23

Pawling, NY Homes for Sale with Acreage

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  • /23

    $799,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    26 Rodina Dr, Pawling, NY 12564

    Welcome to your brand new dream home! Nestled on a beautiful and peaceful two and half acres. Be the first to live in this stunning four bedroom, two and a half bath home. 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 with motion sensor lighting on

    Agent Photo

    Douglas Servello

    Home Sweet Home Properties

    (845) 415-1257

    26 Rodina Dr, 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
  • /46

    $1,995,000 Open Thu 11AM - 1PM

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

    43 Meeting House Rd, Pawling, NY 12564

    A Bucolic Retreat in Prestigious Quaker Hill, nestled among grand equestrian estates in the coveted Quaker Hill community of Pawling, this magnificent country retreat artfully blends modern luxury with rustic charm. Set on five serene acres surrounded by rolling meadows, scenic horse farms, and distinguished country homes, 43 Meeting House Lane offers an inspiring escape that celebrates the best

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    Alicia Goldman

    Christie's Int. Real Estate

    (845) 373-3547

    43 Meeting House 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

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    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
  • /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
  • /15

    $975,000

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

    14 Akindale Rd, Pawling, NY 12564

    TO BE BUILT 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 , there is no better

    Kathryn McCoach Houlihan Lawrence Inc.

    14 Akindale Rd, Pawling, NY 12564
  • /47

    $1,450,000

    • 5 Beds
    • 7.5 Baths
    • 5,470 Sq Ft

    604 N Quaker Hill Rd, Pawling, NY 12564

    Exceptional living awaits in this stately Georgian manor house sitting on 7 acres at the top of prestigious North Quaker Hill Road. This mostly original home offers 9’ ceilings, radiant heating and ownership that has changed hands only once. A Belgian cobblestone driveway has a center focal point awaiting your personal touch.The Living room opens to an elegant wraparound terrace, perfect for the

    Leigh Tripathi Ellis Sotheby's Intl Realty

    604 N Quaker Hill Rd, Pawling, NY 12564
  • /33

    $1,250,000

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

    6 Byrds Hill Rd, Pawling, NY 12564

    Modern Pawling Farmhouse - This beautifully renovated Colonial home near Scenic Quaker Hill offers a perfect blend of charm and modern amenities. The spacious kitchen, complete with a center island with seating, flows seamlessly into an open dining and living area, where a cozy fireplace awaits. A separate light-filled den provides a peaceful retreat for relaxation. The main floor features a

    Stephen Pener William Pitt Sothebys Int Rlty

    6 Byrds Hill 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
  • /23

    $1,445,000

    • 4 Beds
    • 3.5 Baths
    • 4,178 Sq Ft

    29 Marble Ln, Pawling, NY 12564

    Fully Approved Shovel Ready Fabulous ultra private 5 plus acre homesite in a deed restricted, eco-sensitive subdivision. Don't miss the opportunity to have your dream home built by an experienced local builder. Once built, this spacious front porch colonial will be enhanced by light infused rooms, an open floor plan and custom eat in kitchen perfect for preparing scrumptious meals. A family room

    John Ravetto Houlihan Lawrence Inc.

    29 Marble Ln, Pawling, NY 12564
  • /40

    $550,000

    • 2 Beds
    • 2.5 Baths
    • 1,820 Sq Ft

    36 Byrds Hill Rd, Pawling, NY 12564

    Welcome to 36 Byrds Hill Rd, Pawling, NY—a serene 3.95-acre country retreat that feels like home from the moment you arrive. This charming property features a well-designed country house that offers all the comforts of modern living, with the warmth and character of a classic country setting. Step inside and you’re immediately welcomed by a spacious mudroom—perfect for keeping shoes, boots,

    Regan Andrews Houlihan Lawrence Inc.

    36 Byrds Hill Rd, Pawling, NY 12564
  • /46

    $580,000

    • 3 Beds
    • 2.5 Baths
    • 1,893 Sq Ft

    10 Rebecca Dr, Pawling, NY 12564

    Nestled in the charming village of Pawling, this delightful house offers new owners the opportunity to create their dream home with a touch of personal flair. Situated on just over 2 acres, the property boasts 3 spacious bedrooms, 2 full bathrooms, and a convenient powder room.The large eat-in kitchen, illuminated by a skylight, provides abundant natural light and features sliders that open

    Maria Justo Howard Hanna Rand Realty

    10 Rebecca Dr, Pawling, NY 12564
  • /36

    $725,000

    • 3 Beds
    • 2.5 Baths
    • 3,564 Sq Ft

    5 Perri Ln, Pawling, NY 12564

    Nestled in the foothills of the Berkshires, this exquisite front Porch Center Hall Colonial sits perfectly on a beautiful rolling 1.4 acres of private property in the heart of Pawling. With it's amazing Bonus Room above the 2 car garage, it lives like a huge 4 Bedroom, 2 1/2 bath, offering all the amenities anyone could ask for. There is an Open Floor Plan with an Updated Kitchen, Granite

    Kristine Hansmann Jefferson Valley Realty

    5 Perri Ln, Pawling, NY 12564
  • /29

    $699,000

    • 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
  • /47

    $574,900

    • 3 Beds
    • 2 Baths
    • 2,107 Sq Ft

    28 Gobblers Knob Rd, Pawling, NY 12564

    Welcome to 28 Gobblers Knob Road – A Hudson Valley Retreat! Nestled in the heart of the rolling hills of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on over 20 acres, offering peace, privacy, and natural beauty in every direction. Just over 3 miles from the Metro-North line to Manhattan, you can enjoy the quiet of a country escape without sacrificing

    Mark Snyder eXp Realty

    28 Gobblers Knob Rd, 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
  • /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

    Vince Buccieri Today Realty Corp.

    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
  • /36

    $5,500,000

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

    618 Quaker Hill Rd, Pawling, NY 12564

    25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4

    Harriet Norris Douglas Elliman Real Estate

    618 Quaker Hill Rd, 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 &

    John Ravetto Houlihan Lawrence Inc.

    0 S White Rock Rd Unit 6015368, Pawling, NY 12531
  • /2

    $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 6 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

    Angela Briante Briante Realty Group, LLC

    13 Rebecca Dr, Pawling, NY 12564

Home Trends in Pawling, NY

Housing Trends

Median Sale Price
$535,000
Median Single Family Sale Price
$608,500
Median Townhouse Sale Price
$361,000
Median 2 Bedroom Sale Price
$361,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
22
Last 12 months Home Sales
65
Months of Supply
4.10
Median List Price
$590,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
3%
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