Nearby rentals
Renter hub
Property management
Keller Williams Prosperity Realty
Apartment Amenities
| Central Air | Fireplace |
| Hardwood Floor | Office |
Appliances
| In-Unit Laundry |
Building
| Basement | Onsite Laundry |
Grounds
| Outdoor Space | Three Parking Spaces |
Other
| Fourteen Rooms | Multi Units |
One-time.
One-time. Refundable.
Property Status: Active 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! Office Phone: (973) 696-0077 Copyright © 2026 Garden State MLS, LLC. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
How 57 Winding Way compares to other nearby properties.
Positives
| Zip code | 07052 |
|---|---|
| Type | House for rent |
4-bedroom apartments at 57 Winding Way cost about the same as the average rent price for 4-bedroom apartments in West Orange.
| Month | Median Rent |
|---|---|
| February 2024 | $4,750 |
| May 2024 | $3,500 |
| June 2024 | $3,800 |
| July 2024 | $5,025 |
| August 2024 | $4,870 |
| September 2024 | $4,583 |
| October 2024 | $4,375 |
| November 2024 | $4,500 |
| December 2024 | $4,637 |
| January 2025 | $3,987 |
| July 2025 | $4,900 |
| August 2025 | $4,732 |
| September 2025 | $4,320 |
| October 2025 | $4,000 |
| November 2025 | $4,260 |
| December 2025 | $4,918 |
| January 2026 | $5,700 |
Can I afford to live at 57 Winding Way?
Bedrooms
4+ bedroomsRent-to-income ratio
30%
$228,000/yr
301 gregory ave
w orange, NJ, 7052
21 Claremont Ave #2
4 Beds
$4,500
100 Avalon Blvd
3 Beds
$4,698–$4,855
1 Florence Dr
3 Beds
N/A
21 Claremont Ave #2
4 Beds
$4,500
100 Avalon Blvd
3 Beds
$4,698–$4,855
1 Florence Dr
3 Beds
N/A
