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MLS ID KEY1004553Last updated Aug 13, 2026

Single Family

274 River Road

Pending · Smithtown · Suffolk County, NY 11780

Bedrooms
6 Beds
Bathrooms
6 Baths
Year built
1905
Est. monthly taxes
$3,937.08
Property gallery0 / 30
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About this home

Set behind black iron gates and approached by a long sweeping driveway, this extraordinary all-brick estate is a rare offering rich in history, character, and timeless elegance. Originally built in 1905 and set on 8.95 picturesque acres along the scenic Nissequogue River, this landmark property captures the grandeur and old-world appeal of a bygone era while offering an incredible opportunity to restore and reimagine a truly special home. In addition to the main parcel, the property also includes an additional 4.5 acres of wetlands located across the river, creating an exceptionally rare and expansive setting. Steeped in history, the residence once served as a hunting and fishing lodge in the early 1900s and showcases exquisite architectural detailing and craftsmanship rarely found today. Once owned by famed actress Dina Merrill, the estate carries with it a remarkable sense of legacy and prestige. From the moment you enter, the home is filled with warmth and character, featuring impressive millwork, rich wood floors, spacious formal entertaining rooms, and elegant period details throughout. At the heart of the home is the magnificent grand ballroom with soaring ceilings and a stunning stone fireplace — an unforgettable space reminiscent of the estate’s storied past and ideal for grand entertaining. The residence also features a desirable first-floor primary bedroom suite, generously sized rooms throughout, a full basement, and a expansive detached garage. Surrounded by natural beauty and offering exceptional privacy, this remarkable property presents endless potential for those who appreciate historic homes and old-world elegance. Conveniently located just minutes from Long Island beaches, restaurants, shopping, and the LIRR. A truly rare and iconic North Shore estate waiting to be restored to its former glory. Offered in “as is” condition. Please note: Listing photographs reflect the home at the time the current owners purchased the property and do not represent the current interior contents. All contents will be removed prior to closing.

Listing snapshot

Days on site
59 days
Listed on MLS
May 26, 2026
Full baths
5
Half baths
1
Annual property tax (MLS)
$47,245
Tax year
2026
Area source (MLS)
Public Records
Listing brokerage
Daniel Gale Sothebys Intl Rlty
MLS ID
KEY1004553
Last updated
Aug 13, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1905
Garage
Yes
Garage spaces
3
Parking
Driveway, Garage
Water source
Public
Sewer
Cesspool
Utilities
Cable Available, Electricity Connected, Phone Available, Trash Collection Public, Water Connected

Interior features

Basement
Full, Storage Space, Unfinished
Heating
Forced Air, Oil
Cooling
None
Interior
First Floor Bedroom, First Floor Full Bath, Built-in Features, Dry Bar, Eat-in Kitchen, Entrance Foyer, Formal Dining, Primary Bathroom, Recessed Lighting, Storage, Washer/Dryer Hookup
Appliances
Cooktop, Dryer, Oven, Refrigerator
Flooring
Hardwood, Tile
Fireplace
Yes
Fireplaces
3

Exterior features

Architectural style
Colonial
Construction materials
Brick
Private pool
No

Schools (MLS)

Elementary school
Dogwood Elementary School
Elementary school district
Smithtown
Middle school
Nesaquake Middle School
Middle school district
Smithtown
High school
Smithtown High School-East
High school district
Smithtown

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

Recent activity

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

Location

Smithtown · Suffolk County, NY 11780Show interactive map
274 River Road

Smithtown · Suffolk County, NY 11780

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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)
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.