Pawling, NY Homes

/23
$799,000 Pending
- 4 Beds
- 2.5 Baths
- 3,200 Sq Ft
26 Rodina Dr, Pawling, NY 12564

Be the first to live in this stunning four bedroom, two and a half bath home nestled on a beautiful two and a half acre lot. This home is located on the border of Putnam and Duchess counties. Step onto the full length front porch and inside to a light, bright and airy interior boasting a modern open floor plan. Spacious entrance foyer with double coat closets and sleek iron railing staircase with

Douglas Servello

Home Sweet Home Properties

(845) 599-8285

26 Rodina Dr, Pawling, NY 12564
Explore Pawling
/40
$3,000 per month
- 2 Beds
- 2.5 Baths
- 1,413 Sq Ft
- House for Rent
3 Evergreen Way, Pawling, NY 12564

Move right into this beautifully maintained 2-bedroom, 2.5-bathroom townhouse located in the desirable Cedar Valley community. Upon entry, you’re welcomed by a bright, tiled foyer that sets the tone for the home’s inviting layout. To the right, an airy eat-in kitchen features granite countertops, a pantry closet, and a convenient pass-through window to the dining area—perfect for both everyday

Shannon Tully

McGrath Realty Inc

(845) 524-8078

3 Evergreen Way, Pawling, NY 12564
$637,500 Sold Dec 31, 2025

175 Old Quaker Hill Rd, Pawling, NY 12564
- 4 Beds
- 5 Baths
- 4,018 Sq Ft
- Built 1952
Last Sold Summary
- 9% Below List Price
- $159/SF
- 114 Days On Market
Current Estimated Value $837,347

Last Listing Agent Tom Consaga RE/MAX Ace Realty

175 Old Quaker Hill Rd, Pawling, NY 12564

Est $643,000 Not Listed For Sale

135 S Quaker Hill Rd, Pawling, NY 12564
- 2 Beds
- 3.5 Baths
- 2,836 Sq Ft
- Built 1850
135 S Quaker Hill Rd, Pawling, NY 12564

Last Sold Summary
- 14% Above List Price
- $199/SF
- 38 Days On Market
Last Sold Price $565,000

Last Listing Agent Dominick DiFilippo Keller Williams Realty Partner

/37
$775,000 Pending
- 4 Beds
- 2.5 Baths
- 3,611 Sq Ft
4 Mane Way, Pawling, NY 12564

Elegant and Updated Center Hall Colonial, ideally situated in The Highlands—a beautiful and highly sought-after neighborhood in the charming Town of Pawling. This spacious four-bedroom, two-and-a-half-bath home seamlessly blends timeless architectural character with modern luxury, offering comfort, style, and functionality for today’s lifestyle. Gleaming hardwood floors flow throughout the main

Sharon Sheil

Coldwell Banker Realty

(845) 443-7838

4 Mane Way, Pawling, NY 12564
/10
$1,400 total monthly price
- 1 Bed
- 1 Bath
- 300 Sq Ft
- Condo for Rent
23 W Main St Unit 1A, Pawling, NY 12564

Two room studio in the historical Village of Pawling. Ground floor, private entrance. Convenient parking. Walk to Metro-North, shopping, laundry. No smoking/pets Call only

23 W Main St Unit 1A, Pawling, NY 12564
$115,000 Sold Nov 14, 2025

0 Overlook Rd, Pawling, NY 12564
- Land
- 1.4 Acres
- $82,143 per Acre
Last Sold Summary
- 21% Below List Price
- 249 Days On Market
Last Listing Agent Judith 'Judy' Albert BHHS Hudson Valley Properties

0 Overlook Rd, Pawling, NY 12564

Not Listed For Sale

9 Ravine Rd, Pawling, NY 12564
9 Ravine Rd, Pawling, NY 12564

Last Sold Summary
- 1,323 Days On Market
Last Sold Price $190,000

Last Listing Agent Shannon Tully McGrath Realty Inc

/11
$229,000
- Land
- 6.63 Acres
- $34,540 per Acre
Lot 25 Brady Brook Farm Rd, Pawling, NY 12564

