Pawling, NY Homes for Sale with Acreage

/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
/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
/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
/4
$199,000
- Land
- 16.67 Acres
- $11,938 per Acre
1D Margherita Ln, Pawling, NY 12564

Discover an incredible opportunity to build on a rare 16+ acre parcel in the town of Pawling! Located just five minutes from the charming village, which is filled with lively shops and restaurants, this property offers a peaceful retreat in the woods. The parcel is approved by the board of health and is ready for you to construct a home with up to four bedrooms. New York City is conveniently

Colleen McGrath

McGrath Realty Inc

(845) 470-5610

1D Margherita Ln, 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
/4
$169,000
- Land
- 4.87 Acres
- $34,702 per Acre
51 Estate Dr, Pawling, NY 12564

Discover your dream sanctuary at lot #21, now cherished as 51 Estate Drive, nestled within the serene Cushman Farms subdivision in picturesque Pawling, NY. This enchanting property offers nearly 5 acres of secluded, buildable land, beckoning you to design the home you've always envisioned OR take advantage of the current plans in place. Picture waking up surrounded by nature's beauty, while still

Colleen McGrath

McGrath Realty Inc

(845) 622-7384

51 Estate Dr, Pawling, NY 12564
/3
$199,000
- Land
- 17.63 Acres
- $11,288 per Acre
1C Margherita Ln, Pawling, NY 12564

Over 17.6 acres to build your hillside oasis! This private lot is approved by the Board of Health for a four-bedroom home, and is located less than two miles from the charming village of Pawling, which offers shops, restaurants, a train station, and parks! Commute to NYC in under two hours (by car OR train), or explore nearby hiking trails, including the infamous Appalachian Trail.

Colleen McGrath

McGrath Realty Inc

(845) 552-2709

1C Margherita Ln, Pawling, NY 12564
/15
$975,000
- 4 Beds
- 2.5 Baths
- 3,000 Sq Ft
14 Akindale Rd, Pawling, NY 12564

TO BE BUILT Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. Enter onto freshly paved road and stone wall entrance. This beautiful lot is on 8.44 pastoral acres with amazing views of open sky and grassy meadows. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better place

Kathryn McCoach Houlihan Lawrence Inc.

14 Akindale Rd, Pawling, NY 12564
/14
$650,000
- 6 Beds
- 2 Baths
- 2,856 Sq Ft
13 Rebecca Dr, Pawling, NY 12564

THIS HOME WILL NOT BE AVAILABLE FOR OCCUPANCY UNTIL DECEMBER 2026. THERE IS A RESIDENTIAL FACILTY IN PLACE AT THIS SITE UNTIL THEN. This Ranch home offers 5 bedrooms and 2 full baths. There is 2,856 sqft of living space above the walk-out basement. Home is currently being used as a Residential Facility and will be held as a Rental with existing Residents in the home until DECEMBER 2026. This is a

Angela Briante Briante Realty Group, LLC

13 Rebecca Dr, 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 &

John Ravetto Houlihan Lawrence Inc.

0 S White Rock Rd Unit 6015368, Pawling, NY 12531
/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
/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
/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
/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 family 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,

Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

104 N Garden Dr, Pawling, NY 12564
/36
$5,500,000
- 17 Beds
- 13 Baths
- 15,000 Sq Ft
618 Quaker Hill Rd, Pawling, NY 12564

25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4

Harriet Norris Douglas Elliman Real Estate

618 Quaker Hill Rd, Pawling, NY 12564

New York Dutchess County Pawling

Home Trends in Pawling, NY

On average, homes in Pawling, NY sell after 61 days on the market compared to the national average of 53 days. The median sale price for homes in Pawling, NY over the last 12 months is $537,500, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$537,500

Median Single Family Sale Price

$603,500

Median Townhouse Sale Price

$370,750

Median 2 Bedroom Sale Price

$361,000

Average Price Per Sq Ft

$271

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.10

Median List Price

$552,500

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

In Pawling, there are currently 18 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Pawling, NY offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Pawling and discover the potential and freedom that comes with owning your own piece of property.

Pawling Types of Homes for Sale

Pawling Land for Sale

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