3,397

Pawling, NY Homes

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  • 94 S Quaker Hill Rd, Pawling, NY 12564
    94 S Quaker Hill Rd, Pawling, NY 12564
    94 S Quaker Hill Rd, Pawling, NY 12564
    /48

    $749,000 Pending

    • 4 Beds
    • 3 Baths
    • 3,360 Sq Ft

    94 S Quaker Hill Rd, Pawling, NY 12564

    Set on 3.62 acres of picturesque and private land, this expansive 4-bedroom split-level home offers the perfect balance of spacious living and resort-style outdoor amenities, highlighted by a 20’ x 50’ saltwater in-ground pool. As you arrive along the freshly paved driveway, you’ll feel instantly at home in your own private oasis. Inside, a bright foyer with gleaming hardwood floors leads to the

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 253-5932

    94 S Quaker Hill Rd, Pawling, NY 12564
  • 7 Watchhill Rd, Pawling, NY 12564

    $555,000 Sold Aug 22, 2025

    • 3,322 Sq Ft
    • $167/SF
    • 20 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2002

    7 Watchhill Rd, Pawling, NY 12564

    Step into comfort and elegance in this spacious 4-bedroom, 2.5-bath Colonial nestled in the sought-after Deerfield Ponds neighborhood. From the moment you enter the grand foyer, you'll feel right at home. The heart of the house is the expansive kitchen featuring a large center island, light wood cabinetry, and tiled flooring, seamlessly flowing into both the formal dining room and the cozy living

    Shannon Tully McGrath Realty Inc

    7 Watchhill Rd, Pawling, NY 12564
  • 5 Perri Ln, Pawling, NY 12564
    5 Perri Ln, Pawling, NY 12564
    5 Perri Ln, 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
  • 42 Harmony Rd, Pawling, NY 12564

    $415,000 Sold Aug 19, 2025

    • 1,152 Sq Ft
    • $360/SF
    • 33 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1930

    42 Harmony Rd, Pawling, NY 12564

    Located on one of Pawling's most charming country roads, while still within a five-minute drive from the quaint and lively village center, this salt-box style home is awaiting your creativity and love. With a cozy and convenient fireplace in the living room, and a front-porch that overlooks an idyllic forest and beaver-pond across the street, the property feels isolated and quiet while still

    Reid McGrath McGrath Realty Inc

    42 Harmony Rd, Pawling, NY 12564
  • 13 Rebecca Dr, Pawling, NY 12564
    13 Rebecca Dr, Pawling, NY 12564
    /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
  • 8 Ravine Rd, Pawling, NY 12564

    $175,000 Sold Aug 15, 2025

    • Land
    • 6.04 Acres
    • $28,974 per Acre
    • 278 Days On Market

    8 Ravine Rd, Pawling, NY 12564

    Location Location Location in the prestigious Quaker Hill area in Pawling! Come build your private Estate on 6.04 acres. This lot is BOHA for a 5 bedroom home and already have a beautiful stone entry to greet you. Well is drilled and other amenities listed. Close to Everything, horse trails, Metro-North, Route 22, I684 and more.

    Shannon Tully McGrath Realty Inc

    8 Ravine Rd, Pawling, NY 12564
  • 48 W Main St, Pawling, NY 12564
    48 W Main St, Pawling, NY 12564
    48 W Main St, Pawling, NY 12564
    /36

    $699,900 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,152 Sq Ft

    48 W Main St, Pawling, NY 12564

    The PERFECT location for a Weekend/Vacation home or Extended/Large Family. 19th Century Colonial/Farmhouse completely remodeled in 2025. Located in the highly desirable Hudson Valley village of Pawling, NY. The photos tell the story of the updates, but it is the LOCATION that is unbeatable! Imagine a brisk autumn morning, waking up in your oversized Primary Bedroom to the warm glow of the morning

    Christopher Filangeri BHHS Hudson Valley Properties

    48 W Main St, Pawling, NY 12564
  • 37 Spruce St, Pawling, NY 12564

    $361,000 Sold Aug 13, 2025

    • 1,413 Sq Ft
    • $255/SF
    • 51 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1993

