Pawling, NY Homes

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  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,434 Sq Ft

  128 Old Pawling Rd, Pawling, NY 12564

  You finally have the opportunity to own a home with year-round mountain views set on an expansive property. A place where you can bring your vision to life and transform the space into a true masterpiece. 128 Old Pawling Road is a beautifully positioned property in Pawling, NY, offering a rare combination of scenic views, generous land, and the potential to create a truly special home. Set back

  Juliska Martino Compass Greater NY, LLC

  128 Old Pawling Rd, Pawling, NY 12564
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• 

  $410,000 Sold Jul 24, 2025

  11 Birch Terrace, Pawling, NY 12564

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $293/SF
  • 34 Days On Market

  Current Estimated Value $410,070

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  11 Birch Terrace, Pawling, NY 12564
• 

  Est $951,551 Not Listed For Sale

  929 Old Quaker Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 2 Baths
  • 2,093 Sq Ft
  • Built 1929

  929 Old Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 13% Below List Price
  • $526/SF
  • 14 Days On Market

  Last Sold Price $1,100,000

  Last Listing Agent David Turner Compass Greater NY, LLC
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  /46

  $420,000 Pending

  • 2 Beds
  • 2 Baths
  • 2,596 Sq Ft

  7 Juniper Ln, Pawling, NY 12564

  Welcome home to your spacious and cozy tri-level end unit in the Cedar Valley complex! The eat-in kitchen opens to the dining area and bright living room with a cozy fireplace, perfect for everyday living and entertaining. The main level features a primary bedroom with private bath and walk-in closet, plus a second bedroom with a full hall bath. The loft overlooking the living area offers

  Elizabeth Poggiogalle Real Broker NY LLC

  7 Juniper Ln, Pawling, NY 12564
• 

  $350,000 Sold Dec 18, 2025

  33 Spruce St, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 1,413 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $248/SF
  • 51 Days On Market

  Current Estimated Value $354,928

  Last Listing Agent Edmond Albano Keller Williams NY Realty

  33 Spruce St, Pawling, NY 12564
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  Est $734,113 Not Listed For Sale

  572 Quaker Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 3.5 Baths
  • 2,900 Sq Ft
  • Built 1999

  572 Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 20% Above List Price
  • $210/SF
  • 37 Days On Market

  Last Sold Price $610,000

  Last Listing Agent Barbara Allen HomeSmart Homes & Estates
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  /50

  $619,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  322 Old Route 22, Pawling, NY 12564

  Multi-family in Pawling! This spacious, newly remodeled 2-family home is located just a few minutes from the Village of Pawling - a great opportunity for owner-occupants, investors, or extended families! Each unit features 2 bedrooms, a full bath, living room, dining area, kitchen and bright, enclosed sunporches, providing plenty of space and natural light throughout. Inside, both units are

  Susan Stevens BHHS Hudson Valley Properties

  322 Old Route 22, Pawling, NY 12564
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  $490,000 Sold May 16, 2025

  17 Fenwood Dr, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $286/SF
  • 85 Days On Market

  Current Estimated Value $519,819

  Last Listing Agent Shannon Tully McGrath Realty Inc

  17 Fenwood Dr, Pawling, NY 12564
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  Est $693,953 Not Listed For Sale

  270 N Quaker Hill Rd, Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • Built 1976

  270 N Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 12% Above List Price
  • $325/SF
  • 39 Days On Market

  Last Sold Price $620,000

  Last Listing Agent Claudia Jiskra McGrath Realty Inc
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  $2,500,000

  • 6 Beds
  • 6.5 Baths
  • 6,625 Sq Ft

  3302 Route 55, Pawling, NY 12564

  Welcome to your forever home, serene retreat and mini estate. Enjoy the 88 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 expansive living space, luxury and customize finishes throughout. A true

