274 River Road
Smithtown, NY 11787
The Landing
6 Beds
5.5 Baths
6,268 sqft (on 8.95 acres)
6 Beds
5.5 Baths
6,268 sqft
(on 8.95 acres)
Local Information
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Description
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.
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.
Home Highlights
Parking
Garage
Outdoor
Patio
A/C
Heating only
HOA
None
Price/Sqft
$287
Listed
9 days ago
Last check for updates: about 14 hours ago
Listing by: Daniel Gale Sothebys Intl Rlty, (631) 584-6600
Bonnie Glenn, (631) 921-1494
Source: OneKey® MLS as distributed by MLS GRID, MLS#1004553
Also Listed on OneKey® MLS as distributed by MLS GRID.
Home Details for 274 River Road
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Interior Details Basement: Full,Storage Space,UnfinishedNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Master Bathroom, Bathroom 1, Basement, Den, Dining Room, Kitchen, Laundry, Living Room |
Beds & Baths Number of Bedrooms: 6Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 6268 Square Feet |
Appliances & Utilities Utilities: Cable Available, Electricity Connected, Phone Available, Trash Collection Public, Water ConnectedAppliances: Cooktop, Dryer, Oven, RefrigeratorDryerLaundry: Washer/Dryer Hookup,Electric Dryer Hookup,Laundry Room,Washer HookupRefrigerator |
Heating & Cooling Heating: Forced Air,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 3Fireplace: Family Room, Living Room, Wood BurningHas a Fireplace |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Flooring: Hardwood, Tile |
Levels, Entrance, & Accessibility Levels: TwoFloors: Hardwood, Tile |
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Exterior Home Features Patio / Porch: PatioOther Structures: Garage(s)No Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas Open ParkingParking Spaces: 3Parking: Driveway,Garage |
Frontage WaterfrontWaterfront: River Front, WaterfrontRoad Frontage: MunicipalResponsible for Road Maintenance: Public Maintained RoadOn Waterfront |
Water & Sewer Sewer: Cesspool |
Farm & Range Not Allowed to Raise Horses |
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Cumulative Days on Market: 1Days on Market: 9 |
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Year Built Year Built: 1905 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial |
Building Construction Materials: BrickNot Attached Property |
Property Information Condition: ActualNot Included in Sale: See listing agentParcel Number: 0800080000100001007 |
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Price List Price: $1,800,000Price Per Sqft: $287 |
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MLS Status: Active |
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Direction & Address City: Saint James |
School Information Elementary School: Dogwood Elementary SchoolJr High / Middle School: Nesaquake Middle SchoolHigh School: Smithtown High School-EastHigh School District: Smithtown |
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Listing Agent Listing ID: 1004553 |
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Building Area Building Area: 6268 Square Feet |
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Not Senior Community |
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No HOA |
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Lot Area: 8.95 Acres |
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Special Conditions: None |
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Listing Agreement Type: Exclusive Right To Sell |
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BasementMls Number: 1004553Attic: UnfinishedAttribution Contact: 631-584-6600Showing Requirements: Appointment Only, Call Listing Agent, Occupied, Restricted Hours, See Remarks |
Market trends in Smithtown
Last updated April 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
65 14MoM
Price History for 274 River Road
| Date | Price | Event | Source |
|---|---|---|---|
| 05/26/2026 | $1,800,000 | Listed For Sale | OneKey® MLS as distributed by MLS GRID #1004553 |
| 11/23/1994 | $625,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $2,175,000 |
Home facts updated by county records
Comparable Sales for 274 River Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.39 | Single-Family Home | $2,000,000 | 03/20/26 | 6 | 4.5 | 6,000 | |
0.39 | Single-Family Home | $1,450,000 | 02/13/26 | 6 | 4.5 | 4,800 | |
0.40 | Single-Family Home | $999,600 | 02/06/26 | 5 | 3.5 | 2,800 | |
0.56 | Single-Family Home | $1,750,000 | 02/09/26 | 6 | 5 | 4,479 | |
0.42 | Single-Family Home | $620,000 | 12/31/25 | 4 | 2.5 | 2,546 | |
0.50 | Single-Family Home | $980,000 | 10/29/25 | 5 | 4.5 | 3,066 | |
0.38 | Single-Family Home | $1,200,000 | 10/09/25 | 5 | 3 | 2,800 | |
0.26 | Single-Family Home | $825,000 | 11/20/25 | 4 | 2 | 2,200 | |
0.55 | Single-Family Home | $969,000 | 10/10/25 | 4 | 2.5 | 3,876 | |
0.42 | Single-Family Home | $950,000 | 12/17/25 | 4 | 2.5 | 2,581 |
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Assigned Schools
These are the assigned schools for 274 River Road.
- Dogwood Elementary School
- K-5
- Public
- 350 Students
7/10GreatSchools RatingParent Rating AverageN/AParent Review16y ago - Nesaquake Middle School
- 6-8
- Public
- 466 Students
6/10GreatSchools RatingParent Rating AverageThis school had good teachers BUT the guidance system SUCKED!!!! It was rigged against actual bullying victims, victim blaming them for being harassed, I speak for me and my friends who have dealt with this exact situation. They don’t punish kids for harassing other students, a little ‘talk’ is all they do and it does NOTHING! Please… for the love of god… be fair to the victims. I hardly felt safe there my years of middle school due to the counselors not being helpful. If the school sees this, please stop blaming the victims, I guarantee you 99% of the time it isn’t their fault that they’re being harassed. Get a better system <3Other Review10mo ago - Smithtown High School East
- 9-12
- Public
- 1403 Students
9/10GreatSchools RatingParent Rating Averageits really bad and boring to be atOther Review2y ago 
Check out schools near 274 River Road.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Bonnie Glenn, Daniel Gale Sothebys Intl Rlty, (631) 584-6600
Agent Phone: (631) 921-1494
Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information
274 River Road, Smithtown, NY 11787 is a 6 bedroom, 6 bathroom, 6,268 sqft single-family home built in 1905. 274 River Road is located in The Landing, Smithtown. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on May 26, 2026. The MLS # for this home is MLS# 1004553.