGRATH PREMIER REAL ESTATE
View 41 and 43 Meeting House Road Pawling, NY MLS# 875119
1 of 48
OPEN HOUSE: Sunday 6/7 1:00 PM - 4:00 PM
$1,799,000
5

Beds

5.1

Baths

5,390

Sq.Ft.

41 and 43 Meeting House Road

Pawling, NY

Courtesy of DOUGLAS ELLIMAN REAL ESTATE
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
5

Beds

4.1

Baths

3,920

Sq.Ft.

120 Harmony Road

Pawling, NY

Courtesy of HILLSIDE REALTY & DEVELOPMENT
View Old Quaker Hill Road Pawling, NY MLS# 986977
$999,000
Studio

Beds

0.0

Baths

2,979,068

Sq.Ft.

Old Quaker Hill Road

Pawling, NY

Courtesy of MCGRATH REALTY INC
View 56 Route 22 Pawling, NY MLS# 980198
$919,900
3,300

Sq.Ft.

56 Route 22

Pawling, NY

Courtesy of MCGRATH REALTY INC
View 128 Old Pawling Road Pawling, NY MLS# 952512
$900,000
4

Beds

3.1

Baths

3,434

Sq.Ft.

128 Old Pawling Road

Pawling, NY

Courtesy of COMPASS GREATER NY, LLC
View 117 S Quaker Hill Road Pawling, NY MLS# 991553
$859,000
2

Beds

2.0

Baths

2,278

Sq.Ft.

117 S Quaker Hill Road

Pawling, NY

Courtesy of MCGRATH REALTY INC
View 103 S Harmony Hill Road Pawling, NY MLS# 989668
$775,000
3

Beds

3.0

Baths

3,729

Sq.Ft.

103 S Harmony Hill Road

Pawling, NY

Courtesy of MCGRATH REALTY 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

50

Estimated median home price

$634,950
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 1
$100K - 200K 5
$200K - 300K 4
$300K - 400K 3
$400K - 500K 4
$500K - 600K 7
$600K - 700K 5
$700K - 800K 2
$800K - 900K 2
$900K - 1M 2
$1M - Max 15

Homes for Sale by Type in Pawling, NY

Property Type Count
Single Family 30
Townhouse 0
Condo 1
Commercial 5
Rental 13
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 6/5/2026)

Information deemed reliable but not guaranteed.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Copyright 2026 by the Multiple Listing service of Ulster County, Inc. All Rights Reserved.

The data relating to real estate on this web site comes in part from the IDX of the Multiple Listing service of Ulster County, Inc. Real estate listings held by brokerage firms other that Weichert Realtors are marked with IDX logo and the detailed information about them includes the name of the listing broker.

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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© Copyright 2026 Smart Multiple Listing Service, Inc.

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

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