Pine Plains, NY Homes

/29
$840,000 Sold Mar 14, 2025
- 2,092 Sq Ft
- $402/SF
- 58 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1968
348 Willow Glen Rd, Red Hook, NY 12571

This gorgeous A-frame—featured in both Dwell and Vogue magazines—combines countryside charm with mid-century modernism in the heart of the Hudson Valley. The Red Hook home sits on six wooded acres, around the corner from a natural swimming hole, yet only minutes away from the Taconic State Parkway. A welcoming, cottage-like exterior opens into a thoughtfully designed, architectural home

Sarah Finch The Kinderhook Group, Inc.

348 Willow Glen Rd, Red Hook, NY 12571

Est $422,015 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,884 Sq Ft
35 Pine St, Pine Plains, NY 12567

35 Pine St, Pine Plains, NY 12567

/30
$545,000
- 4 Beds
- 2.5 Baths
- 3,180 Sq Ft
30 N Main St, Pine Plains, NY 12567

Grand 1880 Colonial Estate Sale - Historic Fixer-Upper with Original Features and Garden Oasis Near Town CenterThis rare 1880 Grand Colonial is a dream opportunity for restoration enthusiasts and anyone searching for a historic fixer-upper near the heart of town. Situated on a flat, tree-lined lot, this estate sale is being sold as is and is filled with authentic charm—from original

Arleen Shepley Elyse Harney Real Estate

30 N Main St, Pine Plains, NY 12567
/3
$335,000 Sold Jan 30, 2025
- 1,296 Sq Ft
- $258/SF
- 53 Days On Market
- 3 Beds
- 2 Baths
- Built 1950
599 Bean River Rd, Millerton, NY 12546

Set on a spacious 1.69-acre parcel with captivating farm and mountain views, 3 bedrooms and 2 full baths, this cozy home also includes a cozy wood-burning fireplace and hardwood floors throughout ground floor. The upper-level hosts a 2-bedroom loft space and a second full bath. With a little TLC, this property and location make it ideal for buyers looking to create their own dream home in a

Christopher Virtuoso Keller Williams Realty HV Nort

599 Bean River Rd, Millerton, NY 12546

Est $402,225 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,052 Sq Ft
10 Woodside St, Pine Plains, NY 12567

10 Woodside St, Pine Plains, NY 12567

/13
$4,950,000
- 3 Beds
- 2 Baths
- 5,000 Sq Ft
3362 New York 199, Pine Plains, NY 12567

To-Be-Built Luxury Estate with Infinity Pool & Panoramic Catskill Views – Pine Plains, NY. Elevated high above the valley floor with sweeping, unobstructed Catskill Mountain views, this to-be-built custom estate is a rare opportunity in the heart of the Hudson Valley. Set on an extraordinary piece of land—offering total privacy and dramatic natural beauty—this 5,000+ square foot

Michael Lund Corcoran Country Living

3362 New York 199, Pine Plains, NY 12567
$415,000 Sold Jan 17, 2025
- 1,408 Sq Ft
- $295/SF
- 98 Days On Market
- 2 Beds
- 2 Baths
- Built 1960
21 Hamlet Ln, Red Hook, NY 12571

Welcome to The Red Hook Retreat. An exquisite 2 bedroom split-level home set on just under 1 acre of lush, private land. Step inside to discover an inviting living room with wood burning fireplace and an open-concept kitchen and dining area, perfect for hosting memorable gatherings with family and friends. The versatile bonus room can easily be transformed into a third bedroom, complete with its

Jessica Hill Real Broker NY LLC

21 Hamlet Ln, Red Hook, NY 12571

Est $271,105 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,091 Sq Ft
75 Birch Dr, Pine Plains, NY 12567

75 Birch Dr, Pine Plains, NY 12567

/33
$2,495,000
- 3 Beds
- 3 Baths
- 4,648 Sq Ft
387 Skunks Misery Rd, Millerton, NY 12546

Perched high above Millerton in the Hudson Valley, this exceptional 2020-built contemporary farmhouse estate commands 53± private acres with panoramic western views spanning the Catskills and Berkshire Mountain Range, including Mount Kaaterskill. Wide red oak hardwood floors unite the main level, where abundant natural light floods through expansive windows, creating an atmosphere of

Elyse Morris Elyse Harney Real Estate

387 Skunks Misery Rd, Millerton, NY 12546
/16
Sold Jan 13, 2025
- 1,416 Sq Ft
- 52 Days On Market
- 3 Beds
- 2 Baths
- Built 1870
3066 Church St, Pine Plains, NY 12567

Personalize it to your taste, as much of the groundwork has been laid for an ideal home or business. This property is situated in the H-MS (Hamlet - Main Street Zone), a tranquil area governed by a 35 MPH speed limit. The yard is flat and inviting, featuring a detached garage and an enclosed space perfect for pets or gardening.

