Dutchess, NY Homes in ZIP Code 12564

/29
$575,000
- 2 Beds
- 2.5 Baths
- 1,820 Sq Ft
36 Byrds Hill Rd, Pawling, NY 12564

Set on a quiet, scenic road in the prestigious Quaker Hill area, this home offers the perfect blend of seclusion and accessibility. You're only 3 miles from the serene waters of Quaker Lake, 2 miles from the Connecticut border, and just 20 minutes from charming CT towns like Sherman, New Milford, and Kent. From the outside, it’s a barn-like farmhouse surrounded by rolling green acreage and space

Colleen McGrath

McGrath Realty Inc

(845) 630-1049

36 Byrds Hill Rd, Pawling, NY 12564
/29
$3,200 per month
- 2 Beds
- 2 Baths
- 2,256 Sq Ft
- House for Rent
559 Quaker Hill Rd, Pawling, NY 12564

October 1st, the most romantic log cabin rental on coveted Quaker Hill becomes available for you to rent. Situated far back from Quaker Hill Road, the 5 acre rustic retreat offers two levels of living space with 2,256 SF with a unique layout. Steps in reveal a large entry with hall closet, a family room, bedroom, full bath, and laundry room. Stairs up take you to the highlight of the rental, a

Reid McGrath McGrath Realty Inc

559 Quaker Hill Rd, Pawling, NY 12564
$555,000 Sold Aug 22, 2025
- 3,322 Sq Ft
- $167/SF
- 20 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2002
7 Watchhill Rd, Pawling, NY 12564

Step into comfort and elegance in this spacious 4-bedroom, 2.5-bath Colonial nestled in the sought-after Deerfield Ponds neighborhood. From the moment you enter the grand foyer, you'll feel right at home. The heart of the house is the expansive kitchen featuring a large center island, light wood cabinetry, and tiled flooring, seamlessly flowing into both the formal dining room and the cozy living

Shannon Tully McGrath Realty Inc

7 Watchhill Rd, Pawling, NY 12564

Est $1,141,000 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,150 Sq Ft
711 Old Quaker Hill Rd, Pawling, NY 12564

711 Old Quaker Hill Rd, Pawling, NY 12564

/49
$595,000
- 3 Beds
- 2.5 Baths
- 2,318 Sq Ft
7 Glen Ct, Pawling, NY 12564

Welcome to this beautifully renovated 3-bedroom, 2.5-bath Colonial home offering over 2,300 sq ft of stylish and comfortable living space. Nestled in a quiet cul-de-sac and private setting in Pawling, this move-in-ready residence blends classic charm with modern upgrades. Step into the heart entryway where you can hang your coat, kick your shoes off, and feel right where you need to be. Make your

Colleen McGrath

McGrath Realty Inc

(845) 584-8385

7 Glen Ct, Pawling, NY 12564
/23
$3,200 per month
- 3 Beds
- 2.5 Baths
- 1,600 Sq Ft
- House for Rent
39 Nathan Pierce Ct, Pawling, NY 12564

Welcome to 39 Nathan Pierce Court – a beautifully updated 3-Bedroom, 2.5 Bath townhouse located in the desirable Deerfield Ponds Community. Offering 1,600 sq ft of thoughtfully designed living space, this home combines modern upgrades with everyday comfort and convenience! The kitchen features stainless steel appliances, generous cabinet space, and a bright eat-in area perfect for casual meals or

LAUREL MASCIA BHHS Hudson Valley Properties

39 Nathan Pierce Ct, Pawling, NY 12564
$415,000 Sold Aug 19, 2025
- 1,152 Sq Ft
- $360/SF
- 33 Days On Market
- 2 Beds
- 1 Bath
- Built 1930
42 Harmony Rd, Pawling, NY 12564

Located on one of Pawling's most charming country roads, while still within a five-minute drive from the quaint and lively village center, this salt-box style home is awaiting your creativity and love. With a cozy and convenient fireplace in the living room, and a front-porch that overlooks an idyllic forest and beaver-pond across the street, the property feels isolated and quiet while still

Reid McGrath McGrath Realty Inc

42 Harmony Rd, Pawling, NY 12564

Est $406,227 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,518 Sq Ft
48 W Main St, Pawling, NY 12564

48 W Main St, Pawling, NY 12564

/33
$9,750,000
- Land
- 558 Acres
- $17,462 per Acre
225 Route 22, Pawling, NY 12564

Unparalleled Opportunity Awaits! Discover this breathtaking 558+ acre parcel, just 90 minutes from Manhattan, offering a canvas of endless possibilities for personal and commercial endeavors. Whether you envision a sprawling family compound or a premier commercial facility, this land is primed for your dreams. Featuring level terrain, extensive trails, and vibrant pastures, this property is

Shaylene Neumann

Houlihan Lawrence Inc.

