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$715,000
2 Beds ⋅ 2 Baths ⋅ 1027903 MLS
Welcome to Glassbury Court of Cold Spring! Stunning Highland model features one floor living in a pristinely kept 55+ adult community. Nestled in the gorgeous Hudson Valley just 50 miles from Manhattan, live in convenience at the midpoint between Cold Spring village and Fishkill village with exciting Beacon just minutes away. Have the easy access to restaurants and every amenity you can imagine, together with the gorgeous surrounding Hudson Highlands and natural landscape. This home features a stunning en suite setup with a second guest bedroom, a third room for an office or den, open kitchen and living concept with fireplace, radiant heat throughout the home as well as in the garage, and a community clubhouse featuring a heated outdoor swimming pool and tennis/pickleball courts. All new furnace installed this year. Top line builder upgrade finishes make this a unique home in this community.

1 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
$659,999
4 Beds ⋅ 3 Baths ⋅ 997105 MLS
Welcome to 21 East Mountain Road South in Cold Spring, NY — a beautifully maintained 4-bedroom, 2.5-bath ranch set on 1.1 flat private acres in the highly sought-after Haldane Central School District. This warm and inviting home offers effortless single-level living with original hardwood floors, skylights, central air, 3-zone heating, and a bright open-concept layout designed for everyday comfort. The spacious open basement provides endless possibilities for recreation, fitness, media, or additional living space, while the large attic offers abundant storage. Step outside to your private backyard oasis featuring an enclosed patio, expansive usable yard, and above-ground pool perfect for entertaining. A 2-car attached garage includes generator and trailer hookups. Conveniently located just minutes from the historic Village of Cold Spring, Metro-North, shopping, dining, hiking trails, and the scenic Hudson River, this property offers the perfect blend of privacy, charm, and commuter convenience.

21 E Mountain Road S, 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
$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

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.