Pawling, NY Homes

/30
$440,000
- 3 Beds
- 3 Baths
- 1,556 Sq Ft
978 W Dover Rd, Pawling, NY 12564

Welcome to 978 W Dover Road in Pawling, NY—where comfort, space, and scenic beauty come together effortlessly. This inviting home features 3 generously sized bedrooms, 3 full bathrooms, and a dedicated home office, making remote work both productive and enjoyable. The open-concept main level creates a seamless flow between living spaces, perfect for hosting gatherings or simply spending quality

Regan Andrews Coldwell Banker Realty

978 W Dover Rd, Pawling, NY 12564
$430,000

Sold Sep 11, 2025

19 Cushing Green S, Pawling, NY 12564
- 3 Beds
- 2.5 Baths
- 1,835 Sq Ft
- Built 1987
Last Sold Summary
- 6% Below List Price
- $234/SF
- 64 Days On Market
Current Estimated Value $446,182

Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

19 Cushing Green S, Pawling, NY 12564

Est $929,046

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
- 14 Days On Market

/43
$629,900

$20K PRICE DROP
- 3 Beds
- 2 Baths
- 1,768 Sq Ft
57 Buhleir Rd, Pawling, NY 12564

Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side.

Carolyn Ridenour Berkshire Hathaway HS NE Prop.

57 Buhleir Rd, Pawling, NY 12564
$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 $416,172

Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

11 Birch Terrace, Pawling, NY 12564

Est $925,394

Not Listed For Sale

9 Strawberry Hill Rd, Pawling, NY 12564
- 3 Beds
- 3.5 Baths
- 2,768 Sq Ft
- Built 1967
9 Strawberry Hill Rd, Pawling, NY 12564

Last Sold Summary
- 103 Days On Market

/45
$600,000
- 4 Beds
- 2.5 Baths
- 2,924 Sq Ft
5 Red Tail Ct, Pawling, NY 12564

Single family home in the Squire Green Community with many amenities to enjoy. Need space? This home delivers. From the oversized living area to the spacious bedrooms and flexible floor plan, there's plenty of room. If space is what you're looking for, you've come to the right place. This home offers generous living areas and plenty of room to comfortably accommodate everyone, entertain guests,

Susan Salamone Houlihan Lawrence Inc.

5 Red Tail Ct, 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 $357,160

Last Listing Agent Edmond Albano Keller Williams NY Realty

33 Spruce St, Pawling, NY 12564

Est $801,125

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
- 37 Days On Market

/29
$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
$775,000

Sold May 01, 2026

36 Horseshoe Path, Pawling, NY 12564
- 3 Beds
- 2.5 Baths
- 4,627 Sq Ft
- Built 2003
Last Sold Summary
- $167/SF
- 32 Days On Market
Current Estimated Value $782,431

Last Listing Agent Neeta Saraswat Weichert Realtors

36 Horseshoe Path, Pawling, NY 12564

Est $697,386

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
- 39 Days On Market

/21
$595,000
- 3 Beds
- 2.5 Baths
- 2,636 Sq Ft
188 N Quaker Hill Rd, Pawling, NY 12564

Fantastic weekend getaway or full time residence, hard to find Quaker Hill, situated on 5.00 secluded acres with babbling brook running through. Master bedroom with bath, walk in closet. 2 additional bedrooms & full bath. The living room, dining area & eat in kitchen are bright & spacious with hardwood floors throughout. Finished walkout basement with powder room. This property is mostly level,

Gillian Stewart Gillian Stewart Real Estate

188 N Quaker Hill Rd, 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 $566,988

Last Listing Agent Patrycja Warda Corcoran Country Living

32 Elm St, Pawling, NY 12564

Est $727,266

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
- 24 Days On Market

/9
$140,000

$10K PRICE DROP
- Land
- 20,037 Sq Ft
- $304,348 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
$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 $406,716

Last Listing Agent Vicki Reinach BHHS Hudson Valley Properties

18 Evergreen Way, Pawling, NY 12564

Est $1,428,332

Not Listed For Sale

54 Burgess Rd, Pawling, NY 12564
- 4 Beds
- 3.5 Baths
- 2,910 Sq Ft
- Built 1926
54 Burgess Rd, Pawling, NY 12564

Last Sold Summary
- 60 Days On Market

/5
$399,000

$30K PRICE DROP 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
$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 $348,798