  STACI MACKIN Dixon Smith Realty

  3302 Route 55, Pawling, NY 12564
• 

  $645,000 Sold Jun 13, 2025

  32 Elm St, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1880

  Last Sold Summary

  • 3% Above List Price
  • $339/SF
  • 20 Days On Market

  Current Estimated Value $569,331

  Last Listing Agent Patrycja Warda Corcoran Country Living

  32 Elm St, Pawling, NY 12564
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  Est $704,010 Not Listed For Sale

  64 Game Farm Rd, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 2,209 Sq Ft
  • Built 1950

  64 Game Farm Rd, Pawling, NY 12564

  Last Sold Summary

  • 15% Above List Price
  • $276/SF
  • 24 Days On Market

  Last Sold Price $610,000

  Last Listing Agent Vince McGough McGough Realty Corp
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  /8

  $150,000

  • Land
  • 0.46 Acre
  • $326,087 per Acre

  20 Hickory Ln, Pawling, NY 12564

  Build your dream home on this exceptional 0.46-acre parcel, offering a rare blend of privacy, nature, and convenience. The property is BOH approved (3 bedroom residential dwelling), providing a smooth path to construction, and is landlocked at the rear, creating a peaceful, secluded setting. Enjoy access to two nearby lakes for fishing or swimming, or relax at the clubhouse. Drive into Pawling

  Tela Cook McGrath Realty Inc

  20 Hickory Ln, Pawling, NY 12564
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  $376,500 Sold Jun 18, 2025

  18 Evergreen Way, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 1,427 Sq Ft
  • Built 1997

  Last Sold Summary

  • 2% Above List Price
  • $264/SF
  • 13 Days On Market

  Current Estimated Value $395,854

  Last Listing Agent Vicki Reinach BHHS Hudson Valley Properties

  18 Evergreen Way, Pawling, NY 12564
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  Est $1,079,749 Not Listed For Sale

  382 Old Quaker Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 3.5 Baths
  • 6,052 Sq Ft
  • Built 2007

  382 Old Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 12% Above List Price
  • $159/SF
  • 74 Days On Market

  Last Sold Price $960,000

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
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  /5

  $399,000 Pending

  • Land
  • 61.82 Acres
  • $6,454 per Acre

  0 S White Rock Rd Unit 6015368, Pawling, NY 12531

  Approved 7 lot residential subdivision: Pristine, secluded, quiet area with DCBOH approved residential building lots 3.02-6.41 acres surroundinga 31 acre open space area. All lot sites selected for privacy. Partial physical improvements (over $350K) to include 2 (partially complete) roads and storm water works in place. Tax assessments in appeal. HOA established, shared fees for roads & storm

  John Ravetto Houlihan Lawrence Inc.

  0 S White Rock Rd Unit 6015368, Pawling, NY 12531
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  $949,900 Sold May 02, 2025

  14 Little Pond Rd, Pawling, NY 12564

  • 4 Beds
  • 4.5 Baths
  • 3,798 Sq Ft
  • Built 2000

  Last Sold Summary

  • $250/SF
  • 6 Days On Market

  Current Estimated Value $981,883

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  14 Little Pond Rd, Pawling, NY 12564
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  Est $774,933 Not Listed For Sale

  112 S Quaker Hill Rd, Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 2,758 Sq Ft
  • Built 1985

  112 S Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 5% Above List Price
  • $268/SF
  • 34 Days On Market

  Last Sold Price $740,000

  Last Listing Agent Claudia Jiskra McGrath Realty Inc
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  /22

  $425,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,776 Sq Ft

  40 Walnut St, Pawling, NY 12564

  Spacious 4 BR Home is located in the Village of Pawling. Nice property has a wonderful western view with amazing sunsets! Sunny Living Rm with picture window is open to the Dining Rm. The Kitchen has space for a breakfast table or island. The main floor has been freshly painted and has solid oak hardwood floors. Walking distance to Metro-North Train Station, Library, Medical Offices, Village

  Lisa Liffland McGrath Realty Inc

  40 Walnut St, Pawling, NY 12564
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  $345,000 Sold Jul 09, 2025

  88 Lakeview Dr, Pawling, NY 12564

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Above List Price
  • $383/SF
  • 26 Days On Market

  Current Estimated Value $348,015

  Last Listing Agent Martha Woodhouse Howard Hanna Rand Realty

  88 Lakeview Dr, Pawling, NY 12564
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  Est $802,114 Not Listed For Sale

