Pawling, NY Homes

Est $381,561

Not Listed For Sale

4 Juniper Ln, Pawling, NY 12564
- 2 Beds
- 2.5 Baths
- 2,100 Sq Ft
- Built 1988
4 Juniper Ln, Pawling, NY 12564

Last Sold Summary
- 20 Days On Market

/50
$5,000,000
- 8 Beds
- 13 Baths
- 15,000 Sq Ft
618 Quaker Hill Rd, Pawling, NY 12564

Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations.

Jake Garay Serhant LLC

618 Quaker Hill Rd, Pawling, NY 12564
$820,000

Sold Jul 28, 2025

12 Berry Ln, Pawling, NY 12564
- 4 Beds
- 3 Baths
- 3,304 Sq Ft
- Built 1965
Last Sold Summary
- 6% Below List Price
- $248/SF
- 52 Days On Market
Current Estimated Value $840,582

Last Listing Agent Brian McGrath McGrath Realty Inc

12 Berry Ln, Pawling, NY 12564

Est $397,803

Not Listed For Sale

5 Hemlock Cir, Pawling, NY 12564
- 2 Beds
- 2.5 Baths
- 2,113 Sq Ft
- Built 1988
5 Hemlock Cir, Pawling, NY 12564

Last Sold Summary
- 15 Days On Market

/37
$14,995,000
- 4 Beds
- 3.5 Baths
- 3,942 Sq Ft
15 Kirby Hill Rd, Pawling, NY 12564

Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct

Brian McGrath McGrath Realty Inc

15 Kirby Hill Rd, Pawling, NY 12564
$430,000

Sold Jul 22, 2025

26 Fenwood Dr, Pawling, NY 12564
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
- Built 1963
Last Sold Summary
- 7% Below List Price
- $287/SF
- 177 Days On Market
Current Estimated Value $441,997

Last Listing Agent Vicki Reinach BHHS Hudson Valley Properties

26 Fenwood Dr, Pawling, NY 12564

Est $377,441

Not Listed For Sale

7 Evergreen Way, Pawling, NY 12564
- 2 Beds
- 2.5 Baths
- 1,413 Sq Ft
- Built 1998
7 Evergreen Way, Pawling, NY 12564

Last Sold Summary
- 37 Days On Market

/33
$9,750,000

$7M PRICE DROP
- Land
- 558.35 Acres
- $17,462 per Acre
225 Route 22, Pawling, NY 12564

Unparalleled Opportunity Awaits! Discover this breathtaking 558+ acre parcel, just 90 minutes from Manhattan, offering a canvas of endless possibilities for personal and commercial endeavors. Whether you envision a sprawling family compound or a premier commercial facility, this land is primed for your dreams. Featuring level terrain, extensive trails, and vibrant pastures, this property is

Shaylene Neumann Houlihan Lawrence Inc.

225 Route 22, Pawling, NY 12564
$575,000

Sold Dec 22, 2025

7 Glen Ct, Pawling, NY 12564
- 3 Beds
- 2.5 Baths
- 2,318 Sq Ft
- Built 1997
Last Sold Summary
- 3% Below List Price
- $248/SF
- 136 Days On Market
Current Estimated Value $590,686

Last Listing Agent Colleen McGrath McGrath Realty Inc

7 Glen Ct, Pawling, NY 12564

Est $1,175,557

Not Listed For Sale

10 Cox Rd, Pawling, NY 12564
- 4 Beds
- 3.5 Baths
- 4,500 Sq Ft
- Built 2000
10 Cox Rd, Pawling, NY 12564

Last Sold Summary
- 28 Days On Market

/29
$525,000
- 3 Beds
- 1.5 Baths
- 1,955 Sq Ft
37 W Deer Trail, Pawling, NY 12564

When you think about Deerfield Ponds in Pawling, this home is it.From the moment you drive up, you’re welcomed by a picture-perfect lot with breathtaking mountain views and a pond right in your backyard. Enjoy the private trails just steps away, along with kayaking in the warmer months and ice skating and ice fishing during the winter. This 3-bedroom, 1.5 bath home is packed with potential.

Pete Rodriguez William Raveis Real Estate

37 W Deer Trail, Pawling, NY 12564
$465,000

Sold Sep 15, 2025

14 Summit Ave, Pawling, NY 12564
- 2 Beds
- 2 Baths
- 1,706 Sq Ft
- Built 1957
Last Sold Summary
- 17% Above List Price
- $273/SF
- 31 Days On Market
Current Estimated Value $463,359

Last Listing Agent Karen Gundelach Keller Williams NY Realty

14 Summit Ave, Pawling, NY 12564

Est $636,278

Not Listed For Sale

55 Akindale Rd, Pawling, NY 12564
- 3 Beds
- 2 Baths
- 2,152 Sq Ft
- Built 1965
55 Akindale Rd, Pawling, NY 12564

Last Sold Summary
- 52 Days On Market

/36
$699,000

$16K PRICE DROP
- 3 Beds
- 3.5 Baths
- 3,629 Sq Ft
921 W Dover Rd, Pawling, NY 12564

