Pawling Homes for Sale

/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
/28
$537,500
- 3 Beds
- 3.5 Baths
- 2,106 Sq Ft
101 Bundy Hill Rd, Holmes, NY 12531

Nestled in between trees and rocks, privacy abounds in this Contemporary Colonial style dwelling with numerous upgrades. A down to the studs remodel in 2016, the home boasts generous open concept living, dining and kitchen areas all with recessed lighting. Kitchen includes butcherblock counter tops and stainless-steel appliances. Entry nook convenient for coats, purses, backpacks and shoes. First

Judith 'Judy' Albert

BHHS Hudson Valley Properties

(845) 299-9362

101 Bundy Hill Rd, Holmes, NY 12531
/25
$469,000
- 4 Beds
- 2.5 Baths
- 1,608 Sq Ft
120 South Rd, Holmes, NY 12531

Welcome to 120 South Rd/40 Great Bear Rd, a charming home at the end of a quiet cul-de-sac, offering peace, privacy, and a stunning lake view from the deck. Set on just under 3 acres, this property features a spacious front yard shaded by mature trees, perfect for outdoor gatherings, gardening, or simply relaxing in your own private oasis. Enjoy the comfort and efficiency of new windows

Omar Harper

Epique Realty

(845) 552-1998

120 South Rd, Holmes, NY 12531
/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
/32
$1,400,000
- 11 Beds
- 8 Baths
750 Route 292, Holmes, NY 12531

Multi-generational housing opportunity with 3 individual homes on one property. 3 distinct home styles with plenty of options. The perfect balance of togetherness and privacy. And investors - you may want to give this property some serious consideration as well.Unit A: Colonial style renovated home. Hardwood floors, crown molding and recessed lighting throughout. Spacious Living Room with

Judith 'Judy' Albert

BHHS Hudson Valley Properties

(845) 957-9518

750 Route 292, Holmes, NY 12531
/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
/45
$505,000
- 4 Beds
- 2 Baths
- 1,210 Sq Ft
23 Lakeview Dr, Holmes, NY 12531

You get to enjoy the Lakehouse lifestyle all year round at this newly updated raised ranch. Convenient to the restaurants and shops of downtown Pawling and your pick of the Pawling, Patterson, or Southeast Metro North stations as well as I-84 and the Taconic State Parkway. The current owner has made extensive improvements to the property, including all new baths and a master bedroom with

Lisbeth Furke

World Homes Realty

(845) 851-0605

23 Lakeview Dr, Holmes, NY 12531
/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
/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
/38
$889,900
- 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

1125 Old Quaker Hill Rd, Pawling, NY 12564
/42
$675,000
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
1098 New York 292, Holmes, NY 12531

Here's a fantastic opportunity to own a piece of waterfront paradise, perfect for those seeking a tranquil escape without sacrificing convenience! This charming ranch-style home boasts three comfortable bedrooms and three full baths, ensuring ample space and privacy for everyone. You'll love the dedicated office, ideal for remote work, and a cozy den for a quiet reading nook while enjoying the

John Derevjanik BHHS Hudson Valley Properties

1098 New York 292, Holmes, NY 12531
/41
$595,000
- 3 Beds
- 2 Baths
- 2,254 Sq Ft
79 W Main St, Pawling, NY 12564

One of the prettiest homes you will see! Lovingly maintained home has all the original character and charm yet offers desired modern updates. Truly park-like property features a babbling brook, stone walls and perennial gardens. Special interior features throughout the home include solid hardwood floors, vintage doors with glass doorknobs, original trim work, all new windows, central air. A

Lisa Liffland McGrath Realty Inc

79 W Main St, Pawling, NY 12564
/26
$699,000
- 3 Beds
- 2 Baths
- 1,822 Sq Ft
379 S White Rock Rd, Holmes, NY 12531

Welcome to 379 South White Rock Road — a completely renovated country home in the charming town of Pawling, NY, offering a truly distinctive blend of modern luxury and timeless rural character. Rebuilt from the foundation up in 2023, every inch of this home has been meticulously reimagined by a master builder using only premium, top-quality materials and finishes. The result is a living

Laurence Wallace Coldwell Banker Realty

379 S White Rock Rd, Holmes, NY 12531
/46
$420,000
- 2 Beds
- 2 Baths
- 2,596 Sq Ft
7 Juniper Ln, Pawling, NY 12564

Welcome home to your spacious and cozy tri-level end unit in the Cedar Valley complex! The eat-in kitchen opens to the dining area and bright living room with a cozy fireplace, perfect for everyday living and entertaining. The main level features a primary bedroom with private bath and walk-in closet, plus a second bedroom with a full hall bath. The loft overlooking the living area offers

Elizabeth Poggiogalle Real Broker NY LLC

7 Juniper Ln, 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
/17
$228,000
- 2 Beds
- 1 Bath
- 672 Sq Ft
5 Birch Dr, Holmes, NY 12531

2 bedroom home on Whaley Lake in Shore Haven Civic Association. Access to 3 beaches and dock. Winter (and a little summer) views of the lake.

