Pawling, NY Homes for Sale

Q: What are the most popular zip codes in Pawling, NY?

The most popular zip codes in Pawling, NY include 12564 , 12563 , 12531 , 12570 and 06784 .

/42
$598,500
- 4 Beds
- 4.5 Baths
- 2,361 Sq Ft
126 Old Route 55, Pawling, NY 12564

Back on the market, the deal fell through from the buyer side. 9/17/2025 This house is owned by a church and in New York a sale has to be approved by the Attorney Generals office which can take up to six months. This can work to your benefit depending on your own timeline. This can also be set up a s a short term rental as well while waiting for the approvals WITH PORTION OF RENT GOING TOWARDS

Philip Bisesto

HomeSmart Homes & Estates

(845) 576-1665

126 Old Route 55, Pawling, NY 12564
Explore Pawling
/23
$799,000
- 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
/38
$875,000
- 3 Beds
- 2 Baths
- 2,048 Sq Ft
1125 Old Quaker Hill Rd, Pawling, NY 12564

Tucked away in the prestigious Quaker Hill area of Pawling, this cozy ranch-style country home offers a private setting, on 6.8 wooded acres, where time slows and weekends linger. Thoughtfully renovated in 2018, the residence is rich in character, featuring 100-year-old reclaimed posts and beams from a barn in Western PA and 150-year-old wide-board floors reclaimed from a CT tobacco barn that

Diana Murphy

HomeSmart Homes & Estates

(845) 583-0180

1125 Old Quaker Hill Rd, Pawling, NY 12564
/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
/48
$1,200,000
- 5 Beds
- 4 Baths
- 4,248 Sq Ft
64 S Quaker Hill Rd, Pawling, NY 12564

Welcome to Country Living at Its Finest!Nestled on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential for those looking to restore a piece of history. A long, tree-lined driveway leads to this charming 4-bedroom, 4-bath home surrounded by open fields, mature trees, and peaceful country views. The property features a spacious 4-car garage with finished living space with

Shannon Tully

McGrath Realty Inc

(845) 415-7723

64 S Quaker Hill Rd, Pawling, NY 12564
/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
/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) 328-6866

Lot 21 Cox Rd, Pawling, NY 12564
/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) 378-9417

Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
/50
$599,000
- 2 Beds
- 2 Baths
- 1,428 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
/42
$775,000 Coming Soon
- 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
/24
$950,000
- 4 Beds
- 3.5 Baths
- 3,434 Sq Ft
128 Old Pawling Rd, Pawling, NY 12564

Welcome to 128 Old Pawling Road, a beautifully situated property in Pawling, NY. Set back from the road, the home is approached by a long private driveway and gated entrance, offering a sense of privacy while still being part of a neighborhood setting. Resting on over 5 acres, the property showcases stunning mountain views that create an impressive backdrop to everyday living year-round. Whether

Juliska Martino Compass Greater NY, LLC

128 Old Pawling Rd, Pawling, NY 12564
/15
$1,250,000
- 4 Beds
- 4.5 Baths
- 3,200 Sq Ft
120 Harmony Rd, Pawling, NY 12564

New construction 4 bedroom, 4.5 bathroom home on 5 acres. Don't miss this opportunity to customize your dream home. This home features a open floor plan with large kitchen, perfect for entertaining. The main living area has exposed beams and high ceilings. The primary bedroom has large walk in closet and ensuite. There is also a junior suite with ensuite. See attached floor plans for full detail.