A One-of-a-Kind Custom Ranch on Nearly 4 Private Acres. Discover exceptional space, quality, and versatility in this expansive custom-built 3+ bedroom ranch, perfectly tucked away in a serene country setting. Designed for comfort and flexibility, this home is ideal for extended family living, multi-generational needs, or a spacious mother-daughter layout. The main floor offers true single-level

Joyce Brennan-Zolnik BHHS Hudson Valley Properties

921 W Dover Rd, Pawling, NY 12564
$415,000

Sold Aug 19, 2025

42 Harmony Rd, Pawling, NY 12564
- 2 Beds
- 1 Bath
- 1,152 Sq Ft
- Built 1930
Last Sold Summary
- 2% Below List Price
- $360/SF
- 33 Days On Market
Current Estimated Value $420,832

Last Listing Agent Reid McGrath McGrath Realty Inc

42 Harmony Rd, Pawling, NY 12564

Est $536,000

Not Listed For Sale

173 Quaker Hill Rd, Pawling, NY 12564
- 4 Beds
- 3 Baths
- 3,620 Sq Ft
- Built 1989
173 Quaker Hill Rd, Pawling, NY 12564

Last Sold Summary
- 39 Days On Market

/10
$135,000

Pending
- Land
- 18,730 Sq Ft
- $313,953 per Acre
0 Prospect St Unit KEY985758, Pawling, NY 12564

First time on market! BOHA not required - Town Water and Sewer must be hooked-up. Nice level lot, the majority of which is mostly cleared. Great location! Short drive to Metro-North, great restaurants and shops, Pawling schools, Lakeside Park with beach, playground area, trails, and pickleball courts. Dutcher Golf Course is a 9-hole gem, the oldest public course in America. Also close to grocery

Lisa Liffland McGrath Realty Inc

0 Prospect St Unit KEY985758, Pawling, NY 12564
$100,000

Sold May 11, 2026

3 Pine Dr, Pawling, NY 12564
- Land
- 13,503 Sq Ft
- $322,581 per Acre
Last Sold Summary
- 20% Below List Price
- 136 Days On Market
Last Listing Agent Brandon Doswell-Stephens Silverside Realty LLC

3 Pine Dr, Pawling, NY 12564

Est $527,779

Not Listed For Sale

45 Fenwood Dr, Pawling, NY 12564
- 3 Beds
- 2 Baths
- 1,824 Sq Ft
- Built 1976
45 Fenwood Dr, Pawling, NY 12564

Last Sold Summary
- 74 Days On Market

$420,000

Sold Aug 01, 2025

7 Holiday St, Pawling, NY 12564
- 3 Beds
- 1 Bath
- 1,056 Sq Ft
- Built 1961
Last Sold Summary
- 2% Below List Price
- $398/SF
- 29 Days On Market
Current Estimated Value $421,556

Last Listing Agent Lisa Liffland McGrath Realty Inc

7 Holiday St, Pawling, NY 12564

Est $534,229

Not Listed For Sale

17 Fenwood Dr, Pawling, NY 12564
- 3 Beds
- 2.5 Baths
- 1,716 Sq Ft
- Built 1986
17 Fenwood Dr, Pawling, NY 12564

Last Sold Summary
- 85 Days On Market

$1,405,000

Sold Jul 24, 2025

7 Tower Hill Rd, Pawling, NY 12564
- 4 Beds
- 3 Baths
- 3,038 Sq Ft
- Built 1999
Last Sold Summary
- 8% Above List Price
- $462/SF
- 49 Days On Market
Current Estimated Value $1,399,801

Last Listing Agent Ryan Arket Compass Greater NY, LLC

7 Tower Hill Rd, Pawling, NY 12564

Est $1,437,139

Not Listed For Sale

49 S Quaker Hill Rd, Pawling, NY 12564
- 5 Beds
- 4 Baths
- 4,480 Sq Ft
- Built 1840
49 S Quaker Hill Rd, Pawling, NY 12564

Last Sold Summary
- 78 Days On Market

$860,000

Sold Apr 14, 2026

1125 Old Quaker Hill Rd, Pawling, NY 12564
- 3 Beds
- 2 Baths
- 2,048 Sq Ft
- Built 1972
Last Sold Summary
- 3% Below List Price
- $420/SF
- 39 Days On Market
Current Estimated Value $860,864

Last Listing Agent Diana Murphy HomeSmart Homes & Estates

1125 Old Quaker Hill Rd, Pawling, NY 12564

Est $581,515

Not Listed For Sale

85 W Deer Trail, Pawling, NY 12564
- 4 Beds
- 2.5 Baths
- 2,341 Sq Ft
- Built 2001
85 W Deer Trail, Pawling, NY 12564

Last Sold Summary
- 23 Days On Market

$385,000

Sold Dec 02, 2025

23 Juniper Ln, Pawling, NY 12564
- 2 Beds
- 2.5 Baths
- 2,130 Sq Ft
- Built 1988
Last Sold Summary
- 1% Below List Price
- $181/SF
- 31 Days On Market
Current Estimated Value $397,245