Brad Rebillard Dutchess Country Realty, Inc.

3066 Church St, Pine Plains, NY 12567

Est $218,264 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,088 Sq Ft
144 N Main St, Pine Plains, NY 12567

144 N Main St, Pine Plains, NY 12567

/7
$145,000
- Land
- 3.45 Acres
- $42,029 per Acre
66 Ryan Rd, Pine Plains, NY 12567

Build your dream home in the heart of Pine Plains, surrounded by nature, history, and vibrant Hudson Valley living, on this exceptional 3.45 Acre elevated homesite, Board of Health approved for a 4-bedroom residence, with sweeping views of majestic Stissing Mountain. This remarkable parcel offers the perfect blend of tranquility, natural beauty, and convenience, presenting a rare opportunity to

Vida Odescalchi Legacy Land & Homes LLC

66 Ryan Rd, Pine Plains, NY 12567
$970,000 Sold Dec 23, 2024
- 2,268 Sq Ft
- $428/SF
- 147 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1988
102 Hall Hill Rd, Ancram, NY 12502

Calling all barndominium lovers! Welcome to this income-producing horse boarding facility with indoor arena, large 14-stall barn, hay storage capacity, training round pen, 8-stall paddock/stall building, dog kennel, chicken coop, andpastures. Unique opportunity to own an equestrian property on 26 acres, with trail on the RoeJan Kill River. Off the beaten path and nicely nestled in a quiet

Antoinette Caruso Stonewall Realty Group LLC

102 Hall Hill Rd, Ancram, NY 12502

Est $488,495 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,012 Sq Ft
16 Meusel Rd, Pine Plains, NY 12567

16 Meusel Rd, Pine Plains, NY 12567

/50
$8,475,000
- 6 Beds
- 7.5 Baths
- 12,418 Sq Ft
367 Prospect Hill Rd, Ancramdale, NY 12503

First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation,

George Langa Houlihan Lawrence Inc.

367 Prospect Hill Rd, Ancramdale, NY 12503
/38
$2,000,000 Sold Dec 19, 2024
- 3,804 Sq Ft
- $526/SF
- 202 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1880
88 Friar Tuck Rd, Ancramdale, NY 12503

Enjoy country living at its best in this1880 Victorian located down a quiet country lane in the Ancram area which is convenient to all the Berkshire's and surrounding areas have to offer. The home features generous size rooms with high ceilings. Enter through a large foyer area that opens into the kitchen with a built-in breakfast nook, viking stove for the serious chef and an adjacent cozy

Ann Simmons Compass Greater NY, LLC d/b/a

88 Friar Tuck Rd, Ancramdale, NY 12503

Est $427,693 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,002 Sq Ft
32 Britton St, Pine Plains, NY 12567

32 Britton St, Pine Plains, NY 12567

/25
$535,000
- 2 Beds
- 2 Baths
- 1,336 Sq Ft
618 Bean River Rd, Millerton, NY 12546

PINE PLAINS 2-3 LOT DEVELOPMENT, 15+ acres for Family Compound or upscale development between Pine Plains Village and Millerton on quiet road off Route 199. The Development includes a 1400 SF 2BR/2BA RANCH with new well, w/2 large decks, all wood floors, wood siding + detached 2 car garage on 7+ acres subdividable into 4 acres with house and 3 acre vacant lot. Included is additional approved 8

David Birch Barns and Farms Realty LLC

618 Bean River Rd, Millerton, NY 12546
$2,200,000 Sold Dec 19, 2024
- 4,207 Sq Ft
- $523/SF
- 377 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2023
570 Bean River Rd, Pine Plains, NY 12567

The approach to this spectacular contemporary barn-style home takes you up a long, winding private driveway past open fields & woods that are part of this special 22+ acre property. At the top of the hill, sits this incredibly private, recently completed, custom, stick built, 3-bedroom, 3.5-bath, contemporary home boasting approximately 4,000 sf of total square footage. This stunning home is

Ann Stettner Neil Charles Real Estate, LLC

570 Bean River Rd, Pine Plains, NY 12567

Est $400,777 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,632 Sq Ft
53 Britton St, Pine Plains, NY 12567

53 Britton St, Pine Plains, NY 12567

/20
$375,000
- 2 Beds
- 2 Baths
- 1,176 Sq Ft
1814 Route 199, Stanfordville, NY 12581

One level living. 2 Acres partially wooded. Lots of privacy. Put in a few updates and a little elbow grease and make this home your style.

