Pawling, NY Homes

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  /23

  $799,000

  • 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

  (845) 415-1257

  26 Rodina Dr, Pawling, NY 12564
• Explore Pawling

• 

  

  

  /25

  $3,250 per month

  • 2 Beds
  • 2 Baths
  • 1,387 Sq Ft
  • Property for Rent

  63 River Rd Unit A, Pawling, NY 12564

  A secluded oasis – come home to this 39 acre working horse farm without sacrificing convenience! Lovely 2 bedroom raised ranch single family house waiting for your personal touches. Light & bright Living Room with new luxury vinyl flooring; Eat-in-Kitchen with plenty of cabinets and room for a large table & chairs to entertain family and guests. Refrigerator, gas stove and dishwasher included.

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  (845) 253-5697

  63 River Rd Unit A, Pawling, NY 12564
• 

  $688,000 Sold Nov 24, 2025

  • 2,920 Sq Ft
  • $236/SF
  • 146 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1986

  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, offering

  Doris Jean William Raveis Real Estate

  12 W Wind Rd, Pawling, NY 12564
• 

  Est $547,000 Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 2,836 Sq Ft

  135 S Quaker Hill Rd, Pawling, NY 12564

  135 S Quaker Hill Rd, 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

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 576-1665

  126 Old Route 55, Pawling, NY 12564
• 

  

  /11

  $1,400 per month

  • 1 Bed
  • 1 Bath
  • 300 Sq Ft
  • Condo for Rent

  23 W Main St Unit 1A, Pawling, NY 12564

  Two room studio Ground floor, private entrance. Convenient parking. Walk to shopping, laundry. No smoking/pets Call only

  23 W Main St Unit 1A, Pawling, NY 12564
• 

  $400,000 Sold Nov 21, 2025

  • 1,620 Sq Ft
  • $247/SF
  • 41 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1965

  96 Lakeview Dr, Pawling, NY 12564

  Welcome to this renovated 1,620 SF raised ranch in Pawling Lake Estates, a charming lake community nestled atop West Mountain and adjacent to West Mountain State Park. Steps in reveal freshly painted walls and refinished hardwood flooring throughout the 1,120 SF first floor. The living room has a massive stone fireplace and wood-burning stove insert, which opens to the dining area. A renovated

  Claudia Jiskra McGrath Realty Inc

  96 Lakeview Dr, Pawling, NY 12564
• 

  Not Listed For Sale

  9 Ravine Rd, Pawling, NY 12564

  9 Ravine Rd, Pawling, NY 12564
• 

  

  /49

  $575,000 Pending

  • 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 entryway that

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 584-8385

  7 Glen Ct, Pawling, NY 12564
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  /34

  $2,950 per month

  • 3 Beds
  • 1 Bath
  • 1,186 Sq Ft
  • House for Rent

  112 Charles Colman Blvd, Pawling, NY 12564

  Delightful C1900 Farmhouse Colonial located on the prettiest streets in the Village. Updated, renovated, & designed to perfection. There are period wood flrs, an updated airy kitchen w/quartz counters, open to a country dining area w/sunny bay window & back dr to patio. The large LR runs front to back w/deep windows, lots of light & sliders to the patio. The covered front porch w/vintage millwork

  Gillian Stewart Gillian Stewart Real Estate

  112 Charles Colman Blvd, Pawling, NY 12564
• 

  $115,000 Sold Nov 14, 2025

  • Land
  • 1.4 Acres
  • $82,143 per Acre

  • 249 Days On Market

  0 Overlook Rd, Pawling, NY 12564

  Build your dream home in Pawling with this Board of Health approved location, blending the charm of an established neighborhood while providing a blank building canvas. This 1.4 acre lot is approved for up to 4 bedrooms and offers potential peek-a-boo mountain views and colorful sunsets. The partially wooded lot provides natural privacy with mature landscaping from day one. The driveway has been

  Judith 'Judy' Albert BHHS Hudson Valley Properties

  0 Overlook Rd, Pawling, NY 12564
• 

  Est $325,492 Not Listed For Sale

  7 Birch Ln, Holmes, NY 12531

  7 Birch Ln, Holmes, 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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 378-9417

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
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  /36

  $8,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,942 Sq Ft
  • House for Rent

  15 Kirby Hill Rd, Pawling, NY 12564

  Now for rent is one of Quaker Hill's most prestigious estate homes. The main estate at Kirby Hill Farm is available as a year-round, or seasonal winter rental, impeccably furnished and equipped residential rental with an in-ground pool. Set on close to 250 acres and one of the region's finest equestrian facilities. The circa 1860 colonial farmhouse boasts 3,942 square feet. There are two separate

