5 Downer Ln
Listing Notes
Set on six bucolic acres along one of Woodstock's most scenic country roads, this extraordinary barn residence captures sweeping views of Overlook Mountain, the timeless beauty of the Hudson Valley landscape, and the quiet rhythm of a true farm setting. Reimagined from a historic 19th-century barn that was carefully disassembled and relocated from farther north, the home is a remarkable example of craftsmanship, creativity, and preservation. Following the tradition of Woodstock's celebrated handmade houses, the interiors were assembled over many years from salvaged architectural elements, reclaimed materials, and one-of-a-kind finds - each room richly layered with hand-hewn timbers, antique details, stained glass, and finishes that create an atmosphere unlike anything on the market. The grand living spaces are anchored by soaring timber-frame construction, warm gathering areas inside and out, open meadows, and unobstructed mountain views. The property comfortably accommodates farm animals, making it well-suited for a small hobby farm, equestrian use, or simply a deeper connection to the land. A heated pool, sauna, gym, and generous entertaining spaces complete the picture - along with proximity to Woodstock's beloved swimming holes, hiking trails, and village life. For those seeking a weekend escape, this is the kind of place you stop looking once you find it. For investors, the numbers speak clearly: the property carries a proven short-term rental track record in one of the Hudson Valley's most in-demand markets. Woodstock's STR environment has tightened considerably, making an established, permitted rental operation here a genuine asset - not a starting point. More than a residence, this is a work of art and a sound investment - an authentic expression of Woodstock's creative spirit with the income history to back it up.
Price in context
Cheaper than 29% of the 24 homes listed nearby right now, which run $684,000 to $1,700,000.
See all 24 nearby listings
| Address | Asking | Size |
|---|---|---|
| 24 Ryan Dr | $684,000 | 4 bd · 3 ba |
| 18 Playhouse Ln | $725,000 | 3 bd · 2 ba |
| 17 Knolls Ct | $725,000 | 3 bd · 3 ba |
| 72 Van Dale Rd | $749,000 | 3 bd · 3 ba |
| 364 John Joy Rd | $749,000 | 3 bd · 3 ba |
| 276 Chestnut Hill Rd | $755,000 | 2 bd · 1 ba |
| 31 Pond Park Rd | $775,000 | 3 bd · 2 ba |
| 12 Oriole Dr | $785,000 | 4 bd · 3 ba |
| 25 Pine Grove St | $795,000 | 2 bd · 2 ba |
| 5 Lazy Brook Ln | $799,000 | 4 bd · 3 ba |
| 1 Stone Ridge Ct | $799,000 | 4 bd · 3 ba |
| 5 Maverick Ter | $799,900 | 3 bd · 3 ba |
| 29 Maurizi Ln | $799,999 | 4 bd · 3 ba |
| 97 John Joy Rd | $825,000 | 3 bd · 2 ba |
| 95 W Saugerties Woodstock Rd | $850,000 | 2 bd · 4 ba |
| 15 Chipmunk Ln | $915,000 | 3 bd · 3 ba |
| 9 Chesters Pl | $950,000 | 3 bd · 2 ba |
| 27 Old Wagon Rd | $1,275,000 | 4 bd · 5 ba |
| 94 Chestnut Hill Rd | $1,325,000 | 3 bd · 1 ba |
| 60 Boggs Hill Rd | $1,375,000 | 3 bd · 2 ba |
| 19 Blues Quarry Rd | $1,400,000 | 4 bd · 4 ba |
| 19 Blues Quarry | $1,400,000 | 4 bd · 4 ba |
| 18 Ryan Dr | $1,595,000 | 3 bd · 4 ba |
| 5 7 Downer Ln | $1,700,000 | 5 bd · 5 ba |
Where it is
For sale Coming soon Recently sold— zoom out for more
OpenRealtor, a RealtyLens company. Listing facts are drawn from public feeds and enriched with NYC public records. This is not the original listing site.