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$6,500,000
8 Beds 8 Baths 1039174 MLS
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 stretch out to your left. When the house comes into view along the ridge, you begin to enter a different state of mind. Blood pressure drops, worries fade, and you are home. This is the home you have always wanted. A home where you can welcome family and friends. Built in 1883 for Rev. Walter Thompson and restored and modernized for use as an office over the past decade by a team of skilled architects, designers and craftsmen, Winter Hill emerges in full view as you crest the ridge. Park in either the sprawling forty space lot, perfect for entertaining many guests, or under the porte-cochere, connected to the wrap-around porch. Open the double doors and enter the main foyer, with a unique wall design, and find yourself in an elegant living room, centered on a huge wood-burning fireplace. Original details - pocket doors, gleaming hardwood floors and walls of multi-paned windows - are accentuated by the modern glass chandelier. Beyond is the front parlor, with striking bay window seating. Behind, you will find the massive central dining room, with amazing original fireplace details, then a perfect home office space or potential formal library, with its own fireplace. All of these rooms flow together to make an amazing space for entertaining. Imagine friends, family and community gathering here, in your home. Off the central hall, find the chef's dream kitchen, with beautifully unique light fixtures, stainless appliances, two ovens, a prep sink and abundant counter space. More on this level: a back room that would be a great first floor bedroom, two half baths and a bonus room. Everywhere are open or wooded views. Step out to the covered front porch and slate patio. Here, you'll host drinks in the evening, or simply sit with a cup of tea in the morning, looking over the serene fields. On the second level, arrived at via the convenient, full four-floor elevator, or gorgeous front staircase, opportunity abounds. Currently used as offices, the many large and bright rooms here can be converted into guest bedrooms, family rooms, playrooms and more. Two of the rooms have fireplaces. Other 1800's details, like wood floors and leaded glass windows, are here, as elsewhere. Most rooms have views to the gorgeous grounds. One floor up, find even more bright spaces - bedrooms, guest areas, artist and craft rooms, or wherever your vision takes you. Let’s hop in the elevator and jet down to the lowest level, to discover large spaces that are perfect for home gyms and media rooms. There are huge storage rooms and the new utility systems, including state of the art electrical and a/v rooms. Leaving the basement through the walkout, we exit to the side yard and look out to the fields flowing before us. At the side is the private guest cottage above the two-car garage. This cottage has views of its own, a kitchen and full bathroom. This is a perfect spot for your guests, or extended family. Nearby, the large water tower ensures never running out of fresh water. From here, we can see the property at a different angle. The home’s cedar shingle siding and roof, with stately brick chimneys, rises before us. To our right, protected land, to our left the park-like land and rolling hills stretching out to the tree line, almost as far as you can see. All of this, just minutes to the train and the heart of Cold Spring. Come, visit Winter Hill and join its living story.

