Pine Plains, NY Houses for Sale

Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an

Susan Whalen George T Whalen Real Estate

Rare opportunity to own 160 breathtaking acres in the heart of Pine Plains, featuring rolling fields, wooded terrain, and scenic wetlands. Anchoring the property is an antique farmhouse awaiting restoration, set within a 7 plus acre residential area offering privacy and pastoral charm. Most of the property is protected under a conservation easement, preserving the natural landscape while allowing

Richard Brenner Rich Brenner Realty, LLC

This c. 1880 three-story farmhouse seamlessly blends historic charm with modern luxury, meticulously cared for and thoughtfully curated to offer both timeless elegance and contemporary comfort.Step inside and be greeted by the inviting, light-filled living room. This spacious area exudes classic sophistication, centered around a warming wood-burning fireplace and boasting large windows that

Jill Rose Houlihan Lawrence Inc.

Nestled on 13 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom cottage combines historical character with contemporary amenities, featuring gleaming wood and wide board floors, beamed ceilings, stone fireplace, central air and a gourmet

Jeannine Simmons Corcoran Country Living

This architect designed and custom built passive solar home and guest house is sited privately on 17.90 acres with panoramic views of the of the eastern valley plains to Stissing Mountain and beyond. The tree lined driveway leads you to both houses that sit high on the land, facing south over looking the property fields & pond. Perfectly sited for the passive solar design and the solar panel

Kimberly Baker BHHS Hudson Valley Properties

Sunlight streams through the many windows and the vaulted ceilings with exposed beams create an airy, open atmosphere in this 1924 Ranch which has been beautifully renovated. Your mornings begin in the primary suite, where French doors open to a private deck overlooking a tranquil yard. Imagine sipping coffee while listening to birdsong and watching the changing seasons across your peaceful

Linda Lindsay Upstate Down

Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming

HOMER STALEY JR. Staley Real Estate, LLC

Welcome to Fallkill Farm, an incredible 37 acre oasis with expansive meadows, wooded buffers, mountain backdrop and Roeliff Jansen Kill frontage. Historic significance and modern amenities converge with the impeccably restored circa 1800 farmhouse featuring updated kitchen w/center island, designer cabinetry, Subzero refrigerator, Wolfe range and soapstone counters. Loaded with period features

Dan Axtmann BHHS Hudson Valley Properties

Nestled on 56 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, sizeable barn, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom cottage combines historical character with contemporary amenities, featuring gleaming wood and wide board floors, beamed ceilings, stone fireplace, central air

Jeannine Simmons Corcoran Country Living

Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This

Diana Bisselle William Pitt Sothebys Int Rlty

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

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

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 seamless

Elyse Morris Elyse Harney Real Estate

Available: 7.5 lush acres on the Roe-Jan! A rustic-style late mid-century three-bedroom, two bath home sits in a beautifully landscaped property with nearly 300 feet of footage on the Roeliff Jansen Kill in Gallatin, New York. You approach this quiet and serene hideaway by a long a private drive through shady woods. The home, built by a local lumber dealer, provides a warm and inviting interior.

David Norman Hall Houlihan Lawrence Inc.

Charming Renovated Ranch with Scenic Views and Endless Potential, l with extra additional side lot!! Welcome to this beautifully renovated ranch-style home offering 1,200 square feet of comfortable, single-level living. Featuring 3 spacious bedrooms and 2 full baths, this thoughtfully updated home boasts a functional and versatile layout with multiple private entrances—perfect for

Jason Schobert eXp Realty

An artist's delight, a gardener's dream and a naturalist's paradise. A thoughtfully designed and exceptionally well-built home set on 78 acres of woodlands and farmland with agricultural exemptions in place. This 4,250 SF architect designed home features multiple structures centered around a landscaped courtyard. Connected to the main home, by way of a covered portico, is a private guest suite

Michael Stasi Corcoran Country Living

Welcome to 37 Stissing Mountain Drive. Perfectly nestled on 6.9 acres of peaceful woodland, this newly built 2-bedroom, 2-bath home is a modern sanctuary that beautifully balances simplicity, sustainability, and style—just minutes from the heart of Pine Plains NY.Inside you will find a sun-filled, open-concept living space with soaring 22-foot vaulted ceilings that frame sweeping views of the

Jason Nadeau Compass Greater NY, LLC

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.

