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MLS ID KEY831283Last updated Feb 28, 2026

Single Family

75 Hill 99

Active · Woodstock · Ulster County, NY 12498

Monthly rent$16,500/monthRequest a Showing
Bedrooms
4 Beds
Bathrooms
4 Baths
Year built
1973
Property gallery0 / 36
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About this home

Secluded Mountain Chalet with Breathtaking Views and Poolside Lodge - Set atop nine private acres, this stunning mountaintop chalet offers a rare combination of serenity, seclusion, and spectacular views. A long, private driveway winds through the property, leading to a retreat unlike any other. The property features a three-story main house and a separate two-story Poolside Lodge, both connected by an expansive deck with a heated pool, open from mid-May through November 1st, and a built-in outdoor grill station perfect for entertaining. Inside the main house, soaring cathedral ceilings and wide-plank wooden floors create an immediate sense of warmth and grandeur. The second floor spacious living room is anchored by a striking double-sided wood-burning fireplace, which also serves a cozy alcove office lined with picture windows—a peaceful and inspiring workspace. The adjoining kitchen is fully equipped with modern appliances, including an induction stovetop, oven, and two refrigerators. A large island with seating for four offers a casual spot for dining, while the adjacent alcove provides a more formal space with a handcrafted wooden table positioned to capture stunning views of the Hudson Valley. Step onto the wooden terrace for a peaceful morning coffee, watching the sunrise over the mountains. On clear days, the view stretches as far as the Berkshires. Behind the living room, two serene bedrooms, each with a queen-size bed, offer restful retreats. One overlooks the pool and deck area, while the other gazes out at the garden and bocce court. A beautifully designed modern bathroom sits just across the hall. A spiral staircase leads to the top floor, where the expansive primary suite is a sanctuary unto itself. Cathedral ceilings create an airy feel, while the en-suite bathroom is a luxurious escape, featuring a bubble-stream tub and a sunlit glass block windowed shower brings the outdoors in. A grand staircase leads to the first-floor great room, where another working fireplace, plush leather seating, and a cozy library plus corner bench seating reading nook create an inviting atmosphere. Behind the living area, a ground-floor bedroom offers a private retreat with french doors opening to nature and a handcrafted solid cherry Le Grange bed. An elegant en-suite Porcelanosa bathroom enhances this space, making it feel like a mini-suite. Stepping outside and crossing the pool deck brings you to the Poolside Lodge, an inviting space designed for relaxation and entertaining. The upper level is dominated by a grand room with walls of windows and private terrace that capture sweeping 180-degree mountian views. Luxurious leather seating and an open, airy layout make it the perfect place to gather. On warm days, four large french doors open to let in the fresh mountain air, creating an effortless indoor-outdoor flow. Downstairs, the lower level of the Poolside Lodge offers a spacious retreat with a piano, pool table, and gym equipment, providing plenty of space for recreation and entertainment. Beyond the homes, the lower portion of the property features a tranquil pond, ideal for rowing a boat or enjoying a picnic at the shaded table by the dock. The front of the main house opens to a vast, open lawn surrounded by wooded land, with a fire pit that invites guests to gather under the star-filled sky. For those who love the outdoors, the chalet is perfectly situated. Hunter and Belleayre ski resorts are just a 30-40 minute drive away, while nearby hiking trails offer endless opportunities to explore nature. Despite its secluded feel, the property is only two hours from New York City, making it an accessible escape from the hustle and bustle. This remarkable retreat is available for rent for high season rates (inquire) July 7 - August 1, then on a month-to-month or long-term basis starting September 3, 2025. This is more than just a rental—it's an experience.

Listing snapshot

Days on site
59 days
Listed on MLS
Mar 4, 2025
Full baths
3
Half baths
1
Area source (MLS)
Other
Listing brokerage
Corcoran Country Living
MLS ID
KEY831283
Last updated
Feb 28, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1973
Garage
No
Water source
Well
Sewer
Septic Tank
Utilities
None

Interior features

Heating
Forced Air, Wood
Cooling
Central Air
Interior
First Floor Bedroom
Appliances
Dishwasher, Dryer, Refrigerator, Stainless Steel Appliance(s), Washer
Fireplace
Yes
Fireplaces
2

Exterior features

Architectural style
Chalet
Construction materials
Wood Siding
Private pool
Yes

Schools (MLS)

Elementary school
Phoenicia Elementary School
Elementary school district
Onteora
Middle school
Onteora Middle School
Middle school district
Onteora
High school
Onteora High School
High school district
Onteora

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. First seen on this site
  2. Listing updated from MLS
  3. MLS status changed

Location

Woodstock · Ulster County, NY 12498Show interactive map
75 Hill 99

Woodstock · Ulster County, NY 12498

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Listing data is supplied by the MLS and may change without notice.