Country Homes for Sale in Pawling Town, NY

17 Homes for Sale

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Photo 3 of Single family home for sale at 139 Harmony Rd, Pawling, NY 12564 | MLS# 1045580 | Listing updated on 2026-10-06

Photo 1 of Single family home for sale at 139 Harmony Rd, Pawling, NY 12564 | MLS# 1045580 | Listing updated on 2026-10-06

Photo 2 of Single family home for sale at 139 Harmony Rd, Pawling, NY 12564 | MLS# 1045580 | Listing updated on 2026-10-06

$985,000

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4Bds

3Ba

3,831sqft

Single family home for sale

139 Harmony Rd, Pawling, NY 12564

Mcgrath Realty Inc

Price Drop: $26K

Photo 3 of Single family home for sale at 1080 Route 292, Pawling, NY 12531 | MLS# 978111 | Listing updated on 2026-10-03

Photo 1 of Single family home for sale at 1080 Route 292, Pawling, NY 12531 | MLS# 978111 | Listing updated on 2026-10-03

Photo 2 of Single family home for sale at 1080 Route 292, Pawling, NY 12531 | MLS# 978111 | Listing updated on 2026-10-03

$699,000

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2Bds

2Ba

1,722sqft

Single family home for sale

1080 Route 292, Pawling, NY 12531

Mcgrath Realty Inc

Photo 3 of Single family home for sale at 401 W Dover Rd, Pawling, NY 12564 | MLS# 1056846 | Listing updated on 2026-10-04

Photo 1 of Single family home for sale at 401 W Dover Rd, Pawling, NY 12564 | MLS# 1056846 | Listing updated on 2026-10-04

Photo 2 of Single family home for sale at 401 W Dover Rd, Pawling, NY 12564 | MLS# 1056846 | Listing updated on 2026-10-04

$369,000

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2Bds

1Ba

768sqft

Single family home for sale

401 W Dover Rd, Pawling, NY 12564

Daniel Gale Sothebys Intl Rlty

Photo 3 of Single family home for sale at 823 N Quaker Hl Rd, Pawling, NY 12564 | MLS# 1053203 | Listing updated on 2026-10-03

Photo 1 of Single family home for sale at 823 N Quaker Hl Rd, Pawling, NY 12564 | MLS# 1053203 | Listing updated on 2026-10-03

Photo 2 of Single family home for sale at 823 N Quaker Hl Rd, Pawling, NY 12564 | MLS# 1053203 | Listing updated on 2026-10-03

$2,400,000

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4Bds

4Ba

3,660sqft

Single family home for sale

823 N Quaker Hl Rd, Pawling, NY 12564

Houlihan Lawrence, Inc

Photo 3 of Sale Pending at 5 Henry St, Pawling, NY 12564 | MLS# 1044575 | Listing updated on 2026-09-29

Photo 1 of Sale Pending at 5 Henry St, Pawling, NY 12564 | MLS# 1044575 | Listing updated on 2026-09-29

Photo 2 of Sale Pending at 5 Henry St, Pawling, NY 12564 | MLS# 1044575 | Listing updated on 2026-09-29

$399,000

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4Bds

3Ba

2,424sqft

Sale Pending

5 Henry St, Pawling, NY 12564

Mcgrath Realty Inc

3D Tour

Photo 3 of Sale Pending at 3846 Route 55, Pawling, NY 12564 | MLS# 1035919 | Listing updated on 2026-09-28

Photo 1 of Sale Pending at 3846 Route 55, Pawling, NY 12564 | MLS# 1035919 | Listing updated on 2026-09-28

Photo 2 of Sale Pending at 3846 Route 55, Pawling, NY 12564 | MLS# 1035919 | Listing updated on 2026-09-28

$639,000

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4Bds

4Ba

1,696sqft

Sale Pending

3846 Route 55, Pawling, NY 12564

Ellis Sotheby'S Intl Realty

Hot

Photo 3 of Single family home for sale at 194 South Rd, Holmes, NY 12531 | MLS# 964060 | Listing updated on 2026-09-26

Photo 1 of Single family home for sale at 194 South Rd, Holmes, NY 12531 | MLS# 964060 | Listing updated on 2026-09-26

Photo 2 of Single family home for sale at 194 South Rd, Holmes, NY 12531 | MLS# 964060 | Listing updated on 2026-09-26

$949,000

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4Bds

4Ba

3,768sqft

Single family home for sale

194 South Rd, Holmes, NY 12531

Houlihan Lawrence Inc.

Photo 3 of Single family home for sale at 5 Red Tail Ct, Pawling, NY 12564 | MLS# 945476 | Listing updated on 2026-09-25

Photo 1 of Single family home for sale at 5 Red Tail Ct, Pawling, NY 12564 | MLS# 945476 | Listing updated on 2026-09-25

Photo 2 of Single family home for sale at 5 Red Tail Ct, Pawling, NY 12564 | MLS# 945476 | Listing updated on 2026-09-25

$575,000

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4Bds

3Ba

2,924sqft

Single family home for sale

5 Red Tail Ct, Pawling, NY 12564

Houlihan Lawrence Inc.

