Pawling, NY Homes

• 

  $750,000 Sold Feb 27, 2025

  • 2,719 Sq Ft
  • $276/SF
  • 104 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2004

  197 Highlands Dr, Pawling, NY 12564

  Stunning Sun-Drenched Postmodern Home with Elegant Features and Curb Appeal Nestled on a lush, private lot, this beautifully maintained postmodern home offers striking curb appeal with its classic facade, landscaped gardens, and welcoming front porch-perfect for morning coffee or evening relaxation. Step inside to a bright, open-concept floor plan filled with natural light. The cathedral

  Mary Capria Shawn Michael Realty

  197 Highlands Dr, Pawling, NY 12564
• 

  Est $465,279 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft

  1 Westmount Ave, Pawling, NY 12564

  1 Westmount Ave, Pawling, NY 12564
• 

  

  

  /31

  $367,000 Open Sat 12PM - 2PM

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

  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
• 

  $692,500 Sold Feb 26, 2025

  • 3,078 Sq Ft
  • $225/SF
  • 144 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  31 Millstream Ct, Pawling, NY 12564

  Discover this charming 4-bedroom 2 1/2 bath, 3078 Sq Ft home on 1.57 acres minutes from the quaint Village of Pawling. At entry, step onto a beautiful wrap-around front porch, perfect for enjoying your morning coffee or unwinding in the evening. The inside foyer leads you to this bright first level, where a spacious double-sized family room awaits. Abundant natural light floods the space,

  Mary Craig Coldwell Banker Realty

  31 Millstream Ct, Pawling, NY 12564
• 

  Est $391,081 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,260 Sq Ft

  25 Reservoir Rd, Pawling, NY 12564

  25 Reservoir Rd, Pawling, NY 12564
• 

  

  /32

  $329,999

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

  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 living

  Vincent Reda Keller Williams Realty

  24 Timberline Trail, Pawling, NY 12564
• 

  $610,000 Sold Feb 20, 2025

  • 2,900 Sq Ft
  • $210/SF
  • 37 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1999

  572 Quaker Hill Rd, Pawling, NY 12564

  Set on over 3 acres in Quaker Hill, this beautiful Colonial offers flexibility, privacy, and endless potential. The open floor plan includes a formal dining room, inviting family room with a gas fireplace, and a kitchen with granite countertops and stainless steel appliances.A mudroom accessed from the 2 gar garage helps keep messy shoes and coats organized and out of sight. Upstairs, the primary

  Barbara Allen HomeSmart Homes & Estates

  572 Quaker Hill Rd, Pawling, NY 12564
• 

  Est $407,971 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,344 Sq Ft

  336 Old Route 22, Pawling, NY 12564

  336 Old Route 22, Pawling, NY 12564
• 

  

  /47

  $1,485,000 Open Sun 12PM - 3PM

  • 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
• 

  $150,000 Sold Feb 20, 2025

  • Land
  • 4.43 Acres
  • $33,860 per Acre

  • 151 Days On Market

  Unlisted Address

  Explore this exceptional 4+ acre level lot on Estate Drive, nestled further into the peaceful Cushman Road subdivision in Pawling, NY. Enjoy the privacy of this serene setting while benefiting from shared access with two other similar properties via a common driveway. This lot is equipped with underground utilities and a well, offering a smooth building process. Located just 6 minutes from the

  Colleen McGrath McGrath Realty Inc

  Unlisted Address
• 

  Est $654,241 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,428 Sq Ft

  8 Mallow Ct, Pawling, NY 12564

  8 Mallow Ct, Pawling, NY 12564
• 

  

  /50

  $5,450,000

  • 8 Beds
  • 11 Baths
  • 11,301 Sq Ft

  955 Old Quaker Hill Rd, Pawling, NY 12564

  Perched atop historic Quaker Hill, MAIN TOP, is a private oasis of 20 gated acres with a stately manor, heated saltwater pool, tennis court, and endless mountain vistas that reach across 5 states. The 11,301 sq. ft. residence blends timeless elegance with high ceilings, oak floors, and fine details. Inside, you’ll find stunning formal rooms including a dramatic 47 ft living room, an entertaining

  Gladys Disisto Christie's Int. Real Estate

  955 Old Quaker Hill Rd, Pawling, NY 12564
• 

  $746,000 Sold Feb 14, 2025

  • 2,600 Sq Ft
  • $287/SF
  • 56 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2021

