Within the Hudson Valley, Philipstown, 58 miles from New York City, is known for its recreation and hamlets. “You have a sense of living in the country with proximity to the city and other great places,” says Steven Gray, a real estate agent with Compass Greater NY, LLC. Gray has worked in the industry for five years. The area has a rolling, mountainous terrain with swaths of preserved land and hiking trails. Diana Polack, a Realtor with Compass Greater NY, LLC who has over 35 years of experience and lives in the Hudson Valley, says most people know the area for the hamlets of Cold Spring and Garrison. Cold Spring has a Main Street with shopping and dining, and Garrison is mainly residential and surrounded by nature. “The downtown district of Cold Spring is very much city living, there’s a little bit of everything,” says Gray.
Philipstown’s incorporation in 1812 marked the start of its civic history.
Rolling hills and quiet woods define the rural charm of Philipstown’s countryside.
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Lots of trails to explore
Polack says the area offers world-class trails. “People come from all over to hike there,” she says. Hudson Highlands State Park has over 70 miles of trails, including a 5-mile section of the Appalachian Trail. Outside Cold Spring is the Constitution Marsh and Audubon Center and Sanctuary, a fish and bird habitat that offers educational programs and public trails. Castle Rock Park includes the Glenclyffe Trailhead and Sugarloaf Hill, where visitors may catch a glimpse of the 1881 castle built by railroad executive William H. Osborn.
Hikers frequently hike the "Lemon Squeezer" trail at Harriman State Park.
Philipstown residents get outside for fresh air at the Constitution Marsh Sanctuary.
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Homes range from condos to estates with river views
Most homes are spaced far apart among the rolling greenery of Philipstown or clustered together in hamlets. Multifamily, single-family, condos and townhouses are available in the Colonial Revival, split-level and farmhouse styles. Most townhouses and condos are along U.S. Route 9 and in the hamlet of Cold Spring. They range from $370,000 to $745,000. Single-family and multifamily homes range from $325,000 to $975,000. Larger estate homes in Colonial Revival, Tudor Revival and custom styles range from $1 million to $3.5 million. “There are also vacation homes or second homes and some estate-level properties along the Hudson River. Some of the finest properties in Garrison may have Hudson River views.” Most houses here use septic tanks and well water. While the Hudson River may flood during inclement weather, Polack says it's not likely to flood residential areas.
Some Philipstown residents make the most of their properties on spacious lots.
Multifamily homes offer flexible living options in scenic Philipstown.
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Thriving arts scene in Philipstown
“If you're outdoorsy, it's an endless opportunity for nature lovers,” says Gray. “And it also has a robust arts community.” The Boscobel House and Gardens combine art and nature on the grounds of a rebuilt 1800s Neoclassical manor. The inside of the house offers a collection of Federal-style art and furniture. Outside, garden tours, festivals and concerts keep visitors busy. Also on the site, the Cold Spring Farmers’ Market sells fresh produce every Saturday. In Garrison, the Art Center offers workshops, exhibits and events all year, including a craft show each October. The Depot Theater hosts plays, drag shows, musicals, concerts and other live entertainment from local directors and performers. From June to September, the Hudson Valley Shakespeare Festival performs in an open-air tent at The Garrison, a hotel and venue.
Pumpkin Glow visitors sing along to live tunes in the heart of Philipstown.
Residents enjoy all the local shopping and dining options in historic Philipstown.
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Top marks for schools in the Philipstown area
The Haldane Central School District, which gets an A from Niche, serves the northern half of Philipstown, and the Garrison Union Free School District, which also receives an A-minus, partially serves the southern half. Children may attend Haldane Elementary, which gets an A-minus and Haldane Middle, which gets an A. The Garrison Union Free School District has just one facility, the Garrison School, which teaches prekindergarten through eighth grade and gets an A. Haldane High gets an A and is listed as the best public high school in Putnam County. Those in Garrison may attend Haldane High or two other public schools: Putnam Valley High, which gets a B-plus, and James I. O’Neill High, which gets an A.
Haldane Elementary Middle School serves students in the Putnam County community.
