Recently Sold Pawling, NY Homes

• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $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
• 

  $360,000 Sold Jan 13, 2025

  • 1,413 Sq Ft
  • $255/SF
  • 65 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  13 Juniper Ln, Pawling, NY 12564

  Welcome to your sunlit home in the desirable Cedar Valley Subdivision! This beautifully updated 2-bedroom, 2.5-bath condo offers a perfect blend of modern upgrades and comfortable living. Enjoy abundant natural light throughout. Recent upgrades include new Pella windows and front door, water filtration system, new hot water tank, new carpeting, and new hallway and living room flooring. All

  Nanci Kubik Houlihan Lawrence Inc.

  13 Juniper Ln, Pawling, NY 12564
• 

  $535,000 Sold Jan 10, 2025

  • 3,620 Sq Ft
  • $148/SF
  • 39 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1989

  173 Quaker Hill Rd, Pawling, NY 12564

  Welcome to this immaculate and spacious Pawling colonial. The first thing you see is the beautiful, mature landscaping on over an acre of land. And the views! The first floor offers a living room with a fireplace and bay window to enjoy the far reaching view. The kitchen opens into the dining room where you will find sliding glass doors to the large back patio. Also on this floor is a

  Regan Andrews Houlihan Lawrence Inc.

  173 Quaker Hill Rd, Pawling, NY 12564
• 

  $467,000 Sold Dec 27, 2024

  • 1,824 Sq Ft
  • $256/SF
  • 74 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  45 Fenwood Dr, Pawling, NY 12564

  Your search is over! Charming 3 bedrm, 2 bath home on 1.15 acres, fenced-in private yard, perfect for your little ones or four-legged family members enjoy nature in safety. Savor morning coffee on the wrap-around deck overlooking tranquil gardens, beautiful natural landscaping & your own greenhouse! Bright open floor plan w/cathedral ceilings, hardwoods make this home feel like an artist’s

  Peggy MacLeay-Generoso McGrath Realty Inc

  45 Fenwood Dr, Pawling, NY 12564
• 

  $795,000 Sold Dec 26, 2024

  • 3,287 Sq Ft
  • $242/SF
  • 58 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1979

  206 N Quaker Hill Rd, Pawling, NY 12564

  Perched on 3 wooded acres high above a natural stream, this 4-bedroom 3.5 bath Contemporary offers more than meets the eye. Natural landscaping sweeps down the drive, guiding visitors to a fresh stone path leading to the front door. The entry features a cathedral ceiling featuring a charming wood stove, set-off by large windows, soaring ceilings, hardwood floors, and a floor to ceiling stone

  Shannon Tully McGrath Realty Inc

  206 N Quaker Hill Rd, Pawling, NY 12564
• 

  $260,000 Sold Dec 23, 2024

  • 1,640 Sq Ft
  • $159/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  85 Harmony Hill Rd, Pawling, NY 12564

  Three bedroom, two bathroom ranch in T/Pawling on 2.9 acres! Additional 1800 square foot structure with potential for added living space adjacent to main house. See agent remarks for more information prior to showing. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent

  Brian Smith River Realty Services, Inc.

  85 Harmony Hill Rd, Pawling, NY 12564
• 

  $114,900 Sold Dec 18, 2024

  • Land
  • 0.76 Acre
  • $151,184 per Acre

  • 112 Days On Market

  15 Dykeman St, Pawling, NY 12564

  Don't miss this great opportunity! Lovely vacant lot in Pawling, NY. Book your appointment to see this great property today! This is a FannieMae HomePath property.