(845) 377-2512

225 Route 22, Pawling, NY 12564
/31
$2,500 per month
- 1 Bed
- 1 Bath
- 500 Sq Ft
- Apartment for Rent
71 E Main St Unit 303, Pawling, NY 12564

Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

Claudia Jiskra McGrath Realty Inc

71 E Main St Unit 303, Pawling, NY 12564
$175,000 Sold Aug 15, 2025
- Land
- 6 Acres
- $28,974 per Acre
- 278 Days On Market
8 Ravine Rd, Pawling, NY 12564

Location Location Location in the prestigious Quaker Hill area in Pawling! Come build your private Estate on 6.04 acres. This lot is BOHA for a 5 bedroom home and already have a beautiful stone entry to greet you. Well is drilled and other amenities listed. Close to Everything, horse trails, Metro-North, Route 22, I684 and more.

Shannon Tully McGrath Realty Inc

8 Ravine Rd, Pawling, NY 12564

Est $429,110 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,190 Sq Ft
37 Old Route 55, Pawling, NY 12564

37 Old Route 55, Pawling, NY 12564

/42
$599,000
- 4 Beds
- 4.5 Baths
- 2,361 Sq Ft
126 Old Route 55, Pawling, NY 12564

FULLY AVAIIABLE This house is owned by a church and in New York a sale has to be approved by the Attorney Generals office which can take up to six months. This can work to your benefit depending on your own timeline. This can also be set up a s a short term rental as well while waiting for the approvals WITH PORTION OF RENT GOING TOWARDS THE COST OF THE SALE. . This charming,

Philip Bisesto

HomeSmart Homes & Estates

(845) 576-1665

126 Old Route 55, Pawling, NY 12564
/43
$2,900 per month
- 2 Beds
- 2 Baths
- 997 Sq Ft
- Apartment for Rent
71 E Main St Unit 204, Pawling, NY 12564

Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

Claudia Jiskra McGrath Realty Inc

71 E Main St Unit 204, Pawling, NY 12564
$361,000 Sold Aug 13, 2025
- 1,413 Sq Ft
- $255/SF
- 51 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1993
37 Spruce St, Pawling, NY 12564

Discover comfort and convenience in this beautifully maintained 2-bedroom, 2.5-bath townhouse nestled in the sought-after Cedar Valley Complex in Pawling, NY. The sun-drenched, open-concept living and dining area features a charming fireplace, offering the perfect setting for cozy nights in or easy entertaining. The kitchen is generously sized for a townhouse, offering ample cabinet space and

Nick Selca Lakeshore Realty International

37 Spruce St, Pawling, NY 12564

Not Listed For Sale
9 Ravine Rd, Pawling, NY 12564

9 Ravine Rd, Pawling, NY 12564

/17
$975,000
- 4 Beds
- 2.5 Baths
- 3,000 Sq Ft
14 Akindale Rd, Pawling, NY 12564

TO BE BUILT Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. Enter onto freshly paved road and stone wall entrance. This beautiful lot is on 8.44 pastoral acres with amazing views of open sky and grassy meadows. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better

Kathryn McCoach Houlihan Lawrence Inc.

