19

Pawling, NY Homes for Sale with Acreage

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  • /50

    $775,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,729 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

    103 S Harmony Hill Rd, Pawling, NY 12564
  • /38

    $899,000

    Open Sun 12PM - 2PM
    • 4 Beds
    • 3.5 Baths
    • 3,434 Sq Ft

    128 Old Pawling Rd, Pawling, NY 12564

    Beautifully situated on 5.5 private acres, this impressive home offers a gated entrance and a long private driveway leading to breathtaking mountain views and a peaceful setting. Relax on the charming rocking-chair front porch and enjoy the serenity of the surrounding landscaped front lawn. Step inside to a dramatic two-story foyer and an abundance of natural light. The spacious kitchen features

    Agent Photo

    Teddie Leonaggeo

    McGrath Realty Inc

    128 Old Pawling 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

    Lot 21 Cox Rd, Pawling, NY 12564
  • /44

    $450,000

    • 2 Beds
    • 2 Baths
    • 2,096 Sq Ft

    35 Gobblers Knob Rd, Pawling, NY 12564

    Welcome to 35 Gobblers Knob, a charming Contemporary Cape set on 1.67 beautifully landscaped acres. This spacious 2,009 square foot home offers an open and inviting floor plan featuring a bright Living Room, updated Kitchen, and Dining Area perfect for everyday living and entertaining. The Kitchen opens to a private patio overlooking the scenic property. The main level includes a lovely office

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    35 Gobblers Knob Rd, 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

    Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
  • /41

    $1,300,000

    • 5 Beds
    • 4 Baths
    • 4,248 Sq Ft

    64 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to country living at its finest. Set on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential and timeless charm. A long tree-lined driveway leads to the 4 bedroom, 4 bathroom home surrounded by open fields, mature trees, and peaceful countryside views. The property includes a spacious 5-car garage (3 in front and additional 2 car tandum in back) with finished living

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    64 S Quaker Hill Rd, Pawling, NY 12564
  • /22

    $1,350,000

    $50K PRICE INCREASE
    • 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.

    178 Charles Colman Blvd, Pawling, NY 12564
  • /43

    $629,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,768 Sq Ft

    57 Buhleir Rd, Pawling, NY 12564

    Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side.

    Carolyn Ridenour Berkshire Hathaway HS NE Prop.

    57 Buhleir Rd, Pawling, NY 12564
  • /21

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 2,636 Sq Ft

    188 N Quaker Hill Rd, Pawling, NY 12564

    Fantastic weekend getaway or full time residence, hard to find Quaker Hill, situated on 5.00 secluded acres with babbling brook running through. Master bedroom with bath, walk in closet. 2 additional bedrooms & full bath. The living room, dining area & eat in kitchen are bright & spacious with hardwood floors throughout. Finished walkout basement with powder room. This property is mostly level,

    Gillian Stewart Gillian Stewart Real Estate

    188 N Quaker Hill 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
  • /45

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,172 Sq Ft

    7 Holm Run, Pawling, NY 12564

    Charming Cape Cod on a private cul de sac right on the outskirts of the Village of Pawling yet located in the Town of Pawling. Walking distance to the Village, trains, golf, and easy access to the highways. The open country kitchen with bay window is open to the dining area, central a/c, screened in porch overlooks private yard, multiple decks, mature landscaping with lots of perennials, wood

    Anthony Anzalone RE/MAX Classic Realty

    7 Holm Run, Pawling, NY 12564
  • /31

    $995,000

    • 3 Beds
    • 2.5 Baths
    • 3,035 Sq Ft

    6 Byrds Hill Rd, Pawling, NY 12564

    Renovated Colonial near Quaker Hill, less than two hours from NYC and minutes from Metro-North. Board-and-batten exterior with black-trimmed windows set the tone: clean lines and deliberate detail. Inside, the kitchen anchors the main level - marble island with seating, patterned tile backsplash behind the range, double wall ovens, and a layout that opens naturally to dining and living spaces.

    Stephen Pener William Pitt Sothebys Int Rlty

    6 Byrds Hill Rd, Pawling, NY 12564
  • /50

    $499,000

    • 4 Beds
    • 2.5 Baths
    • 1,968 Sq Ft

    40 Harmony Rd, Pawling, NY 12564

    Set on 5.6 acres in Pawling within the Pawling Central School District, this Colonial-style home offers a rare combination of acreage, character, and versatile living space. With 4 bedrooms, 2 baths, and 1,872 square feet, buyers searching for a home with land in Dutchess County, a property surrounded by mature trees, or a house with multiple indoor and outdoor gathering spaces will appreciate

    Virginia Corbett eXp Realty

    40 Harmony Rd, Pawling, NY 12564
  • /46

    $1,799,000

    Open Sun 1PM - 3PM
    • 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
  • /56

    $3,100,000

    • 3 Beds
    • 3 Baths
    • 3,600 Sq Ft

    809 N Quaker Hill Rd, Pawling, NY 12564

    Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property's idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling

    Raj Kumar Four Seasons Sotheby's Int.

    809 N Quaker Hill Rd, Pawling, NY 12564
  • /50

    $5,000,000

    • 8 Beds
    • 13 Baths
    • 15,000 Sq Ft

    618 Quaker Hill Rd, Pawling, NY 12564

    Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations.

    Jake Garay Serhant LLC

    618 Quaker Hill Rd, 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
  • /33

    $9,750,000

    $7M PRICE DROP
    • 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.

    225 Route 22, Pawling, NY 12564
  • /36

    $699,000

    $16K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,629 Sq Ft

    921 W Dover Rd, Pawling, NY 12564

    A One-of-a-Kind Custom Ranch on Nearly 4 Private Acres. Discover exceptional space, quality, and versatility in this expansive custom-built 3+ bedroom ranch, perfectly tucked away in a serene country setting. Designed for comfort and flexibility, this home is ideal for extended family living, multi-generational needs, or a spacious mother-daughter layout. The main floor offers true single-level

    Joyce Brennan-Zolnik BHHS Hudson Valley Properties

    921 W Dover Rd, Pawling, NY 12564

Home Price Trends

Median Sale Price
$511,250
Median Single Family Sale Price
$600,000
Median Townhouse Sale Price
$387,500
Median 2 Bedroom Sale Price
$396,000
Average Price Per Sq Ft
$330
Number of Homes for Sale
19
Last 12 months Home Sales
62
Months of Supply
3.70
Median List Price
$559,500
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-9%
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