Bliss Voutsinas Hillside Realty & Development

120 Harmony Rd, Pawling, NY 12564
/50
$619,000
- 4 Beds
- 2 Baths
- 1,950 Sq Ft
322 Old Route 22, Pawling, NY 12564

Multi-family in Pawling! This spacious, newly remodeled 2-family home is located just a few minutes from the Village of Pawling - a great opportunity for owner-occupants, investors, or extended families! Each unit features 2 bedrooms, a full bath, living room, dining area, kitchen and bright, enclosed sunporches, providing plenty of space and natural light throughout. Inside, both units are

Susan Stevens BHHS Hudson Valley Properties

322 Old Route 22, Pawling, NY 12564
/29
$2,500,000
- 6 Beds
- 6.5 Baths
- 6,625 Sq Ft
3302 Route 55, Pawling, NY 12564

Welcome to your forever home, serene retreat and mini estate. Enjoy the 88 private acres with breath taking views. Mother Nature is at her best. Exceptional beauty for all four seasons. The unique and exquisite architectural design of this home lends to expansive living space, tucked behind gated entry. This home offers expansive living space, luxury and customize finishes throughout. A true

STACI MACKIN Dixon Smith Realty

3302 Route 55, Pawling, NY 12564
/8
$150,000
- Land
- 0.46 Acre
- $326,087 per Acre
20 Hickory Ln, Pawling, NY 12564

Build your dream home on this exceptional 0.46-acre parcel, offering a rare blend of privacy, nature, and convenience. The property is BOH approved (3 bedroom residential dwelling), providing a smooth path to construction, and is landlocked at the rear, creating a peaceful, secluded setting. Enjoy access to two nearby lakes for fishing or swimming, or relax at the clubhouse. Drive into Pawling

Tela Cook McGrath Realty Inc

20 Hickory Ln, Pawling, NY 12564
/5
$399,000
- Land
- 61.82 Acres
- $6,454 per Acre
0 S White Rock Rd Unit 6015368, Pawling, NY 12531

Approved 7 lot residential subdivision: Pristine, secluded, quiet area with DCBOH approved residential building lots 3.02-6.41 acres surroundinga 31 acre open space area. All lot sites selected for privacy. Partial physical improvements (over $350K) to include 2 (partially complete) roads and storm water works in place. Tax assessments in appeal. HOA established, shared fees for roads & storm

John Ravetto Houlihan Lawrence Inc.

0 S White Rock Rd Unit 6015368, Pawling, NY 12531
/27
$450,000
- 4 Beds
- 1.5 Baths
- 1,776 Sq Ft
40 Walnut St, Pawling, NY 12564

Spacious 4 BR Home is located in the Village of Pawling. Nice property has a wonderful western view with amazing sunsets! Sunny Living Rm with picture window is open to the Dining Rm. The Kitchen has space for a breakfast table or island. The main floor has been freshly painted and has solid oak hardwood floors. Walking distance to Metro-North Train Station, Library, Medical Offices, Village

Lisa Liffland McGrath Realty Inc

40 Walnut St, Pawling, NY 12564
/24
$485,000
- 3 Beds
- 3.5 Baths
- 2,503 Sq Ft
20 Saratoga St, Pawling, NY 12564

Welcome to this stunning 3-bedroom, 3.5-bath end-unit townhome in the highly desirable Deerfield Ponds community. Bright, warm, and beautifully maintained, this home offers an ideal blend of comfort, convenience, and modern living. Step inside to an inviting living room that seamlessly flows into the dining area and a charming kitchen with a cozy breakfast nook, all appliances updated within the

Julia Lear Coldwell Banker Realty

20 Saratoga St, Pawling, NY 12564
/6
$225,000
- Land
- 0.76 Acre
- $296,053 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

15 Dykeman St, Pawling, NY 12564
/20
$3,900,000
- Land
- 108 Acres
- $36,111 per Acre
57 S Quaker Hill Rd, Pawling, NY 12564

Seldom does a property like this become available. Two parcels totaling 108 acres create the most idyllic setting on Quaker Hill. Imagine a pastoral retreat blanketed by farmed fields, well-maintained trails, and productive land. With approximately 56 cleared acres, the possibilities are endless. Build your dream country estate, an extended family compound, or an equestrian paradise with ample

Brian McGrath McGrath Realty Inc

57 S Quaker Hill Rd, Pawling, NY 12564
/16
$387,000
- 2 Beds
- 2.5 Baths
- 1,413 Sq Ft
10 Timberline Trail, Pawling, NY 12564