MICHAEL MORRISON Corcoran Country Living

1814 Route 199, Stanfordville, NY 12581
$285,000 Sold Dec 19, 2024
- 750 Sq Ft
- $380/SF
- 52 Days On Market
- 1 Bed
- 1 Bath
- Built 1950
Unlisted Address

Fully updated and renovated cottage sitting back on a long beautiful driveway on 3 acres this modern NYC loft style house is perfect for someone who loves privacy and a scenic view. This property was originally part of a winery with limitless potential for landscaping and views. Brand new vinyl siding, roof, floors, windows, quartz countertops, appliances, tile work and more this is move in

Lorraine Little LITTLE LORRAINE ML

Unlisted Address

Est $386,128 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,010 Sq Ft
26 Bowman Rd, Pine Plains, NY 12567

26 Bowman Rd, Pine Plains, NY 12567

/19
$995,000
- Land
- 28.7 Acres
- $34,669 per Acre
5-8 Lakeside Ln, Pine Plains, NY 12567

Welcome to your own slice of paradise! This beautiful 29-acre waterfront property offers the perfect canvass for your dream home. Nestled in the shadow of Stissing Mountain, you'll enjoy country views and ample space to build your oasis. Boasting approximately 800 feet of waterfront on Twin Island Lake, enjoy fishing, kayaking or just observing natures glory. Privacy is paramount on this property

Richard Brenner Rich Brenner Realty, LLC

5-8 Lakeside Ln, Pine Plains, NY 12567
/33
$407,500 Sold Dec 18, 2024
- 2,456 Sq Ft
- $166/SF
- 55 Days On Market
- 5 Beds
- 2.5 Baths
1420 Route 83, Pine Plains, NY 12567

Surrounded by rolling hills in the Pine Plains hamlet of Shekomeko sits this beautiful, spacious colonial house with preserved original detail and tasteful recent updates that fuse a modern feeling with original character. Built in 1865, the home has 5 bedrooms and 2.5 baths, a large living room, separate family room and a formal dining area. The kitchen was recently updated with stainless

Adam Ecker ECKER ADAM D

1420 Route 83, Pine Plains, NY 12567

Est $364,239 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,700 Sq Ft
14 Myrtle Ave, Pine Plains, NY 12567

14 Myrtle Ave, Pine Plains, NY 12567

/39
$399,000
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
107 Near Rd, Red Hook, NY 12571

A true Hudson Valley treasure! Step into this enchanting 1934 Hudson Valley home, where vintage charm meets modern sophistication. Set on nearly 2 peaceful acres, this 2-bedroom, 2-bath retreat features a cozy open floor plan with an inviting fireplace/woodstove, multiple skylights, exposed beams, incredible architectural lines, and beautiful Doug fir wood floors. Offering a perfect blend of

Margaret Niekrewicz Margaret Mondello Real Estate

107 Near Rd, Red Hook, NY 12571
/36
$2,578,000 Sold Dec 17, 2024
- 4,724 Sq Ft
- $546/SF
- 313 Days On Market
- 5 Beds
- 5.5 Baths
- Built 1980
182 Silvernails Rd, Pine Plains, NY 12567

Fly into this private, hilltop country estate with its own airstrip. This five bedroom, five and one half bath home has stunning bucolic views to Stissing Mountain and provides a layout that has an airy and elegant ambiance. The cathedral living room is centered around a soaring stone fireplace and leads to a cozy library and the formal dining room. Top of the line appliances, marble countertops,

Paula Redmond Corcoran Country Living - Mill

182 Silvernails Rd, Pine Plains, NY 12567

Est $383,940 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,142 Sq Ft
36 Briarcliff Ln, Pine Plains, NY 12567

36 Briarcliff Ln, Pine Plains, NY 12567

/49
$699,000
- 7 Beds
- 5 Baths
80 County Route 7, Pine Plains, NY 12567

This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds,

Margaret Niekrewicz Margaret Mondello Real Estate

80 County Route 7, Pine Plains, NY 12567
/22
$845,000 Sold Dec 13, 2024
- 1,455 Sq Ft
- $581/SF
- 39 Days On Market
- 2 Beds
- 2 Baths
- Built 1943
Unlisted Address

Light and bright serene and charming Cape Cod-style home on 4 acres nestled in the peaceful town of Ancramdale, NY. With its cozy living room featuring a fireplace insert, it promises warmth and comfort during the colder months. The formal dining room and dining nook provide ample space for entertaining guests, while the main floor bedroom and full bath offer convenience. The second floor houses