Come build your dream home on this 6.63-acre Board of Health–approved lot in the desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom home, this property offers the perfect setting for those seeking privacy while remaining just minutes from all the conveniences the Town of Pawling has to offer. Enjoy easy access to Route 22, Route 55, Metro-North, shopping, the charming

Shannon Tully

McGrath Realty Inc

(845) 684-9806

Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
/35
$2,600 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- House for Rent
332 Quaker Hill Rd, Pawling, NY 12564

Adorable 2 bedroom cottage at the end of a long private drive (which the owner plows!) overlooking 13 acres of open fields alongside an apple orchard. Views for days, covered back porch for those BBQ's & just watching the sun set. Wide wood floors throughout, a fireplace with a wood burning stove insert which heats the whole house (landlord has plenty of wood). The living room is huge with

Gillian Stewart Gillian Stewart Real Estate

332 Quaker Hill Rd, Pawling, NY 12564
$200,000 Sold Oct 21, 2025

Lot #2 Dodge Rd, Pawling, NY 12564
- Land
- 9.73 Acres
- $20,555 per Acre
Last Sold Summary
- 20% Below List Price
- 312 Days On Market
Last Listing Agent Brian McGrath McGrath Realty Inc

Lot #2 Dodge Rd, Pawling, NY 12564

Est $168,211 Not Listed For Sale

7 Birch Ln, Holmes, NY 12531
7 Birch Ln, Holmes, NY 12531

Last Sold Summary
- 1,194% Above List Price
- 234 Days On Market
Last Sold Price $13,000

Last Listing Agent Pauline Angrisani Coldwell Banker Realty

/6
$220,000
- Land
- 0.76 Acre
- $289,474 per Acre
15 Dykeman St, Pawling, NY 12564

Rare opportunity to build in the heart of the Village of Pawling! Cleared and ready for development, this residential lot at 15 Dykeman Street offers municipal water and sewer available at the street — a major advantage for new construction. The property features a defined driveway lined with item four stone, providing immediate access and a head start on site work. Level and open, the lot offers

Joanne Debellis

Debellis Real Estate LLC

(845) 660-6758

15 Dykeman St, Pawling, NY 12564
/9
$1,500 per month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Apartment for Rent
104 E Main St Unit 5, Pawling, NY 12564

Spacious one bedroom apartment close to the Village of Pawling available for immediate occupancy.

Bethany Cole HomeSmart Homes & Estates

104 E Main St Unit 5, Pawling, NY 12564
$400,000 Sold Jan 28, 2026

2 Spruce St, Pawling, NY 12564
- 2 Beds
- 2.5 Baths
- 1,838 Sq Ft
- Built 1993
Last Sold Summary
- $218/SF
- 37 Days On Market
Current Estimated Value $399,319

Last Listing Agent Robin Butler-Koschei Hanson Real Estate Partners

2 Spruce St, Pawling, NY 12564

Est $624,386 Not Listed For Sale

68 W Main St, Pawling, NY 12564
- 7 Beds
- 3 Baths
- 3,400 Sq Ft
- Built 1920
68 W Main St, Pawling, NY 12564

Last Sold Summary
- 69% Above List Price
- $109/SF
- 20 Days On Market
Last Sold Price $370,000

Last Listing Agent Ronald Green KW MidHudson

/28
$530,000
- 3 Beds
- 1.5 Baths
- 1,706 Sq Ft
58 Pine Dr, Pawling, NY 12564

Tucked away at the end of a quiet cul-de-sac, this beautifully maintained home sits on 2.87 acres of mostly level, private property—offering the perfect blend of peaceful surroundings and everyday convenience. Step into a bright and welcoming main living area featuring a sun-filled living room with an oversized picture window framing peaceful views of the front lawn, and a dining room with