20 Nazareth Way, Garrison

$6,500,000
1039176 MLS
Winter Hill, a flagship property in the Hudson Highlands, is a meeting of two amazing worlds. A marriage of stately 19th century craftsmanship and 21st century cutting edge construction techniques, these buildings offer tremendous opportunity for both investors and end-users. Set on twenty rolling acres of verdant, natural beauty, with stone walls, mature trees and well maintained plantings, the main house was built in 1883 for Rev. Walter Thompson. It has been restored and modernized for use as an office over the past decade by a team of skilled architects, designers and craftsmen. Off a quiet, country road and down a long, gently curving driveway, Winter Hill emerges in full view as you crest the ridge. The well lit, paved parking lot has space for forty cars, with additional parking elsewhere. The main original double door entrance, under a classic porte-cochere, has been enhanced with a keyless entrance security system. Inside, the large, grand lobby is centered around a huge wood-burning fireplace. Original details - pocket doors, gleaming hardwood floors and walls of multi-paned windows are accentuated by the contemporary glass chandelier. Beyond is a library, waiting room or potentially a private office, with a fireplace of its own. Next, is the massive conference room, with a projector and screen for presentations. Another fireplace, with amazing original woodworking surrounding it, is at the head of this room. Behind, there is a large, open office space with moveable dividers. Another private office and a copier room complete this area. Nearby, a full chef's kitchen, well suited for catered events, can be found. Also on this level are two half bathrooms and a separate, accessible entrance. There are open or wooded views from every room. The covered porch and slate patio is a perfect spot to host client events, or to simply relax between meetings. On the second level, arrived at via the convenient, full four-floor elevator, or gorgeous front staircase, there is additional abundant office space. At the top of the stairs, find a potential second lobby or open office space. Off of this, there are two large offices, one with a second, private office connected. All of these rooms are brilliantly lit with both natural light and an automatic, energy conscious lighting system. Two of the rooms have original fireplaces and views to the rolling grounds. Other original details, like wood floors and stained glass windows, are here as well. There is also a kitchenette, copier room and two more bathrooms. One floor up, find four more offices. As with the rest of the building, a fire suppression system keeps this level safe and nearly every room has its own heating zone. Let’s jump in the elevator and jet down to the lowest level, to find two more large offices, one with it's own separate entrance. There are also huge storage rooms, access to the new utility systems, including state of the art electrical and a/v rooms, a kitchenette, janitor's room and a bathroom. Leaving the basement through the walkout, we climb up to the second building, a garage/ with residential unit above. This space has views of its own, a kitchen and full bathroom. Nearby, the 22,000 gallon water tower ensures never running out of fresh water. Let’s not forget the storage shed with a backup generator next to it. From here, we can see the property at a different angle. The building's cedar shingle siding and roof, with stately brick chimneys rises before us. To our right, protected land, to our left the park-like fields and rolling hills stretching out to the tree line, almost as far as you can see. All of this, just minutes to the train and the heart of Cold Spring. The entire Hudson Valley opens before us, with NYC one hour south and Albany less than two hours north. Don't miss this opportunity.

20 Nazareth Way, Garrison

$2,300,000
6 Beds 7 Baths 1041990 MLS
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, stone cottages, original details, and a striking three-story barn that has been thoughtfully adapted as a pool house and game room overlooking the in-ground pool. Beyond the main residence, two additional cottages and three outbuildings offer tremendous flexibility for guests, studios, or other creative pursuits. The surrounding acreage accented with native meadows and mature fruit trees gives total privacy while remaining close to everything that makes the Hudson Valley so desirable. The Hudson River, Cold Spring Village, Metro-North trains, hiking trails, shops and restaurants, are all just minutes away, with New York City accessible in just over an hour by train or car. A one-of-one historic estate with acreage, architectural integrity, privacy, and proximity, Normandy Grange offers the opportunity to create a distinctive Hudson Valley legacy property. Property is being sold as-is.

15-18 Normandy Grange, Garrison

$1,300,000
4 Beds 3 Baths 1020810 MLS
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 kitchen with stainless steel appliances opens to a durable, low-maintenance deck overlooking the backyard, creating an easy indoor-outdoor flow. The inviting living room features a wood-burning fireplace, adding warmth and character to the main living space. Upstairs, the generous primary suite offers a large walk-in closet and an en-suite bath with double vanity, separate shower, and Jacuzzi tub. Two additional bedrooms, each with double closets, share a full hall bath, while a finished bonus room above the attached two-car garage provides versatile space for work, recreation, or storage. Recent improvements include a new roof, Renewal by Andersen replacement windows, new siding, a Buderus boiler and hot water heater, an automatic whole-house generator, and owned solar panels that deliver exceptional energy efficiency with little to no electric costs. Conveniently located just minutes from Cold Spring, Metro-North, hiking trails, and the Hudson River, this special home offers comfort, efficiency, and ease of living in a highly desirable Hudson Valley setting.