~ Welcome to your spacious and cozy tri-level townhome in the desirable Cedar Valley Community. ~This rare end unit provides you with an abundance of light and additional outdoor space. Featuring 2 spacious bedrooms and 2.5 bathrooms, this home boasts an open and versatile layout ideal for everyday living and entertaining. The dining area and bright living room with its cozy fireplace opens

Giorgio Palmisano Howard Hanna Rand Realty

10 Timberline Trail, Pawling, NY 12564
/33
$495,000
- 2 Beds
- 2 Baths
- 1,088 Sq Ft
17 Townsend Blvd, Pawling, NY 12564

Fall in Love with this Charming Mediterranean Style Garden Home. A Private Oasis Hidden Away and Nestled among a Grove of Mature Trees. Follow meandering paths that lead to Splashes of Color from the Cultivated Perennial Gardens of a Lifetime and a Gentle Woodland Stream. This Home is Sparkling Clean, Freshly Polished, Newly Painted, Move-In Ready and awaits your Arrival. Tucked in at the end of

Martha Woodhouse Howard Hanna Rand Realty

17 Townsend Blvd, Pawling, NY 12564
/11
$125,000
- Land
- 0.31 Acre
- $403,226 per Acre
3 Pine Dr, Pawling, NY 12564

This property offers endless possibilities, whether for development, investment, or creating a personalized mobile home environment. Key features include: Expansive Lot: 13,500 sq ft for development, investment, or personal use.Prime Location: Close to town with shops, dining, and community events.Transportation Access: Near major routes and public transit (Dover Plains Metro North

Brandon Doswell-Stephens Silverside Realty LLC

3 Pine Dr, Pawling, NY 12564
/3
$149,900
- Land
- 4.21 Acres
- $35,606 per Acre
0 South Rd Unit KEY853088, Pawling, NY 12531

Beautiful 4.21-acre lot in Pawling, NY presents a unique opportunity to build your dream home. This secluded property offers the ideal blend of privacy and convenience, situated just minutes from the charming Village of Pawling, Metro-North train station, restaurants, shopping, and all the amenities the historic Hudson Valley has to offer. Only three miles off I-84. Perfect for a year-round

Michael Knecht Howard Hanna Rand Realty

0 South Rd Unit KEY853088, Pawling, NY 12531
/3
$189,000
- Land
- 11.4 Acres
- $16,579 per Acre
0 Kirby Hill Rd, Pawling, NY 12564

Great 11 acre BOHA property in Quaker Hill area of Pawling. Great views. Located quiet area next to historic library (not active. Shown as museum in warmer weather). Fantastic getaway area or permanent dream house.

Richard Castro Howard Hanna Rand Realty

0 Kirby Hill Rd, Pawling, NY 12564
/14
$345,000
- 2 Beds
- 2.5 Baths
- 1,567 Sq Ft
1 Cushing Green N, Pawling, NY 12564

This great 2 bedroom 2.5 bath townhome is a must see. Many great amenities including attached garage, formal dining room, fireplace, rear deck and more. This is a Fannie Mae HomePath property.

Matthew Cave Hudson Property Services, LLC

1 Cushing Green N, Pawling, NY 12564
/29
$705,000
- 4 Beds
- 3 Baths
- 3,888 Sq Ft
12 Rebecca Dr, Pawling, NY 12564

Surrounded by the natural beauty of the Hudson Valley region, this Multi-Family home benefits from a private environment that outdoor enthusiasts will find irresistible. This property's location offers convenient access to the Lakeside Park Disc Golf Course, the nearby Appalachian Trail which provides endless hiking opportunities for nature lovers and the Metro-North Railroad being about a 5

Kevin Sanabria eRealty Advisors, Inc

12 Rebecca Dr, Pawling, NY 12564
/46
$39,000,000
- 9 Beds
- 15 Baths
- 55,000 Sq Ft
104 N Garden Dr, Pawling, NY 12564

Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it

Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

104 N Garden Dr, Pawling, NY 12564
/49
$425,000
- 2 Beds
- 2.5 Baths
- 1,567 Sq Ft
13 Cushing Green S, Pawling, NY 12564

A rare find and an incredible opportunity awaits in Squire Green with this two-story end-unit townhome featuring the highly sought-after attached garage. Townhomes are seldom available in the Squire Green section of the Deerfield Ponds community, and end units are even more uncommon, making this offering especially desirable. Steps inside reveal a spacious entry foyer leading to an updated

