Refine Search
Sort by
$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

$1,150,000
4 Beds 3 Baths 1043322 MLS
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 recessed lighting and vaulted ceilings that create an open and airy feel. The chef’s kitchen features marble countertops, a large center island, stainless steel appliances, dishwasher, electric cooktop, and exhaust fan, making it both functional and ideal for entertaining. The home also offers a welcoming entrance foyer, formal dining room, ceiling fans, generous storage, and walk-in closets. The primary bedroom is conveniently located on the first floor, offering added privacy and accessibility. Additional highlights include in-home washer and dryer, a dedicated wine cellar and wine bar, and plenty of storage throughout. Comfort is enhanced by Mitsubishi mini-split systems for heating and cooling, complemented by backup oil heating. Outdoor living includes both a balcony and deck, while covered carport parking provides convenient protection from the elements. The property also features a shed for additional storage, four exterior security cameras, and a four-zone music system for added convenience and entertainment. Located in scenic Cold Spring, this home offers easy access to the area's charming village atmosphere, restaurants, cafés, boutique and antique shopping, and the Hudson River waterfront. Outdoor enthusiasts will appreciate the nearby hiking, kayaking, parks, and Hudson Highlands recreation. The Metro-North Hudson Line provides convenient access toward New York City, while attractions such as Boscobel House and Gardens, West Point Foundry Preserve, and the Hudson Highlands are all nearby. Enjoy the best of Hudson Valley living with modern comforts, entertaining spaces, and the charm of Cold Spring right at your doorstep.

24 Babbling Brook Lane, Cold Spring

$712,000
2 Beds 2 Baths 1027839 MLS
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. The welcoming foyer features a raised ceiling and opens to an elegant formal dining room with a tray ceiling. The vaulted great room, highlighted by a gas fireplace, flows seamlessly into the kitchen with a granite center island, stainless steel appliances, and a spacious pantry. Wood floors extend throughout the main living areas and primary bedroom, while the second bedroom and den feature carpeting. Additional amenities include radiant-floor and hydro-air heating, central air, central vacuum, a heated two-car garage, and a convenient storage room off the patio. Residents enjoy a clubhouse, fitness center, movie theater, heated swimming pool, and tennis courts. North Highlands Park of Philipstown, with its scenic pond and hiking trails, is nearby, while the Metro-North train station is approximately five miles away—offering an ideal balance of natural beauty, recreation, and convenience.

5 Maggie May Way, Cold Spring

$698,000
2 Beds 2 Baths 1024506 MLS
If you have been patiently waiting for the perfect Hudson Valley home that checks every single box—from effortless one-floor living and high-end barefoot luxury to a vibrant, resort-style social scene—your wait is officially over! Welcome to 10 Maggie May Way, an exceptional single-level residence that seamlessly pairs next-generation green technology with an unparalleled lifestyle. Offering rare privacy and sweeping curb appeal, fully heated garage design, this eco-luxury end-unit delivers the classic, stately aesthetic of a detached home with all the maintenance free ease of a premier condominium association. Step inside to an expansive, sun-drenched floor plan warmed from the ground up by radiant heated floors and anchored by the ambient glow of an elegant gas fireplace. The gourmet kitchen is a true centerpiece, with double oven and stove top, beautifully appointed with premium granite countertops that offer both timeless durability and sophisticated style. Advanced geothermal technology ensures flawless climate control year-round with an incredibly small carbon footprint and radically low utility costs. When it's time to unwind, retreat to a luxurious primary suite featuring a magnificent spa-style bathtub—your own private sanctuary for long, soothing soaks. Need an extra room? Here you have a flex space you can use for a den, office or hobby room. Beyond your front door lies a vibrant, 20-acre playground designed for wellness and connection. Here you have one of Hudson Valley’s premier 55+ luxury lifestyle communities. Glassbury Court’s spectacular luxury clubhouse serves as your extended living room, featuring a fully equipped fitness center, a billiards room with a premium pool table and bar, a private movie theater, a sparkling heated outdoor pool and so much more. Whether you are starting your morning with a fast-paced match on the tennis or pickleball courts, watching your pup play in the dedicated community dog park, hiking the scenic trails around the lake, or gathering with neighbors, the lifestyle here is rich, active, and entirely maintenance-free. Minutes from historic downtown Cold Spring and the Metro-North, this is the ultimate Hudson Valley retreat you've been searching for.

10 Maggie May Way, Cold Spring

$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

$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

$75,000
2 Beds 1 Baths 928789 MLS
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 of the surrounding area while being just minutes from local shops, dining, Metro-North, and the Hudson River. Ideal as a primary residence or weekend retreat, this property offers an affordable opportunity to enjoy all that Cold Spring has to offer. Land rent of $620/month covers water, sewer, garbage, plowing & real estate taxes. This sale is subject to court approval (not a short sale). Property to be sold in "as is" condition. Please verify all info.

3485 US 9, Cold Spring

$625,000
6 Beds 3 Baths 941328 MLS
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 walk-out below, ideal for extended family, guests, or flexible living arrangements. Outdoor space abounds, with room to garden, relax, or simply enjoy the tranquil woodland setting. A detached work shed at the rear of the property provides additional storage or creative space, while a separate front storage area adds convenience. The long driveway offers ample parking, making it easy to host visitors while maintaining privacy. Whether you’re drawn to the charm of a classic Dutch Colonial, the flexibility of a multi-unit layout, or the calming presence of nature just outside your door, this unique property captures the essence of Hudson Valley living.

11 Cross Creek Road, Cold Spring

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.