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- Description
- Property Details
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Street View
$1,419,999
Monthly Est:$7,068
4 Beds
- 4 Baths
3 full baths + 1 half bath
2,905sqft
21 Wilderness Rd, Smithtown, NY 11780
$1,419,999
$7,068/moEst:
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Single Family Residence
Built in 1965
$70.83/mo HOA
2 acres lot
$489/sq.ft
Description
Welcome to 21 Wilderness Road, an exceptional Colonial set on two private acres in the Village of Nissequogue, where timeless design and thoughtful updates come together in a private, serene setting. Offering 4 bedrooms and 4 bathrooms, this residence delivers generous living spaces, refined finishes, and effortless everyday comfort.
Hardwood floors, detailed crown molding, and an inviting floor plan create a warm yet elegant atmosphere throughout. The updated kitchen is appointed with granite countertops, abundant cabinetry, and flows seamlessly into the main living areas, making it ideal for both entertaining and everyday living. A fireside sitting area offers the perfect place to gather, while a dedicated home office provides the flexibility to function as a fifth bedroom, guest suite, or private study. One of the home’s most desirable features is its private deeded access to the pristine Long Island Sound, where scenic water views and shoreline access offer an exceptional coastal lifestyle. Along with Additional highlights include, LOW TAXES, Horse property, an oversized two-car garage with attic storage, a newer Peerless boiler with a Riello burner, and an indirect hot water system for added efficiency. This home is surrounded by natural beauty, yet exceptionally connected, this residence is moments from boating, Nissequogue Golf Club, Stony Brook University and charming villages of St. James.
- Houzeo last checked: 12 hours ago
- Listing updated: October 9, 2026 at 1:38 pm
- Listing Provided by: Jennifer Keenan (631) 459-6100 | Serhant East End LLC (646) 480-7665
- Source: OneKey MLS-NY | MLS#: 1027742

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1965
HOA Fees
$70.83/mo
Finished Area
2,905 sqft
Lot Size
2 acres lot
Basement Area
- sqft
MLS Name
OneKey MLS
MLS Number
1027742
MLS Status
Active
Days on Market
79
Cumulative Days on Market
79
Open House

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Location
HOA Management
Nissequogue Wilderness Property Association
HOA Fees
$850/ Annually
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Other
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 4
Interior
Appliances
Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Washer
Sewer
Cesspool
Exterior Features
Garden, Mailbox, Rain Gutters
Cooling
Central Air
Interior Features
Built In Features, Crown Molding, Double Vanity, Formal Dining, Natural Woodwork, Open Kitchen, Other, Primary Bathroom, Stone Counters, Storage, Walk In Closet(s), Washer/dryer Hookup
Heating
Baseboard, Other
Flooring
Hardwood
Construction
Year Built
Year Built: 1965
Home type
Single Family Residence
Property Condition
Actual
Construction Materials
Frame
Architectural Style
Colonial
Utilities & Energy
Water Source
Public
Laundry Features
Electric Dryer Hookup, Gas Dryer Hookup, Laundry Room, Other
Parking Features
Driveway, Garage, Oversized, Private
Fireplace Features
Gas
Utilities
Cable Connected, Electricity Connected, Phone Connected, Trash Collection Public, Water Connected
Basement
Partial
Other Features
Patio And Porch Features
Porch
Subdivision Name
Northwoods
Price History
| Date | Event | Price |
|---|---|---|
09/17/2026 Source: | Price Decreased | $1,419,999 -4.70% $489/sqft |
07/22/2026 Source: | Listed for Sale | $1,489,999 $513/sqft |
07/22/2026 Source: | Price Increased | $1,489,999 +88.61% $513/sqft |
12/01/2024 Source: | Price Increased | $790,000 +21.54% $272/sqft |
11/27/2024 Source: | Sold | $650,000 $224/sqft |
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Based on information from OneKey MLS, through Oct 09, 2026, 02:32PM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.
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