    37 Spruce St, Pawling, NY 12564

    Discover comfort and convenience in this beautifully maintained 2-bedroom, 2.5-bath townhouse nestled in the sought-after Cedar Valley Complex in Pawling, NY. The sun-drenched, open-concept living and dining area features a charming fireplace, offering the perfect setting for cozy nights in or easy entertaining. The kitchen is generously sized for a townhouse, offering ample cabinet space and

    Nick Selca Lakeshore Realty International

    37 Spruce St, Pawling, NY 12564
  • 29 Cunningham Ln, Pawling, NY 12564
    29 Cunningham Ln, Pawling, NY 12564
    29 Cunningham Ln, Pawling, NY 12564
    /34

    $699,000 Pending

    • 4 Beds
    • 5 Baths
    • 4,199 Sq Ft

    29 Cunningham Ln, Pawling, NY 12564

    Harmony Woods, an enclave of beautiful homes on the outskirts of the Village. This contemporary home has so much living space. Meticulously & continuously maintained by the current owners, there is nothing to be done! The 2 story foyer w/tile floors leads to the sunken LR which has high ceilings, a 2 sided fireplace, large windows & w/w carpet. There is formal DR, 2 powder rooms, then on to the

    Gillian Stewart Gillian Stewart Real Estate

    29 Cunningham Ln, Pawling, NY 12564
  • 24 Timberline Trail, Pawling, NY 12564

    $315,000 Sold Aug 05, 2025

    • 2,130 Sq Ft
    • $148/SF
    • 51 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1997

    24 Timberline Trail, Pawling, NY 12564

    Welcome to 24 Timberline Trail—Located in a peaceful, sought-after neighborhood in Pawling, NY. This residence offers the perfect blend of comfort, functionality, and modern updates. Featuring 3 spacious bedrooms and 2.5 bathrooms, the home boasts an open and versatile layout ideal for everyday living and entertaining.Step outside to a generous first-floor deck that seamlessly extends your

    Vincent Reda Keller Williams Realty

    24 Timberline Trail, Pawling, NY 12564
  • 27 Millstream Ct, Pawling, NY 12564
    27 Millstream Ct, Pawling, NY 12564
    27 Millstream Ct, Pawling, NY 12564
    /43

    $734,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,283 Sq Ft

    27 Millstream Ct, Pawling, NY 12564

    Welcome to your new home in the neighborhood you want and with all the amenities you want. Imagine waking in your Oversized Primary bedroom to the sounds of birds chirping and the sun warming your face. Get the day going in your Primary Bath Suite with Double Vanity, Heated Floors, Heated Towel Rack and Jacuzzi Tub. Smell the coffee brewing in your Chef's kitchen where you can prepare meals that

    Christopher Filangeri BHHS Hudson Valley Properties

    27 Millstream Ct, Pawling, NY 12564
  • 38 Old Route 55, Pawling, NY 12564

    $430,000 Sold Aug 01, 2025

    • 1,608 Sq Ft
    • $267/SF
    • 126 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1900

    38 Old Route 55, Pawling, NY 12564

    Turn back the hands of time with this beautiful home built in 1798 reminiscent of the deep south! It's 3 stories, two of which have gorgeous wrap around newly redone porches, that you can envision with rocking chairs, sipping mint juleps or enjoying a summer meal. The 3-story farmhouse has a newly refurbished kitchen, two living rooms, 3 bedrooms, two and a half bathrooms, a cozy fireplace and

    Teddie Leonaggeo McGrath Realty Inc

    38 Old Route 55, Pawling, NY 12564
  • 85 Harmony Hill Rd, Pawling, NY 12564
    85 Harmony Hill Rd, Pawling, NY 12564
    85 Harmony Hill Rd, Pawling, NY 12564
    /46

