57 Winding Way

Sq. Ft.
/ Sq. Ft.
Sq. Ft.
per Sq. Ft.

Description

Welcome to 57 Winding Way, a timeless 4-bedroom, 3.5-bath brick Colonial with over 3,300 sq. ft. of living space, plus a finished basement with walk-out access to a tree-lined backyard. Located on a 0.33-acre lot in the desirable Gregory section of West Orange, just 17 miles from Manhattan, this home offers classic charm, generous space, and a peaceful setting near top-rated schools and NYC transit. Inside, you'll find original hardwood floors, custom built-ins, and a stone fireplace anchoring the...Welcome to 57 Winding Way, a timeless 4-bedroom, 3.5-bath brick Colonial with over 3,300 sq. ft. of living space, plus a finished basement with walk-out access to a tree-lined backyard. Located on a 0.33-acre lot in the desirable Gregory section of West Orange, just 17 miles from Manhattan, this home offers classic charm, generous space, and a peaceful setting near top-rated schools and NYC transit. Inside, you'll find original hardwood floors, custom built-ins, and a stone fireplace anchoring the spacious living room. The main level features a dining room, bright breakfast nook, half bath, laundry room, and galley kitchen with stainless steel appliances and wooded views. A flexible-use bonus room and full bath complete the floor. Upstairs, four bedrooms include a large primary suite with fireplace, built-ins, and private bath. The finished basement offers a 36' x 25' rec room with sliders to the yard and a spacious utility/workshop area. Additional highlights include a carport, screened-in porch, and mid-century character throughout. Close to South Mountain Reservation, and minutes to South Orange, Maplewood, and Montclair. A rare opportunity in a sought-after neighborhood!
  1. Listed by Tang Ho • Keller Williams Prosperity Realty • (908) 494-0877

Property Details for 57 Winding Way

Style
Single Family Residence
Sub style
Other
Waterfront
None
Garage
Carport
LISTING UPDATED: 01/10/2026 09:57 AM

Property Details for 57 Winding Way

StatusActive - Active
MLS #25025360
Days on Market193
Taxes$27,560 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built-
Lot Size-
CountyEssex County

Location

Listing Courtesy of Keller Williams Prosperity Realty, Tang Ho
Add your commute

Payment Calculator

$6,678 per month

30 year fixed, 6.15% Interest

Principal and Interest

$4,382

Property Taxes

$2,297

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 57 Winding Way

Summary
Location and General Information
  • Area name: West Orange
  • Flood plain: None
  • Street Name: Winding
  • County Name: ESSEX
  • Status: Active
  • Street Number Numeric: 57
  • Street Direction: East
  • Zip Code: 07052
Taxes and HOA Information
  • Other Charges: True
  • Association: None
  • Additional subst: None
  • Tax: $27,560
Owner
  • Ownership: Private
Property
Lot Information
  • Lot description: Corner Lot
  • Year Built: 1900-1939, Build Prior to 1978
  • Views exposure: East
  • Miscellaneous: Deck / Patio
  • Average Acres: 0.33
Property and Assessments
  • Photo Number: 30
  • CourtAppYN: No
Utilities
  • Sewer: Public Sewer
  • Heatcool: Natural Gas, Forced Air
  • Cooling Type: Central Air
Interior and Exterior Features
Interior Features
  • Bedrooms: 4
  • Baths full: 3
  • Baths partial: 0
  • Basement: Partially Finished
  • Basement Description: Recreational, Utility
  • Number of rooms: 14
  • Lifestyle: Close/Parks
  • Full Baths Total: 3
  • Num of Baths: 3.0
Exterior Features
  • Fireplace: 2 Fireplaces
  • Exterior: Brick
  • Miscellaneous: Deck / Patio
  • Pool Type: None
Agent
Sale and Listing Information
  • Management Phone: (908) 494-0877
  • Search Class: RES, Residential
  • List Price: $899,000.00
  • Listing Date: 07-17-2025
  • Expired Date: 07-16-2026
  • Status Date: 01-06-2026
Showing Information
  • Internet Remarks: Welcome to 57 Winding Way, a timeless 4-bedroom, 3.5-bath brick Colonial with over 3,300 sq. ft. of living space, plus a finished basement with walk-out access to a tree-lined backyard. Located on a 0.33-acre lot in the desirable Gregory section of West Orange, just 17 miles from Manhattan, this home offers classic charm, generous space, and a peaceful setting near top-rated schools and NYC transit. Inside, you'll find original hardwood floors, custom built-ins, and a stone fireplace anchoring the spacious living room. The main level features a dining room, bright breakfast nook, half bath, laundry room, and galley kitchen with stainless steel appliances and wooded views. A flexible-use bonus room and full bath complete the floor. Upstairs, four bedrooms include a large primary suite with fireplace, built-ins, and private bath. The finished basement offers a 36' x 25' rec room with sliders to the yard and a spacious utility/workshop area. Additional highlights include a carport, screened-in porch, and mid-century character throughout. Close to South Mountain Reservation, and minutes to South Orange, Maplewood, and Montclair. A rare opportunity in a sought-after neighborhood!