  8 Birch Hill Rd, Pawling, NY 12564

  • 4 Beds
  • 4 Baths
  • 2,772 Sq Ft
  • Built 1985

  8 Birch Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 7% Above List Price
  • $271/SF
  • 7 Days On Market

  Last Sold Price $752,500

  Last Listing Agent Liza Reiss Elyse Harney Real Estate
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  /24

  $485,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,503 Sq Ft

  20 Saratoga St, Pawling, NY 12564

  Welcome to this stunning 3-bedroom, 3.5-bath end-unit townhome in the highly desirable Deerfield Ponds community. Bright, warm, and beautifully maintained, this home offers an ideal blend of comfort, convenience, and modern living. Step inside to an inviting living room that seamlessly flows into the dining area and a charming kitchen with a cozy breakfast nook, all appliances updated within the

  Julia Lear Coldwell Banker Realty

  20 Saratoga St, Pawling, NY 12564
• 

  $674,900 Sold May 21, 2025

  24 Sheridan Dr, Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 2,876 Sq Ft
  • Built 1930

  Last Sold Summary

  • $235/SF
  • 134 Days On Market

  Last Listing Agent John Gabriel Jr KW MidHudson

  24 Sheridan Dr, Pawling, NY 12564
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  Est $363,357 Not Listed For Sale

  62 S Quaker Hill Rd, Pawling, NY 12564

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1991

  62 S Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 9% Above List Price
  • $370/SF
  • 110 Days On Market

  Last Sold Price $333,000

  Last Listing Agent Reid McGrath McGrath Realty Inc
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  /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 Hillside Realty & Development

  120 Harmony Rd, Pawling, NY 12564
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  $240,000 Sold Nov 12, 2025

  51 Kirby Hill Rd, Pawling, NY 12564

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

  Last Sold Summary

  • 4% Below List Price
  • 80 Days On Market

  Last Listing Agent Donna Kennedy Compass Greater NY, LLC

  51 Kirby Hill Rd, Pawling, NY 12564
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  Est $712,800 Not Listed For Sale

  83 Hurds Corners Rd, Pawling, NY 12564

  • 3 Beds
  • 3 Baths
  • 3,300 Sq Ft
  • Built 1986

  83 Hurds Corners Rd, Pawling, NY 12564

  Last Sold Summary

  • 2% Above List Price
  • $212/SF
  • 93 Days On Market

  Last Sold Price $700,000

  Last Listing Agent Beth Yoon Sherwood Hill Realty LLC
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  /35

  $549,222 Open Sat 2:30PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  5 Old Field Cir, Pawling, NY 12564

  Welcome to this beautifully maintained Victorian-style home, ideally situated in the highly sought-after Deerfield Ponds community at Squire Green in Pawling. From the inviting wraparound porch to the thoughtfully designed interior, this home offers timeless character paired with modern updates. The first floor features hardwood floors throughout, a formal dining room, and a sun-filled living

  Mark Seiden Mark Seiden Real Estate Team

  5 Old Field Cir, Pawling, NY 12564
• 

  $2,700,000 Sold Jan 10, 2026

  30 Dewey Ln, Pawling, NY 12564

  • 6 Beds
  • 6 Baths
  • 6,460 Sq Ft
  • Built 1860

  Last Sold Summary

  • 28% Below List Price
  • $418/SF
  • 146 Days On Market

  Current Estimated Value $2,388,821

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  30 Dewey Ln, Pawling, NY 12564
• 

  Est $739,559 Not Listed For Sale

  1104 Route 22, Pawling, NY 12564

  • 4 Beds
  • 2.5 Baths
  • 2,944 Sq Ft
  • Built 1986

  1104 Route 22, Pawling, NY 12564

  Last Sold Summary

  • 87% Above List Price
  • $134/SF
  • 9 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Ernie Acampora River Realty Services, Inc.
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  /13

  $368,888 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,960 Sq Ft

  21 Kings Way, Pawling, NY 12564

  Welcome to 21 Kings Way, a charming 3-bedroom, 2.5-bathroom townhome nestled in a wonderful community in Pawling, NY. This beautifully maintained home offers a perfect blend of comfort, style, and convenience. Step inside to discover an inviting open floor plan with spacious living areas, perfect for both entertaining and everyday living. The large windows flood the space with natural light,