14 Akindale Rd, Pawling, NY 12564
/43
$2,850 per month
- 2 Beds
- 2 Baths
- 960 Sq Ft
- Apartment for Rent
71 E Main St Unit 102, Pawling, NY 12564

Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

Claudia Jiskra McGrath Realty Inc

71 E Main St Unit 102, Pawling, NY 12564
$315,000 Sold Aug 05, 2025
- 2,130 Sq Ft
- $148/SF
- 51 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1997
24 Timberline Trail, Pawling, NY 12564

Welcome to 24 Timberline Trail—Located in a peaceful, sought-after neighborhood in Pawling, NY. This residence offers the perfect blend of comfort, functionality, and modern updates. Featuring 3 spacious bedrooms and 2.5 bathrooms, the home boasts an open and versatile layout ideal for everyday living and entertaining.Step outside to a generous first-floor deck that seamlessly extends your

Vincent Reda Keller Williams Realty

24 Timberline Trail, Pawling, NY 12564

Est $1,603,566 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,347 Sq Ft
82 S Quaker Hill Rd, Pawling, NY 12564

82 S Quaker Hill Rd, Pawling, NY 12564

/29
$869,000
- 4 Beds
- 2.5 Baths
- 3,200 Sq Ft
26 Rodina Dr, Pawling, NY 12564

Welcome to your brand new dream home! Nestled on a beautiful and peaceful two and half acres. Be the first to live in this stunning four bedroom, two and a half bath home. Step onto the full length front porch and inside to a light, bright and airy interior boasting a modern open floor plan. Spacious entrance foyer with double coat closets and sleek iron railing with motion sensor lighting on

Douglas Servello Home Sweet Home Properties

26 Rodina Dr, Pawling, NY 12564
/22
$3,500 per month
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- Apartment for Rent
63 River Rd Unit B, Pawling, NY 12564

Barndominium Bliss! Captivating views and the unique opportunity to live your best life on a 39 acre working horse farm. Beautifully renovated 2nd floor of a large barn with all the rustic charm and latest amenities you need. Open living and dining areas with gleaming hardwood floors throughout. Rough hewn beams add charm and character. Niche space for sitting, reading or relaxing. Chef’s

Judy Albert BHHS Hudson Valley Properties

63 River Rd Unit B, Pawling, NY 12564
$420,000 Sold Aug 01, 2025
- 1,056 Sq Ft
- $398/SF
- 29 Days On Market
- 3 Beds
- 1 Bath
- Built 1961
7 Holiday St, Pawling, NY 12564

Wonderful mid-century ranch enjoys beautiful, park-like property in the scenic town of Pawling! Nearby Lakeside Park is open for the summer! 36 acre lake with beach, pickle ball courts, Snack Shack, more. Now, back to the house! Large, sun-filled living rm features a bay window and hardwood floor. The spacious kitchen and dining area are lovely! Beautiful cabinetry, quartz-like countertops,

Lisa Liffland McGrath Realty Inc

7 Holiday St, Pawling, NY 12564

Est $459,397 Not Listed For Sale
- 7 Beds
- 3 Baths
- 3,400 Sq Ft
68 W Main St, Pawling, NY 12564

68 W Main St, Pawling, NY 12564

/47
$1,250,000
- 4 Beds
- 6 Baths
- 3,012 Sq Ft
16 Anderson Rd, Pawling, NY 12564

Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping

Ryan Arket Compass Greater NY, LLC

16 Anderson Rd, Pawling, NY 12564
$430,000 Sold Aug 01, 2025
- 1,608 Sq Ft
- $267/SF
- 126 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1900
38 Old Route 55, Pawling, NY 12564

Turn back the hands of time with this beautiful home built in 1798 reminiscent of the deep south! It's 3 stories, two of which have gorgeous wrap around newly redone porches, that you can envision with rocking chairs, sipping mint juleps or enjoying a summer meal. The 3-story farmhouse has a newly refurbished kitchen, two living rooms, 3 bedrooms, two and a half bathrooms, a cozy fireplace and

Teddie Leonaggeo McGrath Realty Inc

38 Old Route 55, Pawling, NY 12564

Est $2,101,618 Not Listed For Sale
- 5 Beds
- 5 Baths
- 8,331 Sq Ft
73 Cunningham Ln, Pawling, NY 12564

73 Cunningham Ln, Pawling, NY 12564

/48
$799,900
- 4 Beds
- 2.5 Baths
- 3,350 Sq Ft
134 Old Pawling Rd, Pawling, NY 12564

Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

Drita Shala Howard Hanna Rand Realty

134 Old Pawling Rd, Pawling, NY 12564
$820,000 Sold Jul 28, 2025
- 3,304 Sq Ft
- $248/SF
- 52 Days On Market
- 4 Beds
- 3 Baths
- Built 1965
12 Berry Ln, Pawling, NY 12564