Property History for 57 Winding Way

DateEvent & SourcePriceAppreciation
Jan 7, 2026

Price Change

NJMLS #25025360

$899,000
Dec 11, 2025

Listed (Active)

NJMLS #25025360

Dec 7, 2025

Under Contract

NJMLS #25025360

Nov 19, 2025

Price Change

NJMLS #25025360

$950,000
Nov 19, 2025

Price Change

GSMLS #3976038

$950,000
Sep 22, 2025

Price Change

NJMLS #25025360

$999,000
Sep 22, 2025

Price Change

GSMLS #3976038

$999,000
Aug 20, 2025

Price Change

NJMLS #25025360

$1,059,000
Aug 20, 2025

Price Change

GSMLS #3976038

$1,059,000
Aug 6, 2025

Price Change

NJMLS #25025360

$1,079,000
Aug 6, 2025

Price Change

GSMLS #3976038

$1,079,000
Jul 17, 2025

Price Change

GSMLS #3976038

$1,099,000
Jul 17, 2025

Price Change

GSMLS #3976038

$1,079,000
Jul 17, 2025

Price Change

GSMLS #3976038

$1,059,000
Jul 17, 2025

Price Change

GSMLS #3976038

$999,000
Jul 17, 2025

Price Change

GSMLS #3976038

$950,000
Jul 17, 2025

Listed (Active)

GSMLS #3976038

$899,000
Jul 16, 2025

Listed (Active)

NJMLS #25025360

$1,099,000
Apr 24, 2025

Sold (Public Record)

Public Record #1558542821

$858,000

+2.2% / yr

Oct 17, 2003

Sold (Public Record)

Public Record #250163946

$535,000
DateEvent & SourcePrice
01/07/2026

Price Change

NJMLS #25025360

$899,000
12/11/2025

Listed (Active)

NJMLS #25025360

12/07/2025

Under Contract

NJMLS #25025360

11/19/2025

Price Change

NJMLS #25025360

$950,000
11/19/2025

Price Change

GSMLS #3976038

$950,000
09/22/2025

Price Change

NJMLS #25025360

$999,000
09/22/2025

Price Change

GSMLS #3976038

$999,000
08/20/2025

Price Change

NJMLS #25025360

$1,059,000
08/20/2025

Price Change

GSMLS #3976038

$1,059,000
08/06/2025

Price Change

NJMLS #25025360

$1,079,000
08/06/2025

Price Change

GSMLS #3976038

$1,079,000
07/17/2025

Price Change

GSMLS #3976038

$1,099,000
07/17/2025

Price Change

GSMLS #3976038

$1,079,000
07/17/2025

Price Change

GSMLS #3976038

$1,059,000
07/17/2025

Price Change

GSMLS #3976038

$999,000
07/17/2025

Price Change

GSMLS #3976038

$950,000
07/17/2025

Listed (Active)

GSMLS #3976038

$899,000
07/16/2025

Listed (Active)

NJMLS #25025360

$1,099,000
04/24/2025

Sold (Public Record)

Public Record #1558542821

$858,000

+2.2% / yr

10/17/2003

Sold (Public Record)

Public Record #250163946

$535,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 57 Winding Way

Taxable ValueLand$341,000Additions$592,000Total$933,000
Tax Record2024$27,561 ($2,297 / month)
Home Facts
Beds0Total Finished SqFt3,198 SqFtAbove Grade Finished SqFt3,198 SqFtStories2Lot Size14,440 SqFtStyleSingle Family ResidenceYear Built1937ZoningR-5CountyESSEXAPN22 00052-0000-00001- 02

Schools near 57 Winding Way

This home is within West Orange Public School District.
Rating
School
Type
Grades
Distance
Public - 6
Public - 9 to 12
Public - K to 5
Public - K to 5
Rating
School
Distance
Edison Middle School
Public6

West Orange High School
Public9 to 12

Redwood Elementary School
PublicK to 5

Pleasantdale Elementary School
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Neighborhood Map and Transit

Similar Homes

Similar Sold Homes

57 Winding Way is a single family home for sale in West Orange, NJ 07052. This property was listed for sale on July 17, 2025 by Keller Williams Prosperity Realty, it's currently listed at $899,000. It has been on the market for a total of 193 days and was last sold on April 24, 2025. This listing's school district is West Orange Public School District. Nearby schools include Edison Middle School, West Orange High School and Redwood Elementary School. 57 Winding Way is a 4-bed, 3-bath, single family home.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Keller Williams Prosperity Realty, Tang Ho

The data relating to the real estate for sale on this website comes in part from the Internet Data Exchange Program of the NJMLS. Real estate listings held by brokerage firms other than (insert office name) aremarked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website. All information deemed reliable but not guaranteed. Last date updated: 01/30/2026 12:21 PM. Source: New Jersey Multiple Listing Service, Inc. © 2026 New Jersey Multiple Listing Service, Inc. All rights. The data relating to the real estate for sale and sold listing information on this website comes from the New Jersey Multiple Listing Service, Inc. Virtual Office Website (VOW) program. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. Sold listings may have been listed and/or sold by a real estate brokerage other than (insert office name). All information deemed reliable but not guaranteed. NLMLS makes no representation or warranty regarding the accuracy of the data. This data and information is protected under federal copyright laws which prohibit the unauthorized copying or alternation of all or any part of copyrighted materials, including certain compilations of data and information. Copyright violators may be subject to severe fines and penalties under federal law. Source: New Jersey Multiple Listing Service Inc. Last date updated: 01/30/2026 12:21 PM © 2026 New Jersey Multiple Listing Service Inc. All rights reserved.