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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!
| DAYS ON MARKET | 181 | LAST UPDATED | 1/7/2026 |
|---|---|---|---|
| YEAR BUILT | 0 | COMMUNITY | 300 |
| GARAGE SPACES | 2.0 | COUNTY | ESSEX |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| PRICE HISTORY | |
| Prior to Aug 6, '25 | $1,099,000 |
|---|---|
| Aug 6, '25 - Aug 20, '25 | $1,079,000 |
| Aug 20, '25 - Sep 22, '25 | $1,059,000 |
| Sep 22, '25 - Nov 19, '25 | $999,000 |
| Nov 19, '25 - Jan 7, '26 | $950,000 |
| Jan 7, '26 - Today | $899,000 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| AREA | 300 |
| BASEMENT | Partially Finished, Yes |
| CONSTRUCTION | Brick |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Forced Air, Natural Gas |
| LOT DESCRIPTION | Corner Lot |
| POOL DESCRIPTION | None |
| TAXES | 27560 |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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All information deemed reliable but not guaranteed. Last date updated: 1/14/26 5:13 AM PST Source: New Jersey Multiple Listing, Inc.
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