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39 N Chestnut Street, New Paltz, NY, 12561

9beds
4baths
3,273sqft
$999,999
$306price/sqft
$7,335/moest. monthly cost
$293,400/yrincome needed

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

84
WalkingVery Walkable
0
TransitVery Limited Transit
58
BikeBikeable

Schools

--
Duzine SchoolGrades PK-20.8 mi
9/10
New Paltz Middle SchoolGrades 6-80.5 mi
8/10

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
    Strong WindRelatively High
  • Cold Wave
    Cold WaveModerate
  • Inland Flooding
    Inland FloodingModerate
  • Lightning
    LightningModerate
  • Tornado
    TornadoModerate
  • Winter Weather
    Winter WeatherModerate

How This Home’s Risks Compare

Strong Wind
Cold Wave
Inland Flooding
Lightning
Tornado
Winter Weather

FEMA Declared Disasters in Ulster County and New York

Flood
Severe Storm

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

MonthlyAnnual
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
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$251,485/yr
40% on housing$220,050/yr
45% on housing$195,600/yr

New York FAIR Plan Programs

New York Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 20,669Commercial: 1,556
Total Premiums$32.27M
Total Exposure$7.63B

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.

Insurance Growth Rate5-year average: 2.7%
2.7%
0%30.0%
Electricity Growth Rate10-year average: 7.1%
7.1%
0%15.0%
Property Taxes Growth Rate2-year average: -1.2%
-1.2%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$306This listing

vs Other Active Listings

Avg $/sqft

ZIP 12561$277
Ulster County$304

vs Homes Sold Last Month

Median $/sqft

ZIP 12561$289
Ulster County$261

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

DateEventPrice
2026-07-10Price change$999,999
2026-05-20Listed for sale$1,199,999

For Sale by Agent

AgentJacob M. Cohen
BrokerageeXp Realty

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