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MLS ID KEY1052611Last updated Oct 10, 2026

Single Family

39 Orchard Drive

Pending · Ossining · Westchester County, NY 10562

Bedrooms
4 Beds
Bathrooms
2 Baths
Year built
1929
Est. monthly taxes
$1,672.08
Property gallery0 / 40
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About this home

Set back on a lush, level .43-acre property and framed by mature trees, this classic 1929 Dutch Colonial offers a wonderful sense of privacy and calm. Quiet and tucked away, yet convenient to the many amenities that make Ossining such a desirable place to call home, the setting is one of this property’s standout features. Inside, the gracious traditional layout reflects the craftsmanship and character of an earlier era, with solid wood doors, wood floors, ample closets, and charming architectural details throughout. A welcoming foyer opens to the formal living room with fireplace and formal dining room. The eat-in kitchen connects to a bright family room addition with vaulted ceiling and direct access to the yard, while a fabulous screened-in porch just off the dining room provides an inviting seasonal space for morning coffee, casual meals, or summer evenings. A convenient half bath completes the first floor. Upstairs are four comfortably sized bedrooms with generous closet space and a full hall bath, along with access to a large walk-up attic offering exceptional storage. The full basement provides laundry, utilities, additional storage, and a dedicated workshop area. Outdoors, the expansive level property features mature plantings, open lawn, ample driveway parking, and a spacious detached 2 1/2 car garage with attic storage. Lovingly maintained by its longtime owners, this nearly century-old home combines period character, substantial property, comfortable living space, and thoughtful updates made over the years including New Boiler and radiant floor heating system (main) + radiant baseboard on second floor (2023) and New Roof (2024). A truly special Ossining home ready for its next chapter.

Listing snapshot

Days on site
40 days
Listed on MLS
Sep 23, 2026
Full baths
1
Half baths
1
Annual property tax (MLS)
$20,065
Tax year
2026
Area source (MLS)
Public Records
Listing brokerage
Compass Greater NY, LLC
MLS ID
KEY1052611
Last updated
Oct 10, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1929
Garage
Yes
Garage spaces
2
Parking
Detached, Driveway, Garage, Oversized
Water source
Public
Sewer
Public Sewer
Utilities
Cable Connected, Electricity Connected, Phone Connected, Sewer Connected, Trash Collection Public, Water Connected

Interior features

Basement
Bilco Door(s), Full, Storage Space, Unfinished
Heating
Oil, Radiant, Radiant Floor
Cooling
None
Interior
Cathedral Ceiling(s), Ceiling Fan(s), Eat-in Kitchen, Entrance Foyer, Formal Dining, Pantry, Storage, Walk Through Kitchen
Appliances
Dishwasher, Dryer, Electric Range, Refrigerator, Washer
Flooring
Combination, Hardwood, Laminate, Wood
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Colonial
Construction materials
Vinyl Siding
Exterior
Basketball Hoop, Garden, Mailbox
Private pool
No

Schools (MLS)

Elementary school
Brookside
Elementary school district
Ossining
Middle school
Anne M Dorner Middle School
Middle school district
Ossining
High school
Ossining High School
High school district
Ossining

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

Ossining · Westchester County, NY 10562Show interactive map
39 Orchard Drive

Ossining · Westchester County, NY 10562

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Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
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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.