Teddie Leonaggeo

McGrath Realty Inc

(845) 299-0848

58 Pine Dr, Pawling, NY 12564
/17
$3,250 per month
- 3 Beds
- 2.5 Baths
- 1,700 Sq Ft
- Apartment for Rent
10 Fenwood Dr Unit B, Pawling, NY 12564

Bright & Spacious 3-Bedroom Apartment in Private Setting – Close to Train, Shopping & Schools Enjoy privacy and convenience in this light-filled 3-bedroom, 2.5-bath apartment located in a well-maintained three-family home on a quiet, secluded road just off the main thoroughfare. This spacious apartment offers the perfect balance of peaceful living while being minutes from shopping centers,

Clayton Livingston McGrath Premier Real Estate

10 Fenwood Dr Unit B, Pawling, NY 12564
$435,000 Sold Jun 06, 2025

103 Mohawk Trail, Pawling, NY 12564
- 3 Beds
- 2.5 Baths
- 1,917 Sq Ft
- Built 2001
Last Sold Summary
- 2% Above List Price
- $227/SF
- 13 Days On Market
Current Estimated Value $462,714

Last Listing Agent Claudia Jiskra McGrath Realty Inc

103 Mohawk Trail, Pawling, NY 12564

Est $2,180,817 Not Listed For Sale

73 Cunningham Ln, Pawling, NY 12564
- 5 Beds
- 5 Baths
- 8,331 Sq Ft
- Built 2009
73 Cunningham Ln, Pawling, NY 12564

Last Sold Summary
- 36% Above List Price
- $192/SF
- 121 Days On Market
Last Sold Price $1,600,000

Last Listing Agent Helen Murray William Pitt Sothebys Int Rlty

/50
$599,000
- 2 Beds
- 2 Baths
- 2,196 Sq Ft
168 Old Route 55, Pawling, NY 12564

Step into the very year our nation was born and own a piece of American history! Originally constructed in 1776, this iconic stone residence later became the "Pawling Toll Gate and Toll House," serving as a vital gateway for travelers, a general store, a post office, and a legendary tavern. It is even whispered that George Washington himself once proved his strength within these walls, winning a

Colleen McGrath

McGrath Realty Inc

(845) 932-0435

168 Old Route 55, Pawling, NY 12564
/8
$2,000 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Apartment for Rent
10 Fenwood Dr Unit C, Pawling, NY 12564

Charming and spacious 2-bedroom, 1-bath apartment featuring high ceilings, skylights, and ceramic tile floors throughout, creating a bright and open living environment. This inviting home offers a private entry, providing added privacy and convenience. The apartment is filled with natural light thanks to the skylights and generous ceiling height, giving the living spaces an airy and comfortable

Clayton Livingston McGrath Premier Real Estate

10 Fenwood Dr Unit C, Pawling, NY 12564
$436,000 Sold Dec 18, 2025

36 Elm St, Pawling, NY 12564
- 3 Beds
- 1.5 Baths
- 1,680 Sq Ft
- Built 1900
Last Sold Summary
- 17% Below List Price
- $260/SF
- 133 Days On Market
Current Estimated Value $431,730

Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

36 Elm St, Pawling, NY 12564

Est $762,140 Not Listed For Sale

34 Harmony Hill Rd, Pawling, NY 12564
- 4 Beds
- 4.5 Baths
- 3,340 Sq Ft
- Built 2007
34 Harmony Hill Rd, Pawling, NY 12564

Last Sold Summary
- 23% Above List Price
- $185/SF
- 88 Days On Market
Last Sold Price $619,500

Last Listing Agent Lawrence Zacks Keller Williams Realty Partner

/22
$1,350,000
- Land
- 3.9 Acres
- $346,154 per Acre
178 Charles Colman Blvd, Pawling, NY 12564

Exclusive Mixed-Use Property in Pawling N.Y.! Incredible Investment or Business Opportunity offering a rare blend of Residence, Greenhouse, Floral Shop, & Nursery.This beautiful Sprawling estate boasts a Commercial c & Residential component? with a 2,500 sqft greenhouse fully-equipped floral shop with retail space There is Ample parking & easy accessibility for Commercial

Vince Buccieri

Today Realty Corp.

