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39 Orchard Drive

Ossining, NY 10562 · Westchester County

Beds
4
Baths
1.5
Sqft
2,448
Status
Coming Soon
On site
Today

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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. A special Ossining home ready for its next chapter.

Listed with Compass Greater NY, LLC · Valerie Cascione · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 19, 2026, 2:07 PM ET. ©2026 One Key MLS.

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Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and Private Mortgage Insurance.

$5,709.23Total / mo

Estimated Monthly Payment

Principal & interest
$3,837.15 (67.2%)
Taxes
$1,672.08 (29.3%)
Insurance
$200.00 (3.5%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

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Market Insights

The market around Ossining, NY

Current Listings

New in the last 30 days

24

Sep 2026

Average Price

Active listings

$913,640

Sep 2026

Average Days on Market

Active listings

101 days

Sep 2026

Computed from 104 active OneKey MLS listings in Ossining, NY.

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