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Houses for Sale in 12564

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  • /29

    $575,000

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

    36 Byrds Hill Rd, Pawling, NY 12564

    Set on a quiet, scenic road in the prestigious Quaker Hill area, this home offers the perfect blend of seclusion and accessibility. You're only 3 miles from the serene waters of Quaker Lake, 2 miles from the Connecticut border, and just 20 minutes from charming CT towns like Sherman, New Milford, and Kent. From the outside, it’s a barn-like farmhouse surrounded by rolling green acreage and space

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 630-1049

    36 Byrds Hill Rd, Pawling, NY 12564
  • /49

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 2,318 Sq Ft

    7 Glen Ct, Pawling, NY 12564

    Welcome to this exquisitely renovated 3-bedroom, 2.5-bath Colonial home, showcasing over 2,300 square feet of elegant and comfortable living space. Perfectly situated in a serene cul-de-sac within the picturesque town of Pawling, this move-in-ready residence masterfully blends timeless charm with modern enhancements.As you step through the front door, you are greeted by a gracious

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 584-8385

    7 Glen Ct, Pawling, NY 12564
  • /49

    $1,299,000

    • 4 Beds
    • 2.5 Baths
    • 4,880 Sq Ft

    53 Dugway Dr, Pawling, NY 12564

    Tucked away on 4.5 acres with hundreds of Acres of landlocked State land behind us in the iconic rolling hills of Pawling Lake Estates, 53 Dugway Drive is more than a house—it's a lifestyle. Just a bit over an hour to NYC by Metro North.... Pull into Our gated fully blacktopped driveway, Nestled in the mountains of Dutchess County. Built in 2025 boasting lifestyle with 10’

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    Jeannie Shipman

    NextGen Real Estate LLC

    (845) 415-7093

    53 Dugway Dr, Pawling, NY 12564
  • /42

    $599,000

    • 4 Beds
    • 4.5 Baths
    • 2,361 Sq Ft

    126 Old Route 55, Pawling, NY 12564

    FULLY AVAIIABLE 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 THE COST OF THE SALE. . This charming,

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

    126 Old Route 55, Pawling, NY 12564
  • /41

    $450,000

    • 2 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    27 Washington Ct, Pawling, NY 12564

    Welcome to 27 Washington Court, located in the sought-after Deerfield Ponds community!This end-unit 2-bedroom, 2.5-bath townhome offers spacious living with beautiful pond views. Step inside from the inviting front porch and you’ll be greeted by a bright, airy entryway featuring a mudroom area, half bath, and a window opening into the pass-through kitchen. The eat-in kitchen boasts stainless

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 444-3725

    27 Washington Ct, Pawling, NY 12564
  • /48

    $769,000

    • 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
  • /34

    $699,000

    • 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
  • /17

    $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
  • /37

    $699,000

    • 4 Beds
    • 5 Baths
    • 4,018 Sq Ft

    175 Old Quaker Hill Rd, Pawling, NY 12564

    A Stately Cape Cod Estate with exceptional Potential awaits. Set on an expansive, flat parcel of land surrounded by farms, rolling hills, and mountain views, this once grand and elegant residence offers a rare opportunity to restore and reimagine a home of timeless distinction. A property of this caliber, featuring grand proportions, architectural charm, and breathtaking grounds, is a true gem

    Tom Consaga RE/MAX Ace Realty

    175 Old Quaker Hill Rd, Pawling, NY 12564
  • /29

    $869,000

    • 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

    Douglas Servello Home Sweet Home Properties

    26 Rodina Dr, Pawling, NY 12564
  • /47

    $1,250,000

    • 4 Beds
    • 6 Baths
    • 3,012 Sq Ft

    16 Anderson Rd, Pawling, NY 12564

    Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping

    Ryan Arket Compass Greater NY, LLC

    16 Anderson Rd, Pawling, NY 12564
  • /50

    $699,000

    • 4 Beds
    • 4.5 Baths
    • 2,920 Sq Ft

    12 W Wind Rd, Pawling, NY 12564

    Nestled on over two serene acres and backing to a tranquil nature preserve, this beautifully maintained home offers the perfect blend of peace, privacy, and natural beauty. With breathtaking seasonal views of the surrounding woodlands, the setting is ideal for quiet reflection or lively gatherings.Though the tax card shows four-bedrooms, this spacious home lives like a five-bedroom,

