- 4 beds
- 3.5 baths
- 3,400 sqft
- 14,375 sqft lot
- $323 per sqft
- 1937 build
- – on site
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!
Last checked:
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Last updated Jul 17, 2025
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MLS# 3976038 —
This home is listed in more than one place. See it here.
The Building
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Construction Date/Year Built:Renovated
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Construction Date/Year Built:1937
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Renovated Year:2025
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Style:Colonial
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Primary Style:Colonial
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Roof Description:Slate
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Exterior Description:Brick
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Color of Building:White
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Basement:Yes
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Building #:57
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Possible Other Uses:Home-Office
Interior
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Interior Features:Carbon Monoxide Detector, Fire Extinguisher, Walk-In Closet, Window Treatments
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Flooring:Laminate, Tile, Wood
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# of Rooms:14
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Level 1 Rooms:Bath(s) Other, Dining Room, Kitchen, Living Room, Office
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Level 2 Rooms:4 Or More Bedrooms, Bath Main, Bath(s) Other
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Kitchen Level:First
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Kitchen Area:Galley Type
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Living Room Level:First
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Dining Room Level:First
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Family Room Level:Ground
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Basement Description:Finished-Partially
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Other Room 1 Level:First
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Other Room 1:Office
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Other Room 2 Level:Ground
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Other Room 2:Rec Room
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Other Room 3:Utility Room
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Ground Level Rooms:Laundry Room, Rec Room, Utility Room, Walkout
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# of Fireplaces:2
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Fireplace Description:Non-Functional, See Remarks, Wood Burning
Room Dimensions
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Living Room Dimensions:28x26
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Kitchen Dimensions:9x22
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Dining Room Dimensions:13x17
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Family Room Dimensions:36 Sqft
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Bedroom 1 Dimensions:18x16
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Bedroom 2 Dimensions:13 Sqft
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Bedroom 3 Dimensions:13x9
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Bedroom 4 Dimensions:16x13
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Other Room 1 Dimensions:12x12
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Other Room 2 Dimensions:37x25
Financial & Terms
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Possession:Closing
Location
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Directions:Gregory Ave to Winding Way
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Latitude:40.76894
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Longitude:-74.25953
The Property
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Property Subtype:Single Family
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Approx Lot Size:76 Sqft
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Lot Description:Level Lot, Wooded Lot
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Approx SqFt:3,400 Sqft
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Total Acres:0 Sqft
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Lot Identifier:1.02
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Zoning:Residential
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Exterior Features:Deck, Patio
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Easements:Unknown
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Farm Assessment:No
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Assessment Land:341000
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Assess Amount Land Tax:*
Listing Agent
- Contact info:
- Office phone:
- (973) 696-0077
Taxes
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Tax ID:*
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Tax ID For Property:1622-00052-0000-00001-0002-
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Tax Year:2024
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Tax Year:*
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Tax Rate:*
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Tax Rate Year:2024
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Tax Rate Amount:4.684
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Tax Amount:$27,560
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Tax Amount:$*
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Lot ID Tax:*
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Lot Size Tax:*
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Acres Tax:$*
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Block ID Tax:*
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City Tax:$*
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City Code Tax:*
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County Tax:$*
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County Code Tax:*
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Zip Code Tax:*
Beds
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# of Bedrooms:4
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Master Bedroom Description:Walk-In Closet
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Bedroom 1 Level:Second
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Bedroom 2 Level:Second
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Bedroom 3 Level:Second
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Bedroom 4 Level:Second
Baths
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# of Baths:3.10
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# of Full Baths:3
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# of Half Baths:1
The Listing
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Home Warranty:No
Heating & Cooling
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Cooling:2 Units, Central Air
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Heating:1 Unit
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Water Heater:Gas
Utilities
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Utilities:All Underground, Electric, Gas-Natural
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Water:Public Water
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Fuel Type:Gas-Natural
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Sewer:Public Sewer
Appliances
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Appliances:Carbon Monoxide Detector, Cooktop - Gas, Dishwasher, Dryer, Refrigerator, Wall Oven(s) - Gas, Washer
The Community
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Community Living:No
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Pets Allowed:Yes
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Assessment Total:933000
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Assessment Total Tax:*
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Assessment Bldg:592000
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Assess Amount Building Tax:*
Parking
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# of Garage Spaces:2
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Garage Description:Carport-Attached
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# of Parking Spaces:6
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Parking/Driveway Description:1 Car Width, Blacktop
Monthly cost estimate

Asking price
$1,099,000
Expense | Monthly cost |
---|---|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$5,884
|
Taxes | N/A |
Insurance | $302 |
Utilities | $263 See report |
Total | $6,449/mo.* |
*This is an estimate |
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
---|---|---|---|---|
7/17/25
Jul 17, 2025
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Listed / Active | GSMLS | $1,099,000 |

84% of nearby similar homes sold for over asking price
Similar homes that sold in bidding wars went $171k above asking price on average, but some went as high as $603k over asking price.