Dutchess, NY Homes

• 

  $499,850 Sold Apr 28, 2025

  • 1,876 Sq Ft
  • $266/SF
  • 14 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  56 Gristmill Ln, Pawling, NY 12564

  Escape to your own private sanctuary in the heart of Pawling! This unique and multi-functional split ranch is situated on over an acre of meticulously maintained lawns, offering exceptional privacy and breathtaking natural beauty. Just minutes away from nature reserves and the historic Dutcher Golf Course, this home provides the perfect blend of serenity and recreation. Inside, discover a

  Gino Bello Howard Hanna Rand Realty

  56 Gristmill Ln, Pawling, NY 12564
• 

  Est $447,263 Not Listed For Sale

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

  1 Westmount Ave, Pawling, NY 12564

  1 Westmount Ave, Pawling, NY 12564
• 

  

  

  /34

  $625,000

  • 3 Beds
  • 3 Baths
  • 1,450 Sq Ft

  54 Nanny Hill Rd, Pawling, NY 12564

  This stunning home is brand new from Westchester modular, built with top-of-the-line finishes and quality materials. As soon as you step inside, you'll be greeted by a bright and airy open floor plan that creates a spacious and inviting atmosphere. The chef's kitchen is a standout feature, featuring an oversized island with a prep sink and high-end appliances that are sure to appeal to the

  Kaye Saglibene

  54 Nanny Hill Rd, Pawling, NY 12564
• 

  $840,000 Sold Apr 28, 2025

  • 2,768 Sq Ft
  • $303/SF
  • 103 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1967

  9 Strawberry Hill Rd, Pawling, NY 12564

  Nestled on 7 serene acres, this exceptional property offers complete privacy and tranquility. Designed by renowned local architect William Berkley, known for his mid-century modern and contemporary designs on Quaker Hill, this 2,768 SF home, built in 1967, is bathed in natural light and surrounded by stunning landscapes. The property’s design integrates walls of windows and sliding glass doors,

  Brian McGrath McGrath Realty Inc

  9 Strawberry Hill Rd, Pawling, NY 12564
• 

  Est $398,044 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,260 Sq Ft

  25 Reservoir Rd, Pawling, NY 12564

  25 Reservoir Rd, 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 Equestrian Retreat! Nestled in the heart of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on a breathtaking 20+ acre property offering peace, privacy, and natural beauty in every direction. Whether you're looking for a serene country getaway or a horse property, this one-of-a-kind home is the perfect match. The

  Mark Snyder eXp Realty

  28 Gobblers Knob Rd, Pawling, NY 12564
• 

  $335,000 Sold Apr 21, 2025

  • 1,639 Sq Ft
  • $204/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  34 Spruce St, Pawling, NY 12564

  End unit townhome in Cedar Valley. Living room has cathedral ceilings, fireplace and french doors to patio. Primary bedroom/bath suite on first floor. Second floor bedroom/bath guest suite. Only one step from curb to entrance. Easy access to Route 22 and Route 55. Close to the Village of Pawling, shopping, schools and services.

  James Bergstraser RE/MAX Classic Realty

  34 Spruce St, Pawling, NY 12564
• 

  Est $397,147 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
• 

  

  /45

  $456,600

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  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
• 

  $365,000 Sold Apr 10, 2025

  • 2,100 Sq Ft
  • $174/SF
  • 20 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  4 Juniper Ln, Pawling, NY 12564

  Welcome to this cozy and well-maintained 2-bedroom, 2.5-bathroom townhouse with finished basement, offering a perfect blend of comfort, functionality, and extra living space. The open-concept living area with fire place is filled with natural light, creating a warm, inviting atmosphere that’s perfect for relaxing or entertaining. The kitchen is thoughtfully designed with efficient storage and

  Josephine Diego K. Fortuna Realty, Inc.