(845) 280-5951

178 Charles Colman Blvd, Pawling, NY 12564
/37
$30,000 per month
- 4 Beds
- 3.5 Baths
- 4,233 Sq Ft
- House for Rent
121 N Quaker Hill Rd, Pawling, NY 12564

$30k/month summer. Inquire for other terms. 4 bedroom 3.5 designer inspired home intended to complement the splendor of its natural surroundings. Fully furnished for comfortable luxury. 3 fireplaces and awe inspiring panoramic views. Soak in a breathtaking scene spanning the great meadow, rolling hills and mountains beyond. Long driveway with mature landscape, this hideaway provides pure

Joseph Lorino Brown Harris Stevens HV LLC

121 N Quaker Hill Rd, Pawling, NY 12564
$361,000 Sold Aug 13, 2025

37 Spruce St, Pawling, NY 12564
- 2 Beds
- 2.5 Baths
- 1,413 Sq Ft
- Built 1993
Last Sold Summary
- 3% Below List Price
- $255/SF
- 51 Days On Market
Current Estimated Value $369,759

Last Listing Agent Nick Selca Lakeshore Realty International

37 Spruce St, Pawling, NY 12564

Est $869,987 Not Listed For Sale

6 di Pietro Ln, Pawling, NY 12564
- 4 Beds
- 4.5 Baths
- 6,042 Sq Ft
- Built 2002
6 di Pietro Ln, Pawling, NY 12564

Last Sold Summary
- 16% Above List Price
- $124/SF
- 46 Days On Market
Last Sold Price $750,000

Last Listing Agent Tony Zaccardo Coldwell Banker Realty

/33
$9,750,000
- 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.

(845) 377-2512

225 Route 22, Pawling, NY 12564
$330,000 Sold Oct 02, 2025

36 Spruce St, Pawling, NY 12564
- 2 Beds
- 2.5 Baths
- 1,414 Sq Ft
- Built 1993
Last Sold Summary
- 3% Below List Price
- $233/SF
- 41 Days On Market
Current Estimated Value $441,909

Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

36 Spruce St, Pawling, NY 12564

Est $863,253 Not Listed For Sale

809 N Quaker Hill Rd, Pawling, NY 12564
- 3 Beds
- 3 Baths
- 3,600 Sq Ft
- Built 1759
809 N Quaker Hill Rd, Pawling, NY 12564

Last Sold Summary
- 62% Below List Price
- $639/SF
- 20 Days On Market
Last Sold Price $2,300,000

Last Listing Agent Raj Kumar Four Seasons Sothebys Intl

/8
$229,000
- Land
- 5.57 Acres
- $41,113 per Acre
Lot 21 Cox Rd, Pawling, NY 12564

Come build your dream home on this 5.6-acre Board of Health–approved lot in the highly desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom residence, this property offers both privacy and convenience—just minutes from Route 22, the Village of Pawling, shopping, Metro-North, Route 55, and even the Appalachian Trail. Nestled within the Oblong Trails, residents of Brady Brook

Shannon Tully

McGrath Realty Inc

(845) 412-9125

Lot 21 Cox Rd, Pawling, NY 12564
$725,000 Sold Dec 17, 2025

27 Millstream Ct, Pawling, NY 12564
- 4 Beds
- 2.5 Baths
- 3,283 Sq Ft
- Built 2000
Last Sold Summary
- $221/SF
- 162 Days On Market
Current Estimated Value $719,914

