Multi-family homes are a rare find in the Village of Pawling, making this two-family, two-story property an exceptional opportunity for an owner-occupant or investor seeking income-producing real estate in a highly convenient location. The building offers two apartments, including a spacious 3-bedroom, 2-bath residence with approximately 1,680 square feet spanning the first and second floors, and a 1-bedroom, 1-bath apartment with approximately 679 square feet located on the rear of the first floor. Both units are occupied by long-term tenants who would like to remain, while flexible month-to-month leases provide options for a new owner. Apartment 5A is entered through a covered front porch and features an entry with a hall closet, large living room, nicely sized kitchen with dining area, full bath, and access to the basement. Upstairs are three bedrooms, a large bedroom with two closets, a smaller bedroom in the middle and a spacious rear bedroom offering two walk-in closets plus an additional closet. A second full bath completes the upper level. The tenant is responsible for oil heat, electricity and cable, as does the lawn maintenance and snow removal. Apartment 5B has a private rear entrance into a large living room with a hall closet and a convenient closet with a combination washer and dryer. The bedroom features a large walk-in closet, while the kitchen provides space for a table. The full bath includes a walk-in shower. The tenant is responsible for electricity (electric heat), and cable. The landlord is responsible for the propane for the two gas stoves, quarterly municipal water and sewer, and annual garbage service through the Village of Pawling. Each apartment has two tandem parking spaces, with convenient three-hour municipal parking available directly across the street for guests. A large shed provides additional storage, and both tenants enjoy use of the backyard. The location is especially appealing for those who want to enjoy village living without relying on a car. Boutique shops, fine dining, casual eateries, local pubs and the seasonal farmers' market are all just a short distance away, while the Pawling Metro-North train station is less than half a mile from the property. A rare opportunity to own a well-located multi-family property in the heart of the Village of Pawling with established tenants and flexible lease arrangements.
For sale
$399,000
5 Henry Street, Pawling, NY 12564
4beds
2,424sqft
Duplex, Multi Family
Built in 1900
-- sqft lot
$464,500 Zestimate®
$165/sqft
$-- HOA
What's special
- 8 days
- 1,412
- 104
Zillow last checked:
Listing updated:
Listed by:
McGrath Realty Inc 845-855-5550,
Claudia Jiskra 914-447-3761
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1044575
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Electric, Oil
Cooling
- None
Features
- First Floor Bedroom, First Floor Full Bath, Eat-in Kitchen
- Flooring: Vinyl, Wood
- Basement: Partial,Unfinished
- Has fireplace: No
Interior area
- Total structure area: 2,424
- Total interior livable area: 2,424 sqft
Property
Parking
- Total spaces: 4
- Parking features: Driveway
- Has uncovered spaces: Yes
Features
- Patio & porch: Covered, Porch
- Has view: Yes
- View description: Neighborhood
Lot
- Size: 4,356 Square Feet
- Features: Back Yard, Corner Lot, Front Yard, Level, Near Golf Course, Near Public Transit, Near School, Near Shops
Details
- Additional structures: Shed(s)
- Parcel number: 1340016956089979560000
- Special conditions: None
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Colonial
- Property subtype: Duplex, Multi Family
Materials
- Frame, Stone
Condition
- Actual
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Connected, Electricity Connected, Sewer Connected, Trash Collection Public, Water Connected
Community & HOA
Location
- Region: Pawling
Financial & listing details
- Price per square foot: $165/sqft
- Tax assessed value: $98,100
- Annual tax amount: $8,594
- Date on market: 9/1/2026
- Cumulative days on market: 8 days
- Listing agreement: Exclusive Right To Sell
- Tenant pays: Electricity, Heat, See Remarks
- Electric utility on property: Yes
Estimated market value
$464,500
$418,000 - $516,000
$2,364/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/1/2026 | Listed for sale | $399,000+99.5%$165/sqft |
Source: | ||
| 6/18/2018 | Sold | $200,000-14.9%$83/sqft |
Source: | ||
| 4/26/2018 | Pending sale | $235,000+49.7%$97/sqft |
Source: BHHS HUDSON VALLEY PROPERTIES PW #369393 Report a problem | ||
| 4/19/2018 | Sold | $157,000-33.2%$65/sqft |
Source: Public Record Report a problem | ||
| 3/15/2018 | Listed for sale | $235,000-37%$97/sqft |
Source: BHHS Hudson Valley Properties #4810027 Report a problem | ||
| 3/8/2011 | Listing removed | $372,900$154/sqft |
Source: Houlihan Lawrence #263080 Report a problem | ||
| 3/7/2011 | Listed for sale | $372,900+9.7%$154/sqft |
Source: Houlihan Lawrence #263080 Report a problem | ||
| 1/5/2011 | Listing removed | $340,000$140/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 4/20/2010 | Price change | $340,000-3.7%$140/sqft |
Source: Houlihan Lawrence #263080 Report a problem | ||
| 4/17/2010 | Price change | $353,000-0.6%$146/sqft |
Source: Houlihan Lawrence #263080 Report a problem | ||
| 1/30/2010 | Price change | $355,000-5.3%$146/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 11/26/2009 | Price change | $375,000+5.6%$155/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 11/23/2009 | Price change | $355,000-5.3%$146/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 10/6/2009 | Price change | $375,000+5.6%$155/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 10/4/2009 | Price change | $355,000-5.3%$146/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 9/27/2009 | Price change | $375,000+5.6%$155/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 9/26/2009 | Price change | $355,000-5.3%$146/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 6/22/2009 | Price change | $375,000+5.6%$155/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 6/20/2009 | Price change | $355,000-5.3%$146/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 6/6/2009 | Price change | $375,000+0.6%$155/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 4/30/2009 | Price change | $372,900-0.6%$154/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 4/18/2009 | Price change | $375,000+0.6%$155/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 12/21/2008 | Price change | $372,900-0.6%$154/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 12/15/2008 | Price change | $375,000+0.6%$155/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 10/26/2008 | Price change | $372,900-0.6%$154/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 10/25/2008 | Listed for sale | $375,000$155/sqft |
Source: Houlihan Lawrence #2803925 Report a problem | ||
| 8/3/2005 | Sold | $375,000+82%$155/sqft |
Source: Public Record Report a problem | ||
| 5/31/2001 | Sold | $206,000+83.1%$85/sqft |
Source: Public Record Report a problem | ||
| 11/15/1996 | Sold | $112,500$46/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $98,100 |
| 2024 | -- | $98,100 |
| 2023 | -- | $98,100 |
| 2022 | -- | $98,100 |
| 2021 | -- | $98,100 |
| 2020 | -- | $98,100 |
| 2019 | -- | $98,100 +18.1% |
| 2018 | -- | $83,100 |
| 2017 | $5,403 | $83,100 |
| 2016 | -- | $83,100 |
| 2015 | -- | $83,100 |
| 2014 | -- | $83,100 |
| 2012 | -- | $83,100 |
| 2011 | -- | $83,100 |
| 2010 | -- | $83,100 |
| 2009 | -- | $83,100 |
| 2008 | -- | $83,100 |
| 2005 | -- | $83,100 |
| 2004 | -- | $83,100 |
| 2003 | -- | $83,100 |
| 2002 | -- | $83,100 |
Find assessor info on the county website
Monthly payment
Climate risks
Neighborhood: 12564
Nearby schools
Schools provided by the listing agent
- Elementary: Pawling Elementary School
- Middle: Pawling Middle School
- High: Pawling High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.




