Historic Homes for Sale in Pawling, NY

19 Homes for Sale

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Photo 3 of Single family home for sale at 11 Stanley Dr, Pawling, NY 12564 | MLS# 1058860 | Listing updated on 2026-10-09

Photo 1 of Single family home for sale at 11 Stanley Dr, Pawling, NY 12564 | MLS# 1058860 | Listing updated on 2026-10-09

Photo 2 of Single family home for sale at 11 Stanley Dr, Pawling, NY 12564 | MLS# 1058860 | Listing updated on 2026-10-09

$250,000

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4Bds

2Ba

2,096sqft

Single family home for sale

11 Stanley Dr, Pawling, NY 12564

Mcgrath Realty Inc

Photo 3 of Sale Pending at 265 Old Pawling Rd, Pawling, NY 12564 | MLS# 1045289 | Listing updated on 2026-10-06

Photo 1 of Sale Pending at 265 Old Pawling Rd, Pawling, NY 12564 | MLS# 1045289 | Listing updated on 2026-10-06

Photo 2 of Sale Pending at 265 Old Pawling Rd, Pawling, NY 12564 | MLS# 1045289 | Listing updated on 2026-10-06

$404,444

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2Bds

1Ba

1,000sqft

Sale Pending

265 Old Pawling Rd, Pawling, NY 12564

K. Fortuna Realty, Inc.

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 2026-10-09

Photo 1 of Single family home for sale at 401 W Dover Rd, Pawling, NY 12564 | MLS# 1056846 | Listing updated on 2026-10-09

Photo 2 of Single family home for sale at 401 W Dover Rd, Pawling, NY 12564 | MLS# 1056846 | Listing updated on 2026-10-09

$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

Hot

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

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 Sale Pending at 28 Birch Ter, Pawling, NY 12564 | MLS# 1020651 | Listing updated on 2026-08-29

Photo 1 of Sale Pending at 28 Birch Ter, Pawling, NY 12564 | MLS# 1020651 | Listing updated on 2026-08-29

Photo 2 of Sale Pending at 28 Birch Ter, Pawling, NY 12564 | MLS# 1020651 | Listing updated on 2026-08-29

$375,000

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2Bds

1Ba

816sqft

Sale Pending

28 Birch Ter, 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 2026-10-10

Photo 1 of Single family home for sale at 64 S Quaker Hl Rd, Pawling, NY 12564 | MLS# 1010537 | Listing updated on 2026-10-10

Photo 2 of Single family home for sale at 64 S Quaker Hl Rd, Pawling, NY 12564 | MLS# 1010537 | Listing updated on 2026-10-10

$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

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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Pawling, NY Housing Market Overview

Pawling is moving fast, and is a seller's market. Just 1 months of supply and 23 days on the market mean less competition for buyers and more leverage for you.

Status

Seller's Market

Days on Market

Inventory

Sep 2021Jan 2024Mar 2026

Median Home Price

$455,000 0.00%

In Mar 2026 · YoY

Sep 2021Jan 2024Mar 2026

Mortgage Rates 30-Yr Fixed

6.23% 0.58%

Current rate · YoY

Loan Type

30-Year Fixed

Housing Supply

Homes For Sale: 2 Down 0.00%
Newly Listed Homes: 0 Down 0.00%
Months of Supply: 1 Down 0.00%

Housing Demand

Homes Sold: 2 Down 0.00%
Sale-to-List Ratio: 99.5% Down 0.00%
Homes Sold Above List: 50% Down 0.00%

30-yr fixed rate 6.23% · Data as of Mar 2026 · Source: Houzeo Research.

View Full Pawling Market Report

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

Homes for Sale in Pawling With AC

Homes With Acreage in Pawling

Country Homes for Sale in Pawling

Ranch Homes for Sale in Pawling

Patio Homes for Sale in Pawling

Houses for Sale in Pawling With Pool

Land for Sale in Pawling

Waterfront Houses for Sale in Pawling

Cheap Houses for Sale in Pawling

Luxury Homes in Pawling

Cabins for Sale in Pawling

Open Houses in Pawling

Duplex Homes for Sale in Pawling

Multi Family Homes for Sale in Pawling

No. of Homes

1 Bedroom Homes for Sale in Pawling, NY

2 Bedroom Homes for Sale in Pawling, NY

3 Bedroom Homes for Sale in Pawling, NY

4 Bedroom Homes for Sale in Pawling, NY

5 Bedroom Homes for Sale in Pawling, NY

8 Bedroom Homes for Sale in Pawling, NY

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Based on information from OneKey MLS, through Oct 10, 2026, 6:17 PM. 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.