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$399,000 Sale Pending
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Property Description
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.
Full Property Details
Full Property Details for 5 Henry St
General
- Price: $399,000
- Taxes: $8,594
- Status: Pending
- Type: Multi-Family
- Source: Long_Island
- MLS ID: 1044575
- Updated: 9/29/2026
- Added to Site: 40 day(s) ago
Interior
- Interior Features: First Floor Bedroom, First Floor Full Bath, Eat-in Kitchen
- Flooring: Vinyl, Wood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Exterior
- Porch/Patio/Deck: Covered, Porch
Parking
- Total Spaces: 4
- Parking Features: Driveway
Location
- County: Dutchess County
- Cross Streets: Dutcher Avenue
- Driving Directions: Dutcher Avenue to Henry Street. Home on the corner, see sign. Park across the street in the 3 hour parking spots.
School Information
- High School District: Pawling
- Elementary School: Pawling Elementary School
- Middle School: Pawling Middle School
- High School: Pawling High School
Heating & Cooling
- Cooling Type: None
- Heating Type: Electric, Oil
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Sewer Connected, Trash Collection Public, Water Connected
Structural Information
- Architectural Style: Colonial
- Detached/Attached: Detached
- Construction: Frame, Stone
- Basement: Yes
- Basement Desc.: Partial, Unfinished
- Building Size: 2424
- Square Feet: 2,424
- Year Built: 1900
Additional Structures
- Other Structures: Shed(s)
Lot Features
- Property View: Neighborhood
- Lot Size (Acres): 0.1
- Lot Size (Sq. Ft.): 4,356
- Frontage: Municipal
- Lot Features: Back Yard, Corner Lot, Front Yard, Level, Near Golf Course, Near Public Transit, Near School, Near Shops
Financial Considerations
- Tax Amount: $8,594
- Tenant Pays: Electricity, Heat, See Remarks
Disclosures and Reports
- Special Conditions: None
- Property ID: 134001-6956-08-997956-0000
Listed by McGrath Realty Inc
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Schools
Schools serving 5 Henry St
School District:Pawling Central School District
| Name | Grades | Distance |
|---|---|---|
Pawling Elementary School 7 Haight Street, Pawling, NY 12564 | K-4 | 0.4 mi |
Pawling Middle School 80 Wagner Drive, Pawling, NY 12564 | 5-8 | 1.6 mi |
Pawling High School 30 Wagner Drive, Pawling, NY 12564 | 9-12 | 1.5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5 Henry St
Date
Details
Price
Change
Source
9/01/2026
Listed
$399,000
99.5%
MLS
6/18/2018
Sold
$200,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 5 Henry St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,873
29%
$98,100
—
2024
$6,881
365%
$98,100
—
2020
$1,481
-49%
$98,100
—
2021
$2,910
-64%
$98,100
—
2020
$8,009
-9%
$98,100
18%
2018
$8,847
33%
$83,100
—
2017
$6,668
-1%
$83,100
—
2016
$6,735
-2%
$83,100
—
2015
$6,869
—
$83,100
—
2015
$6,889
1%
$83,100
—
2013
$6,853
—
$83,100
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5 Henry St
5 Henry Street, Pawling, NY 12564 (MLS# 1044575) is a Multi-Family property with 2 units containing 4 bedrooms and 3 full bathrooms. 5 Henry Street is currently listed for $399,000 and was received on September 01, 2026. Want to learn more about 5 Henry Street? Do you have questions about finding other Multi-Family real estate for sale in Pawling? You can browse all Pawling real estate or contact a Coldwell Banker agent to request more information.