  4 Juniper Ln, Pawling, NY 12564
• 

  Est $684,225 Not Listed For Sale

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

  8 Mallow Ct, Pawling, NY 12564

  8 Mallow Ct, 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
• 

  $355,000 Sold Apr 08, 2025

  • 720 Sq Ft
  • $493/SF
  • 82 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  26 Taber Knolls Dr, Pawling, NY 12564

  Nestled in a serene country setting just a few miles from the charming village of Pawling, this delightful bungalow offers the perfect blend of tranquility and convenience. Located close to the Metro North Train Station, local shops, restaurants, and parks, this home makes both commuting and leisure readily accessible. With the ease of one level living and charming details like hardwood floors, a

  Reid McGrath McGrath Realty Inc

  26 Taber Knolls Dr, Pawling, NY 12564
• 

  Est $531,996 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
• 

  

  /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
• 

  $975,000 Sold Apr 07, 2025

  • 4,615 Sq Ft
  • $211/SF
  • 21 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2000

  11 Birch Hill Rd, Pawling, NY 12564

  An incredible opportunity awaits atop Quaker Hill. Set on a park-like 1.34-acre parcel framed by picturesque stone walls, this custom-built colonial spans 4,615 SF over three floors. The home is complemented by a stunning 24 x 36 two-story post-and-beam barn, a serene pond, raised garden beds, and expansive outdoor spaces. The home's design is incredibly functional, with a flexible floor plan

  Claudia Jiskra McGrath Realty Inc

  11 Birch Hill Rd, Pawling, NY 12564
• 

  Est $430,242 Not Listed For Sale

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

  2 Mallow Ct, Pawling, NY 12564

  2 Mallow Ct, Pawling, NY 12564
• 

  

  /3

  $150,000

  • Land
  • 4.21 Acres
  • $35,629 per Acre

  0 South Rd Unit KEY853088, Pawling, NY 12531

  Beautiful 4.21-acre lot in Pawling, NY presents a unique opportunity to build your dream home. This secluded property offers the ideal blend of privacy and convenience, situated just minutes from the charming Village of Pawling, Metro-North train station, restaurants, shopping, and all the amenities the historic Hudson Valley has to offer. Only three miles off I-84. Perfect for a year-round

  Michael Knecht Howard Hanna Rand Realty

  0 South Rd Unit KEY853088, Pawling, NY 12531
• 

  $100,000 Sold Mar 11, 2025

  • Land
  • 0.36 Acre
  • $277,778 per Acre

  • 129 Days On Market

  1074 W Dover Rd, Pawling, NY 12564

  Come build your Dream Home and experience the Good Life at this Wonderful Parcel of Land for Sale in Dutchess County! This is the ideal location to come home to for some peace and relaxation, underneath your lush, Crimson Maple Tree! You'll have a head start with your preparation plans. Not only is this a BOE approved property, but it boasts a 1250 foot drilled well (Pump is located 600 ft down &

  Robert Pape Keller Williams NY Realty

  1074 W Dover Rd, Pawling, NY 12564
• 

  Est $838,265 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
• 

  

  /47

  $1,450,000

  • 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
• 

  $367,500 Sold Mar 04, 2025

  • 1,572 Sq Ft
  • $234/SF
  • 68 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1945

  27 Gobblers Knob Rd, Pawling, NY 12564

  Welcome home to this light and airy 4 Bedroom, 2 Bath Cape located on over 1 acre of level property. House sits on an expansive lot with mature plantings in a quiet and peaceful setting. Spend relaxing days on the deck or serene evenings on the rear enclosed screened in porch. Enter into an amazing living room with stone fireplace that is perfect for family gatherings. The kitchen opens into a

  Douglas McGowan Coldwell Banker Realty

  27 Gobblers Knob Rd, Pawling, NY 12564
• 

  Est $903,909 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
• 

  

  /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
• 

  $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 $935,610 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
• 

  /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
• 

  $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 $663,709 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
• 

  

  /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
• 

  $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 $454,722 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
• 

  

  /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
• 

  $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 $518,799 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,324 Sq Ft

  17 San Souci Dr, Pawling, NY 12564

  17 San Souci Dr, 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
• 

  $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 $441,759 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,166 Sq Ft

  9 San Souci Dr, Pawling, NY 12564

  9 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
• 

  $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

Showing Results 81 - 120, Page 3 of 18