Claudia Jiskra McGrath Realty Inc

13 Cushing Green S, Pawling, NY 12564
/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
/26
$299,500
- 3 Beds
- 1 Bath
- 1,653 Sq Ft
14 Old Route 55, Pawling, NY 12564

Welcome HOME to this charming and historic 3-bedroom, 1-bath residence located in the heart of Pawling in the Pawling School District. This beautifully updated antique home offers the perfect blend of timeless character and modern convenience. Recent updates include brand-new carpeting, refinished hardwood floors, fresh paint, updated fixtures, an updated bathroom, and a renovated kitchen with

Ronald Green KW MidHudson

14 Old Route 55, Pawling, NY 12564

New York Dutchess County Pawling

Why Live in Pawling

Pawling, NY, spans 45 square miles in Dutchess County, offering residents a blend of rural solitude and accessibility to New York City via an MTA station for an hour-long commute. The town features over 1,000 acres of protected parklands, including the Pawling Nature Reserve, where locals can hike the Appalachian Trail. Recreational options also include Dutcher Golf Course and Whaley Lake, the largest lake in the county, ideal for swimming, kayaking, and fishing. The Maybrook Trailway, part of the Empire State Trail system, provides scenic hiking opportunities. Pawling's housing market includes upscale single-family homes such as Colonial Revivals, ramblers, raised ranches, and split-levels, with exclusive areas like Quaker Hill offering large farms and multimillion-dollar properties. The central village features Craftsman and Victorian homes, while waterfront cottages are available in Holmes. Pawling Central School District serves the community with highly rated schools, including Pawling Elementary, Pawling Middle, and Pawling High. The private Trinity-Pawling School, an all-boys Episcopal boarding school, is also highly rated. Local amenities include grocery stores like Acme Markets and Hannaford along NY-22, and dining options such as O’Connor’s Public House downtown. Community traditions include the Pawling Farmers Market and the Pawling Concert Series, along with Decemberfest and Tree Lighting events. Commuters can reach Manhattan in an hour and a half by train or car, and New Haven, Connecticut, is accessible within two hours.

Learn more about living in Pawling

Frequently Asked Questions

What is the average home price in Pawling, NY?

Homes for sale in Pawling, NY have an average home price of $1,303,469.

How many homes have sold over the last 12 months in Pawling, NY?

65 homes have sold in Pawling, NY over the last 12 months.

What are the most popular zip codes in Pawling, NY?

The most popular zip codes in Pawling, NY include 12564, 12563, 12531, 12570 and 06784.

How much do you need to make to afford a house in Pawling?

The median home price in Pawling is $540,000. If you put a 20% down payment of $108,000 and had a 30-year fixed mortgage with an interest rate of 5.98%, your estimated principal and interest payment would be $2,580 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in Pawling. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Pawling, NY?

Pawling, NY has highly rated public and private schools. Some of the best schools in Pawling based on Niche Grades are Trinity-Pawling School, Mizzentop Day School and Pawling High School. Browse all the schools in Pawling, NY to learn more.

Home Trends in Pawling, NY

On average, homes in Pawling, NY sell after 67 days on the market compared to the national average of 54 days. The median sale price for homes in Pawling, NY over the last 12 months is $510,000, down 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$510,000

Median Single Family Sale Price

$598,500

Median Townhouse Sale Price

$380,750

Median 2 Bedroom Sale Price

$363,000

Average Price Per Sq Ft

$317

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.30

Median List Price

$540,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-5%

How to Buy a Home How to Finance a Home How to Sell a Home

Pawling Types of Homes for Sale

Pawling Land for Sale

More About Living in Pawling

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