  Matthew Cave Hudson Property Services, LLC

  15 Dykeman St, Pawling, NY 12564
• 

  $995,000 Sold Dec 13, 2024

  • 2,716 Sq Ft
  • $366/SF
  • 94 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1850

  138 Harmony Rd, Pawling, NY 12564

  Welcome to a truly unique and private retreat nestled on 66+ acres of verdant grounds along a scenic country road in Pawling, NY. This estate transports you back in time, with impeccably maintained landscapes featuring ancient stately trees, expansive lawns, and picturesque stone walls that wind through the property. The beauty of the land is unparalleled, offering absolute privacy and a serene

  Brian McGrath McGrath Realty Inc

  138 Harmony Rd, Pawling, NY 12564
• 

  $430,000 Sold Dec 12, 2024

  • 1,286 Sq Ft
  • $334/SF
  • 104 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1971

  25 Frenchmans Ln, Pawling, NY 12564

  A/O, CTS for backup. Where the blacktop ends, a lovely split level Ranch nestled on 1 level acre. The setting couldn't be lovelier. This 3 BR, 1 bath home has many new improvements such as a new furnace, new central AC unit, electric upgraded to 200 Amps. There are wood floors underneath the tile in the hallway & the carpeting in the living room/dining area. The home is conveniently located to

  Gillian Stewart Gillian Stewart Real Estate

  25 Frenchmans Ln, Pawling, NY 12564
• 

  $752,500 Sold Dec 10, 2024

  • 2,772 Sq Ft
  • $271/SF
  • 7 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1985

  8 Birch Hill Rd, Pawling, NY 12564

  Stunning sunsets and panoramic mountain views await at this 4+ acre home on Birch Hill Road in Pawling, NY. This beautifully maintained 4-bedroom, 3.5-bath colonial includes a finished guest space above the 2-car garage, featuring a private office and separate living room. Enjoy breathtaking views from the wrap-around porch, living room, and kitchen. The first floor offers a spacious living room

  Liza Reiss Elyse Harney Real Estate

  8 Birch Hill Rd, Pawling, NY 12564
• 

  $662,500 Sold Dec 10, 2024

  • 2,344 Sq Ft
  • $283/SF
  • 195 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1950

  54 Old Route 55, Pawling, NY 12564

  PRICE IMPROVEMENT!!!! Head to your very own countryside getaway just 60 miles from NYC! This peaceful retreat offers privacy and relaxation surrounded by nature's beauty. Set on 19 acres, this updated 3 bed 3 bath home boasts a modern kitchen and a luxurious spa-like bathroom in the main suite. With high ceilings and plenty of windows, natural light floods the space, offering tranquil woodland

  Suzanne Browne-Shilling Coldwell Banker Realty

  54 Old Route 55, Pawling, NY 12564
• 

  $13,000 Sold Nov 20, 2024

  • Land
  • 0.26 Acre
  • $50,000 per Acre

  • 234 Days On Market

  7 Birch Ln, Holmes, NY 12531

  Please note: Tiny Homes are not allowed per Town Code. The min. size dwelling that can be built, provided you meet all the other requirements including BOH approval, is 800/sf. Trailers are only allowed in Mobil Home Parks in the Town of East Fishkill . Vacant land for sale CurrentUses: Single Family,

  Pauline Angrisani Coldwell Banker Realty

  7 Birch Ln, Holmes, NY 12531
• 

  $440,000 Sold Nov 18, 2024

  • 1,818 Sq Ft
  • $242/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  52 Gristmill Ln, Pawling, NY 12564

  Property like this doesn't hit the market often! This charming three bedroom ranch is surrounded by one acre of park-like grounds on a quiet, bucolic street with no through-traffic. Inside, you'll find everything you want in a home: a large eat-in Kitchen with granite counters and stainless steel appliances; spacious living room and dining room with sliding doors to the deck; primary bedroom with

  Vanessa Longo Briante Realty Group, LLC

  52 Gristmill Ln, Pawling, NY 12564
• 

  $680,000 Sold Nov 15, 2024

  • 2,599 Sq Ft
  • $262/SF
  • 38 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  Unlisted Address