  Bopaul Sookdeo YourHomeSold Guaranteed Realty

  21 Kings Way, Pawling, NY 12564
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  $660,000 Sold Jan 16, 2026

  29 Cunningham Ln, Pawling, NY 12564

  • 4 Beds
  • 5 Baths
  • 4,199 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $157/SF
  • 72 Days On Market

  Current Estimated Value $680,464

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

  29 Cunningham Ln, Pawling, NY 12564
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  Est $464,563 Not Listed For Sale

  1 Westmount Ave, Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft
  • Built 1948

  1 Westmount Ave, Pawling, NY 12564

  Last Sold Summary

  • 9% Above List Price
  • $292/SF
  • 40 Days On Market

  Last Sold Price $428,000

  Last Listing Agent Brian McGrath McGrath Realty Inc
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  /16

  $387,000

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

  10 Timberline Trail, Pawling, NY 12564

  ~ Welcome to your spacious and cozy tri-level townhome in the desirable Cedar Valley Community. ~This rare end unit provides you with an abundance of light and additional outdoor space. Featuring 2 spacious bedrooms and 2.5 bathrooms, this home boasts an open and versatile layout ideal for everyday living and entertaining. The dining area and bright living room with its cozy fireplace opens

  Giorgio Palmisano Howard Hanna Rand Realty

  10 Timberline Trail, Pawling, NY 12564
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  $1,400,000 Sold Sep 04, 2025

  21 Brady Brook Farm Rd, Pawling, NY 12564

  • 4 Beds
  • 3.5 Baths
  • 4,683 Sq Ft
  • Built 2003

  Last Sold Summary

  • 17% Below List Price
  • $299/SF
  • 139 Days On Market

  Current Estimated Value $1,414,642

  Last Listing Agent Brian McGrath McGrath Realty Inc

  21 Brady Brook Farm Rd, Pawling, NY 12564
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  Est $478,215 Not Listed For Sale

  2 Mallow Ct, Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1984

  2 Mallow Ct, Pawling, NY 12564

  Last Sold Summary

  • $369/SF
  • 19 Days On Market

  Last Sold Price $480,000

  Last Listing Agent Claudia Jiskra McGrath Realty Inc
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  /38

  $375,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,639 Sq Ft

  16 Juniper Ln, Pawling, NY 12564

  Welcome to Cedar Valley! This bright corner unit offers the perfect blend of comfort and convenience, with potential for easy one-floor living. The main level features both bedrooms, while a spacious loft upstairs provides flexible bonus space—ideal for a home office, gym, guest area, or additional living space.Enjoy the ease of just two steps from the parking lot to your front door, with two

  Vanessa Longo Briante Realty Group, LLC

  16 Juniper Ln, Pawling, NY 12564
• 

  $315,000 Sold Aug 05, 2025

  24 Timberline Trail, Pawling, NY 12564

  • 2 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 1997

  Last Sold Summary

  • 10% Below List Price
  • $148/SF
  • 51 Days On Market

  Current Estimated Value $347,484

  Last Listing Agent Vincent Reda Keller Williams Realty

  24 Timberline Trail, Pawling, NY 12564
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  Est $949,052 Not Listed For Sale

  235 N Quaker Hill Rd, Pawling, NY 12564

  • 5 Beds
  • 2.5 Baths
  • 3,216 Sq Ft
  • Built 1928

  235 N Quaker Hill Rd, Pawling, NY 12564

  Last Sold Summary

  • 5% Above List Price
  • $280/SF
  • 71 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Regan Andrews Coldwell Banker Realty
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  /33

  $495,000

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  17 Townsend Blvd, Pawling, NY 12564

  Fall in Love with this Charming Mediterranean Style Garden Home. A Private Oasis Hidden Away and Nestled among a Grove of Mature Trees. Follow meandering paths that lead to Splashes of Color from the Cultivated Perennial Gardens of a Lifetime and a Gentle Woodland Stream. This Home is Sparkling Clean, Freshly Polished, Newly Painted, Move-In Ready and awaits your Arrival. Tucked in at the end of

  Martha Woodhouse Howard Hanna Rand Realty

  17 Townsend Blvd, Pawling, NY 12564

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