View 29 Cunningham Lane Pawling, NY MLS# 908496
$699,000
4

Beds

3.2

Baths

4,199

Sq.Ft.

29 Cunningham Lane

Pawling, NY

Courtesy of GILLIAN STEWART REAL ESTATE
View 48 David Lane Pawling, NY MLS# 920517
$695,000
3

Beds

2.1

Baths

1,788

Sq.Ft.

48 David Lane

Pawling, NY

Courtesy of HUDSON RIVER LINE REALTY
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 7 Glen Court Pawling, NY MLS# 887124
$575,000
3

Beds

2.1

Baths

2,318

Sq.Ft.

7 Glen Court

Pawling, NY

Courtesy of MCGRATH REALTY INC
View 28 Gobblers Knob Road Pawling, NY MLS# 876715
$574,900
3

Beds

2.0

Baths

2,107

Sq.Ft.

28 Gobblers Knob Road

Pawling, NY

Courtesy of EXP 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.
View 36 Elm Street Pawling, NY MLS# 866409
$449,000
3

Beds

1.1

Baths

1,680

Sq.Ft.

36 Elm Street

Pawling, NY

Courtesy of GILLIAN STEWART REAL ESTATE
View 23 Union Street Pawling, NY MLS# 890553
  • Virtual Tour
1 of 28
$419,900
3

Beds

2.0

Baths

1,480

Sq.Ft.

23 Union Street

Pawling, NY

Courtesy of K FORTUNA LIGHTHOUSE REALTY
View 21 Kings Way Pawling, NY MLS# 938784
  • Recently Listed
1 of 13
$408,888
3

Beds

2.1

Baths

1,960

Sq.Ft.

21 Kings Way

Pawling, NY

Courtesy of YOURHOMESOLD GUARANTEED REALTY
View 2 Spruce Street Pawling, NY MLS# 931295
$399,999
2

Beds

2.1

Baths

1,838

Sq.Ft.

2 Spruce Street

Pawling, NY

Courtesy of HANSON REAL ESTATE PARTNERS
View 215 Little Pond Road Pawling, NY MLS# 872418
$399,000
5

Beds

0.0

Baths

1,062

Sq.Ft.

215 Little Pond Road

Pawling, NY

Courtesy of DOUGLAS ELLIMAN REAL ESTATE
View 12 Anderson Way Pawling, NY MLS# 908608
$399,000
2

Beds

1.0

Baths

1,160

Sq.Ft.

12 Anderson Way

Pawling, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 16 Townsend Boulevard Pawling, NY MLS# 934462
  • Recently Listed with Virtual Tour
1 of 35
$399,000
2

Beds

1.0

Baths

1,080

Sq.Ft.

16 Townsend Boulevard

Pawling, NY

Courtesy of MCGRATH REALTY INC
View 33 Spruce Street Pawling, NY MLS# 862384
  • Virtual Tour
1 of 36
$359,999
2

Beds

2.1

Baths

1,413

Sq.Ft.

33 Spruce Street

Pawling, NY

Courtesy of KELLER WILLIAMS NY REALTY
View Lot 21 Cox Road Pawling, NY MLS# 917652
$229,000
Studio

Beds

0.0

Baths

242,629

Sq.Ft.

Lot 21 Cox Road

Pawling, NY

Courtesy of MCGRATH REALTY INC
View Lot 25 Brady Brook Farm Road Pawling, NY MLS# 918929
$229,000
Studio

Beds

0.0

Baths

288,803

Sq.Ft.

Lot 25 Brady Brook Farm 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

51

Estimated median home price

$619,000
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

PriceCount
$0 - 100K2
$100K - 200K7
$200K - 300K3
$300K - 400K5
$400K - 500K3
$500K - 600K5
$600K - 700K7
$700K - 800K5
$800K - 900K1
$900K - 1M1
$1M - Max12

Homes for Sale by Type in Pawling, NY

Property TypeCount
Single Family31
Townhouse0
Condo0
Commercial5
Rental9
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 12/10/2025)

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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