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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/3
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.
1/2
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
Michael Kahns,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Welcome to your own private retreat in the heart of the Hudson Valley. This warm and inviting 3-bedroom, 2-bath home is filled with charm, natural light, and spectacular treetop views that create a peaceful everyday escape. A spacious entry welcomes you into the home, leading to a bright dining room with breathtaking elevated views and direct access to a large private deck- perfect for relaxing,
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
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. This 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 fireplace is the centerpiece of the open-concept floor plan. A
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:
Welcome to your own private retreat in the heart of the Hudson Valley. This warm and inviting 3-bedroom, 2-bath home is filled with charm, natural light, and spectacular treetop views that create a peaceful everyday escape. A spacious entry welcomes you into the home, leading to a bright dining room with breathtaking elevated views and direct access to a large private deck- perfect for relaxing,
Looking for a Hudson Valley escape with easy access to NYC? This beautifully cared-for home offers the perfect balance of privacy, outdoor living, and commuter convenience. Ideally located between the Garrison train station and the Bear Mountain Bridge—both less than 3 miles away—it’s an easy trip to the city while feeling worlds away from it all. Beautifully expanded and renovated with quality
Hudson River views from every room, walkable to Metro-North, and direct access to 129-acre preserve trails define this c.1890 Arts & Crafts Victorian, thoughtfully expanded and updated for modern living. Set above the river on beautifully landscaped grounds with mature specimen trees, perennial gardens, and stone walls, the home offers privacy, low-maintenance design, and a circular drive framed
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!
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
Set on over 7 private acres just minutes from the village of Cold Spring, this thoughtfully constructed home offers a rare combination of quality craftsmanship, space, and everyday livability. Built with care and designed for longevity, it reflects a level of construction and attention to detail that is increasingly hard to find.The home showcases rich hardwoods and warm wood finishes
First time on the market, 25 East Mountain Rd. S in Cold Spring is a thoughtfully remodeled generational home that retains distinctive original character. The bright, open floor plan offers spacious and inviting living areas, complemented by two fireplaces and ample storage. The custom kitchen features beautiful cabinetry, granite countertops, and stainless-steel appliances, and flows seamlessly
Sabrina ZeoliLimited Editions Realty, 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
Land for sale in Continental Village, NY – 1.046-acre parcel featuring a wooded setting with mature trees, seasonal mountain views, and a natural stream along the property. This unimproved parcel previously had Board of Health approval, with prior development plans available for review, subject to municipal approvals. Conveniently located near local amenities, shopping, recreation, and major
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
Luxurious 1,077 sf apartment in newly completed building. The apartment is absolutely beautiful.It is a Luxury one bedroom apartment with a den, 2 balconies facing north and south, high ceilings, granite counters, and tile bathrooms. Washer and dryer in apartment. One full bathroom and one half bathroom.This new building is part of the Butterfield complex and is on Route 9D and across
Luxurious 1,077 sf apartment in newly completed building. The apartment is absolutely beautiful.It is a Luxury one bedroom apartment with a den, 2 balconies facing north and south, high ceilings, granite counters, and tile bathrooms. Washer and dryer in apartment. One full bathroom and one half bathroom.This new building is part of the Butterfield complex and is on Route 9D and across
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
Nestled in a serene private lake community, this newly updated cottage offers the perfect blend of comfort and outdoor recreation. The unfurnished home features one spacious bedroom plus a second flex room, a bright full bathroom, a well-appointed kitchen, and a basement for storage. Beautiful wood floors flow throughout and complement a cozy masonry fireplace, creating a warm and inviting
If you want to be in the heart of the village this is for you! Charming, spacious, light filled,corner unit with brand new double paned windows to reduce any noise. No need to be concerned about living close to a restaurant, the building has soundproofing. Oversized rooms. Large, fully equipped eat in kitchen with stainless steel appliances. Will be freshly painted and carpets cleaned. More
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 8 and has off street parking for 2 cars. Enjoy outdoor cooking and dining with the gas
Cold Spring NY 2 Bedroom Apartment On Main St close to the train and shops, Restaurants close by. Plenty of Natural light, washer and dryer in unit, Small dogs considered .
Charming one-bedroom apartment located right on Main Street in the heart of Cold Spring, offering an ideal blend of comfort and convenience. Just a five-minute walk to Metro-North, this location makes commuting to NYC simple while still allowing you to enjoy everything the village has to offer, from local shops and cafes to scenic hiking trails and riverfront views. The apartment features a
Charming Updated Cottage Near Cold Spring. This beautifully updated two-bedroom, one-bath cottage offers the perfect blend of comfort and charm. Featuring vaulted ceilings, hardwood floors, and abundant natural light, the home feels both airy and inviting. A mini-split system in the main living space ensures year-round comfort, while the in-home washer and dryer add everyday convenience.Step
Tucked away at the end of a peaceful cul-de-sac, this well-cared-for village home combines privacy with exceptional convenience. Ideally located within walking distance of schools, Metro-North, and the vibrant Main Street of Cold Spring, you'll enjoy easy access to boutique shopping, acclaimed restaurants, and the scenic Hudson River waterfront. Thoughtfully maintained, the home features updated
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
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