    Doris Jean William Raveis Real Estate

    12 W Wind Rd, Pawling, NY 12564
  • /48

    $799,900

    • 4 Beds
    • 2.5 Baths
    • 3,350 Sq Ft

    134 Old Pawling Rd, Pawling, NY 12564

    Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

    Drita Shala Howard Hanna Rand Realty

    134 Old Pawling Rd, Pawling, NY 12564
  • /33

    $1,350,000

    • 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
  • /38

    $699,000

    • 5 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    5 Red Tail Ct, Pawling, NY 12564

    Tucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tail Court is a beautifully maintained 5-bedroom, 2.5-bathroom Colonial offering space, style, and convenience. With 2,924 sq ft of living space, this home features an inviting floor plan, perfect for both everyday living and entertaining.Step inside to find a sun-filled living room with a cozy

    Julius Cooper eXp Realty

    5 Red Tail Ct, 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

    120 Harmony Rd, Pawling, NY 12564
  • /29

    $399,000

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft

    12 Anderson Way, Pawling, NY 12564

    ?This charming cottage is within walking distance of the picturesque village of Pawling and on the market for the first time in over 35 years. Lovingly maintained and enhanced by its owner, this home boasts the ease and convenience of one level living. The renovated front porch welcomes you to the house while the beautiful sundrenched addition features heating, hardwood floor, oversized windows,

    Stacey Cronin Houlihan Lawrence Inc.

    12 Anderson Way, Pawling, NY 12564
  • /46

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 1,518 Sq Ft

    26 Frenchmans Ln, Pawling, NY 12564

    Welcome to this beautifully remodeled Pawling home, perfectly situated on an idyllic 1+ acre property, just minutes to the Village. Whether you’re searching for the perfect starter home or country escape, this residence offers comfort, convenience, and timeless style. Step inside and you’ll immediately feel the open, airy flow connecting the living room, dining area, and kitchen. The heart of the

    Ryan Arket Compass Greater NY, LLC

    26 Frenchmans Ln, Pawling, NY 12564
  • /36

    $359,999

    • 2 Beds
    • 2.5 Baths
    • 1,413 Sq Ft

    33 Spruce St, Pawling, NY 12564

    Welcome to 33 Spruce Lane, a charming 2-bedroom, 2.5-bath home located in the sought-after Cedar Valley community in Pawling. This inviting townhome lives like a single-family home and offers the perfect balance of comfort, convenience, and amenities.Step inside to find a bright and open living space designed for easy living. The home features a spacious living room, a functional kitchen with

    Edmond Albano Keller Williams NY Realty

    33 Spruce St, Pawling, NY 12564
  • /33

    $2,500,000

    • 6 Beds
    • 6.5 Baths
    • 6,094 Sq Ft

    3302 Route 55, Pawling, NY 12564

    Welcome to your forever home, serene retreat and mini estate. Enjoy the 72 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 unique living space, luxury and customize finishes throughout. A true

    STACI MACKIN Dixon Smith Realty

    3302 Route 55, Pawling, NY 12564
  • /34

    $3,750,000

    • 6 Beds
    • 6 Baths
    • 6,460 Sq Ft

    30 Dewey Ln, Pawling, NY 12564

    Westerly is one of the finest estates on Quaker Hill, located on 23.77 private, level acres, all cleared & landscaped, at the end of a truly local road. The expansive fields & meadows are perfect for a horse farm. The original home was built in 1860, the front addition was built in 1920 by the DeWitt-Wallaces of Readers Digest fame. A sensitive whole house renovation was completed in 1990