  Brian McGrath McGrath Realty Inc

  15 Kirby Hill Rd, Pawling, NY 12564
• 

  $240,000 Sold Nov 12, 2025

  • Land
  • 5.36 Acres
  • $44,776 per Acre

  • 80 Days On Market

  51 Kirby Hill Rd, Pawling, NY 12564

  Down a winding country road, across the street from 350 acres of hiking trails and just 10 minutes from the heart of Pawling, this 5.36-acre parcel offers a rare blend of readiness and wildness. This is the kind of place where ideas can take shape beneath a canopy of oaks and mountain laurel. The elevated, partially cleared build site holds promise for views, with a roughed-in driveway already in

  Donna Kennedy Compass Greater NY, LLC

  51 Kirby Hill Rd, Pawling, NY 12564
• 

  Est $436,184 Not Listed For Sale

  • 7 Beds
  • 3 Baths
  • 3,400 Sq Ft

  68 W Main St, Pawling, NY 12564

  68 W Main St, 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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 328-6866

  Lot 21 Cox Rd, Pawling, NY 12564
• 

  

  /14

  $1,900 per month

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  84-88 E Main St Unit 1, Pawling, NY 12564

  Available Immediately. 1 Bedroom, 1 Bath in the Village of Pawling. Upon entering, you're greeted by charming wood-built ins and freshly cleaned carpet. The large living room with a floor to ceiling, corner glass block wall, provides a ton on natural light. You'll be impressed by the large bedroom and laundry room complete with a washer and dryer. The private rental is situated on a flat,

  John DiDio Century 21 Alliance Rlty Group

  84-88 E Main St Unit 1, Pawling, NY 12564
• 

  $200,000 Sold Oct 21, 2025

  • Land
  • 9.73 Acres
  • $20,555 per Acre

  • 312 Days On Market

  Lot #2 Dodge Rd, Pawling, NY 12564

  Nestled within a recently divided 163-acre parcel, this picturesque 9.73-acre property offers an idyllic escape. Enjoy the privacy of your own land while having access to a shared 100-acre common area with scenic trails and natural wonders. Set within a protected area, the eight lots in this division have been transferred to new owners, and none can be further subdivided due to conservation

  Brian McGrath McGrath Realty Inc

  Lot #2 Dodge Rd, Pawling, NY 12564
• 

  Est $2,385,649 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 8,331 Sq Ft

  73 Cunningham Ln, Pawling, NY 12564

  73 Cunningham Ln, 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

  

  Vince Buccieri

  Today Realty Corp.

  (845) 280-5951

  178 Charles Colman Blvd, Pawling, NY 12564
• 

  $160,000 Sold Oct 08, 2025

  • Land
  • 9.65 Acres
  • $16,580 per Acre

  • 212 Days On Market

  16 Brady Brook Farm Rd, Pawling, NY 12564

  Incredible opportunity to build your dream home in the beautiful and prestigious Brady Brook Falls community, a park-like section of Quaker Hill. Located at the end of a private cul-de-sac, this parcel offers serenity and breathtaking surroundings. The property is attached to roughly 100 acres of open space where you can enjoy hiking, horseback riding, cross country skiing, and trout fishing.

  Andrew Stewart Gillian Stewart Real Estate

  16 Brady Brook Farm Rd, Pawling, NY 12564
• 

  Est $823,807 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,340 Sq Ft

  34 Harmony Hill Rd, Pawling, NY 12564

  34 Harmony Hill 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

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (845) 377-2512

  225 Route 22, Pawling, NY 12564
• 

  $560,000 Sold Oct 06, 2025

  • 2,616 Sq Ft
  • $214/SF
  • 50 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2004

  37 Baxter Rd, Pawling, NY 12564

  Welcome to this charming Colonial-style residence, offering 3 bedrooms, 3.5 bathrooms, and a versatile bonus room—ideal for a potential in-law suite. With over 2,600 square feet of comfortable living space, this home is located in the desirable Baxter Green community, nestled in the scenic Village of Pawling.The interior showcases beautiful hardwood floors throughout, while the spacious

  Matt Rose Keller Williams Prestige Prop

  37 Baxter Rd, Pawling, NY 12564
• 

  Est $772,691 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,657 Sq Ft

  30 Horseshoe Path, Pawling, NY 12564

  30 Horseshoe Path, Pawling, NY 12564
• 

  

  /8

  $229,000 Pending

  • Land
  • 7.02 Acres
  • $32,621 per Acre

  Lot 18 Cox Rd, Pawling, NY 12564

  Come build your dream home on this 7.02-acre Board of Health Approved lot in the highly desirable Brady Brook Falls community. Approved for a 5-bedroom residence, this property offers the perfect setting to create your ideal retreat while being just minutes from all the conveniences of Pawling. Enjoy easy access to Route 22, Route 55, shopping, the Village of Pawling, Metro-North, and even the

  

  Shannon Tully

  McGrath Realty Inc

  (845) 516-8037

  Lot 18 Cox Rd, Pawling, NY 12564
• 

  $330,000 Sold Oct 02, 2025

  • 1,414 Sq Ft
  • $233/SF
  • 41 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1993

