189 Ingalside Road, Greenville

Sprawling Mid-Century Retreat on 25 Acres

Set on nearly 25 park-like acres, this sprawling mid-century ranch offers a rare combination of privacy, character, and comfort. Surrounded by towering trees and peaceful natural beauty, the property feels tucked away in its own private setting while still offering easy access to nearby towns and activities. Inside, warm wood floors, exposed beams, arched architectural details, and oversized windows create a home that feels both expansive and inviting, with flexible spaces suited for full-time living, entertaining, or a weekend escape.

The layout begins with two distinct entry experiences - a casual mudroom-style entrance designed for everyday living, the other a welcoming formal foyer that introduces the home's architectural character from the moment you step inside. The main level is anchored by a dramatic eat-in kitchen with soaring ceilings and floor-to-ceiling windows that fill the space with natural light and frame views of the surrounding landscape. Just beyond, the cozy living room features exposed beams, built-in shelving, and a wood-burning fireplace that centers the space with warmth and character. Three bedrooms and two full baths are located on the first floor, including a spacious primary with vaulted ceilings, an en-suite bath, and direct access to the back patio and hot tub. A custom built studio space and attached garage add flexibility for creative work, hobbies, storage, or workshop use.

Upstairs, the finished attic space offers endless potential - equally suited as a private guest suite, entertainment or movie room, home office, recreation space, or creative retreat. Complete with an additional bath and separation from the main living areas, the upper level provides a comfortable and versatile extension of the home that is especially well-suited for hosting or multi-purpose use.

Outside, the property unfolds across nearly 25 acres of beautifully wooded, park-like grounds with open clearings and trails winding through the trees. A thoughtfully cleared 1.4-mile hiking trail with trail markers winds throughout the property, inviting quiet walks and deeper exploration of the landscape. Near the house, the patio and surrounding backyard create an ideal setting for outdoor dining, grilling, evenings around the fire pit, and relaxing beneath the trees. The combination of mature landscaping, privacy, and usable land gives the property a true retreat-like feel.

Recent improvements include: new roof, completely refurbished fireplace including new brick chimney, flue and firebox, new heat pump/furnace, new gutters, new hot water heater, new well pump, new whole house water filter, and Vivint security system.

Greenville and the surrounding Greene County area have become a destination in their own right, offering a mix of small-town charm, great local spots, and easy access to the outdoors. Spend the afternoon browsing antiques at Pidgin, catch a movie at the Greenville Drive-In, or grab a classic Italian dinner at longtime favorite Vince Anna's. Nearby, James Beard Award nominee Casa Susanna at Camptown has become a regional favorite for its artisanal Mexican cuisine, while Julia's Local in Round Top is loved for its cozy atmosphere and garden-to-table meals. Red Star Cafe & Bakery and See & Be Kitchen in nearby Cairo have also built loyal followings for specialty coffee, fresh sourdough, and farm-to-table bites. With Windham and Hunter nearby for skiing, Catskill and Hudson both within easy reach, and plenty of opportunities for hiking, biking, and exploring, the area offers something to enjoy year-round.

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