Beautiful Two Story, 4BR/2BA corner lot home with mountain views & quick walk to post office, shops, Stissing Lake & Stissing Mountain hiking trails. Experience the wonderful life of beautiful Pine Plains living! Wonderful large front, side & back yard on quiet sought after Myrtle Ave. Lovely front porch to sit & enjoy the scenery or head into the private back yard for a BBQ. Walk to school, post

Thomas Zengen Thomas Zengen

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

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

Want country living at its finest? LOOK no further! Nestled halfway between Rhinebeck and Millbrook is this Stanfordville gem! This gorgeous 3 bed 2 & half bath home sits on a majestic acre w/bucolic scenery surrounding you! You even have your own bubbling brook to mesmerize you! Simply sit out on the expansive decking and enjoy the natural beauty that greets you on so many levels that it

Justina Trainor BHHS Hudson Valley Properties

Meticulously maintained 2500+ sq ft 4-bedroom 2.5 bath center hall colonial sits on a beautiful and flat corner lot with stunning mountain views just minutes to the center of the town of Pine Plains. As you enter the home you immediately notice the care and attention to detail that the original owners have shown – Tasteful updates throughout include hardwood floors, chef’s kitchen with quartz

Ronald Green KW MidHudson

Welcome to 43 Stissing Mountain Drive — a peaceful and private retreat set on 2 beautifully wooded acres in the heart of the Hudson Valley. This great contemporary home offers 3 bedrooms and 2 bathrooms across 1,862 square feet of comfortable living space. With an open-concept layout, cathedral ceilings, and abundant natural light, the home blends style and function. A cozy fireplace anchors the

Richard Brenner Rich Brenner Realty, LLC

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

Whether you're beginning retirement or planning a weekend escape, 48 Woodside Street is a charming, move-in-ready home. Pine Plains offers attractions like fine dining at the Stissing House and tranquil kayaking on Thompson Pond. Nearby hiking trails include the challenging Stissing Fire Tower and the peaceful Thompson Preserve, ideal for a leisurely walk. Lions Club Park features a recreation

Brad Rebillard DUTCHESS COUNTRY REALTY INC. M

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.

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone Easy subdivision into 4 and 3 acre lots. Also available as Family Compound with adjoining 8 acre and 4 acre boha parcels for 699,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show unoccupied.

David Birch Barns & Farms Realty, LLC

Nestled on top of Carpenter Hill, with unparalleled views of Stissing Mountain, the Catskills and the surrounding farmland, sits this country estate on 24.78 acres. The traditional, cedar shake 6,310 square foot home exudes elegance exhibited through the well proportioned rooms with 9’4” ceiling height, exceptional craftmanship and attention to detail found throughout the home. A dramatic double

PAULA REDMOND Corcoran Country Living

Located in the picturesque Antlers Club Lake Community, this 2-bedroom, 2-bath Cape Cod offers a peaceful retreat with beach access and your own dock for kayaking, fishing, or relaxing by the water. The home features a bright and inviting layout, with spacious living areas, a well-equipped kitchen, and a full bath on the main level. Upstairs, a large bedroom and another full bath provide a cozy

Michael Cahill HomeSmart Homes & Estates

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone Easy subdivision into 4 and 3 acre lots. Also available as Family Compound with adjoining 8 acre and 4 acre boha parcels for 625,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show unoccupied.

David Birch Barns and Farms Realty LLC

Ingadi, the Zulu word for garden, is a true legacy compound all set within 127 acres of pristine land with a total of 11 bedrooms across four distinct residential structures. A magical journey of the senses where the Roeliff Jansen Kill and the Shekomeko Creek merge, ensuring sustainability while creating one of the most spiritually powerful and visually stunning experiences in the Hudson Valley.

Byron Anderson Compass Greater NY, LLC

Set among the beautiful rolling hills on 203 acres is this private estate that takes you back in time. The farm was built in 2008 around a c.1754 Dutch barn that was dismantled from upstate NY and transformed into an incredible great room with 34' soaring ceilings, a brick fireplace and two huge French doors to take in the view. Designed by Cynthia Filkoff with 6,340 square feet, the main house

Paula Redmond Corcoran Country Living - Mill

A long driveway leads to this imposing Greek Revival style house set high on a hill on 200 + acres of prime land overlooking Hudson Valley's farm country. Open fields and woodland with1600' of frontage on the Roeliff Jansen Kill. The house has 9000 sq ft with 12' ceilings throughout, large areas for entertaining, surrounding balconies for summer living and a 5000 bottle wine cave. The kitchen

HEATHER CRONER William Pitt Sotheby's Interna

You wanted charm? You got it! This vintage 1903 village home in Pine Plains, NY formerly served as both the town pharmacy and library, and many of the bookshelves and all the quaint apothecary drawers remain intact. The large 3000sq foot home on a nicely landscaped yard of nearly a half an acre is filled with period details: wooden moldings, original door knobs and intricate iron hardware, a

David Norman Hall Houlihan Lawrence Inc.

A quaint antique home is for sale in Gallatinville, NY. This rare 1820 home on .68 acres in a quiet hamlet is loaded with quirky charm. With vintage wallpaper, lots of built-in cabinets and bookshelves, the 3-bedroom 1-bath house is as homey as they get. From the glassed-in porch, you step into a cozy entry hall / office, then into a large dining room. The country kitchen and comfortable living

David Norman Hall Houlihan Lawrence Inc.