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Single family home for sale at 21 Wilderness Rd, Smithtown, NY 11780 | MLS# 1027742 | Listing updated on 2026-10-09
Photo 1 of Single family home for sale at 21 Wilderness Rd, Smithtown, NY 11780 | MLS# 1027742 | Listing updated on 2026-10-09
Photo 2 of Single family home for sale at 21 Wilderness Rd, Smithtown, NY 11780 | MLS# 1027742 | Listing updated on 2026-10-09
Photo 3 of Single family home for sale at 21 Wilderness Rd, Smithtown, NY 11780 | MLS# 1027742 | Listing updated on 2026-10-09
Photo 4 of Single family home for sale at 21 Wilderness Rd, Smithtown, NY 11780 | MLS# 1027742 | Listing updated on 2026-10-09
31+
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Street View

$1,419,999

Monthly Est:$7,068

  • Beds Icon4 Beds
  • Beds Icon
    4 Baths
  • Beds Icon2,905sqft

21 Wilderness Rd, Smithtown, NY 11780

$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 perf
ect 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 OneKey MLS-NY

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Suffolk County

  • City

    Smithtown

  • 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

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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 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

DateEventPrice

09/17/2026

Source: mls_logoOneKey MLS-NY #KEY1027742

Price Decreased

$1,419,999 -4.70%

$489/sqft

07/22/2026

Source: mls_logoOneKey MLS-NY #KEY1027742

Listed for Sale

$1,489,999

$513/sqft

07/22/2026

Source: mls_logoOneKey MLS-NY #KEY1027742

Price Increased

$1,489,999 +88.61%

$513/sqft

12/01/2024

Source: mls_logoOneKey MLS-NY #KEYL3016346

Price Increased

$790,000 +21.54%

$272/sqft

11/27/2024

Source: mls_logoOneKey MLS-NY #KEYL2675982

Sold

$650,000

$224/sqft

Nearby Homes

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.

Advertising Broker: Derek Greene | The Greene Realty Group