21

Homes for Sale in 12564

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  • /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
  • /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
  • /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

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    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

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    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

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    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

    Agent Photo

    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

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    Colleen McGrath

    McGrath Realty Inc

    (845) 622-7384

    51 Estate Dr, Pawling, NY 12564
  • /15

    $975,000

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    14 Akindale Rd, Pawling, NY 12564

    TO BE BUILT A/o continue to show! 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 ,

    Kathryn McCoach Houlihan Lawrence Inc.

    14 Akindale Rd, Pawling, NY 12564
  • /47

    $1,175,000

    • 4 Beds
    • 6 Baths
    • 3,012 Sq Ft

    16 Anderson Rd, Pawling, NY 12564

    Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping

    Ryan Arket Compass Greater NY, LLC

    16 Anderson Rd, Pawling, NY 12564
  • /50

    $619,000

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    322 Old Route 22, Pawling, NY 12564

    Welcome to 322 Old Route 22! Spacious, newly remodeled 2-family home is a great opportunity for owner-occupants, investors, or extended families. Great location just a few minutes from the heart of the Village of Pawling! 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,

    Susan Stevens BHHS Hudson Valley Properties

    322 Old Route 22, 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
  • /27

    $489,000

    • 4 Beds
    • 1.5 Baths
    • 1,776 Sq Ft

    40 Walnut St, Pawling, NY 12564

    Spacious 4 BR, 1.5 bath home is located in the Village of Pawling. Nice property has a great view and an inground pool. Walkable distance to Metro-North Train Station, Village shops, Lakeside Park, more! The main level has hardwood floors and has been freshly painted. The walk-out lower level has a bedroom with a half bath, office, laundry area, and large Rec Rm with door to yard. The lower-level

    Lisa Liffland McGrath Realty Inc

    40 Walnut 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
  • /13

    $368,888

    • 3 Beds
    • 2.5 Baths
    • 1,960 Sq Ft

    21 Kings Way, Pawling, NY 12564

    Welcome to 21 Kings Way, a charming 3-bedroom, 2.5-bathroom townhome nestled in a wonderful community in Pawling, NY. This beautifully maintained home offers a perfect blend of comfort, style, and convenience. Step inside to discover an inviting open floor plan with spacious living areas, perfect for both entertaining and everyday living. The large windows flood the space with natural light,

    Bopaul Sookdeo YourHomeSold Guaranteed Realty

    21 Kings Way, Pawling, NY 12564
  • /24

    $399,000

    • 5 Beds
    • 1,062 Sq Ft

    215 Little Pond Rd, Pawling, NY 12564

    Private Lake House on a Private Lake! Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and peaceful environment.

    Jillian Pajer Douglas Elliman Real Estate

    215 Little Pond 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
  • /10

    $154,900

    • Land
    • 0.73 Acre
    • $212,192 per Acre

    0 Walnut St, Pawling, NY 12564

    Great lot in the Village of Pawling! *Board of Health Approval is NOT required because the house will be hooked up to municipal water and sewer! This .73-acre lot offers a lovely western view. Walk to the picturesque Village center with its quaint shops, bakeries, restaurants, library, post office, health care, so much more! Metro-North Train Station (Harlem Line) is located in the Village as

    Lisa Liffland McGrath Realty Inc

    0 Walnut St, 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

    $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 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
  • /27

    $509,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,490 Sq Ft

    66 Fairway Dr, Pawling, NY 12564

    Experience the charm of village living in historic, picturesque Pawling. This convenient .37-acre corner lot offers sidewalk access to local shops, restaurants, the Metro-North Harlem Line station, the library, The Dutcher Golf Course, and Lakeside Park. Enjoy year-round community activities on the Village Green, including the popular, seasonal Farmer’s Market.This well-maintained 3-bedroom,

    Carol Aprile

    66 Fairway Dr, Pawling, NY 12564
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