




39 N Chestnut Street, New Paltz, NY, 12561
About This Home
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.
Getting Around
Schools
Construction
Condition
- Year built: 1890
Materials
- Construction materials: Brick
Type & Style
- Home type: MultiFamily
- Architectural style: Victorian
- Property subType: Triplex,Multi Family
Interior
Basement
- Has basement: Yes
- Basement: Full,Unfinished,Walk-Out Access
Bedrooms & Bathrooms
- Bedrooms: 9
- Bathrooms: 4
- Full bathrooms: 4
Features
- First Floor Bedroom,First Floor Full Bath,Natural Woodwork
- Attic: None
Heating & Cooling
- Heating features: Forced Air
- Cooling features: None
Interior Area
- Total structure area: 3,273
- Total interior livable area: 3,273 sqft
Property
Details
- Parcel number: 3801086.0340001009.1000000
- Special condition: None
Features
- Exterior features: Courtyard
Lot
- Lot size: 6,534 sqft
- Features: Near Golf Course,Near Public Transit,Near School,Near Shops
Parking
- Total spaces: 1
- Parking features: Driveway,Garage,Parking Lot
- Has garage: Yes
- Attached garage spaces: 1
- Covered spaces: 1
- Has uncovered spaces: Yes
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Strong Wind
- Cold Wave
- Inland Flooding
- Lightning
- Tornado
- Winter Weather
How This Home’s Risks Compare
FEMA Declared Disasters in Ulster County and New York
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $5,056 | $60,672 |
| Home Insurance * | $390 | $4,680 |
| Property Taxes | $1,349 | $16,188 |
| Electricity | $540 | $6,490 |
| Total | $7,335 | $88,020 |
Income You'd Need if You Spent...
New York FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
No zestimate history available
Price History
| Date | Event | Price |
|---|---|---|
| 2026-07-10 | Price change | $999,999 |
| 2026-05-20 | Listed for sale | $1,199,999 |
