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$1,399,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 2 Car Garage
  • Updated 1 day ago

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Open House: 2:00 PM - 4:00 PM

Saturday 5/9 2:00 PM - 4:00 PM

21 Winding Way,West Orange Township, NJ 07052

21 Winding WayWest Orange TownshipNJ07052

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  • Open House: 2:00 PM - 4:00 PM

    Sunday 5/10 2:00 PM - 4:00 PM

    21 Winding Way,West Orange Township, NJ 07052
    21 Winding WayWest Orange TownshipNJ07052
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Stunning 5-Bedroom Colonial in West Orange's Upper Gregory Section This beautifully maintained, oversized Colonial is set in the highly sought-after Upper Gregory section of West Orange, offering classic curb appeal with a siding-and-brick exterior and a welcoming front porch. The home blends timeless style with modern functionality in a prime residential setting.Inside, you'll find 5 spacious bedrooms each with generous closet space, 4 full bathrooms, and 2 half baths, providing ample space for comfortable living. The heart of the home is an open-concept kitchen that flows seamlessly into a family room anchored by a cozy gas fireplace perfect for effortless entertaining. Expanding your living options are two bonus levels: a newly finished basement with high ceilings (ideal for a home gym or theater) and a fully finished third floor that serves as a private office suite or additional bedroom. Outside, enjoy a two-car garage, a large front lawn framed by mature trees, and a private setting that offers both space and convenience. Located near top-rated schools, parks, shopping, and major highways, with an easy commute to Manhattan.A rare opportunity to own a move-in-ready home in one of West Orange's most desirable neighborhoods.

Full Property Details for 21 Winding Way

General

  • Price: $1,399,000
  • Taxes: $25,668 (2025)
  • Status: Active
  • Type: Single Family
  • Source: Garden_State
  • MLS ID: 4025153
  • Updated: 5/7/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 17
  • 3rd Floor/Level 3: Office, Powder Room, Storage Room
  • 2nd Floor/Level 2: 4 Or More Bedrooms, Bath Main, Bath(s) Other, Laundry Room
  • 1st Floor/Level 1: Breakfast Room, Den, Dining Room, Family Room, Foyer, Kitchen, Living Room, Pantry, Powder Room
  • Lower Level: Other Bath, Exercise Room, GameRoom, Rec Room, SittngRm
  • Interior Features: Wet Bar, Jacuzzi-Type Tub, Smoke Detector, Stall Shower, Walk-In Closet
  • Number of Fireplaces: 1
  • Fireplace(s): Family Room, Gas Fireplace
  • Appliances: Carbon Monoxide Detector, Cooktop - Gas, Dryer, Washer
  • Flooring: Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 4
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Full Bath, Walk-In Closet
  • Bedroom 1: 16 x 23, Second
  • Bedroom 2: 11 x 15, Second
  • Bedroom 3: 19 x 13, Second
  • Bedroom 4: 13 x 11, Second

Other Rooms

  • Living Room: 15 x 15, First
  • Family Room: 21 x 15, First
  • Kitchen: Center Island, Eat-In Kitchen, 12 x 14, First
  • Dining Room: 13 x 17, First
  • Den: 13 x 11, First
  • Bedroom: 13 x 12, Second
  • Office: 30 x 24, Third
  • Exercise Room: 17 x 15, Basement
  • Game Room: 17 x 15, Basement

Additional Information

  • Shared Amenities: Billiards Room

Exterior

  • Exterior Features: Curbs

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Uncovered Spaces: 4
  • Garage Description: Attached Garage

Location

  • County: Essex
  • Subdivision: Upper Gregory
  • Driving Directions: Gregory to Winding Way

School Information

  • Elementary School: GREGORY
  • Middle School: ROOSEVELT
  • High School: W ORANGE

Heating & Cooling

  • Cooling Type: 4+ Units, Central Air Conditioning
  • Heating Type: 4+ Units, Forced Hot Air
  • Heating Fuel: Natural Gas
  • Water Heater: Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public Water
  • Utility Description: Electric, Gas In Street, Natural Gas

Structural Information

  • Architectural Style: Colonial
  • Basement: Yes
  • Basement Desc.: Finished, Full
  • Roof: Asphalt Shingles
  • Year Built: 2006
  • Remodeled/Updated: 2025

Lot Features

  • Lot Size (Acres): 0.32
  • Lot Size: 13877 SQ. FT
  • Driveway/Sidewalk: 2 Car Width
  • Lot Description: Flag Lot

Financial Considerations

  • Assessment Amount: $977,100
  • Land Assmt: $341,000
  • Tax Amount: $25,668
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: window dressings and wall mounted TV's
  • Disclosures: Yes
  • APN: 1622-00049-0000-00012-0002-
  • Block: 49
  • Lot Number: 12.02

Listed by Prominent Properties Sir

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Listing agent

— 21 Winding Way —

  • Prominent Properties Sir

917-359-8990

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 21 Winding Way

School District:West Orange Town School District
NameGradesDistance
Gregory Elementary School
301 Gregory Avenue, West Orange, NJ 07052
K-50.1 mi
Roosevelt Middle School
36 Gilbert Place, West Orange, NJ 07052
7-80.3 mi
West Orange High School
51 Conforti Avenue, West Orange, NJ 07052
9-122.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 21 Winding Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/07/2026
Listed
$1,399,000
55.44%
MLS
9/29/2023
Sold
$900,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 21 Winding Way

Year
Property Taxes
Change
Tax Assessment
Change
2024
$35,687
10%
$977,100
34%
2022
$32,381
2%
$729,800
—
2021
$31,775
34%
$729,800
—
2021
$23,671
-22%
$729,800
—
2019
$30,367
3%
$729,800
—
2018
$29,469
1%
$729,800
—
2017
$29,090
2%
$729,800
—
2016
$28,389
2%
$729,800
—
2015
$27,856
5%
$729,800
—
2013
$26,623
—
$729,800
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Prominent Properties Sir

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21 Winding Way, West Orange Township, NJ 07052 (MLS# 4025153) is a Single Family property with 5 bedrooms, 4 full bathrooms and 2 partial bathrooms. 21 Winding Way is currently listed for $1,399,000 and was received on May 07, 2026. Want to learn more about 21 Winding Way? Do you have questions about finding other Single Family real estate for sale in West Orange Township? You can browse all West Orange Township real estate or contact a Coldwell Banker agent to request more information.

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