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$950,000
4 Beds ⋅ 3 Baths ⋅ 1045792 MLS
Historic character meets a complete modern transformation at 20 Division Street in the heart of Cold Spring Village. Originally built in 1790, this four-bedroom, two-and-a-half-bathroom home has been thoughtfully reimagined from the inside out, offering 2,000+ square feet of beautifully finished living space. The fully renovated interior features an open, light-filled floor plan designed for both everyday living and entertaining. A brand-new kitchen anchors the main level, complemented by new hardwood floors, custom built-ins, exposed beamed ceilings, and carefully considered architectural details throughout. A newly added powder room completes the first floor. Upstairs, the hall bathroom has been completely updated, while the transformed primary suite features a new private full bathroom. Every space feels fresh, refined, and entirely move-in ready while preserving the character of the home’s historic origins. Outside, updated siding, a newer roof, and new paver work create an inviting exterior with lasting curb appeal. Set within one of the Hudson Valley’s most beloved villages, the home is just moments from Cold Spring’s shops, restaurants, hiking trails, and the Hudson River. This is a rare opportunity to own a fully renovated historic residence offering modern comfort, timeless character, and an exceptional village lifestyle.

20 Division Street, Cold Spring
$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
$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
$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
$599,000
3 Beds ⋅ 2 Baths ⋅ 1002388 MLS
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 living space. This sun-drenched expansion added a spacious sunroom/playroom and a pristine new full bathroom. Beautiful reclaimed wood flooring adds warmth and history throughout, while digital WiFi-enabled thermostats in every room allow you to manage comfort from anywhere. Inside, enjoy a stunning open-concept kitchen with granite countertops, a large island perfect for entertaining and everyday living, a convenient pot filler, high-end appliances, and a reverse osmosis filtration system under the sink for pure drinking water. The primary bedroom offers a private retreat with an en-suite bath featuring a walk-in shower. Peace of mind comes standard with a newly installed septic system for the main residence. Beyond the main house lies a separate 434 square foot cottage, sold as-is, that could potentially be rehabbed. Locate near multiple hiking trails and parks, this property offers a move-in ready mountain-top sanctuary with sophisticated modern upgrades and endless outdoor recreation at your doorstep.

517 E Mountain Road N Unit #515-517, Cold Spring
$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

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.