Arleen Shepley Elyse Harney Real Estate

Unlisted Address

Est $529,223 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,022 Sq Ft
20 Fabrello Ln, Pine Plains, NY 12567

20 Fabrello Ln, Pine Plains, NY 12567

/16
$539,000
- 3 Beds
- 2 Baths
- 1,768 Sq Ft
284 Hall Hill Rd-Stop # 18, Ancram, NY 12502

A ''Real Deal'' log home in Ancram, New York. This listing has been reconfigured to include a separate 3 acre building parcel, across the private dead-end road. Read below the importance of this added acreage. The home has 3 BR, 2 BA, and is 1768 sf. It is surrounded by woods and meadows. There is a brick fireplace, wood stove, open floor plan, and deck out back. Fiber-optic

Lindsay Lebrecht Copake Lake Realty Corp.

284 Hall Hill Rd-Stop # 18, Ancram, NY 12502
/16
$62,000 Sold Nov 21, 2024
- Land
- 4.04 Acres
- $15,347 per Acre
- 133 Days On Market
00WP Hoffman Rd, Pine Plains, NY 12567

This BOH approved 4 acre lot has great potential to build your primary home or country home on acreage. The Approval has been extended until April of 2027 for a 3 Bedroom Dwelling. The land has a beautiful view of the Catskill mountains and is situated on a quiet town road just outside the quaint village of Pine Plains. It is in close proximity to many great places to eat visit and enjoy. Some

Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

00WP Hoffman Rd, Pine Plains, NY 12567

Est $346,270 Not Listed For Sale
- 3 Beds
- 1 Bath
- 2,860 Sq Ft
18 Bfs Ln, Pine Plains, NY 12567

18 Bfs Ln, Pine Plains, NY 12567

/22
$275,000
- 3 Beds
- 2 Baths
- 1,037 Sq Ft
22-28 Ryan Rd, Pine Plains, NY 12567

Looking for a piece of property for a great low price? Looking for two homes for the price of one? Here is a great opportunity for you to acquire one manufactured home, and one mobile home, both on the same plot of land with 2.30 acres! Investors will consider this property for rental income. Those interested in home ownership will consider this property as well, given you can live in one of the

Jorge Lugo Real Broker NY LLC

22-28 Ryan Rd, Pine Plains, NY 12567
$590,000 Sold Nov 15, 2024
- 1,643 Sq Ft
- $359/SF
- 19 Days On Market
- 3 Beds
- 2 Baths
- Built 1960
7760 S Main St, Pine Plains, NY 12567

Mid-Century Perfection This chic reimagination of a 1960 ranch with 3 bedrooms, two baths, and elegant living on one floor is move-in ready. The buyer can throw a party on the day of the closing. This rare find is a fully renovated, meticulously designed 1,788-square-foot modern home in the country. New Italian Bertazzoni stainless steel appliances including induction cook top, wall oven and

CHRISTINE BATES William Pitt Sotheby's Int'l

7760 S Main St, Pine Plains, NY 12567

Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,300 Sq Ft
138 Ryan Rd, Pine Plains, NY 12567

138 Ryan Rd, Pine Plains, NY 12567

/15
$529,000
- 2 Beds
- 2 Baths
- 1,336 Sq Ft
618 Bean River Rd, Pine Plains, NY 12567

PINE PLAINS 2-3 LOT DEVELOPMENT, 15+ acres for Family Compound or upscale development between Pine Plains Village and Millerton on quiet road off Route 199. The Development includes a 1400 SF 2BR/2BA RANCH with new well, w/2 large decks, all wood floors, wood siding + detached 2 car garage on 7+ acres subdividable into 4 acres with house and 3 acre vacant lot. Included is additional approved 8

David Birch Barns & Farms Realty, LLC

618 Bean River Rd, Pine Plains, NY 12567
$475,000 Sold Nov 12, 2024
- 1,714 Sq Ft
- $277/SF
- 8 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1991
154 Woods Dr, Ancramdale, NY 12503

Down a Scenic Country Lane, past Shetland Cattle and Beautiful Farmland, down the long driveway to your Country Contemporary Home in the woods with Seasonal Eastern Vistas of the Taconic Range and a Very Private Setting. Upon entry, the home invites you in with Open Living area, Soaring Ceilings, Beautiful Stone Fireplace, Huge Kitchen. Down the hall is a powder room and a substantial Den

Michael Mondello BHHS Hudson Valley Properties

154 Woods Dr, Ancramdale, NY 12503

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