Historic Homes for Sale in Pawling Town, NY

20 Homes for Sale

Sort by:Newest Listings

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

Price Drop: $40K

Photo 3 of Multi family home for sale at 6 Laurel Dr, Holmes, NY 12531 | MLS# 938285 | Listing updated on 2026-10-01

Photo 1 of Multi family home for sale at 6 Laurel Dr, Holmes, NY 12531 | MLS# 938285 | Listing updated on 2026-10-01

Photo 2 of Multi family home for sale at 6 Laurel Dr, Holmes, NY 12531 | MLS# 938285 | Listing updated on 2026-10-01

$259,900

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5Bds

4Ba

2,790sqft

Multi family home for sale

6 Laurel Dr, Holmes, NY 12531

Ai Realty Brokerage Llc

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 264 Quaker Hl Rd, Pawling, NY 12564 | MLS# 1047901 | Listing updated on 2026-09-28

Photo 1 of Single family home for sale at 264 Quaker Hl Rd, Pawling, NY 12564 | MLS# 1047901 | Listing updated on 2026-09-28

Photo 2 of Single family home for sale at 264 Quaker Hl Rd, Pawling, NY 12564 | MLS# 1047901 | Listing updated on 2026-09-28

$695,000

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4Bds

2Ba

2,160sqft

Single family home for sale

264 Quaker Hl Rd, Pawling, NY 12564

Gillian Stewart Real Estate

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

Photo 3 of Sale Pending at 357 W Dover Rd, Pawling, NY 12564 | MLS# 1026446 | Listing updated on 2026-09-18

Photo 1 of Sale Pending at 357 W Dover Rd, Pawling, NY 12564 | MLS# 1026446 | Listing updated on 2026-09-18

Photo 2 of Sale Pending at 357 W Dover Rd, Pawling, NY 12564 | MLS# 1026446 | Listing updated on 2026-09-18

$365,000

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3Bds

3Ba

2,137sqft

Sale Pending

357 W Dover Rd, Pawling, NY 12564

Vylla Home

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 5 Birch Dr, Pawling, NY 12531 | MLS# 931059 | Listing updated on 2026-09-15

Photo 1 of Sale Pending at 5 Birch Dr, Pawling, NY 12531 | MLS# 931059 | Listing updated on 2026-09-15

Photo 2 of Sale Pending at 5 Birch Dr, Pawling, NY 12531 | MLS# 931059 | Listing updated on 2026-09-15

$216,000

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2Bds

1Ba

672sqft

Sale Pending

5 Birch Dr, Pawling, NY 12531

Re/Max Classic Realty

3D Tour

Photo 3 of Sale Pending at 21 Overlook Dr, Pawling, NY 12564 | MLS# 1029600 | Listing updated on 2026-08-29

Photo 1 of Sale Pending at 21 Overlook Dr, Pawling, NY 12564 | MLS# 1029600 | Listing updated on 2026-08-29

Photo 2 of Sale Pending at 21 Overlook Dr, Pawling, NY 12564 | MLS# 1029600 | Listing updated on 2026-08-29

$699,000

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3Bds

3Ba

1,460sqft

Sale Pending

21 Overlook Dr, Pawling, NY 12564

Mcgrath Realty Inc

Photo 3 of Single family home for sale at 1555 Route 292, Pawling, NY 12531 | MLS# 1031078 | Listing updated on 2026-08-19

Photo 1 of Single family home for sale at 1555 Route 292, Pawling, NY 12531 | MLS# 1031078 | Listing updated on 2026-08-19

Photo 2 of Single family home for sale at 1555 Route 292, Pawling, NY 12531 | MLS# 1031078 | Listing updated on 2026-08-19

$249,000

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1Bd

1Ba

733sqft

Single family home for sale

1555 Route 292, Pawling, NY 12531

Exp Realty

Hot

3D Tour

Photo 3 of Single family home for sale at 64 S Quaker Hl Rd, Pawling, NY 12564 | MLS# 1010537 | Listing updated on 2026-09-30

Photo 1 of Single family home for sale at 64 S Quaker Hl Rd, Pawling, NY 12564 | MLS# 1010537 | Listing updated on 2026-09-30

Photo 2 of Single family home for sale at 64 S Quaker Hl Rd, Pawling, NY 12564 | MLS# 1010537 | Listing updated on 2026-09-30