Haldane Elementary/Middle School serves students from the Philipstown area.
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Shopping and dining in Cold Spring and Garrison
Angelina’s Pizza & Brew is a popular Italian restaurant on Chestnut Street in Cold Spring. Foodtown is nearby for groceries. For more upscale dining, The Bird & Bottle Inn in Garrison serves modern Southern dishes and craft cocktails for brunch and dinner. “If someone needs something special, they’ll head to Woodbury Common,” says Polack. Woodbury Common Premium Outlets, 19 miles from Philipstown, is an open-air mall with restaurants and popular retailers like Gucci, Adidas and Aeropostale.
The Bird & Bottle Inn blends colonial architecture with outdoor dining near Philipstown.
Weekend shoppers browse storefronts in historic Philipstown.
A mix of storefronts and cafés line the streets of Philipstown Square.
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The Hudson line leads to New York City
The Palisades Interstate Parkway leads to New York City, 58 miles south of Philipstown. The area has three train stations on the Hudson line: Cold Spring, Garrison and Manitou. All arrive in Grand Central Terminal in just over an hour.
The Montefiore St. Luke’s Cornwall and the NewYork-Presbyterian Hudson Valley Hospital are both 13 miles away. The New York Stewart International Airport is 20 miles north. Houses of worship such as Cold Spring United Methodist Church, St. Mary’s Episcopal Church in-the-Highlands and Our Lady of Loretto Church are in Cold Spring.
Daily train rides offer scenic views for Philipstown commuters.
The Cold Spring train station connects Philipstown residents to New York City.
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Written By
Isabella Pontecorvo
Photography Contributed By
Matt Pangman
Video By
Sara Warthen
Interested in learning more about homes in this area?
Reach out to
Peter Raider,
an experienced agent in this area.
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Escape to your own private paradise. Tucked away on six lush, wooded acres, this stunning country sanctuary offers the perfect blend of privacy, tranquility, and natural beauty. A seasonal stream meandering through the backyard and preserved farmland bordering the property create a peaceful setting ideal for hiking, relaxing, and enjoying the outdoors. Inside, the expansive contemporary design is
Build your DREAM HOME amongst the relaxing mountain views from every direction! It has an expired 3 bedroom BOHA but maybe can be a 4 Bedroom see attached. This property is located in within the Lakeland School District in Putnam County. 147 Feet of road frontage, nestled in-between 485 and 489 Sprout Brook Rd. Explore Continental Village with a minimal fee to enjoy the Amenities which include:
Opportunity awaits to build your custom single-family home in the desirable Continental Village community on .29 acres. Proposed plans for a 2-bedroom home plus office, with 2024 Board of Health approval already in place - just need to renew and customize your own plans to build. Enjoy all that Continental Village has to offer, including lake and beach access, clubhouse, tennis and basketball
Wooded 1.06-Acre Lot in Garrison – Ideal for a Thoughtfully Designed Home This 1.06-acre wooded parcel on Sprout Brook Road offers a unique opportunity for buyers with vision and an appreciation for the natural landscape. The property features a defined buildable area closer to the road, with dramatic rock outcroppings and a steeper hillside beyond—creating a beautiful, natural backdrop and added
NOTE: Please , DON'T walk property WITHOUT PERMISSION. Surveillance cameras. Also available for rent at $6500/mo, Rental MLS Listing #1009737. Newly renovated and upgraded chalet home offers ambiance and charm from the moment you step through the door. Cathedral ceilings throughout the house give a sense of height and brightness. The large windows in every room bring the outside in. The stone
Gorgeous approved lot on desirable Old Albany Post Rd. in the heart of Garrison! Property borders New York State land and adjacent to Fahnestock Park, with access to Catfish Pond. Private and wooded, but minutes from historic Cold Spring Village. Newly updated board of health approval for a four bedroom home. Driveway and curtain drains installed. Bring your building plans!
