Pawling, NY Homes

/48
$1,200,000
- 5 Beds
- 4 Baths
- 4,248 Sq Ft
64 S Quaker Hill Rd, Pawling, NY 12564

Welcome to Country Living at Its Finest!Nestled on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential for those looking to restore a piece of history. A long, tree-lined driveway leads to this charming 4-bedroom, 4-bath home surrounded by open fields, mature trees, and peaceful country views. The property features a spacious 4-car garage with finished living space with

Shannon Tully

McGrath Realty Inc

(845) 415-7723

64 S Quaker Hill 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 $441,124

Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

19 Cushing Green S, Pawling, NY 12564

Est $962,860 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
- 12% Below List Price
- $526/SF
- 14 Days On Market
Last Sold Price $1,100,000

Last Listing Agent David Turner Compass Greater NY, LLC

/24
$950,000
- 4 Beds
- 3.5 Baths
- 3,434 Sq Ft
128 Old Pawling Rd, Pawling, NY 12564

Welcome to 128 Old Pawling Road, a beautifully situated property in Pawling, NY. Set back from the road, the home is approached by a long private driveway and gated entrance, offering a sense of privacy while still being part of a neighborhood setting. Resting on over 5 acres, the property showcases stunning mountain views that create an impressive backdrop to everyday living year-round. Whether

Juliska Martino Compass Greater NY, LLC

128 Old Pawling Rd, Pawling, NY 12564
$367,500 Sold Mar 04, 2025

27 Gobblers Knob Rd, Pawling, NY 12564
- 4 Beds
- 2 Baths
- 1,572 Sq Ft
- Built 1945
Last Sold Summary
- 14% Below List Price
- $234/SF
- 68 Days On Market
Current Estimated Value $395,117

Last Listing Agent Douglas McGowan Coldwell Banker Realty

27 Gobblers Knob Rd, Pawling, NY 12564

Est $703,636 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
- 15% Above List Price
- $210/SF
- 37 Days On Market
Last Sold Price $610,000

Last Listing Agent Barbara Allen HomeSmart Homes & Estates

/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
$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 $404,140

Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

11 Birch Terrace, Pawling, NY 12564

Est $717,187 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
- 16% Above List Price
- $325/SF
- 39 Days On Market
Last Sold Price $620,000

Last Listing Agent Claudia Jiskra McGrath Realty Inc

/50
$619,000
- 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
$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 $353,937

Last Listing Agent Edmond Albano Keller Williams NY Realty

33 Spruce St, Pawling, NY 12564

Est $708,682 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
- 16% Above List Price
- $276/SF
- 24 Days On Market
Last Sold Price $610,000

Last Listing Agent Vince McGough McGough Realty Corp

/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
$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 $516,520

Last Listing Agent Shannon Tully McGrath Realty Inc

17 Fenwood Dr, Pawling, NY 12564

Est $1,188,341 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
- 24% Above List Price
- $159/SF
- 74 Days On Market
Last Sold Price $960,000

Last Listing Agent Mark Boyland Keller Williams Realty Partner

/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
$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 $510,438

Last Listing Agent Patrycja Warda Corcoran Country Living

32 Elm St, Pawling, NY 12564

Est $804,421 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
- 9% Above List Price
- $268/SF
- 34 Days On Market
Last Sold Price $740,000

Last Listing Agent Claudia Jiskra McGrath Realty Inc

/5
$399,000
- 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
$975,000 Sold Apr 07, 2025

11 Birch Hill Rd, Pawling, NY 12564
- 4 Beds
- 3.5 Baths
- 4,615 Sq Ft
- Built 2000
Last Sold Summary
- $211/SF
- 21 Days On Market
Current Estimated Value $1,044,878

Last Listing Agent Claudia Jiskra McGrath Realty Inc

11 Birch Hill Rd, Pawling, NY 12564

Est $826,806 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
- 10% Above List Price
- $271/SF
- 7 Days On Market
Last Sold Price $752,500

Last Listing Agent Liza Reiss Elyse Harney Real Estate

/27
$450,000
- 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
$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 $381,365

Last Listing Agent Vicki Reinach BHHS Hudson Valley Properties

18 Evergreen Way, Pawling, NY 12564

Est $360,029 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
- 8% Above List Price
- $370/SF
- 110 Days On Market
Last Sold Price $333,000

Last Listing Agent Reid McGrath McGrath Realty Inc

/24
$485,000
- 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
$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 $946,949

Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

14 Little Pond Rd, Pawling, NY 12564

Est $733,605 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
- 5% Above List Price
- $212/SF
- 93 Days On Market
Last Sold Price $700,000

Last Listing Agent Beth Yoon Sherwood Hill Realty LLC

/6
$225,000
- Land
- 0.76 Acre
- $296,053 per Acre
15 Dykeman St, Pawling, NY 12564

Rare opportunity to build in the heart of the Village of Pawling! Cleared and ready for development, this residential lot at 15 Dykeman Street offers municipal water and sewer available at the street — a major advantage for new construction. The property features a defined driveway lined with item four stone, providing immediate access and a head start on site work. Level and open, the lot offers

Joanne Debellis Debellis Real Estate LLC

15 Dykeman St, Pawling, NY 12564
$355,000 Sold Apr 08, 2025

26 Taber Knolls Dr, Pawling, NY 12564
- 2 Beds
- 1 Bath
- 720 Sq Ft
- Built 1955
Last Sold Summary
- 11% Below List Price
- $493/SF
- 82 Days On Market
Current Estimated Value $352,675

Last Listing Agent Reid McGrath McGrath Realty Inc

26 Taber Knolls Dr, Pawling, NY 12564

Est $670,156 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
- 70% Above List Price
- $134/SF
- 9 Days On Market
Last Sold Price $395,000

Last Listing Agent Ernie Acampora River Realty Services, Inc.

/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
$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 $346,045

Last Listing Agent Martha Woodhouse Howard Hanna Rand Realty

88 Lakeview Dr, Pawling, NY 12564

Est $484,588 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
- 13% Above List Price
- $292/SF
- 40 Days On Market
Last Sold Price $428,000

Last Listing Agent Brian McGrath McGrath Realty Inc

/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
$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

Est $413,305 Not Listed For Sale

25 Reservoir Rd, Pawling, NY 12564
- 2 Beds
- 1 Bath
- 1,260 Sq Ft
- Built 1951
25 Reservoir Rd, Pawling, NY 12564

Last Sold Summary
- 21% Above List Price
- $272/SF
- 78 Days On Market
Last Sold Price $342,500

Last Listing Agent Felisha Peralta Keller Williams Realty NYC Grp

/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
$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 $465,196 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
- 3% Below List Price
- $369/SF
- 19 Days On Market
Last Sold Price $480,000

Last Listing Agent Claudia Jiskra McGrath Realty Inc

/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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