by RH Advisors

Check Availability
$1,298,999
● House - For Sale

21 Wilderness Road

Smithtown, NY 11780
bedrooms
4 Beds
bathrooms
3 Baths, 1 Half Bath
square feet
2,905 Ft²
$8,181
Est. Monthly
$71
HOA / Fees

About This Property

Tucked away on a private road in the desirable Village of Nissequogue, this classic 4-bedroom, 3.5-bath Colonial offers timeless charm, a spacious layout and exceptional privacy on two sprawling, usable acres. Set back from the road, the home welcomes you with formal living and dining rooms, ideal for entertaining. The kitchen features granite countertops, peninsula seating and a sunlit dining area overlooking the picturesque grounds, flowing seamlessly into the inviting family room with a brick fireplace. A convenient first-floor office with built-ins and a separate outside entrance provides flexibility for working from home, while a mudroom/laundry room with access to the two-car garage adds everyday functionality.

Upstairs, the spacious primary suite offers a private retreat with an en suite bathroom featuring dual sinks, a dressing area and walk-in closet. Three additional bedrooms and a full bathroom complete the second level.

Enjoy the tranquility of two expansive acres with plenty of room for outdoor entertaining, recreation or simply taking in the natural surroundings. A private beach (dues) on the Long Island Sound is just a stone's throw away, adding to the appeal of this special location. Village amenities include a dedicated Village Police Department and resident-only Short Beach with its beach and playground. Easy access to museums, golf courses, dining and shopping and conveniently located just 3.8 miles from the St. James train station. A wonderful opportunity to enjoy privacy, space and the sought-after North Shore lifestyle.
Unit Size
2,905 Ft²
Days on Market
111 days
Land Size
2.00 acres
Price per sqft
$447
Property Type
House
Property Taxes
$1,731
HOA Dues
$71
Year Built
1966

Listed By

Sari Eidelkind
Lucky to Live Here Realty
Joyce Mennella
Lucky to Live Here Realty

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Last updated: 11 hours ago (OneKey MLS #KEY1027742)

Price History

Date / Event Date Event Price
Nov 6, 2026 Relisted $790,000
Relisted
Nov 5, 2026 Price Decreased $1,298,999
↓ $121K (8.5%)
Price Decreased
Nov 3, 2026 In contract -
In contract
Sep 18, 2026 Price Decreased $1,419,999
↓ $70K (4.7%)
Price Decreased
Jul 17, 2026 Listed by Serhant East End LLC $1,489,999
Listed by Serhant East End LLC
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Property Highlights

Garage
Air Conditioning
Fireplace
Parking Details
Has Garage
Has Open Parking
Parking Features: Driveway, Garage
Garage Spaces: 2
Interior Details
Half Bathrooms: 1
Full Bathrooms: 3
Interior Features: Built-in Features, Double Vanity, Walk-In Closet(s), Formal Dining, Primary Bathroom
Appliances: Dishwasher, Electric Range, Microwave, Refrigerator
Flooring Type: Hardwood
Laundry Features: Laundry Room
Rooms: 9
Has Fireplace
Fireplace Features: Family Room
Fireplaces: 1
Basement: Partial
Exterior Details
Square Footage: 2905
Square Footage Source: $0
Architectural Style: Colonial
Year Built: 1965
Building Area Units: Square Feet
Construction Materials: Frame
Lot Features: See Remarks
Lot Size Area: 87120
Lot Size Units: Square Feet
Lot Size Acres: 2
Lot Size Square Feet: 87120
Tax Lot: 29
Water Source: Public
Financial Details
Tax Assessed Value: $8,305
Tax Annual Amount: $20,775
Utilities Details
Cooling Type: Central Air
Heating Type: Baseboard
Sewer : Cesspool
Location Details
HOA/Condo/Coop Fee Includes: Other
HOA Fee: $850
HOA Fee Frequency: Annually

Building Info

Overview

    General

  • Year Built: 1966
  • Effective Year Built: 1966
  • Bedroom Count: 4
  • Bathroom Count: 3
  • Full Bathrooms: 2
  • Partial Bathrooms: 3
  • Building Condition: 6
  • Building Quality: 7
  • Construction Type: 0
  • Building Style: 5
  • Exterior Walls Type: 17
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 0
  • Floor Count: 200
  • Floor Cover: 0
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 490
  • Parking Space Count: 2
  • Patio Type: 0
  • Porch Type: 6
  • Pool Type: 0

    Dimensions

  • Lot Size Square Feet: 87,120
  • Total Building Area: 2,841
  • Building Area: 2,841
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 0
  • Heating: 10
  • Heated Square Feet: 2,841
  • Heating Fuel Type: 6

    Utilities

  • Sewer System: 4
  • Water Service: 2

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: MAP OF NORTHWOOD
  • Land Acres: 0000002000
  • Standard Land Use Code: 1001
  • County Land Use Code: 210
  • Legal Description 1: 3.-2-12 *3888 LOT 29 NORTHWOODS SEC 2

Neighborhood

  • School District Name: Smithtown Central School District
  • School Tax School District: SMITHTOWN
  • Census Tract: 135004

Geography

  • District: 0802-0
  • Section: 3.00
  • Parcel: 0802-003.00-02.00-012.000
  • Block: 2
  • Lot: 12.000
  • Municipality: SMITHTOWN
  • Latitude: 40.9114
  • Longitude: -73.1963

    Address

  • Full Address: 21 Wilderness Rd
  • Address - House Number: 21
  • Address - Street Name: Wilderness
  • Address - Suffix Type: Rd
  • State: NY
  • City Name: Saint James
  • Carrier Code: R001
  • 4-Digit Zip Code: 4008
  • Zip Code: 11780

Valuation

    Tax

  • Tax Year: 2023
  • Tax Amount: $1,706,099
  • Tax Rate Code Area: 473401

    Appraisal Valuation

  • Standard Deviation: 0.2677
  • Valuation Date: Feb 14, 2024
  • Confidence Score: 61
  • Final Value: 1,205,256
  • High Value: 1,527,982
  • Low Value: 882,530

    Market Valuation

  • Market Total Value: $9,546
  • Market Land Value: $1,379
  • Market Improvement Value: $8,167

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $8,305
  • Assessed Land Value: $1,200
  • Assessed Improvements Value: $7,105

    Sales

  • Current Sale Contract Date: Nov 02, 2018
  • Current Sale Recording Date: Nov 29, 2018
  • Current Sale Price:
  • Current Sale Document Type: 27
  • Previous Sale Recording Date: Jun 28, 2018
  • Previous Sale Contract Date: May 31, 2018
  • Previous Sale Amount: $900,000
  • Previous Sale Document Type: 27
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Nissequogue


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Frequently Asked Questions

When was property at 21 Wilderness Road built and last sold?
The property at 21 Wilderness Road was built in 1966 and last sold on Nov 2, 2018 for $790,000.
How much is this home worth?
The estimated value of the home located at 21 Wilderness Road is $1,315,572.
What are some comparable homes to 21 Wilderness Road?
There are currently no comparable homes to 21 Wilderness Road.

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