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Newest Homes for Sale in Pawling, NY

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  • /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
  • /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
  • /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
  • /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
  • /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

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 932-0435

    168 Old Route 55, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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

    Agent Photo

    Douglas Servello

    Home Sweet Home Properties

    (845) 599-8285

    26 Rodina 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
  • /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
  • /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
  • /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
  • /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

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 415-7723

    64 S Quaker Hill 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
  • /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

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 378-9417

    Lot 25 Brady Brook Farm Rd, 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

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 328-6866

    Lot 21 Cox 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
  • /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
  • /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
  • /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

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

    126 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

    Agent Photo

    Vince Buccieri

    Today Realty Corp.

    (845) 280-5951

    178 Charles Colman Blvd, 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

    $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
  • /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

    Agent Photo

    Shaylene Neumann

    Houlihan Lawrence Inc.

    (845) 377-2512

    225 Route 22, 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

Frequently Asked Questions

What is the average home price in Pawling, NY?
Homes for sale in Pawling, NY have an average home price of $1,126,023.
How many homes have sold over the last 12 months in Pawling, NY?
67 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 $545,000. If you put a 20% down payment of $109,000 and had a 30-year fixed mortgage with an interest rate of 6.01%, your estimated principal and interest payment would be $2,620 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.
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

Housing Trends

Median Sale Price
$512,500
Median Single Family Sale Price
$596,750
Median Townhouse Sale Price
$386,000
Median 2 Bedroom Sale Price
$365,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
17
Last 12 months Home Sales
67
Months of Supply
3.00
Median List Price
$545,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-4%
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