Photo 3 of Single family home for sale at 41 W Deer Trl, Pawling, NY 12564 | MLS# 1047471 | Listing updated on 2026-10-02

Photo 1 of Single family home for sale at 41 W Deer Trl, Pawling, NY 12564 | MLS# 1047471 | Listing updated on 2026-10-02

Photo 2 of Single family home for sale at 41 W Deer Trl, Pawling, NY 12564 | MLS# 1047471 | Listing updated on 2026-10-02

$597,500

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4Bds

3Ba

2,300sqft

Single family home for sale

41 W Deer Trl, Pawling, NY 12564

Mcgrath Realty Inc

Hot

3D Tour

Photo 3 of Single family home for sale at 66 Reservoir Rd, Pawling, NY 12564 | MLS# 1033232 | Listing updated on 2026-09-21

Photo 1 of Single family home for sale at 66 Reservoir Rd, Pawling, NY 12564 | MLS# 1033232 | Listing updated on 2026-09-21

Photo 2 of Single family home for sale at 66 Reservoir Rd, Pawling, NY 12564 | MLS# 1033232 | Listing updated on 2026-09-21

$525,000

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3Bds

3Ba

1,950sqft

Single family home for sale

66 Reservoir Rd, Pawling, NY 12564

Re/Max Town & Country

Photo 3 of Single family home for sale at Lot 5 A S White Rock Rd, Pawling, NY 12564 | MLS# 1024239 | Listing updated on 2026-09-19

Photo 1 of Single family home for sale at Lot 5 A S White Rock Rd, Pawling, NY 12564 | MLS# 1024239 | Listing updated on 2026-09-19

Photo 2 of Single family home for sale at Lot 5 A S White Rock Rd, Pawling, NY 12564 | MLS# 1024239 | Listing updated on 2026-09-19

$1,150,000

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5Bds

4Ba

3,400sqft

Single family home for sale

Lot 5 A S White Rock Rd, Pawling, NY 12564

Houlihan Lawrence Inc.

Photo 3 of Single family home for sale at 136 Bundy Hl Rd, Pawling, NY 12531 | MLS# 1052304 | Listing updated on 2026-09-25

Photo 1 of Single family home for sale at 136 Bundy Hl Rd, Pawling, NY 12531 | MLS# 1052304 | Listing updated on 2026-09-25

Photo 2 of Single family home for sale at 136 Bundy Hl Rd, Pawling, NY 12531 | MLS# 1052304 | Listing updated on 2026-09-25

$395,000

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2Bds

2Ba

920sqft

Single family home for sale

136 Bundy Hl Rd, Pawling, NY 12531

Compass Greater Ny, Llc

Price Drop: $250K

Photo 3 of Mansion for sale at 618 Quaker Hl Rd, Pawling, NY 12564 | MLS# 968589 | Listing updated on 2026-09-17

Photo 1 of Mansion for sale at 618 Quaker Hl Rd, Pawling, NY 12564 | MLS# 968589 | Listing updated on 2026-09-17

Photo 2 of Mansion for sale at 618 Quaker Hl Rd, Pawling, NY 12564 | MLS# 968589 | Listing updated on 2026-09-17

$4,750,000

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8Bds

13Ba

15,000sqft

Mansion for sale

618 Quaker Hl Rd, Pawling, NY 12564

Serhant Llc

Photo 3 of Sale Pending at 17 Spring St, Pawling, NY 12564 | MLS# 1022255 | Listing updated on 2026-08-16

Photo 1 of Sale Pending at 17 Spring St, Pawling, NY 12564 | MLS# 1022255 | Listing updated on 2026-08-16

Photo 2 of Sale Pending at 17 Spring St, Pawling, NY 12564 | MLS# 1022255 | Listing updated on 2026-08-16

$575,000

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3Bds

2Ba

2,202sqft

Sale Pending

17 Spring St, Pawling, NY 12564

Mcgrath Realty Inc

Photo 3 of Single family home for sale at 1564 Route 292, Pawling, NY 12531 | MLS# 1001208 | Listing updated on 2026-08-12

Photo 1 of Single family home for sale at 1564 Route 292, Pawling, NY 12531 | MLS# 1001208 | Listing updated on 2026-08-12

Photo 2 of Single family home for sale at 1564 Route 292, Pawling, NY 12531 | MLS# 1001208 | Listing updated on 2026-08-12

$725,000

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3Bds

2Ba

1,628sqft

Single family home for sale

1564 Route 292, Pawling, NY 12531

Mcgrath Realty Inc

Photo 3 of Single family home for sale at 120 Harmony Rd, Pawling, NY 12564 | MLS# 811617 | Listing updated on 2026-07-16

Photo 1 of Single family home for sale at 120 Harmony Rd, Pawling, NY 12564 | MLS# 811617 | Listing updated on 2026-07-16

Photo 2 of Single family home for sale at 120 Harmony Rd, Pawling, NY 12564 | MLS# 811617 | Listing updated on 2026-07-16

$1,250,000

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5Bds

5Ba

3,920sqft

Single family home for sale

120 Harmony Rd, Pawling, NY 12564

Hillside Realty & Development

3D Tour

Photo 3 of Single family home for sale at 15 Kirby Hl Rd, Pawling, NY 12564 | MLS# 965662 | Listing updated on 2026-05-29

Photo 1 of Single family home for sale at 15 Kirby Hl Rd, Pawling, NY 12564 | MLS# 965662 | Listing updated on 2026-05-29

Photo 2 of Single family home for sale at 15 Kirby Hl Rd, Pawling, NY 12564 | MLS# 965662 | Listing updated on 2026-05-29

$14,995,000

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4Bds

4Ba

3,942sqft

Single family home for sale

15 Kirby Hl Rd, Pawling, NY 12564

Mcgrath Realty Inc

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Single Family Homes for Sale in Pawling Town

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Based on information from OneKey MLS, through Oct 8, 2026, 9:01 AM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.