    Gillian Stewart Gillian Stewart Real Estate

    30 Dewey Ln, Pawling, NY 12564
  • /31

    $275,000

    • 3 Beds
    • 1 Bath
    • 1,653 Sq Ft

    14 Old Route 55, Pawling, NY 12564

    FULLY Available! Welcome home to this historic and charming 3 bedroom, 1 bathroom beauty located above a stunning stream in the heart of Pawling. This beautifully antique home offers a rare blend of historic character and contemporary updates. Walk into the welcoming sunroom with plenty of natural light that opens up to a cozy living room featuring a wood burning fireplace and French doors that

    Ronald Green KW MidHudson

    14 Old Route 55, Pawling, NY 12564
  • /46

    $650,000

    • 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
  • /11

    $280,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    7 Elm St, Pawling, NY 12564

    Home in the Village of Pawling - Come make this your special home - 3 Bedrooms, 2 Full Baths. Located right in the Village, walk to EVERYTHING! Metro North, Shops, Restaurants, Ice Cream, Boutiques. Upstairs has 3 Bedrooms with a full bath. Main floor has Living Room, Dining Room, nice size kitchen with full Bath. Deck off back to fenced in yard. Bring your vision and make your village

    Teddie Leonaggeo McGrath Realty Inc

    7 Elm St, Pawling, NY 12564
  • /28

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,480 Sq Ft

    23 Union St, Pawling, NY 12564

    3 Bed | 2 Bath | Fully Electric | Walkable Village LocationTurnkey, updated, and full of charm—this 3-bedroom, 2-bath home is perfectly situated in the heart of Pawling Village. Whether you're a first-time buyer using FHA or VA financing, a downsizer, or simply seeking a low-maintenance, energy-efficient home, this property offers a flexible layout, thoughtful upgrades, and access to

    Brett David Miller K Fortuna Lighthouse Realty

    23 Union St, Pawling, NY 12564
  • /47

    $649,900

    • 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
  • /24

    $399,000

    • 5 Beds
    • 1,062 Sq Ft

    215 Little Pond Rd, Pawling, NY 12564

    Private Lake House on a Private Lake!Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and

    Jillian Pajer Douglas Elliman Real Estate

    215 Little Pond Rd, Pawling, NY 12564
  • /37

    $449,000

    • 3 Beds
    • 1.5 Baths
    • 1,680 Sq Ft

    36 Elm St, Pawling, NY 12564

    A historic Village Colonial on a quiet street, is a delight to show. Immaculate, well maintained & updated. Downstairs, a formal living room with a gas stove fireplace & bay windows, a formal dining room with built ins for storage, an office with closets & shelves for storage, a foyer, hardwood floors, a stunning eat in chef's kitchen with stone counters, stainless appliances, a big closet &

    Gillian Stewart Gillian Stewart Real Estate

    36 Elm St, Pawling, NY 12564
  • /9

    $1,100,000

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    51 Estate Dr, Pawling, NY 12564

    Don't miss this opportunity to have your dream home built and custom designed to your finishes. As you step inside, you're greeted by a grand foyer entrance with high ceilings open to the second floor. Discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, quartz countertops, and center island. The oversized open floor plan seamlessly

    Tony Zaccardo Coldwell Banker Realty

    51 Estate Dr, Pawling, NY 12564
  • /36

    $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, Grand Prix polo field, over 100 acres of fenced property, and 150 acres of riding trails

    Brian McGrath McGrath Realty Inc

    15 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
  • /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
  • /42

    $519,900

    • 3 Beds
    • 3.5 Baths
    • 3,467 Sq Ft

    2 Bridle Way, Pawling, NY 12564

    Wonderful investment opportunity awaits with this spacious home. The inviting library-style living room showcases nicely finished built-ins, while the expansive kitchen with a dining area seamlessly flows into the family room, highlighted by a cozy fireplace. The primary suite includes a private bathroom, ensuring comfort and convenience. A finished walkout lower level expands the living space

    Jonathan Gineo Jonathan D. Gineo

    2 Bridle Way, Pawling, NY 12564
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