Deer Wood Lodge: Callicoon, NY

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About The Property

Tucked away at the end of a long drive that winds through the woods, this sprawling retreat invites you into a peaceful world of natural beauty with space to roam. Set in complete privacy, you’re surrounded by 65 enchanting acres of open lawns, mature trees, forested trails—and two bodies of water: a large, serene pond just below the house, and the trout-filled Callicoon Creek flowing through the woods beyond. It’s the kind of place where time slows down and every season brings something to savor.

The home itself is gracefully perched on the hillside, offering sweeping views of the pond and park-like landscape from nearly every room. Step inside, and you’ll immediately feel the breadth of the space: vaulted ceilings, picture windows framing idyllic vistas.

The house is laid out in such a way that you get two very different, exciting vibes, in a large open concept space. To one side is an area where the dramatic stone fireplace takes center stage —gather ‘round here during crisp winter evenings, where a cozy seating area turns into your seasonal sanctuary. Around the corner, the space opens up to an airy window-wrapped lounge and dining area, filled with natural light and direct access to the expansive deck — a perfect spot for morning coffee, sunset cocktails, or simply taking in the view. Connecting the two is a sleek, modern, chef’s kitchen with a generous island, stainless appliances (including two wall ovens, gas stove, a wine fridge and two beverage fridges), and plenty of room to prep, with long expanses of counterspace. It’s a killer kitchen for cooking, entertaining, or chatting with friends while you prepare a meal sourced from the local farmers’ market in Callicoon, one of the best around.

The layout is as generous as the land: On the ground floor are three bedrooms and one full bathroom (tub/shower) and a large office/den. Upstairs are two more spacious bedrooms and two full bathrooms. One of these is en suite, and includes a Jacuzzi tub and separate shower.

Thoughtfully renovated with comfort in mind, the home features numerous upgrades throughout—including mini-splits for efficient heating and cooling, radiant heat flooring on the lower floor and in the primary bedroom, and a whole-house generator for year-round peace of mind.

Outside, you’ll never run out of places to explore: paddle on the pond, hike through your private woods, fish in the creek, or simply lie back and watch the clouds drift by. Wildlife abounds, birdsong fills the air, and the rhythm of nature becomes part of your daily soundtrack.

All this privacy and seclusion is just minutes from some of Sullivan County’s most charming hamlets—Callicoon, North Branch, Jeffersonville, Livingston Manor, Roscoe, and Narrowsburg are all within a 5–25 minute drive. Whether it’s fine dining, breweries, markets, music, or art you’re after, it’s all nearby. And the drive there? Absolutely stunning.

This is a place to gather, to retreat, and to connect — with nature, with loved ones, and with a simpler pace of life.

Listing Agent: Jennifer Grimes, 845-593-9524