    $650,000 Pending

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

    85 Harmony Hill Rd, Pawling, NY 12564

    This charming fully remodeled, bright, and sunny ranch—featuring 3 bedrooms, 3 full bathrooms, and 2.90 acres of land. Prepare meals in the beautiful new kitchen, complete with custom cabinets, LG appliances, and quartz countertops. Relax in the family room beside the gorgeous stone fireplace. From there, step out onto the lovely wood deck and savor your morning coffee surrounded by

    Mary Craig Coldwell Banker Realty

    85 Harmony Hill Rd, Pawling, NY 12564
  • 7 Holiday St, Pawling, NY 12564

    $420,000 Sold Aug 01, 2025

    • 1,056 Sq Ft
    • $398/SF
    • 29 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1961

    7 Holiday St, Pawling, NY 12564

    Wonderful mid-century ranch enjoys beautiful, park-like property in the scenic town of Pawling! Nearby Lakeside Park is open for the summer! 36 acre lake with beach, pickle ball courts, Snack Shack, more. Now, back to the house! Large, sun-filled living rm features a bay window and hardwood floor. The spacious kitchen and dining area are lovely! Beautiful cabinetry, quartz-like countertops,

    Lisa Liffland McGrath Realty Inc

    7 Holiday St, Pawling, NY 12564
  • 48 David Ln, Pawling, NY 12564
    48 David Ln, Pawling, NY 12564
    48 David Ln, Pawling, NY 12564
    /41

    $695,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,788 Sq Ft

    48 David Ln, Pawling, NY 12564

    Enjoy private, direct lakefront access and stunning views from this chic 3-bedroom, 2.5-bathroom modern, turnkey dream cabin on lovely Jones Pond! With stylish Mid-century modern designer features and thoughtful updates throughout, 48 David offers an elevated escape, plenty of room for guests, amazing outdoor spaces, and year-round comfort. The sleek open-concept kitchen features smart storage

    Claudia Dizenzo Hudson River Line Realty

    48 David Ln, Pawling, NY 12564
  • 12 Berry Ln, Pawling, NY 12564

    $820,000 Sold Jul 28, 2025

    • 3,304 Sq Ft
    • $248/SF
    • 52 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1965

    12 Berry Ln, Pawling, NY 12564

    Nestled high atop Quaker Hill, this enchanting property offers 8.5 acres of privacy on a serene lane, just two homes away from the 4th hole of the prestigious Quaker Hill Country Club. A mid-century ranch-style home, with its distinct architectural charm and details, awaits a new owner to bring it into its next chapter. Boasting 2,704 square feet on the main floor and an additional 600 square

    Brian McGrath McGrath Realty Inc

    12 Berry Ln, Pawling, NY 12564
  • 16 Townsend Blvd, Pawling, NY 12564
    16 Townsend Blvd, Pawling, NY 12564
    16 Townsend Blvd, Pawling, NY 12564
    /35

    $399,000

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    16 Townsend Blvd, Pawling, NY 12564

    Welcome to 16 Townsend Blvd, a lovely brick home set in the heart of picturesque Pawling, NY. On the end of a quiet, dead-end road, within walking distance of the historic Village of Pawling, this charming domicile will not last long. The Village of Pawling is home to the oldest public-golf course in the United States, George Washington's headquarters during the Revolutionary War, ample eateries

    Reid McGrath McGrath Realty Inc

    16 Townsend Blvd, Pawling, NY 12564
  • 11 Birch Terrace, Pawling, NY 12564

    $410,000 Sold Jul 24, 2025

    • 1,400 Sq Ft
    • $293/SF
    • 34 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1960

    11 Birch Terrace, Pawling, NY 12564

    Welcome to Pawling Lake Estates - a private lake community about 10 minutes outside the Village of Pawling. This adorable cozy Cape is located on a dead-end road. Has 2 bedrooms but can easily live like a 3-bedroom home. Main level has eat in kitchen with breakfast nook, cozy living room with big bay window. 2 Bedrooms and a main bath. Doors in kitchen that lead out to a nice size deck

    Teddie Leonaggeo McGrath Realty Inc

    11 Birch Terrace, Pawling, NY 12564
  • 21 Kings Way, Pawling, NY 12564
    21 Kings Way, Pawling, NY 12564
    21 Kings Way, Pawling, NY 12564
    /11