James Bergstraser RE/MAX Classic Realty

5 Birch Dr, Holmes, 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
/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
/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
/23
$425,000
- 2 Beds
- 1 Bath
- 1,130 Sq Ft
4 Beachway Dr, Holmes, NY 12531

Welcome to 4 Beachway Drive! This charming ranch-style home offers 2 bedrooms and lives like a 3-bedroom, with year-round views of beautiful Whaley Lake and lake access through the HOA. A welcoming front deck invites you inside, where natural light fills the home through abundant windows and skylights. The kitchen features ample cabinets and counter space, and a door leading to the back

Regan Andrews Coldwell Banker Realty

4 Beachway Dr, Holmes, NY 12531
/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
/23
$388,500
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
11 Park Ln, Holmes, NY 12531

Town of Pawling! Looking for a great starter home with privacy? This 3 Bedroom, 1 Bath Raised Ranch located on .58 acres at end of a private road is for you! Commuter's Dream! Close to I-84! Open floor plan with hardwood flooring in living room & dining room, large kitchen with plenty of counter & cabinet space. Large family room on lower level with sliding door to yard. Sold as-is. Buyer to pay

Ernie Acampora River Realty Services, Inc.

11 Park Ln, Holmes, NY 12531
/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
/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
/44
$299,900
- 5 Beds
- 4 Baths
- 2,790 Sq Ft
6 Laurel Dr, Holmes, NY 12531

Fantastic 3-Family Opportunity in Holmes, NY!Discover the potential in this unique multifamily property, featuring a single-family home plus an additional 2-family house on one parcel. Whether you're a homeowner looking for a fixer-upper with rental income potential or an investor seeking a high-demand rental property, this is the one you’ve been waiting for. Both homes need repairs and

Arafat Ibrahim AI Realty Brokerage LLC

6 Laurel Dr, Holmes, NY 12531
/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 Pawling

Why Live in Pawling

Learn more about living in Pawling

Frequently Asked Questions

Is Pawling a good place to live?

Pawling is a good place to live. Pawling is considered somewhat walkable and somewhat bikeable. Pawling is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Pawling has 2 parks for recreational activities. It has a median age of 48. The average household income is $144,805 which is above the national average. College graduates make up 41% of residents. A majority of residents in Pawling are home owners, with 25.7% of residents renting and 74.3% of residents owning their home. A local real estate agent serving Pawling can help you decide if this neighborhood is the right one for you. Learn more on our Pawling neighborhood guide.

Is Pawling, NY a safe neighborhood?

Pawling, NY is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.

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

The median home price in Pawling is $544,500. If you put a 20% down payment of $108,900 and had a 30-year fixed mortgage with an interest rate of 6.01%, your estimated principal and interest payment would be $2,610 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $112K a year to afford the median home price in Pawling. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Pawling is $145K.

What are the best public schools in Pawling?

The best public schools that serve Pawling are:

Arlington High School has an A- Niche grade, a student teacher ratio of 14:1 and an average review score of 3.9.
Pawling High School has an A- Niche grade, a student teacher ratio of 11:1 and an average review score of 3.5.
Pawling Middle School has a B+ Niche grade, a student teacher ratio of 9:1 and an average review score of 4.2.

What are the best private schools in Pawling?

The best private schools that serve Pawling are:

Trinity-Pawling School has an A+ Niche grade, a student teacher ratio of 6:1 and an average review score of 4.0.
Mizzentop Day School has an A Niche grade, a student teacher ratio of 8:1 and an average review score of 4.7.
Mission Church Academy & Preschool has a student teacher ratio of 22:1.

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

The most popular zip codes in Pawling, Pawling, NY include 12564, 12531, 12563, 12570 and 12594.

Home Trends in Pawling, NY

On average, homes in Pawling, NY sell after 65 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 $540,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$540,000

Median Single Family Sale Price

$550,000

Median Townhouse Sale Price

$386,000

Median 2 Bedroom Sale Price

$365,000

Average Price Per Sq Ft

$284

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.50

Median List Price

$544,500

Median Change From 1st List Price

Median Home Sale Price YoY Change

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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Homes in Nearby Counties

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