  25 Liberty Ln, Pawling, NY 12531

  EXQUISITE Bi-level Colonial custom-built in 2021. This ENERGY EFFICIENT & ECO friendly home is an ideal blend of country design with modern characteristics. Situated on 2 ACRES of private level all fenced-in land w/a long driveway, lush lawns and beautiful gardens with patios & decks, a swimming pool, and breathtaking views of the countryside. Enter through a mahogany door to the 2-story foyer

  Magdalena Pawlowska Coldwell Banker Realty

  25 Liberty Ln, Pawling, NY 12531
• 

  Est $549,967 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,454 Sq Ft

  4 Glen Ct, Pawling, NY 12564

  4 Glen Ct, 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
• 

  $999,000 Sold Feb 13, 2025

  • 3,660 Sq Ft
  • $273/SF
  • 27 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1981

  37 San Souci Dr, Pawling, NY 12564

  This unique and beautifully designed 5-bedroom mother-daughter property offers the perfect blend of togetherness and independence surrounded by peace and nature. Nestled in a tranquil, picturesque setting, both homes are separate yet conveniently close, ideal for multi-generational living. As you approach, you’ll be greeted by a beautiful entrance lined with flowering trees and gorgeous

  Colleen McGrath McGrath Realty Inc

  37 San Souci Dr, Pawling, NY 12564
• 

  Est $446,682 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  2 Mallow Ct, Pawling, NY 12564

  2 Mallow Ct, Pawling, NY 12564
• 

  

  /50

  $1,500,000

  • 4 Beds
  • 3.5 Baths
  • 4,683 Sq Ft

  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
• 

  $610,000 Sold Feb 06, 2025

  • 2,240 Sq Ft
  • $272/SF
  • 31 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2006

  141 Dugway Dr, Pawling, NY 12564

  Beautiful four-bedroom, two-and-a-half-bathroom Colonial home nestled on a stunning 2.90-acre corner lot in Pawling Lake Estates, a private community with lake and beach access. Built in 2006, this home features an open floor plan with hardwood flooring throughout. The inviting country kitchen flows into the living room, highlighted by a gorgeous stone wood-burning fireplace. The main level also

  Joseph Kelley Houlihan Lawrence Inc.

  141 Dugway Dr, Pawling, NY 12564
• 

  Est $590,926 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,186 Sq Ft

  1 Mallow Ct, Pawling, NY 12564

  1 Mallow Ct, Pawling, NY 12564
• 

  

  /18

  $135,000

  • Land
  • 1.40 Acres
  • $96,429 per Acre

  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

  Judy Albert BHHS Hudson Valley Properties

  0 Overlook Rd, Pawling, NY 12564
• 

  $287,000 Sold Jan 30, 2025

  • 1,972 Sq Ft
  • $146/SF
  • 45 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1966

  8 Brady Ln, Pawling, NY 12564

  1 Level Living! 3 Bedroom, 1 Bathroom Ranch on 3 acres in Town of Pawling! Living room with brick fireplace. Huge sun room with sliding doors to rear deck area. Close to shopping, schools and amenities. Private road. Sold as-is. Buyer to pay NYS and any local transfer taxes. Cash only with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation

  Ernie Acampora River Realty Services, Inc.

  8 Brady Ln, Pawling, NY 12564
• 

  Est $821,413 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,497 Sq Ft

  71 Sumner Ln, Pawling, NY 12564

  71 Sumner Ln, Pawling, NY 12564
• 

  /2

  $650,000

  • 6 Beds
  • 2 Baths
  • 2,856 Sq Ft

  13 Rebecca Dr, Pawling, NY 12564

  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 is a unique situation where the home can be held as an Invesment until 2026 and thereafter utilized by the new owner. Generator

  Angela Briante Briante Realty Group, LLC

  13 Rebecca Dr, Pawling, NY 12564
• 

  $718,000 Sold Jan 28, 2025

  • 4,354 Sq Ft
  • $165/SF
  • 84 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2006

  26 Chestnut Ln, Pawling, NY 12564

  Welcome to this stunning example of refined elegance and timeless charm! This impressive colonial home features 5 spacious bedrooms and 4 beautifully appointed bathrooms. The oversized windows allow for an abundance of light displaying the high ceilings and hardwood floors that extend throughout the home. The gourmet kitchen features stainless steel appliances and a large island with seating