Last Listing Agent Martha Woodhouse Howard Hanna Rand Realty

88 Lakeview Dr, Pawling, NY 12564

Est $1,147,919

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
- 74 Days On Market

/31
$900,000

$50K PRICE DROP
- 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
$439,370

Sold May 20, 2026

40 Walnut St, Pawling, NY 12564
- 4 Beds
- 1.5 Baths
- 1,776 Sq Ft
- Built 1960
Last Sold Summary
- 10% Below List Price
- $247/SF
- 78 Days On Market
Current Estimated Value $451,237

Last Listing Agent Lisa Liffland McGrath Realty Inc

40 Walnut St, Pawling, NY 12564

Est $900,454

Not Listed For Sale

139 Old Quaker Hill Rd, Pawling, NY 12564
- 3 Beds
- 2 Baths
- 2,538 Sq Ft
- Built 1965
139 Old Quaker Hill Rd, Pawling, NY 12564

Last Sold Summary
- 197 Days On Market

/16
$499,999
- 2 Beds
- 1 Bath
- 1,347 Sq Ft
1141 Old Quaker Hill Rd, Pawling, NY 12564

Welcome Home! Tucked away along storied Old Quaker Hill, this antique charmer invites you to experience a slower, richer pace of living—where history lingers in every beam and modern comfort quietly supports it. Offered fully furnished (or unfurnished) and available for immediate occupancy, this cozy retreat blends timeless character with everyday ease, making it an ideal escape for your weekend

Chinenye Aguoji Real Broker NY LLC

1141 Old Quaker Hill Rd, Pawling, NY 12564
$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

Est $763,534

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
- 34 Days On Market

/50
$689,000

Pending
- 3 Beds
- 3.5 Baths
- 3,175 Sq Ft
24 Overlook Dr, Pawling, NY 12564

Tucked away on nearly two private acres, this inviting and versatile home offers the perfect balance of everyday comfort and refined country living—just down the street from the heart of Pawling and less than five minutes to Metro-North via the Harlem Line, allowing for an easy commute to the city. Thoughtfully designed as a 3-bedroom home that lives like a 4-bedroom, the layout adapts naturally

Eric Staub Keller Williams NY Realty

24 Overlook Dr, 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 $1,880,275

Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

30 Dewey Ln, Pawling, NY 12564

Est $794,899

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 Days On Market

/15
$1,250,000
- 5 Beds
- 4.5 Baths
- 3,920 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
$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 $693,072

Last Listing Agent Gillian Stewart Gillian Stewart Real Estate

29 Cunningham Ln, Pawling, NY 12564

Est $373,243

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
- 110 Days On Market

/35
$549,222

Pending
- 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
$490,000

Sold May 04, 2026

20 Saratoga St, Pawling, NY 12564
- 3 Beds
- 3.5 Baths
- 2,503 Sq Ft
- Built 1999
Last Sold Summary
- 1% Above List Price
- $196/SF
- 35 Days On Market
Current Estimated Value $447,485

Last Listing Agent Julia Lear Coldwell Banker Realty

20 Saratoga St, Pawling, NY 12564

Est $714,375

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
- 93 Days On Market

/29
$859,000

Pending
- 2 Beds
- 2 Baths
- 2,278 Sq Ft
117 S Quaker Hill Rd, Pawling, NY 12564

Tucked away on historic Quaker Hill - known for its picturesque horse farms and country estates - you will find this charming lodge-style home, offering a comfortable blend of character and rustic warmth. The 10.23 acre property is approached by a winding, level driveway that gently opens to a nature lovers dream.At the heart of the home lies an impressive great room, where a soaring stone

Lisa Liffland McGrath Realty Inc

117 S Quaker Hill Rd, Pawling, NY 12564
$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 $1,422,220

Last Listing Agent Brian McGrath McGrath Realty Inc

21 Brady Brook Farm Rd, Pawling, NY 12564

Est $456,829

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
- 40 Days On Market

/16
$387,000

Pending
- 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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Pawling, NY Homes

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