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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
$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
$695,000
3 Beds ⋅ 2 Baths ⋅ 1040231 MLS
Discover timeless charm and modern convenience in this beautifully preserved historic brick home, ideally located in the heart of Cold Spring. Built in 1845, this special residence is just a short walk to village shops, restaurants, the majestic Hudson River, and the Metro-North train station, offering an exceptional blend of village living and Hudson Valley beauty. Original hardwood floors add warmth and character throughout the home. The main level features an inviting living room with a distinctive antique light fixture from Paris, a convenient full bath, and an updated kitchen with stainless steel appliances and a center island. A bright bay window creates a charming dining nook, while the formal dining room is easily accessed from both the kitchen and living room, making everyday living and entertaining effortless. The second floor offers two bedrooms, a full bath, and a versatile sitting room ideal for a home office, reading room, or additional living space. Step outside onto the private balcony overlooking the beautifully maintained courtyard and lush gardens. The light-filled third-floor bedroom is a peaceful retreat, complete with breathtaking mountain views. Outside, a spacious backyard deck provides the perfect setting for dining and entertaining, while the secluded courtyard offers a tranquil escape surrounded by colorful flowers and mature plantings. With hiking trails just minutes away and all that charming Cold Spring has to offer at your doorstep, this distinctive home perfectly balances historic character, modern comforts, and an enviable Hudson Valley lifestyle.

7 Railroad Avenue, 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
$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
$925,000
3 Beds ⋅ 2 Baths ⋅ 1009674 MLS
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 quiet country road. Beyond the home, the land reveals its most captivating treasures: dramatic creek frontage, a picturesque gorge, cascading waterfalls, and the enduring stone remnants of an 18th-century grist mill that once harnessed the power of the rushing waters. Offered as a collective sale totaling nearly 14 acres, the property includes three separate parcels, each with frontage on Clove Creek. In addition to the farmhouse parcel, included are a 3.05-acre parcel on Horton Road and a 2.91-acre parcel located at Mill and Horton Roads. Together, these parcels create a rare opportunity to preserve, enjoy, and explore an extraordinary natural and historic setting. Whether you envision a country retreat, an artist's sanctuary, a place to reconnect with nature, or simply a chance to become the steward of a truly unique piece of history, this property offers endless inspiration. Wander beside the waterfalls, listen to the creek as it winds through the gorge, and discover the traces of a bygone era hidden among the stone mill ruins. Included in the sale are Tax Parcel #17.1-69 and Tax Parcel #17.1-62. Offered together, these three parcels provide an exceptional combination of history, natural beauty, and potential on nearly 14 acres along one of the area's most enchanting waterways. Clove Creek is a watershed district. A rare opportunity to own not just a home, but a chapter of history.

50 Mill Road, Cold Spring
$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
$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

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.