  36 Spruce St, Pawling, NY 12564

  Comfortable Townhouse Living at Cedar Valley36 Spruce Street, Pawling, NY located in cedar valley development. This 2 bedroom, 2 1/2 bath home is just waiting for you to give it a little TLC. The first floor has a dining/living room, door to an open patio, perfect for your morning coffee or your afternoon tea. The kitchen and half bath finish off the 1st floor. The second floor has two

  Peggy MacLeay-Generoso McGrath Realty Inc

  36 Spruce St, Pawling, NY 12564
• 

  Est $833,296 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 6,042 Sq Ft

  6 di Pietro Ln, Pawling, NY 12564

  6 di Pietro Ln, Pawling, NY 12564
• 

  

  /37

  $699,000 Pending

  • 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

  (845) 640-5625

  175 Old Quaker Hill Rd, Pawling, NY 12564
• 

  $399,000 Sold Sep 26, 2025

  • 1,157 Sq Ft
  • $345/SF
  • 44 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1953

  33 Grandview Ave, Pawling, NY 12564

  Charming Cape Cod in the village of Pawling, one owner since it was built in 1953. The home has been well maintained throughout the years. The interior was painted 2 years ago and there are recently installed windows throughout. There are 2 BR's on the first floor, a living room with wood fireplace & hardwood floors. The eat in kitchen has Corian & butcher block counters, a gas range &

  Gillian Stewart Gillian Stewart Real Estate

  33 Grandview Ave, Pawling, NY 12564
• 

  Est $795,631 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,435 Sq Ft

  919 N Quaker Hill Rd, Pawling, NY 12564

  919 N 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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 253-5932

  94 S Quaker Hill Rd, Pawling, NY 12564
• 

  $465,000 Sold Sep 15, 2025

  • 1,706 Sq Ft
  • $273/SF
  • 31 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1957

  14 Summit Ave, Pawling, NY 12564

  Tucked away on a quiet dead-end street in the serene village of Pawling, this meticulously maintained Cape Cod home offers the perfect blend of comfort, charm, and convenience. Bathed in natural light, the freshly painted interior boasts a seamless flow between living spaces, with two spacious bedrooms that live like three—ideal for guests, a home office, or flexible living. The inviting living

  Karen Gundelach Keller Williams Realty Partner

  14 Summit Ave, Pawling, NY 12564
• 

  Est $1,197,035 Not Listed For Sale

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

  809 N Quaker Hill Rd, Pawling, NY 12564

  809 N Quaker Hill Rd, Pawling, NY 12564
• 

  

  /30

  $390,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  23 Juniper Ln, Pawling, NY 12564

  A quiet cul-de-sac welcomes you to a well-maintained town home in the desirable Cedar Valley Community. Easy accessibility to all the Pawling Village amenities: restaurants, shops, Farmer’s Market, professional services and commuting with Metro North. This home has so much to offer – open Living and Dining areas with hardwood floors, working fireplace and pass through to Kitchen. Also glass doors

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  (845) 789-5932

  23 Juniper Ln, Pawling, NY 12564
• 

  $430,000 Sold Sep 11, 2025

  • 1,835 Sq Ft
  • $234/SF
  • 64 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  19 Cushing Green S, Pawling, NY 12564

  Comfortable Townhouse Living at Squire GreenWelcome to this spacious and bright end-unit townhouse featuring 3 bedrooms, 2.5 bathrooms, and a one-car garage—all set within the highly sought-after Squire Green community. The main floor offers a welcoming layout ideal for daily living and entertaining. Enjoy an eat-in kitchen, a living room with cathedral ceilings, cozy fireplace, and a sliding

  Peggy MacLeay-Generoso McGrath Realty Inc

  19 Cushing Green S, Pawling, NY 12564
• 

  Est $541,325 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,262 Sq Ft

  775 N Quaker Hill Rd, Pawling, NY 12564

  775 N Quaker Hill Rd, Pawling, NY 12564
• 

  

  /41

  $450,000 Pending

  • 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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 444-3725

  27 Washington Ct, Pawling, NY 12564
• 

  $1,400,000 Sold Sep 04, 2025

  • 4,683 Sq Ft
  • $299/SF
  • 139 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  21 Brady Brook Farm Rd, Pawling, NY 12564

  Nestled within the prestigious Brady Brook Falls subdivision on sought-after Quaker Hill, this exquisite colonial offers an unparalleled blend of elegance, privacy, and modern convenience. Situated at the end of a serene cul-de-sac, the home is surrounded by picturesque horse farms and country estates. A long, private driveway leads to this stunning 6.65-acre retreat, complete with a heated

  Brian McGrath McGrath Realty Inc

  21 Brady Brook Farm Rd, Pawling, NY 12564

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