39 N Chestnut St
Listing Notes
Charming 1890 brick Victorian triplex in the heart of the Village of New Paltz. Located at 39 N Chestnut St, this well-maintained multi-family property offers a rare opportunity for both owner-occupants and investors seeking strong, consistent rental income in one of the Hudson Valley's most sought-after and high-demand village locations. It also presents a unique tri-family getaway opportunity, ideal for extended family use, multi-generational living, or a shared Hudson Valley retreat with income potential. The location is truly exceptional - set in the vibrant village core where everything is just steps away. Enjoy immediate access to SUNY New Paltz, local cafes, restaurants, shops, and daily conveniences, along with direct proximity to the Rail Trail for recreation and an easy connection to the broader Hudson Valley lifestyle. The Trailways bus station is also nearby, providing direct and convenient access to New York City for commuters and visitors alike. The property features a total of 3,273 square feet with three separate units. The first floor consists of a spacious 2-bedroom apartment with an additional flex room that generates $3,150/month. The second-floor unit is a 3-bedroom apartment with a monthly rental income of $2,625. The third-floor unit is a 4-bedroom apartment generating $2,735/month. Total monthly rental income is $8,510, equating to $102,120 annually. Recent improvements include a new roof installed in 2025. Tenants are responsible for their own heat and electric, helping to minimize owner expenses. The property offers off-street parking at the rear, along with a detached garage. A rare opportunity to own a character-filled 1890 brick Victorian multi-family property in a premier Village of New Paltz location - offering strong income, long-term upside, and unmatched walkability in a consistently in-demand rental market.
Price in context
Cheaper than 29% of the 24 homes listed nearby right now, which run $550,000 to $1,400,000.
See all 24 nearby listings
| Address | Asking | Size |
|---|---|---|
| 91 Mountain Rest Rd | $550,000 | 2 bd · 1 ba |
| 307 Old Kingston Rd | $570,000 | 4 bd · 2 ba |
| 6 Hickory Hill Rd | $599,000 | 3 bd · 2 ba |
| 3 Dogwood Holw | $599,999 | 4 bd · 2 ba |
| 441 N Ohioville Rd | $639,000 | 4 bd · 2 ba |
| 137 Plains Rd | $649,000 | — |
| 83 Jansen Rd | $695,000 | — |
| 189 Horsenden Rd | $695,000 | 3 bd · 3 ba |
| 213 Huguenot St | $729,000 | 3 bd · 3 ba |
| 31 Millbrook Rd | $775,000 | 2 bd · 2 ba |
| 10A Cooper St | $820,000 | 3 bd · 3 ba |
| 10 Cooper St Unit A | $820,000 | 3 bd · 3 ba |
| 86 State Route 32 S | $849,000 | 3 bd · 2 ba |
| 112 Dubois Rd | $850,000 | 4 bd · 4 ba |
| 11 Spies Rd | $875,000 | 3 bd · 3 ba |
| 10 Deerpath Dr | $975,000 | 3 bd · 3 ba |
| 40 Kleine Kill Dr | $997,500 | 3 bd · 3 ba |
| 3 Ann St | $999,999 | 7 bd · 4 ba |
| 1 Rapp Hill Rd | $1,099,000 | 3 bd · 4 ba |
| 10 Taylor St | $1,137,500 | 3 bd · 3 ba |
| 348 Libertyville Rd | $1,250,000 | 3 bd · 2 ba |
| 11-13 Olev Ln | $1,300,000 | 11 bd |
| 161 Mountain Rest Rd | $1,399,000 | 2 bd · 3 ba |
| 239 Springtown Rd | $1,400,000 | — |
Where it is
For sale Coming soon Recently sold— zoom out for more