24

Homes for Sale in 12564

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  • /48

    $1,799,000 Coming Soon

    • 5 Beds
    • 5.5 Baths
    • 5,390 Sq Ft

    41 and 43 Meeting House Rd, Pawling, NY 12564

    Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious

    Richard Esman Douglas Elliman Real Estate

    41 and 43 Meeting House Rd, Pawling, NY 12564
  • /50

    $785,000

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    103 S Harmony Hill Rd, Pawling, NY 12564

    Properties like this don't come along often! As you turn off the road, the world quiets. The driveway pulls you back through a canopy of mature trees, and by the time the house appears, you already feel the privacy with over five acres, buffered on all sides, thoughtfully expanded and upgraded far beyond its 1975 origins. Step inside to a living room anchored by a stone fireplace, original

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 720-4119

    103 S Harmony Hill Rd, Pawling, NY 12564
  • /22

    $599,900

    • 3 Beds
    • 3 Baths
    • 1,640 Sq Ft

    85 Harmony Hill Rd, Pawling, NY 12564

    **Highest & Best 7pm Monday 4/27.** Set on nearly three private acres just minutes from Metro-North, this fully renovated country retreat delivers the space, privacy, and lifestyle buyers are searching for right now. Bright, open, and thoughtfully updated, the home is designed for both everyday living and easy entertaining. The kitchen features custom cabinetry, quartz countertops, and stainless

    Anna Proctor Compass Greater NY, LLC

    85 Harmony Hill Rd, Pawling, NY 12564
  • /16

    $499,999

    • 2 Beds
    • 1 Bath
    • 1,347 Sq Ft

    1141 Old Quaker Hill Rd, Pawling, NY 12564

    Welcome Home! Tucked away along storied Old Quaker Hill, this antique charmer invites you to experience a slower, richer pace of living—where history lingers in every beam and modern comfort quietly supports it. Offered fully furnished (or unfurnished) and available for immediate occupancy, this cozy retreat blends timeless character with everyday ease, making it an ideal escape for your weekend

    Chinenye Aguoji Real Broker NY LLC

    1141 Old Quaker Hill Rd, Pawling, NY 12564
  • /13

    $999,000

    • Land
    • 68.39 Acres
    • $14,607 per Acre

    0 Old Quaker Hill Rd Unit KEY986977, Pawling, NY 12564

    You can stop looking now because this is the piece of land you've been dreaming of. Over 68 acres atop Pawling's prestigious Quaker Hill. Approximately 20 acres clear and level with the remainder old woods crisscrossed by multiple streams and revolutionary era or older trails. In the heart of Quaker Hill's equestrian enclave, your views are the neighboring mountains and large estates. The short

    Brian McGrath McGrath Realty Inc

    0 Old Quaker Hill Rd Unit KEY986977, Pawling, NY 12564
  • /10

    $135,000

    • Land
    • 18,730 Sq Ft
    • $313,953 per Acre

    0 Prospect St, Pawling, NY 12564

    First time on market! BOHA not required - Town Water and Sewer must be hooked-up. Nice level lot, the majority of which is mostly cleared. Great location! Short drive to Metro-North, great restaurants and shops, Pawling schools, Lakeside Park with beach, playground area, trails, and pickleball courts. Dutcher Golf Course is a 9-hole gem, the oldest public course in America. Also close to grocery

    Lisa Liffland McGrath Realty Inc

    0 Prospect St, Pawling, NY 12564
  • /38

    $385,000

    • 2 Beds
    • 2 Baths
    • 1,639 Sq Ft

    16 Juniper Ln, Pawling, NY 12564

    Welcome to Cedar Valley! This bright corner unit offers the perfect blend of comfort and convenience, with potential for easy one-floor living. The main level features both bedrooms, while a spacious loft upstairs provides flexible bonus space—ideal for a home office, gym, guest area, or additional living space.Enjoy the ease of just two steps from the parking lot to your front door, with two

    Vanessa Longo Briante Realty Group, LLC

    16 Juniper Ln, Pawling, NY 12564
  • /34

    $375,000

    • 2 Beds
    • 2.5 Baths
    • 1,723 Sq Ft

    11 Cushing Green S, Pawling, NY 12564

    Welcome to Squire Green, a charming 2 bed, 2.5 bath townhome that’s move-in ready and full of potential. A versatile den offers the flexibility of a third bedroom, making this home a perfect fit whether you’re growing, downsizing, or simply need extra space.Enjoy the convenience of an attached garage and private driveway, plus ample guest parking. The community offers an in-ground pool,

    Taylor Cirillo Howard Hanna Rand Realty

    11 Cushing Green S, Pawling, NY 12564
  • /35

    $549,222

    • 3 Beds
    • 2.5 Baths
    • 2,104 Sq Ft

    5 Old Field Cir, Pawling, NY 12564

    Welcome to this beautifully maintained Victorian-style home, ideally situated in the highly sought-after Deerfield Ponds community at Squire Green in Pawling. From the inviting wraparound porch to the thoughtfully designed interior, this home offers timeless character paired with modern updates. The first floor features hardwood floors throughout, a formal dining room, and a sun-filled living

    Mark Seiden Mark Seiden Real Estate Team

    5 Old Field Cir, 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
  • /13

    $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
  • /6

    $220,000

    • Land
    • 33,105 Sq Ft
    • $289,474 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

    Agent Photo

    Joanne Debellis

    Debellis Real Estate LLC

    (845) 660-6758

    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
  • /49

    $565,000

    • 2 Beds
    • 2 Baths
    • 2,196 Sq Ft

    168 Old Route 55, Pawling, NY 12564

    Step into the year our nation was born and own a piece of living American history. Originally constructed in 1776 by a Scottish stone mason and frontiersman, who fought in two Revolutionary War battles, this enduring stone home is more than a residence; it’s a survivor. Once known as the Pawling Toll Gate and Toll House, it served as a gateway for travelers, a general store, a post office, and 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
  • /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
  • /31

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 3,434 Sq Ft

    128 Old Pawling Rd, Pawling, NY 12564

    You finally have the opportunity to own a home with year-round mountain views set on an expansive property. A place where you can bring your vision to life and transform the space into a true masterpiece. 128 Old Pawling Road is a beautifully positioned property in Pawling, NY, offering a rare combination of scenic views, generous land, and the potential to create a truly special home. Set back

    Juliska Martino Compass Greater NY, LLC

    128 Old Pawling Rd, Pawling, NY 12564
  • /8

    $150,000

    • Land
    • 20,037 Sq Ft
    • $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
  • /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

    $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) 684-9806

    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) 412-9125

    Lot 21 Cox Rd, Pawling, NY 12564
  • /15

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 3,920 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
  • /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
  • /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
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