Nestled high atop Quaker Hill, this enchanting property offers 8.5 acres of privacy on a serene lane, just two homes away from the 4th hole of the prestigious Quaker Hill Country Club. A mid-century ranch-style home, with its distinct architectural charm and details, awaits a new owner to bring it into its next chapter. Boasting 2,704 square feet on the main floor and an additional 600 square

Brian McGrath McGrath Realty Inc

12 Berry Ln, Pawling, NY 12564

Est $792,451 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,340 Sq Ft
34 Harmony Hill Rd, Pawling, NY 12564

34 Harmony Hill Rd, 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
$510,000 Sold Jul 24, 2025
- 1,736 Sq Ft
- $294/SF
- 20 Days On Market
- 4 Beds
- 2 Baths
- Built 1971
74 Harmony Hill Rd, Pawling, NY 12564

Charming Ranch with Scenic Views and Prime Location!Nestled on a quiet street just minutes from the heart of town, this well-maintained 4-bedroom, 2-bath home offers a rare opportunity to own a piece of classic suburban charm on a sprawling 1.86-acre flat lot. Built in 1971 and on the market for the first time, this bright and sunny home combines timeless character with an unbeatable

Patrycja Warda

74 Harmony Hill Rd, Pawling, NY 12564

Est $803,530 Not Listed For Sale
- 4 Beds
- 5 Baths
- 4,657 Sq Ft
30 Horseshoe Path, Pawling, NY 12564

30 Horseshoe Path, Pawling, NY 12564

/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

120 Harmony Rd, Pawling, NY 12564
$410,000 Sold Jul 24, 2025
- 1,400 Sq Ft
- $293/SF
- 34 Days On Market
- 2 Beds
- 2 Baths
- Built 1960
11 Birch Terrace, Pawling, NY 12564

Welcome to Pawling Lake Estates - a private lake community about 10 minutes outside the Village of Pawling. This adorable cozy Cape is located on a dead-end road. Has 2 bedrooms but can easily live like a 3-bedroom home. Main level has eat in kitchen with breakfast nook, cozy living room with big bay window. 2 Bedrooms and a main bath. Doors in kitchen that lead out to a nice size deck

Teddie Leonaggeo McGrath Realty Inc

11 Birch Terrace, Pawling, NY 12564

Est $789,495 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 6,042 Sq Ft
6 di Pietro Ln, Pawling, NY 12564

6 di Pietro Ln, Pawling, NY 12564

/9
$1,100,000
- 5 Beds
- 3.5 Baths
- 3,500 Sq Ft
51 Estate Dr, Pawling, NY 12564

Don't miss this opportunity to have your dream home built and custom designed to your finishes. As you step inside, you're greeted by a grand foyer entrance with high ceilings open to the second floor. Discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, quartz countertops, and center island. The oversized open floor plan seamlessly

Tony Zaccardo Coldwell Banker Realty

51 Estate Dr, Pawling, NY 12564
$1,405,000 Sold Jul 24, 2025
- 3,038 Sq Ft
- $462/SF
- 49 Days On Market
- 4 Beds
- 3 Baths
- Built 1999
7 Tower Hill Rd, Pawling, NY 12564

Nestled among the towering trees, this spacious 4-bedroom, 3-bath custom-designed home offers the perfect blend of privacy, comfort, and modern amenities. Sit back and enjoy the captivating views from the three expansive decks, overlooking the waterfall, ponds, and large yard below. The home's distinctive architecture is shown in its thoughtful design, encompassing the natural setting, while

Ryan Arket Compass Greater NY, LLC

7 Tower Hill Rd, Pawling, NY 12564

Est $805,352 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,435 Sq Ft
919 N Quaker Hill Rd, Pawling, NY 12564

919 N Quaker Hill Rd, Pawling, NY 12564

/30
$875,000 Pending
- 2 Beds
- 1 Bath
- 1,784 Sq Ft
202 Bundy Hill Rd, Holmes, NY 12531

This spectacular property is available for the first time in 2 decades. Currently owned and loved by a cook, artist and true Renaissance Man this home is sure to appeal to those with a sharp eye for design as well as a love for the outdoors. The house sits about a half mile from the road at the end of a gravel driveway. It is situated so as to afford seasonal 360 degree mountain views. The

Daniel Balassone VYLLA Home

202 Bundy Hill Rd, Holmes, NY 12531

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