Renovated Chalet with Hot Tub and Pond

Summary:

Welcome to Winterberry Pond, our completely renovated converted barn nestled on 7+ private acres. This two bedroom, one bathroom home has a modern aesthetic, having undergone a comprehensive renovation in 2022, and a brand new hot tub added in 2025. Spend your evenings soaking under the stars, then gather around the fire pit for s’mores and stories. Located just 10 minutes from Roscoe and 15 minutes from Livingston Manor, this spot is the perfect spot to explore all that the area has to offer.



The Space:

As you step through the front doors, you'll be greeted by a wall of windows on your right, flooding the interior with natural light. The expansive open area seamlessly combines the living room and an inviting eat-in kitchen—perfect for easy conversation while preparing a meal or enjoying a glass of rosé. Vaulted ceilings add to the spacious, airy feel, and sunlight pours into the open floor plan throughout the day. The renovated bathroom features beautiful tile work and a walk-in shower. This home comfortably accommodates 4 guests with 2 spacious bedrooms featuring luxury linens.



Outside, the home is thoughtfully set back from the road, offering a sense of seclusion and privacy on over 7 acres of Catskills land dotted with mature trees just waiting to be explored. The generously sized yard invites outdoor fun and laid-back evenings, with an upgraded hot tub area that’s ideal for soaking under the sky after a day of hiking or skiing. Gather around the fire pit for s’mores and stories, then wind down with the quiet of the woods all around you. Spend summer afternoons row boating on the private pond and keep an eye out for local wildlife. Please note: while you’re welcome to enjoy the pond, we would not recommend swimming in it. The pond is intended for canoeing and fishing only.



Sleeping arrangements:

Bedroom 1: 1 king bed

Bedroom 2: 1 queen bed



- Set off the road on 7+ acres of remote Catskills land.

- Cozy living area with open floor plan for convenient entertaining.

- Fully-stocked kitchen with modern appliances and an island with a breakfast bar.

- Modern renovated bathroom featuring a walk in shower.

- 2 spacious bedrooms with luxury linens.

- Upgraded hot tub area for relaxing and taking in the views

- Spacious backyard for gathering and entertaining including a fire pit, outdoor dining and grill set-up

- Private pond on the property for row boating and various activities. Please note: while you’re welcome to enjoy the pond, we would not recommend swimming in it. The pond is intended for canoeing and fishing only.

- Convenient proximity to hiking trails, nature, and ski mountains for year-round outdoor activities

- Short drive to the towns of Roscoe and Livingston Manor



• The internet at this property is provided by Starlink. While speeds are typically strong, service can occasionally fluctuate due to weather and other factors and may not always allow a perfectly consistent connection.

• Winter Access Notice: The driveway and parking area is plowed in winter. During snowy conditions, a 4WD or AWD vehicle is strongly recommended for reaching the home. If you’re traveling without one, access may be difficult or not possible at times. Portoro Homes cannot be held responsible for weather-related access issues or provide assistance if a vehicle becomes stuck.



Guest Access:

Portoro Homes offers convenient self check-in. Check-in instructions will be sent by email and text prior to arrival with everything you need to access the home easily and on your schedule. You’ll also receive a digital Guest Guide for the home, packed with helpful tips, house info, and local recommendations to make the most of your stay.



• Early check-ins or late check-outs: Standard check-in time is 4:00 p.m. and standard check-out time is 11:00 a.m. If the home is ready earlier on the day of arrival, an early check-in may be available when confirmed with our main office. Late check-outs must be requested and confirmed by our main office prior to departure.



The Neighborhood:

The Catskills and Hudson Valley are fantastic destinations for anyone looking to escape the city and experience a blend of natural beauty, vibrant culture, and small-town charm. This region is famous for its rolling mountains, lush forests, and scenic river views—perfect for hiking, biking, kayaking, or simply soaking up the outdoors. In autumn, the foliage is truly spectacular, painting the landscape in vibrant colors. Throughout the area, you’ll discover a unique mix of history and creativity, with beautifully preserved architecture, art galleries, boutique shops, and a thriving farm-to-table dining scene featuring fresh local produce and artisanal goods. Weekend markets, cozy cafés, and a welcoming community vibe are found in every corner. The region is rich in culture, with attractions like Olana, Clermont State Historic Site, and regular art shows, music events, and seasonal festivals. Whether you’re after adventure, relaxation, or a foodie experience, the Catskills and Hudson Valley deliver it all—making any of these charming towns a perfect home base for exploring this special corner of New York.



