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50 Holly Rd, 
Napanoch, NY 12458

$340,000


2

Beds


1

Bath


1,152

Sq Ft


Single Family

Pending

Listed by

Erica Schupp

Four Seasons Sotheby'S Int.

845-876-5100

Last updated:

January 12, 2026, 08:42 AM

MLS#

20255365

Source:

NY MLSUC

About This Home

50 Holly Rd

Welcome to Twin Bear Chalet, a cozy A-frame retreat tucked along a babbling creek in Napanoch, NY, just under two hours from New York City. Set on a half acre surrounded by native wildflowers, berries, and fruit trees, this 2 bedroom, 1 bath chalet offers the perfect blend of privacy, serenity, and rustic charm. Step inside and you'll find rough-cut pine paneling throughout, crafted by the original owner—a builder and artist whose handmade ironwork staircase tells a whimsical Catskills story of deer, squirrels, and bears. The open living space glows with natural light, while the upstairs loft provides a spacious second bedroom that opens to a three-season sleeping porch overlooking the forest and Trout Creek. Fall asleep to the sounds of the creek and wake to birdsong and mountain air. Recent updates include a new kitchen sink and lighting, upgraded plumbing, septic service (2023), and a new Generac whole-home standby generator (2023) so you can enjoy peace of mind and modern comfort in a timeless setting. Outside, garden boxes and native plantings invite you to harvest blueberries, blackberries, raspberries, grapes, cherries, paw paws and apples right from your yard. The unfinished basement offers room to expand, add a bedroom, studio, or workshop to suit your vision. Backing up to over 10,000 acres of state land just minutes from the Rondout Reservoir, and a short drive to Peekamoose Blue Hole, Minnewaska State Park, and Mohonk Preserve, this home is ideally located for year-round adventure. Whether you're seeking a weekend escape, a creative hideaway, or a vacation home; Twin Bear Chalet is a rare Catskills gem, a place to reconnect with nature and slow down life's pace.

Home Facts

Single Family

1 Bath

2 Bedrooms

Built in 1986

Price Summary

340,000

$295 per Sq. Ft.

MLS #:

20255365

Last Updated:

January 12, 2026, 08:42 AM

Added:

2 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

1

Full Bathrooms:

1

Interior

Living Area:

1,152 Sq. Ft.


Structure

Structure

Architectural Style:

Chalet

Building Area:

1,152 Sq. Ft.

Year Built:

1986


Lot

Lot Size (Sq. Ft):

21,780


Finances & Disclosures

Finances

Price:

$340,000

Price per Sq. Ft:

$295 per Sq. Ft.

Source:NY MLSUC
The information being provided by Hudson Valley Catskill Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Hudson Valley Catskill Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.