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
Exceptional 3-Unit Investment Property in the Heart of Cold SpringRare opportunity to own a well-maintained three-unit residential rental property on a side street in the charming Village of Cold Spring. This income-producing building features three spacious two-bedroom apartments, each with separate electric meters, electric heat, and electric hot water—offering convenience and simplified
William PughHoulihan Lawrence Inc.
$3,249,000
15 Beds
7.5 Baths
6,416 Sq Ft
A Unique Village Compound / Investment Opportunity – An amazing possibility in the Heart of Cold Spring. An exceptional and rarely available offering: four adjacent properties creating a unique compound, investment portfolio, or redevelopment opportunity. Located on tranquil village streets just steps from shops, restaurants, hiking trails, and the commuter rail, this in-town cluster offers
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
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NOTE: DON'T walk the property WITHOUT PERMISSION. Renovated and upgraded Chalet home offers ambiance and charm from the moment you step through the front door. Cathedral ceilings throughout the gathering spaces give a sense of height and airiness. Large windows in every room bring the outside in. The wood burning stone fireplace provides warmth on cool winter nights. A TV room off of the dining
Located right on Main Street in the Middle of the Village of Cold Spring. 2 Bedroom 2 bathroom apartment is in a great location 4 blocks from the train station. Enjoy off street parking and laundry across the hall. It has a large eat in kitchen, a large master suite with private bathroom with tub, a full living room, second full bathroom, and second bedroom. Located on the second floor of the
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Very large one of kind fully renovated loft with soaring 20 ft. ceilings located right on Cold Spring's charming Main St. This unique 2nd floor loft offers original exposed brick and beams, custom built black walnut cabinets, hardwood floors and washer/dryer in unit. You also have your own outdoor patio to enjoy summer bbq's or autumn picnic's.
Spectacular Hudson river views, beautiful grounds, in-ground pool and total privacy. 24 x 16 Living room w. fieldstone frplc, redwood paneling and 20 ft. of glass opening to covered porch. Family rm. w. wood burning stove which opens onto deck. FDR, Den or 1st flr. BR. w. bath. 4 BR's, 3 Bths. A Unique country retreat or full time private residence on 12 acres. Additional Information: Kitchen
Live in this fully furnished, picture perfect Cold Spring home with walkability to hiking trails, train and shopping! This light filled village victorian home with high ceilings and hardwood floors will charm you. Enjoy mountain views, a rocking chair front porch, lovely green yard and a driveway for parking. The renovated eat in kitchen features granite countertops, new appliances and washer
Located within the peaceful Graymoor setting of Garrison, this spacious single-family rental offers a unique opportunity to live in one of the Hudson Valley’s most serene and distinctive environments. Formerly part of the Graymoor community, the home offers a flexible layout with bedrooms, multiple additional rooms, and generous space for work-from-home needs, guests, creative use, storage, or
Nestled in a serene private lake community, this newly updated cottage offers the perfect blend of comfort and outdoor recreation for a fully furnished summer rental. The home features one spacious bedroom with a queen bed, a light-filled living room with a queen pull-out sofa, and a dedicated dining room, comfortably accommodating guests. A bright full bathroom, well-appointed kitchen, washer /
Welcome to Cold Spring village life! This charming brick house in the heart of the Hudson Valley's most charming village is walkable to the Metro North train to Manhattan, Hudson Highlands hiking trails, shops, restaurants, parks and schools. With 3 bedrooms and 1.5 baths, 6 Church Street comfortably sleeps 7 and has off street parking for 2 cars. Enjoy outdoor cooking and dining with the gas
Nestled in the charming village of Cold Spring, this beautiful two-story condominium offers comfort, convenience, and serene surroundings. The spacious living room features gleaming hardwood floors that continue throughout the home, creating a warm and inviting atmosphere. The updated kitchen includes a cozy dining area and opens to a private balcony overlooking peaceful wooded views — the
Enjoy year-round living in this sun-drenched, fully updated riverfront contemporary offered as an annual rental. This inviting home features 3 bedrooms and 2.5 baths, thoughtfully designed with modern finishes and an open, airy feel. Set along the river with direct access, the property offers a seamless connection to nature—perfect for kayaking, relaxing, or simply taking in the views. Adjacent
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