Roscoe, affectionately known as “Trout Town, USA,” is a haven for anglers and outdoor lovers, where the legendary Beaverkill and Willowemoc rivers converge. The town’s unique claim to fame is its world-class fly fishing, drawing visitors from around the globe to its pristine waters and historic fishing lodges. Beyond the rivers, Roscoe offers a classic Catskills experience with rustic inns, local breweries, and a main street lined with gear shops and cozy cafés. The surrounding forests and hills provide endless opportunities for hiking, camping, and wildlife watching. Roscoe’s blend of sporting heritage, natural beauty, and small-town friendliness makes it a must-visit for anyone seeking both adventure and relaxation in the Catskills.



Things to See & Do:

• Things to Do:

- Go fly fishing at Junction Pool or Willowemoc Creek.

- Visit the Catskill Fly Fishing Center & Museum.

- Enjoy craft beer at Roscoe Beer Company.

- Explore the Roscoe O&W Railway Museum.

- Picnic or play at Trout Town USA Park.

- Attend the annual Trout Parade.

- Shop at local outfitters for fishing gear.

- Camp or hike in nearby state forests.



• Things to See:

- The confluence of Beaverkill and Willowemoc at Junction Pool

- Catskill Fly Fishing Center & Museum’s riverside campus

- Roscoe Diner’s classic neon sign

- Willowemoc Creek’s trout-filled waters

- Beaverkill Covered Bridge’s historic wooden span (nearby)

- Trout Town USA Park’s riverfront setting

- Roscoe O&W Railway Museum’s vintage railcars

- Rolling hills and farmland surrounding the hamlet



• Golf Courses: Roscoe Mountain Club, Villa Roma Resort Golf Course, Twin Village Golf Course



• Museums: Catskill Fly Fishing Center & Museum, Roscoe O&W Railway Museum, Time and the Valleys Museum (Grahamsville, nearby)



• Local Markets: Roscoe Farmers Market, Livingston Manor Farmers Market (nearby), Callicoon Farmers Market (nearby), Roscoe Beer Company Market



• Local Restaurants & Shopping

- Restaurants: Roscoe Diner, The Junction, Raimondo’s Restaurant & Pizzeria, Roscoe Beer Co., The Courtyard, Riverside Café, Northern Farmhouse Pasta

- Shops: Beaverkill Angler, Roscoe Beer Co. Shop, Catskill Flies, Prohibition Distillery Shop, Junction Pool Gifts, Roscoe General Store, Northern Farmhouse Pasta Shop



Annual Festivals & Events:

• Roscoe Trout Parade

• Roscoe Rockland Chamber of Commerce Fall Festival

• Catskill Fly Fishing Center Summerfest

• Livingston Manor Trout Parade (Livingston Manor, nearby)

• Callicoon Country Fair (Callicoon, nearby)

• Roscoe Beer Fest

• Roscoe Catskills Pride Festival

• Livingston Manor Ice Carnival (Livingston Manor, nearby)

• Delaware County Fair (Walton, nearby)

• Sullivan County Fair (Liberty, nearby)



Getting Around:

- Winter Access Notice: A 4WD or AWD vehicle is strongly recommended to access the home during the snowy season. Guests without the appropriate vehicle may be unable to reach the property. Portoro cannot be held responsible for access issues or assist if a vehicle becomes stuck.



Getting around Roscoe is part of the adventure—quiet roads follow trout streams and wind through wooded hills, making each drive peaceful and picturesque. With a car, you can easily reach fishing spots, breweries, and neighboring towns, with minimal traffic and plenty of places to stop.



Route 17 provides quick access to other Catskills destinations, while local byways lead to scenic overlooks and the heart of “Trout Town, USA.” Every drive offers a chance to spot wildlife, cross a covered bridge, or discover a new picnic spot by the river.



Cell service is generally reliable in town, but can fade in remote areas, so download maps ahead of time. Parking is easy and free, and the relaxed pace means you can truly enjoy the journey as much as the destination.



Airports:

• Stewart International Airport (SWF): 1 hour 40 minutes

• Albany International Airport (ALB): 2 hours

• New York City Airports (JFK/LGA/EWR): 2.5–3 hours

• Wilkes-Barre/Scranton International Airport (AVP), PA: 1 hour 45 minutes



Popular Landmarks:

• Roscoe Diner (classic eatery)

• Junction Pool (famous fly-fishing spot)

• Catskill Fly Fishing Center & Museum (nearby)

• Trout Town USA Park (recreation)

• Roscoe O&W Railway Museum (railroad history)

• Roscoe Beer Company (brewery)

• Beaverkill Covered Bridge (historic, nearby)

• Willowemoc Creek (fishing, nature)

• Roscoe Campsite Park (camping, events)

• Catskill Scenic Trail (biking/hiking, nearby)

• Trout Parade (annual event)