Pine Plains Homes for Sale

Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has a proven track record as a highly successful Airbnb. Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on

KELLY ROMANO Keller Williams Realty

COMING SOON: Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary.A Home Infused

KELLY ROMANO Keller Williams Realty

Discover the charm and possibilities of this private lakefront property set on 5.9 picturesque acres. This updated 1950's cottage features three plus bedrooms and two baths, with a bright, inviting interior that immediately feels like home. As soon as you step inside, you're welcomed by a direct view of Twin Island Lake, creating a stunning first impression. Relax on the decks and take in the

ANN SIMMONS Compass Greater NY, LLC

Thoughtfully restored while preserving its historic character, this circa-1820 farmhouse blends timeless craftsmanship with modern comfort and efficiency. Original hand-hewn beams and a fieldstone foundation anchor the home's authentic charm, while extensive upgrades throughout create a move-in ready retreat designed for year-round living. The open floor plan seamlessly connects the dining room,

Kyle Irwin Corcoran Country Living

Step into the charm and character of a bygone era with this spacious early-1900s Colonial-style home located in the heart of the hamlet of Pine Plains. Offering over 3,000 square feet of living space, this 4-bedroom, 1.5-bath residence sits on approximately 0.47 acres and is filled with history, warmth, and timeless architectural details.Once home to both the town pharmacy and library, this

Richard Brenner Rich Brenner Realty, LLC

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

SET ON A NICELY LANDSCAPED AND PRIVATE YARD IDEAL FOR GARDENING WITH 1.37 ACRES TOTAL-(HOUSE ON .65 ACRE AND AN ADJACENT BUILDING PARCEL OF .72 ACRE). THIS INVITING WELL MAINTAINED 3-BEDROOM, 2-BATH RANCH OFFERS COMFORT AND FEATURES A LIVINGROOM WITH A FIREPLACE, LOVELY WOOD FLOORS THROUGHOUT AND A LARGE BASEMENT PERFECT FOR A WORKSHOP, RECREATION ROOM OR ADDITIONAL STORAGE. THE ATTACHED GARAGE

ANN SIMMONS Compass Greater NY, LLC

Sweet and solid, one level Ranch home on a bucolic setting with rolling hills and farmland framing your homestead. Walk into your open living room with built ins and lovely bay window. Through to the dining room and eat in kitchen, perfect for hosting with ease. Sliders to the back covered porch off the dining room allows for al fresco living and enjoying your coffee while watching the sunrise.

Chelsea Pollard-Seiler Mondello Upstate Properties

Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley

Diana Bisselle William Pitt Sotheby's Int'l

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors, ornamented wood siding painted + detached 2 car garage on 7 acres. Parcel is subdividable in Hamlet zone. New well installed.also available with 8 additional acres for 588000 with additional 12 acres (3 building lots) for 713000

David Birch Barns & Farms Realty, LLC

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 Compound with adjoining 8 acre parcel for $588.000 and additional 4 acre boha parcel for $713,000. Adjoining parcels can be purchased separately for . Great location between Pine Plains Village and Millerton on quiet

David Birch Barns and Farms Realty LLC

We welcome this 1834 restored farm into our Luxury Collection of Hudson Valley properties. This magnificent property makes the perfect country compound. Completely updated, restored and improved to also include a new addition on the main house. This 200 acre farm has all the privacy and beauty of a true country retreat. With such amenities as a converted dairy barn to an indoor tennis court

George Langa Houlihan Lawrence Inc.

Cedar Ridge Farm is a premier 246-acre equestrian estate set in the heart of Dutchess County, offering exceptional land quality, extensive infrastructure, and the rare scale required for a top tier equestrian operation or private country estate. The farm encompasses approximately 110 acres of fenced paddocks supported by thoughtfully designed facilities that ensure efficiency, functionality, and

George Langa Houlihan Lawrence Inc.

Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

Ernie Acampora River Realty Services, Inc.

A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite

MICHELLE FRANCESE Corcoran Country Living

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 office,

Susan Whalen George T Whalen Real Estate