23

Pawling, NY Homes for Sale

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  • /6

    $220,000

    • Land
    • 0.76 Acre
    • $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

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    Joanne Debellis

    Debellis Real Estate LLC

    (845) 660-6758

    15 Dykeman St, Pawling, NY 12564
  • /28

    $530,000

    • 3 Beds
    • 1.5 Baths
    • 1,706 Sq Ft

    58 Pine Dr, Pawling, NY 12564

    Tucked away at the end of a quiet cul-de-sac, this beautifully maintained home sits on 2.87 acres of mostly level, private property—offering the perfect blend of peaceful surroundings and everyday convenience. Step into a bright and welcoming main living area featuring a sun-filled living room with an oversized picture window framing peaceful views of the front lawn, and a dining room with

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    Teddie Leonaggeo

    McGrath Realty Inc

    (845) 299-0848

    58 Pine Dr, Pawling, NY 12564
  • /50

    $599,000

    • 2 Beds
    • 2 Baths
    • 2,196 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

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    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

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    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

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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

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    Shannon Tully

    McGrath Realty Inc

    (845) 412-9125

    Lot 21 Cox Rd, Pawling, NY 12564
  • /6

    $87,500

    • Land
    • 0.46 Acre
    • $190,217 per Acre

    0 Lakeview Dr Unit KEY962482, Pawling, NY 12531

    Build your ideal home on this prime .46-acre lot perfectly situated within the sought-after Pawling Lake Estates community. Offering a rare blend of beauty and value, this property boasts picturesque views of Jones Pond and benefits from the lower property taxes of the Dover Union Free School District. Nature enthusiasts will love being surrounded by the sprawling West Mountain State Forest,

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    Colleen McGrath

    McGrath Realty Inc

    (845) 385-2808

    0 Lakeview Dr Unit KEY962482, Pawling, 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

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    Shannon Tully

    McGrath Realty Inc

    (845) 684-9806

    Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
  • /28

    $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
  • /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
  • /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
  • /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
  • /35

    $549,222 Open Sat 2:30PM - 4PM

    • 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
  • /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
  • /38

    $375,000 Open Sat 12PM - 2PM

    • 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
  • /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
  • /4

    $151,000

    • Land
    • 4.21 Acres
    • $35,867 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
  • /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
  • /14

    $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
  • /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
  • /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
  • /10

    $135,000

    • Land
    • 0.43 Acre
    • $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

Why Live in Pawling

Pawling, NY, spans 45 square miles in Dutchess County, offering residents a blend of rural solitude and accessibility to New York City via an MTA station for an hour-long commute. The town features over 1,000 acres of protected parklands, including the Pawling Nature Reserve, where locals can hike the Appalachian Trail. Recreational options also include Dutcher Golf Course and Whaley Lake, the largest lake in the county, ideal for swimming, kayaking, and fishing. The Maybrook Trailway, part of the Empire State Trail system, provides scenic hiking opportunities. Pawling's housing market includes upscale single-family homes such as Colonial Revivals, ramblers, raised ranches, and split-levels, with exclusive areas like Quaker Hill offering large farms and multimillion-dollar properties. The central village features Craftsman and Victorian homes, while waterfront cottages are available in Holmes. Pawling Central School District serves the community with highly rated schools, including Pawling Elementary, Pawling Middle, and Pawling High. The private Trinity-Pawling School, an all-boys Episcopal boarding school, is also highly rated. Local amenities include grocery stores like Acme Markets and Hannaford along NY-22, and dining options such as O’Connor’s Public House downtown. Community traditions include the Pawling Farmers Market and the Pawling Concert Series, along with Decemberfest and Tree Lighting events. Commuters can reach Manhattan in an hour and a half by train or car, and New Haven, Connecticut, is accessible within two hours.

Frequently Asked Questions

What is the average home price in Pawling, NY?
Homes for sale in Pawling, NY have an average home price of $1,343,965.
How many homes have sold over the last 12 months in Pawling, NY?
65 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, 12531, 12570, 12563 and 12594.
How much do you need to make to afford a house in Pawling?
The median home price in Pawling is $535,000. If you put a 20% down payment of $107,000 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $2,670 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $114K 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
$532,000
Median Single Family Sale Price
$560,000
Median Townhouse Sale Price
$375,000
Median 2 Bedroom Sale Price
$361,000
Average Price Per Sq Ft
$322
Number of Homes for Sale
13
Last 12 months Home Sales
65
Months of Supply
2.40
Median List Price
$535,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-2%
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