  This delightful home, set on a peaceful cul-de-sac and close to the quaint Village of Pawling, offers the perfect blend of modern convenience and timeless elegance. Built in 2005, the property feels like new, boasting 2,599 square feet across its first two levels, with three bedrooms, a finished bonus room, and two and a half baths. The unfinished walk-out basement with high ceilings and sliders

  Claudia Jiskra McGrath Realty Inc

  Unlisted Address
• 

  $439,999 Sold Oct 24, 2024

  • 1,079 Sq Ft
  • $408/SF
  • 36 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1977

  85 Fairway Dr, Pawling, NY 12564

  Welcome to your dream home in the charming Village of Pawling! This delightful 3-bedroom, 1.5-bathroom house offers the perfect blend of comfort and convenience. Step inside and be greeted by a spacious eat-in kitchen, boasting elegant granite countertops that will inspire your inner chef. The primary bedroom, complete with its own half bath, provides a peaceful retreat after a long day. All

  Anna Proctor Compass Greater NY, LLC

  85 Fairway Dr, Pawling, NY 12564
• 

  $360,000 Sold Oct 16, 2024

  • 1,200 Sq Ft
  • $300/SF
  • 39 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1945

  11 Allison Dr, Pawling, NY 12564

  Looking for a charming and cozy home in the heart of Pawling Village? Look no further than this adorable property, featuring two bedrooms, a full bathroom, and a living room with a warm and inviting stone fireplace. The dining area leads out to a spacious patio, perfect for entertaining, and the galley kitchen provides access to the backyard and basement. The full, unfinished basement offers

  Teddie Leonaggeo McGrath Realty Inc

  11 Allison Dr, Pawling, NY 12564
• 

  $270,000 Sold Oct 11, 2024

  • 1,950 Sq Ft
  • $138/SF
  • 51 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1929

  322 Old Route 22, Pawling, NY 12564

  Looking for a project, this 2 family property could shine with the right owner. Property sold as-is-where-is with all faults. Pipe on second floor burst, first floor suffered water damage, radiators on first floor are cracked, condition of boiler is unknown, hot water heaters are not operational, house NEEDS work but has tremendous potential. This spacious 2 unit property boasts 2 bedrooms,

  Kelly Campbell Century 21 Alliance Rlty Group

  322 Old Route 22, Pawling, NY 12564
• 

  $1,125,000 Sold Oct 01, 2024

  • 2,441 Sq Ft
  • $461/SF
  • 120 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  39 Overlook Dr, Pawling, NY 12564

  Get ready to feel the All-American dream come to life as you make your way up to this impeccably maintained 5.77-acre property just minutes from the bucolic Village of Pawling. As you pass the 4-stall horse barn (crafted by Old Town Barns) and riding ring to your right, you’ll find the inviting, contemporary home accompanied by the gleaming, freshly epoxy coated 2-bay garage with workshop, two

  Colleen McGrath McGrath Realty Inc

  39 Overlook Dr, Pawling, NY 12564
• 

  $740,000 Sold Sep 30, 2024

  • 2,758 Sq Ft
  • $268/SF
  • 34 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1985

  112 S Quaker Hill Rd, Pawling, NY 12564

  Set high atop Quaker Hill with million-dollar views. Perfectly situated on a 3-acre parcel to enjoy the coveted far-reaching mountain views, pastoral horse farms and nightly awe-inspiring westerly sunsets. This lovely 2,758 SF two-story colonial home is being offered for the first time by its original owner. Inside, the residence offers a harmonious blend of formal and casual spaces, accentuated

  Claudia Jiskra McGrath Realty Inc

  112 S Quaker Hill Rd, Pawling, NY 12564
• 

  $740,000 Sold Mar 27, 2025

  • 3,739 Sq Ft
  • $198/SF
  • 20 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2004

  147 Highlands Dr, Pawling, NY 12564

  Beautiful Colonial home in the Highlands. Exquisite Community. Amenities include a heated pool, tennis court and a fishing pond.

  Pete Rodriguez William Raveis Real Estate

  147 Highlands Dr, Pawling, NY 12564

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