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Properties

  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
  • 86 Chester Ave, Winthrop, Massachusetts, 6 Bedrooms Bedrooms, 12 Rooms Rooms,2.5 BathroomsBathrooms,Residential Income,For Sale,Chester Ave,73361929
Property Description

Experience a complete transformation in this meticulously renovated 2-family home. Perched on a prized corner lot, this residence has undergone extensive updates, including new flooring, walls, electrical, kitchen, plumbing, and a newer roof. The result is a modern, move-in-ready space. Enjoy breathtaking, unobstructed views of Winthrop’s verdant Golf Course from all three levels. This oversized property offers flexible living arrangements. Winthrop itself is a coastal gem, boasting beautiful beaches, scenic parks, and convenient access to Deer Island and downtown Boston via the water ferry. A vibrant dining scene and thriving yacht clubs contribute to the area’s dynamic atmosphere. Commuting is made easy with brand-new MBTA bus lines. Plus, a new middle and high school, along with a state-of-the-art track and football field, enhance the community’s appeal.

Features
Basement:
Full
Parking:
Tandem, Off Street, Paved, Paved Drive
Appliances:
Disposal, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Washer/dryer
Flooring:
Tile, Wood, Hardwood
Sewer:
Public Sewer
Water:
Public
Disclosure:
hardwood floors and laundry in unit., Amazing 4 Bedrooms 1 bath with eat in kitchen, AC and heating changed 5 years ago. Hardwood floors were changed from carpet. New windows (2020). 3rd bedroom and an extra room are in the finished basement, walk out lower level. Roof is about 9 years old. The bedrooms on the second-floor feature bamboo flooring
Garage Parking:
2
Interior Features:
Crown Molding, Kitchen, Stone/granite/solid Counters, Upgraded Cabinets, Dining Room, Open Floorplan, Pantry, Ceiling Fan(s), Family Room, Living Room, Sunroom, Upgraded Countertops, Remodeled, Laundry Room
Lead Paint:
Unknown
Road Type:
Paved
Additional Information
Market Time:
54
Parking Spaces:
9
Tax Year:
2025
Status:
Closed
Price Per Sqft:
$394
Zoning:
RAS
No Units:
2
Orig Price:
$1,099,000
LEASE:
No
Waterfront:
No
MlsStatus:
Sold
Address Map
City:
Winthrop
State:
MA
County:
Suffolk
Postal Code:
02152
Longitude:
W71° 1' 12.7''
Latitude:
N42° 22' 31.7''
  • Google Map

Residential Income

86 Chester Ave, Winthrop, Massachusetts

6 Bedrooms
2.5 Total Bathrooms
2,692 Sqft
$1,099,000
Listing ID #73361929
Basic Details
Property Type :
Residential Income
Listing Type :
For Sale
Price :
$1,099,000
Bedrooms :
6
Rooms :
12
Total Bathrooms :
2.5
Full Bathrooms :
2
Half Bathrooms :
1
Square Footage :
2,692 Sqft
Year Built :
1900
Lot Area :
0.10 Acre
Listing ID :
73361929
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

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