    $408,888

    • 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
  • 7 Tower Hill Rd, Pawling, NY 12564

    $1,405,000 Sold Jul 24, 2025

    • 3,038 Sq Ft
    • $462/SF
    • 49 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1999

    7 Tower Hill Rd, Pawling, NY 12564

    Nestled among the towering trees, this spacious 4-bedroom, 3-bath custom-designed home offers the perfect blend of privacy, comfort, and modern amenities. Sit back and enjoy the captivating views from the three expansive decks, overlooking the waterfall, ponds, and large yard below. The home's distinctive architecture is shown in its thoughtful design, encompassing the natural setting, while

    Ryan Arket Compass Greater NY, LLC

    7 Tower Hill Rd, Pawling, NY 12564
  • 2 Spruce St, Pawling, NY 12564
    2 Spruce St, Pawling, NY 12564
    2 Spruce St, Pawling, NY 12564
    /50

    $399,999

    • 2 Beds
    • 2.5 Baths
    • 1,838 Sq Ft

    2 Spruce St, Pawling, NY 12564

    Welcome home to 2 Spruce St.! 2 full floors plus a completely finished walk out basement. Home has central air and heat. Completely updated and freshly painted, all you need to do is move in. Living room features a built in flue that can be opened up for adding a wood burning fireplace. 2 full primary bedrooms, each with it's own full bathroom, plus a powder room on the first floor. One of the

    Robin Butler-Koschei Hanson Real Estate Partners

    2 Spruce St, Pawling, NY 12564
  • 74 Harmony Hill Rd, Pawling, NY 12564

    $510,000 Sold Jul 24, 2025

    • 1,736 Sq Ft
    • $294/SF
    • 20 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1971

    74 Harmony Hill Rd, Pawling, NY 12564

    Charming Ranch with Scenic Views and Prime Location! Nestled on a quiet street just minutes from the heart of town, this well-maintained 4-bedroom, 2-bath home offers a rare opportunity to own a piece of classic suburban charm on a sprawling 1.86-acre flat lot. Built in 1971 and on the market for the first time, this bright and sunny home combines timeless character with an unbeatable location

    Patrycja Warda

    74 Harmony Hill Rd, Pawling, NY 12564
  • 322 Old Route 22, Pawling, NY 12564
    322 Old Route 22, Pawling, NY 12564
    322 Old Route 22, 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
  • 26 Fenwood Dr, Pawling, NY 12564

    $430,000 Sold Jul 22, 2025

    • 1,500 Sq Ft
    • $287/SF
    • 177 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1963

    26 Fenwood Dr, Pawling, NY 12564

    Welcome to this delightful sunlit Ranch style home nestled on a beautiful and quiet corner lot. This home features 3 nice size bedrooms, a full bath and convenient half bath off the dining/family room. The eat in kitchen offers upscale stainless steel appliances along with ample counter and cabinet space for all your culinary needs. The full size attic can be used for storage or even transformed

    Vicki Reinach BHHS Hudson Valley Properties

    26 Fenwood Dr, Pawling, NY 12564
  • 10 Rebecca Dr, Pawling, NY 12564
    10 Rebecca Dr, Pawling, NY 12564
    10 Rebecca Dr, 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
  • 104 Mohawk Trail, Pawling, NY 12564

    $532,000 Sold Jul 18, 2025

    • 2,175 Sq Ft
    • $245/SF
    • 23 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1999

    104 Mohawk Trail, Pawling, NY 12564

    Charming 3-Bedroom Home in Pawling’s Desirable Deerfield Ponds Community.Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom single-family home nestled in the sought-after Deerfield Ponds Community in Pawling, NY. Offering 2,175 sq. ft. of living space, this home boasts both comfort and convenience.Step inside to find a thoughtfully designed floor plan with renovated bathrooms

    Pete Rodriguez William Raveis Real Estate

    104 Mohawk Trail, Pawling, NY 12564

Showing Results 41 - 80, Page 2 of 18

New York Dutchess County Pawling

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