Last Listing Agent Christopher Filangeri BHHS Hudson Valley Properties

27 Millstream Ct, Pawling, NY 12564

Est $538,474 Not Listed For Sale

775 N Quaker Hill Rd, Pawling, NY 12564
- 5 Beds
- 2 Baths
- 2,262 Sq Ft
- Built 1960
775 N Quaker Hill Rd, Pawling, NY 12564

Last Sold Summary
- 7% Above List Price
- $223/SF
- 13 Days On Market
Last Sold Price $505,000

Last Listing Agent ALEXIS MALSBURY Coldwell Banker Realty

/6
$87,500
- Land
- 0.46 Acre
- $190,217 per Acre
0 Lakeview Dr Unit KEY962482, Pawling, NY 12531

Build your ideal home on this prime .46-acre lot perfectly situated within the sought-after Pawling Lake Estates community. Offering a rare blend of beauty and value, this property boasts picturesque views of Jones Pond and benefits from the lower property taxes of the Dover Union Free School District. Nature enthusiasts will love being surrounded by the sprawling West Mountain State Forest,

Colleen McGrath

McGrath Realty Inc

(845) 385-2808

0 Lakeview Dr Unit KEY962482, Pawling, NY 12531
$540,000 Sold May 23, 2025

85 W Deer Trail, Pawling, NY 12564
- 4 Beds
- 2.5 Baths
- 2,341 Sq Ft
- Built 2001
Last Sold Summary
- $231/SF
- 23 Days On Market
Current Estimated Value $570,993

Last Listing Agent Shannon Tully McGrath Realty Inc

85 W Deer Trail, Pawling, NY 12564

Est $913,384 Not Listed For Sale

16 Anderson Rd, Pawling, NY 12564
- 2 Beds
- 3 Baths
- 2,008 Sq Ft
- Built 2023
16 Anderson Rd, Pawling, NY 12564

Last Sold Summary
- 60% Above List Price
- $284/SF
- 100 Days On Market
Last Sold Price $570,000

Last Listing Agent Brian McGrath McGrath Realty Inc

/42
$775,000 Pending
- 3 Beds
- 2.5 Baths
- 4,627 Sq Ft
36 Horseshoe Path, Pawling, NY 12564

Welcome home to the highly sought- after The Highlands in Pawling. This beautifully designed 3 BR, 3 Bath residence is tailored for today's discerning buyers, offering comfort, flexibility and effortless living. The open concept main level features an expansive Living Room, spacious Dining Room and a Chef's Kitchen , ideal for everything from Sunday pancakes to entertaining on a grand scale! The

Neeta Saraswat Weichert Realtors

36 Horseshoe Path, Pawling, NY 12564
$430,000 Sold Sep 11, 2025

19 Cushing Green S, Pawling, NY 12564
- 3 Beds
- 2.5 Baths
- 1,835 Sq Ft
- Built 1987
Last Sold Summary
- 6% Below List Price
- $234/SF
- 64 Days On Market
Current Estimated Value $445,856

Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

19 Cushing Green S, Pawling, NY 12564

Est $661,029 Not Listed For Sale

8 Brady Ln, Pawling, NY 12564
- 3 Beds
- 1.5 Baths
- 1,972 Sq Ft
- Built 1966
8 Brady Ln, Pawling, NY 12564

Last Sold Summary
- 130% Above List Price
- $146/SF
- 45 Days On Market
Last Sold Price $287,000

Last Listing Agent Ernie Acampora River Realty Services, Inc.

Showing Results 1 - 40, Page 1 of 18

New York Dutchess County Pawling

Home Trends in Pawling, NY

On average, homes in Pawling, NY sell after 64 days on the market compared to the national average of 55 days. The median sale price for homes in Pawling, NY over the last 12 months is $532,000, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$532,000

Median Single Family Sale Price

$560,000

Median Townhouse Sale Price

$375,000

Median 2 Bedroom Sale Price

$361,000

Average Price Per Sq Ft

$323

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.50

Median List Price

$535,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-2%

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Pawling, NY Homes

Real Estate & Homes

Home Trends in Pawling, NY

Housing Trends