Last Listing Agent Judith 'Judy' Albert BHHS Hudson Valley Properties

23 Juniper Ln, Pawling, NY 12564

Est $468,000

Not Listed For Sale

10 John Kane Ct, Pawling, NY 12564
- 2 Beds
- 2 Baths
- 1,564 Sq Ft
- Built 2000
10 John Kane Ct, Pawling, NY 12564

Last Sold Summary
- 43 Days On Market

$399,000

Sold Sep 26, 2025

33 Grandview Ave, Pawling, NY 12564
- 4 Beds
- 1 Bath
- 1,157 Sq Ft
- Built 1953
Last Sold Summary
- 1% Above List Price
- $345/SF
- 44 Days On Market
Current Estimated Value $402,734

Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

33 Grandview Ave, Pawling, NY 12564

Est $553,772

Not Listed For Sale

92 W Deer Trail, Pawling, NY 12564
- 3 Beds
- 3.5 Baths
- 2,992 Sq Ft
- Built 2002
92 W Deer Trail, Pawling, NY 12564

Last Sold Summary
- 65 Days On Market

$485,000

Sold Feb 11, 2026

2 Bridle Way, Pawling, NY 12564
- 3 Beds
- 3.5 Baths
- 3,467 Sq Ft
- Built 1992
Last Sold Summary
- 4% Below List Price
- $140/SF
- 27 Days On Market
Current Estimated Value $581,248

Last Listing Agent Arafat Ibrahim AI Realty Brokerage LLC

2 Bridle Way, Pawling, NY 12564

Est $562,789

Not Listed For Sale

86 W Deer Trail, Pawling, NY 12564
- 4 Beds
- 4 Baths
- 3,550 Sq Ft
- Built 2001
86 W Deer Trail, Pawling, NY 12564

Last Sold Summary
- 10 Days On Market

$790,000

Sold May 15, 2026

26 Rodina Dr, Pawling, NY 12564
- 4 Beds
- 2.5 Baths
- 3,200 Sq Ft
- Built 2025
Last Sold Summary
- 1% Below List Price
- $247/SF
- 51 Days On Market
Current Estimated Value $778,505

Last Listing Agent Douglas Servello Home Sweet Home Properties

26 Rodina Dr, Pawling, NY 12564

Est $565,452

Not Listed For Sale

48 W Deer Trail, Pawling, NY 12564
- 4 Beds
- 2.5 Baths
- 3,898 Sq Ft
- Built 2000
48 W Deer Trail, Pawling, NY 12564

Last Sold Summary
- 41 Days On Market

$410,000

Sold Apr 27, 2026

13 Cushing Green S, Pawling, NY 12564
- 2 Beds
- 2.5 Baths
- 1,567 Sq Ft
- Built 1987
Last Sold Summary
- 4% Below List Price
- $262/SF
- 66 Days On Market
Current Estimated Value $415,118

Last Listing Agent Claudia Jiskra McGrath Realty Inc

13 Cushing Green S, Pawling, NY 12564

Est $702,297

Not Listed For Sale

69 W Deer Trail, Pawling, NY 12564
- 4 Beds
- 4.5 Baths
- 4,898 Sq Ft
- Built 2001
69 W Deer Trail, Pawling, NY 12564

Last Sold Summary
- 13 Days On Market

$532,000

Sold Jul 18, 2025

104 Mohawk Trail, Pawling, NY 12564
- 3 Beds
- 2.5 Baths
- 2,175 Sq Ft
- Built 1999
Last Sold Summary
- 3% Below List Price
- $245/SF
- 23 Days On Market
Current Estimated Value $549,918

Last Listing Agent Pete Rodriguez William Raveis Real Estate

104 Mohawk Trail, Pawling, NY 12564

Est $706,035

Not Listed For Sale

Unlisted Address
- 3 Beds
- 2.5 Baths
- 2,599 Sq Ft
- Built 2005
Unlisted Address

Last Sold Summary
- 38 Days On Market

$615,000

Sold Apr 02, 2026

79 W Main St, Pawling, NY 12564
- 3 Beds
- 2 Baths
- 2,254 Sq Ft
- Built 1931
Last Sold Summary
- 3% Above List Price
- $273/SF
- 11 Days On Market
Current Estimated Value $600,314

Last Listing Agent Lisa Liffland McGrath Realty Inc

79 W Main St, Pawling, NY 12564

Est $664,235

Not Listed For Sale

57 Millstream Ct, Pawling, NY 12564
- 3 Beds
- 2.5 Baths
- 3,000 Sq Ft
- Built 2000
57 Millstream Ct, Pawling, NY 12564

Last Sold Summary
- 16 Days On Market

$360,000

Sold Jun 20, 2025

53 Mohawk Trail, Pawling, NY 12564
- 2 Beds
- 2 Baths
- 1,115 Sq Ft
- Built 1999
Last Sold Summary
- 3% Above List Price
- $323/SF
- 27 Days On Market
Current Estimated Value $378,364

Last Listing Agent Pamela Blecker Keller Williams Realty Partner

53 Mohawk Trail, Pawling, NY 12564

Showing Results 121 - 160, Page 4 of 18

New York Dutchess County Pawling

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