$1,199,000

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5Bds

4Ba

4,248sqft

Single family home for sale

64 S Quaker Hl Rd, Pawling, NY 12564

Mcgrath Realty Inc

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

Hot

Photo 3 of Single family home for sale at 392 Old Quaker Hl Rd, Pawling, NY 12564 | MLS# 1037768 | Listing updated on 2026-08-15

Photo 1 of Single family home for sale at 392 Old Quaker Hl Rd, Pawling, NY 12564 | MLS# 1037768 | Listing updated on 2026-08-15

Photo 2 of Single family home for sale at 392 Old Quaker Hl Rd, Pawling, NY 12564 | MLS# 1037768 | Listing updated on 2026-08-15

$1,400,000

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4Bds

3Ba

4,136sqft

Single family home for sale

392 Old Quaker Hl Rd, 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 Sale Pending at 122 Dutchess Dr, Holmes, NY 12531 | MLS# 999182 | Listing updated on 2026-07-12

Photo 1 of Sale Pending at 122 Dutchess Dr, Holmes, NY 12531 | MLS# 999182 | Listing updated on 2026-07-12

Photo 2 of Sale Pending at 122 Dutchess Dr, Holmes, NY 12531 | MLS# 999182 | Listing updated on 2026-07-12

$875,000

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2Bds

2Ba

1,793sqft

Sale Pending

122 Dutchess Dr, Holmes, NY 12531

Houlihan Lawrence Inc.

Photo 3 of Multi family home for sale at 750 Route 292, Holmes, NY 12531 | MLS# 1004618 | Listing updated on 2026-09-30

Photo 1 of Multi family home for sale at 750 Route 292, Holmes, NY 12531 | MLS# 1004618 | Listing updated on 2026-09-30

Photo 2 of Multi family home for sale at 750 Route 292, Holmes, NY 12531 | MLS# 1004618 | Listing updated on 2026-09-30

$1,350,000

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11Bds

8Ba

--sqft

Multi family home for sale

750 Route 292, Holmes, NY 12531

Bhhs Hudson Valley Properties

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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No. of Homes

Historic Homes for Sale in New York

20,900

Historic Homes for Sale in York

15,324

Historic Homes for Sale in Manhattan

8,999

Historic Homes for Sale in Queens

6,408

Historic Homes for Sale in Manhattan Borough

4,830

Historic Homes for Sale in Queens Borough

4,528

Historic Homes for Sale in Nassau

3,609

Historic Homes for Sale in Brooklyn

3,313

Historic Homes for Sale in Hempstead

2,521

Historic Homes for Sale in Bronx

2,068

Historic Homes for Sale in Brooklyn Borough

1,982

Historic Homes for Sale in Bronx Borough

1,495

Historic Homes for Sale in Buffalo City

1,425

Historic Homes for Sale in Brookhaven Town

1,245

Historic Homes for Sale in Brookhaven

893

Historic Homes for Sale in Albany

848

Historic Homes for Sale in Rochester City

818

Historic Homes for Sale in Oyster Bay Town

718

Historic Homes for Sale in Islip Town

661

Historic Homes for Sale in North Hempstead Town

639

No. of Homes

Single Family Homes for Sale in Pawling Town

Homes for Sale in Pawling Town With AC

Homes With Acreage in Pawling Town

Country Homes for Sale in Pawling Town

Ranch Homes for Sale in Pawling Town

Patio Homes for Sale in Pawling Town

Houses for Sale in Pawling Town With Pool

Land for Sale in Pawling Town

Waterfront Houses for Sale in Pawling Town

Cheap Houses for Sale in Pawling Town

Multi Family Homes for Sale in Pawling Town

Luxury Homes in Pawling Town

Cabins for Sale in Pawling Town

Open Houses in Pawling Town

Duplex Homes for Sale in Pawling Town

No. of Homes

1 Bedroom Homes for Sale in Pawling Town, NY

2 Bedroom Homes for Sale in Pawling Town, NY

3 Bedroom Homes for Sale in Pawling Town, NY

4 Bedroom Homes for Sale in Pawling Town, NY

5 Bedroom Homes for Sale in Pawling Town, NY

8 Bedroom Homes for Sale in Pawling Town, NY

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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.