  Vicki Reinach BHHS Hudson Valley Properties

  26 Chestnut Ln, Pawling, NY 12564
• 

  Est $895,171 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,612 Sq Ft

  60 Sumner Ln, Pawling, NY 12564

  60 Sumner Ln, Pawling, NY 12564
• 

  

  /6

  $165,000

  • Land
  • 10 Acres
  • $17,098 per Acre

  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
• 

  $545,000 Sold Jan 27, 2025

  • 4,502 Sq Ft
  • $121/SF
  • 49 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2002

  10 Watchhill Rd, Pawling, NY 12564

  Perched at the end of a cul-de-sac in Deerfield Ponds, this sprawling 4-bedroom, 3.5-bath Colonial offers more than meets the eye. Welcomed by the large front porch, the front door entry opens to a bright hallway, cathedral ceilings showing off the second floor, a powder room, and large entries to the Family and Living Room. Straight down the hall, you will arrive in the spacious, centrally

  Shannon Tully McGrath Realty Inc

  10 Watchhill Rd, Pawling, NY 12564
• 

  Est $957,657 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,216 Sq Ft

  235 N Quaker Hill Rd, Pawling, NY 12564

  235 N Quaker Hill Rd, Pawling, NY 12564
• 

  

  /14

  $250,000

  • Land
  • 10 Acres
  • $25,694 per Acre

  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
• 

  $650,000 Sold Jan 27, 2025

  • 2,840 Sq Ft
  • $229/SF
  • 53 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1987

  10 di Pietro Ln, Pawling, NY 12564

  This bright and spacious Mediterranean style home was designed and built by the owners. It's nestled on a peaceful and private cul-de-sac. As you step inside, discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, double wall oven, granite countertops, and center island. The oversized open floor plan seamlessly connects the formal dining and

  Tony Zaccardo Coldwell Banker Realty

  10 di Pietro Ln, Pawling, NY 12564
• 

  Est $642,776 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,314 Sq Ft

  77 N Quaker Hill Rd, Pawling, NY 12564

  77 N Quaker Hill Rd, Pawling, NY 12564
• 

  

  /22

  $1,350,000

  • Land
  • 3.90 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
• 

  $600,000 Sold Jan 24, 2025

  • 1,824 Sq Ft
  • $329/SF
  • 71 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1979

  92 E Main St, Pawling, NY 12564

  Welcome to your dream home nestled in the vibrant heart of the village of the picturesque Pawling. The beautiful flow of your main floor boasts natural light, giving a perfect blend of practicality and charm. Your backyard will become a perfect venue for entertaining with its expansive and level setting. This labor of love includes many new upgrades: Roof (2018), windows (2018), sliding glass

  Karen Gundelach Keller Williams Realty Partner

  92 E Main St, Pawling, NY 12564
• 

  Est $698,703 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,626 Sq Ft

  55 River Rd, Pawling, NY 12564

  55 River Rd, 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
• 

  $685,000 Sold Jan 24, 2025

  • 3,246 Sq Ft
  • $211/SF
  • 133 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1993

  15 Stirrup Trail, Pawling, NY 12564

  Prepare to be stunned by this immaculately maintained residence! From the moment you step inside, you’ll notice that shoes have never been worn in this pristine home, reflecting a true sense of care and pride of ownership. The current owner has thoughtfully selected and updated every aspect of this home, creating a warm and inviting atmosphere that welcomes you with open arms. Welcome to 15

  Anthony DeBellis Douglas Elliman Real Estate

  15 Stirrup Trail, Pawling, NY 12564
• 

  Est $453,997 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  19 San Souci Dr, Pawling, NY 12564

  19 San Souci 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
• 

  $485,000 Sold Jan 23, 2025

  • 1,170 Sq Ft
  • $415/SF
  • 42 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  94 David Ln, Pawling, NY 12564

  Relax on your deck, high above the shimmering lake, or amble down the hillside to your private dock and dangle your toes in the cool water. At the end of David Lane is this 2 bed, 1 3/4 bath contemporary house. On the main floor three huge skylights sit high above a terracotta tile floor.and an open kitchen with views of the lake below. Also on the main floor is a guest bedroom and bathroom.

  Shannon Tully McGrath Realty Inc

  94 David Ln, Pawling, NY 12564

Showing Results 81 - 120, Page 3 of 18