Philipstown, NY Homes for Sale with Acreage

Where History Meets the Sound of a Waterfall.Step into a landscape that feels lifted from another century. Nestled along the banks of Clove Creek, this remarkable property invites you to own a piece of local history and imagine the stories that have unfolded here for generations.At its heart stands a historic 1700s farmhouse, a timeless 3-bedroom residence set on 7.94 scenic acres along a

Abbie Carey Houlihan Lawrence Inc.

Deep within the Hudson Highlands, along the historic Old Albany Post Road, this extraordinary 28-acre estate offers a rare union of architectural significance, enduring privacy, and natural beauty. Beyond handcrafted iron gates framed by stone pillars, a winding drive disappears into mature woodlands before revealing a residence that feels quietly woven into the landscape. Stone and timber

Craig Watters Compass Greater NY, LLC

Beyond its rustic stone wall, discover 212 Old Albany Post Road, a charming split-level three-bedroom, two-bath ranch tucked back on a lovely, level two-acre parcel in Garrison, New York. A generous setback provides both privacy and wonderful curb appeal along this historic country lane as it meanders through Garrison's bucolic landscape.Cheerful and inviting, the home offers a

Austin Wright Moore Compass Greater NY, LLC

Just 60 minutes from Manhattan, this exceptional Hudson Highlands retreat offers a rare combination of architectural character, protected natural surroundings, and direct access to some of the region’s most celebrated outdoor destinations. Set on 13 private acres across two separate lots—including a second vacant, buildable parcel—the property is tucked away on a quiet dirt road known for its

Annabel Taylor Four Seasons Sothebys Intl

Privately set on nearly 20 acres in Garrison, 19 Twin Bridges Road offers an incredible sense of space and seclusion surrounded by the natural beauty of the Hudson Highlands.Inside, nearly 6,000 square feet of living space centers around a dramatic great room with soaring ceilings, clerestory windows, a stone fireplace and walls of glass overlooking the wooded property. The spacious kitchen

Katherine Cucchiarella Houlihan Lawrence Inc.

Set on just over 4 tree-lined acres in the heart of Garrison, this beautifully maintained Colonial offers a spacious and thoughtfully designed layout with timeless appeal. A dramatic two-story foyer welcomes you into a freshly painted interior featuring hardwood floors throughout the main level, a first-floor bedroom, and a full bath—ideal for guests, a home office, or flexible living. The

Kathyrine Tomann Houlihan Lawrence Inc.

Set upon a private rise within the Hudson Highlands, Evarts Hill is a restored 1929 French Normandy style estate distinguished by its provenance, craftsmanship, and natural and formal landscapes. Encompassing 53.65 acres and bordered by conserved lands of the Hudson Highlands Land Trust, the property offers exceptional privacy and an unspoiled natural setting just 50 miles from New York

Anthony Cutugno William Pitt Sothebys Int Rlty

Winter Hill, a flagship property in the Hudson Highlands, stands at the intersection of preservation, nature conservation and modern design. This timeless Tudor Revival in the heart of Garrison is a one-of-a-kind home, perched atop twenty acres of verdant, natural beauty.As you enter the property and approach the house on the long, winding drive, open fields flanked by stately trees

Paul Leis North Country Sothebys Int Rlt

Welcome to this recently updated single-family home offering comfort, style, and modern amenities in the beautiful Hudson Valley community of Cold Spring. Featuring 4 bedrooms and 3 full bathrooms, this spacious residence combines thoughtful updates with inviting living spaces and exceptional entertaining features.Inside, oak hardwood flooring runs throughout the home, complemented by

Rupinder Singh Iconic Pros

A nature lover’s paradise on 3.8 private acres, just minutes from the Village of Cold Spring.Set on a quiet mountain road bordering Fahnestock State Park, this character-filled contemporary home offers serenity, seclusion, and direct access to one of the Hudson Valley’s most treasured outdoor playgrounds — over 14,000 acres and 50 miles of hiking trails right at your doorstep.Inside,

Bill Hussung Robert A. McCaffrey Realty Inc

A rare opportunity to own over 5.9 acres across three separate parcels in the heart of Garrison. The main residence at 111 Philipse Brook Road is a 4-bedroom, 2.5-bath Colonial built in 1987, offering approximately 2,294 square feet of living space on 1.83 acres. The home features a gracious layout with spacious living and dining areas, wood-beamed ceilings, two fireplaces, a finished lower-level

Dalia Valdes Julia B Fee Sothebys Int. Rlty

Gothic Revival Country House.Welcome to the Hurst-Pierrepont Estate. This Gothic beauty, situated in the picturesque Hudson Valley is truly a one of a kind offering. The house completed in 1867, designed by Alexander Jackson Davis for Edwards Pierrepont as a country home, sits on almost 20 verdant acres with pool, patio, pond, perennial gardens and specimen trees. Preserving the home's rich

Heather Fitzgerald Coldwell Banker Realty

Discover 515-517 East Mountain Road North—a turnkey ranch perched atop the mountain, where timeless charm meets contemporary living on over 2 acres. This exceptional home artfully blends old-world details with modern additions, creating a perfect harmony of character and comfort.The main house has been beautifully renovated and expanded, featuring a brand-new addition that transforms the

Natalia Rathbauer Julia B Fee Sothebys Int. Rlty

Set on 22+ acres in Garrison, NY, this extraordinary historic Hudson Valley estate offers a rare opportunity to restore and reimagine a one-of-a-kind country property. Once part of the storied c.1900s Dick’s Castle estate, the property served as servants’ quarters and a working farm. More than a century later, the estate retains an incredible degree of architectural integrity, with slate roofs,

Melissa Carlton Houlihan Lawrence Inc.

Nestled just off Route 9 and bordered by a gently rolling creek, this charming Dutch Colonial offers a rare opportunity to experience the natural beauty and quiet lifestyle Cold Spring, NY is known for. Set on over an acre of land, the home is surrounded by mature trees and open lawn, creating a private and peaceful retreat. The property features a versatile 4-bedroom residence with a 2-bedroom

Andy Khan Silverside Realty LLC