310 Avery Road, Garrison

$15,000
1020060 MLS
Tucked along a quiet stretch of Steuben Road in Garrison, NY, this .303-acre parcel offers a rare opportunity for a buyer who understands land, zoning, and long-term potential. Set within the R-40 zoning district, the property measures approximately 60 feet of road frontage and is being sold strictly as is, with no existing approvals in place. This is not a turnkey building lot — and that’s exactly what makes it interesting. At just under one-third of an acre, the parcel will most likely require a variance to support residential development. For the right buyer, builder, or investor, this represents a chance to step into a project with eyes wide open and create value through proper planning, zoning review, and town-level approvals. Parcels like this don’t appeal to everyone — but for those who understand the process, they often present some of the most rewarding opportunities. The surrounding area reflects the charm Garrison is known for: mature trees, established homes, and a strong sense of place within the Hudson Highlands. The location offers privacy and character while still being convenient to major routes, Metro-North, and the natural beauty that draws people to this part of Putnam County. This property is best suited for a buyer who is comfortable doing due diligence, and collaborating with local professionals, and engaging with the zoning and variance process. Whether the end goal is a modest residence, a long-term hold, or a carefully designed home that fits the neighborhood, the potential lies in the vision — not in prepackaged approvals. Vacant land with road frontage in Garrison is increasingly scarce. Opportunities like this don’t come with guarantees — they come with possibilities. For those willing to navigate the path forward, 57 Steuben Road offers a blank canvas in one of the Hudson Valley’s most desirable communities.

57 Steuben Road, Garrison

$100,000
1011915 MLS
Discover a prime opportunity to build your “meant-to-be” home on this expansive parcel of unimproved land in the Town of Philipstown. Located within the R-40 zoning district, the property offers approximately 3.4 acres in a low-density residential setting—ideal for those seeking privacy, space, and tranquility. The R-40 designation allows for the construction of one single-family detached residence per lot, with a minimum required lot size of 40,000 square feet (approximately one acre), subject to Board of Health approval and all necessary building permits. The generous acreage provides ample room for outdoor living, gardens, and future enhancements. Enjoy the peaceful surroundings of Philipstown while remaining conveniently close to local amenities, outdoor recreation, and scenic natural landscapes. This is a rare opportunity to create a custom home in a highly desirable community. Why search for a home when you can build one?

50 Winston Lane, Garrison

$3,200,000
5 Beds 5 Baths 1009485 MLS
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 strong sense of community, minimal traffic, and remarkable tranquility. Bordering the 8,000-acre Hudson Highlands State Park Preserve with more than 70 miles of trails, the estate enjoys a setting that feels both deeply secluded and endlessly connected to nature. Outdoor recreation begins at your doorstep. The property features its own trail network and private trailhead connecting directly to the Appalachian Trail, offering true hike-on, hike-off access. Walk to nearby lakes, explore the trails of the Russel Wright Design Center, hike to Anthony’s Nose, or cycle directly from the property to Bear Mountain, one of the Northeast’s premier road biking destinations. A seasonal stream, private campsite, and campfire area further enhance the experience of living immersed in the landscape. Designed by noted Hudson Valley architect Frank Dushin, the residence blends the warmth and craftsmanship of the Arts and Crafts tradition with the clean lines and thoughtful spatial design of modernism. Dramatic exposed beams, natural materials, and a striking sunken living room create spaces that feel both timeless and distinctly connected to their surroundings. The home has been extensively renovated, including a complete reimagining of the primary suite and bath, beautifully updated bathrooms throughout, and a thoughtfully designed laundry room. Two fireplaces, a screened porch, and expansive views of the surrounding gardens and woodlands create inviting spaces for every season. Outside, more than two decades of garden design by a beloved local horticulturist have shaped the landscape into a living extension of the home. Mature plantings, curated garden rooms, and woodland paths unfold across the property, creating beauty and interest throughout the year. A separate wellness pavilion includes a gym, steam room, dedicated shower facilities, outdoor hot tub, and connections for a future sauna, while a detached two-bedroom guest house with its own kitchen offers comfortable accommodations for family and visitors. Rarely does a property combine architectural pedigree, buildable acreage, direct trail access, protected parkland, established gardens, and resort-style amenities so close to New York City. This is a true Hudson Highlands sanctuary—private, peaceful, and connected to the landscape in every direction.

