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MLS ID KEY1035919Last updated Sep 28, 2026

Single Family

3846 Route 55

Pending · Pawling · Dutchess County, NY 12564

Bedrooms
4 Beds
Bathrooms
4 Baths
Year built
1963
Est. monthly taxes
$937.92
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About this home

Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to purchase wo additional buildable parcels are available from the same family. MLS and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.

Listing snapshot

Days on site
59 days
Listed on MLS
Aug 11, 2026
Full baths
3
Half baths
1
Annual property tax (MLS)
$11,254.98
Tax year
2025
Area source (MLS)
Public Records
Listing brokerage
Ellis Sotheby's Intl Realty
MLS ID
KEY1035919
Last updated
Sep 28, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1963
Garage
Yes
Garage spaces
2
Total parking
6
Parking
Attached, Detached, Driveway, Garage, Off Street, Private
Water source
Well
Sewer
Septic Tank
Utilities
Electricity Connected, See Remarks

Interior features

Basement
Finished, Full, See Remarks, Walk-Out Access
Heating
Baseboard, Electric
Cooling
Wall/Window Unit(s)
Interior
Eat-in Kitchen, Entrance Foyer, Formal Dining, Open Floorplan, Original Details, Storage, Walk-In Closet(s), Wet Bar
Appliances
Dishwasher, Dryer, Electric Oven, Refrigerator, Washer
Flooring
Carpet, Hardwood, Wood
Fireplace
Yes

Exterior features

Architectural style
Colonial
Construction materials
Advanced Framing Technique, Shingle Siding
Private pool
No

Schools (MLS)

Elementary school
Pawling Elementary School
Elementary school district
Pawling
Middle school
Pawling Middle School
Middle school district
Pawling
High school
Pawling High School
High school district
Pawling

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. MLS status changed
  3. First seen on this site

Location

Pawling · Dutchess County, NY 12564Show interactive map
3846 Route 55

Pawling · Dutchess County, NY 12564

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.