Rare Reimagined Two-Family Farmhouse in the Heart of Woodstock

One property, so many options. We’re excited to share the latest listing from Judith Steinfeld, of Halter Associates Realty. Nestled in the heart of Woodstock, New York, this professionally designed and legally configured two-family residence is only 90 miles from New York City. This unique property embodies a rare opportunity to embrace an immediate live/work lifestyle, create a multi-generational retreat, or invest in a prosperous rental opportunity in one of the Hudson Valley’s most desirable towns.

INSIDE+OUT

Situated on a spacious, beautifully landscaped corner lot along a tranquil, tree-lined street, this home combines vintage charm with modern functionality. Whether you’re looking to make it your permanent residence, enjoy weekend getaways, or invest wisely, this unique and impeccably restored 1920s farmhouse invites you to live, work, and play in one of the most creative and acclaimed small towns in the world.

8 Pine Grove Street, Woodstock, NY | Asking $990,000 | See the full listing HERE
Listing Courtesy of Halter Associates Realty
Judith Steinfeld, Associate Broker | Email [email protected] | Cell 917-596-8533
Gary Heckelman, RE Salesperson | Email [email protected] | Cell 845.532.1178

INSIDE | 5 Beds | 4 Bathrooms | 2426 Square Feet

ABOUT THE APARTMENTS
Throughout this two-family residence, the original wide-plank pine floors and whitewashed ceiling beams radiate warmth and character, while custom finishes throughout infuse an inspiring touch of sophistication. Every room is individually climate-controlled, offering comfort and year-round efficiency. With five bedrooms, four full bathrooms, and a dedicated office, there is abundant space for creativity, relaxation, and entertaining. Furnishings in both apartments are available for purchase, offering a turnkey solution for immediate occupancy or rental.

The Lower Garden Apartment

The lower apartment is a 3-bedroom, 2-bath retreat that includes an open-plan living and dining area overlooking the private garden. It’s beautiful primary suite features cathedral ceilings, skylights, an ensuite bath, and a private deck built around a living tree—an enchanting detail that underscores the home’s harmony with nature. A vintage clawfoot tub, a fully equipped kitchen, and an additional office complete the space, making it equally functional and charming.

The Upper Treetop Apartment

This upper apartment is a serene 2-bedroom, 2-bath haven. The open-concept layout flows seamlessly to a private balcony perched among the trees. A sleek new kitchen, a spacious primary bedroom with a meditation or office nook, and a bright guest room with an ensuite bath make this a truly tranquil space.

OUTSIDE: 0.16 Acres | Corner Lot | Garden | Fire Pit | Private Yard

Each unit features a private entrance and a fully fenced, landscaped backyard, complete with a fire pit. These outdoor spaces create peaceful, separate sanctuaries perfect for lounging or hosting gatherings under the stars.

Off-street parking adds convenience, and the location puts you just minutes away from Woodstock’s iconic restaurants, galleries, shops, and live music venues, as well as the Trailways bus service to New York City. A short drive leads to Catskill Mountain hiking trails, ski areas, swimming holes, and the historic Hudson River waterfront.

“ My husband and I bought this property in 2014, and it’s been a wonderful experience! We met and welcomed many people from around the world when we had it as a seasonal vacation rental. We loved living there because we were right in town and could walk everywhere. Our kids loved having a place to stay, separate but close. My husband passed away last year, and it’s time for me to pass it on to the next owners. I’m a licensed real estate agent and psychotherapist with a lifelong passion for homes, design, and the power of place. Please call me if you’re interested!” – Judith Steinfeld.

This extraordinary property is far more than a home—it’s a versatile sanctuary that offers the perfect blend of style, privacy, and community.

Photos: Franco Vogt

Contact Listing Agents:

Judith Steinfeld, Associate Broker | Email [email protected] | Cell 917-596-8533
Gary Heckelman, RE Salesperson | Email [email protected] | Cell 845.532.1178
8 Pine Grove Street, Woodstock, NY
Listing Courtesy of Halter Associates Realty

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This post is in partnership with Judith Steinfeld | Halter Associates Realty