20 S Mountain Pass Spur, Garrison

$8,950,000
6 Beds 6 Baths 972365 MLS
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 City. The setting preserves the integrity of one of Garrison's last original country estates. The estate was held by a single family for generations before its recent renewal. The main residence, a stone-and-stucco chateau with a slate roof, draws inspiration from rural Normandy and the Loire Valley. Designed with restraint and classic proportions, it combines formal architecture with a sense of intimacy, and ease suited to its surroundings. A three-story rotunda anchors the interior and introduces a classic curved staircase that rises through the center of the home. The floor plan unfolds in a balanced sequence of rooms. Grand entertaining spaces are complemented by more intimate private rooms. Approximately 6,200 square feet, which includes six bedrooms/five baths, and one half bath. Original features—deep-set windows, sleeping porches, and period millwork—remain intact, supported by a full restoration completed in 2018. Modern systems include radiant heating, central climate control, fiber-optic connectivity, and discreet security integration. The estate comprises a series of interconnected structures and landscapes. A converted carriage house of approximately 4,000 square feet serves as a guest residence, offering five bedrooms/bathrooms, a garage, and an artist’s studio marked by a distinctive tower element. Outdoor areas include a gunite pool surrounded by stone terraces, established gardens, a parterred rose garden, and an open lawn. A separate Billiards Lodge with a large stone fireplace offers a private retreat. Evarts Hill represents a rare continuity of architecture, land, and history. It is an early-20th-century Hudson Highlands estate reimagined for modern living, set amid lasting beauty and privacy.

61 Evarts Hill Unit #41, Garrison

$1,300,000
4 Beds 3 Baths 962616 MLS
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 recreation room, open and screened porches, and an attached two-car garage. Included in this offering are two additional separately deeded parcels: 2.25-acre lot 1.83-acre lot All three parcels together provide flexibility for estate expansion, compound living, long-term investment, or preservation of privacy. The combined acreage offers a rare opportunity to control surrounding land in this highly desirable Garrison location. Located within the Garrison School District and just minutes to Metro-North, hiking trails, the Hudson River, and the cultural attractions of Cold Spring and Beacon. A unique offering with exceptional potential — available as a package with all three parcels included in the sale.

111 Philipse Brook Road, Garrison

$4,995,000
8 Beds 7 Baths 871871 MLS
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 history inside, the period features continue throughout. Beginning with the dramatic entrance showcasing the grand, keyhole staircase, the generous public spaces with many fine trim details, paned windows , archways and niches abound. A layout that offers great flow for entertaining as well as many nooks in which to retreat to relax. A slice of country life without being too remote. This hidden sanctuary in the center of Garrison awaits its next owner to enjoy all the history and beauty it has to offer. Privacy without sacrificing convenience. A perfect retreat.

1070 Route 9D, Garrison

$400,000
895215 MLS
The Scenic Hamlet of Garrison in Putnam Valley has long been a refuge from the city with its never ending natural beauty, serenity, and cultural hub for many non-profits. It’s the perfect gateway town to all the Hudson Valley has to offer with amazing access to New York City. And now you can build your dream home in this sought after town where inventory of existing homes is sparse. Situated on Rt 9D - this 2.89 acre lot has full board of health approval. Your mountainous backyard is a wooded haven to hike and explore. You can even catch up to the Appalachian trail or the beautiful trails of Manitoga and Anthony’s Nose - without ever getting in your car. There is a beautiful babbling brook which is so meditative and rock deposits that look perfectly curated. And with western exposure you would catch the most beautiful sunlight all afternoon, not to mention those sunsets over the Hudson River. The property is 5 minutes from the Garrison Train Station, The Philipstown Depot, Dolly's Restaurant, the Garrison School, The Garrison Library and the Bear Mountain Bridge. 10 minutes Cold Spring and 20 minutes to Beacon. Garrison is just 50 miles north of the George Washington Bridge.

TBD Rt-9d, Garrison

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.