$918,584Average Value$495Average Price per Sq Ft1Home For Sale
Hiking and hamlets in mountainous Philipstown
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
Phyllis Lerner,
an experienced agent in this area.
GreatSchools:
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On average, homes in Philipstown, NY sell after 28 days on the market compared to the national average of 55 days. The median sale price for homes in Philipstown, NY over the last 12 months is $428,400, down 44% from the median home sale price over the previous 12 months.
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
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
Set on a peaceful one-acre parcel in the heart of the Hudson Valley, this spacious raised ranch offers room to settle in, gather, and enjoy the surrounding landscape. With 3,132 square feet, 4 bedrooms, and 2.5 baths, there is plenty of space for everyday living, working from home, hosting friends, or simply having room to spread out. The updated kitchen and bathrooms bring a fresh feel to the
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
Experience upscale, carefree living in Glassbury Court at Cold Spring, a premier 55+ active-adult community. This beautifully appointed Highland model enjoys a prime location within the complex, surrounded by lush flowerbeds and mature landscaping. Designed for comfortable one-level living, the home offers two bedrooms, a versatile den, and an expanded patio ideal for relaxing and entertaining.
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
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
Move right in to this beautifully maintained raised ranch home offering the perfect blend of comfort, style and functionality. Filled with natural light, this inviting home features three bedrooms, one-and-a-half bath, hardwood floors, central air conditioning and a spacious 2 car garage. The heart of the home is the expansive great room with vaulted ceiling and skylights creating an open and
Christine DiChiaraColdwell Banker Realty
$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
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
Welcome to The Cold Spring Mobile Home Park in the charming village of Cold Spring, New York. Nestled in a peaceful setting, this home offers comfortable, easy living with a functional layout and abundant natural light. The interior features a welcoming living room with a fireplace, dining area, kitchen, 2 bedrooms & a bath. There is also a deck, shed and 2 parking spaces. Enjoy the tranquility
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
Large 3 Bedroom, 2 Bathroom Apartment located on border of Cold Spring and Garrison. Light, bright and open Kitchen/Living Room area with cathedral ceilings. Spacious bedrooms with large closets. Hardwood floors. New efficient heat & a/c units. Hot water included. 4 miles to train station, conveniently located. Washer and dryer on premises. Off street parking.
Nature Lover’s Dream — Beautiful Cold Spring Rental with Mountain ViewsWelcome home to this beautiful, spacious, unfurnished apartment in Cold Spring, NY, surrounded by lush gardens, peaceful natural scenery, and stunning mountain views. Offering privacy, comfort, and plenty of indoor and outdoor space, this unique rental is a wonderful place to call home.Start your mornings with coffee
Townhouse style home in walking distance to train station and Main Street. Quaint street with off street parking for one car. Wide plank hardwood floors throughout give such charm to this cozy unit. Large eat in kitchen with newer stove. Laundry in the unit on the first floor just off the kitchen in the powder room. Garbage ,lawn mowing, water and sewer included in the rent. Tenant maintains
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
Nora PreusserA.D.Preusser, Inc.
$2,350 per month
1 Bed
1 Bath
800 Sq Ft
Roomy one bedroom updated apartment in lower level with private entrance of Garrison home. Owners live upstairs. All utilities included . Spacious bedroom, large bathroom , big walk in closet. Beautiful open floor kitchen / living space. Laundry room with extra storage. Radiant floor heat with mini splits for backup heat and AC. Nice outdoor dedicated space. Propane Vermont Castings stove for
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
Sun filled first floor, two bedroom, one and a half bath condo in the charming village of Cold Spring. Excellent location allowing for easy access to Main street shops and restaurants, Metro North train station, Hudson river waterfront, hiking trails, parks and many necessities. Hardwood floors. Updated eat in kitchen. Washer/dryer in unit. Beautiful views. Amenities include: Pool , additional
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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