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You are here:
Home Winthrop Multi-Family Homes for Sale

86 Chester Ave Winthrop, MA 02152

$1,099,000
2 Unit
6 Beds
3 Baths
2692 SQFT
0.10 Acre
86 Chester Ave
Winthrop, MA 02152

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.

Property Overview

Property Details click or tap to expand

Building Information

  • Total Units: 2
  • Total Floors: 3
  • Total Bedrooms: 6
  • Total Full Baths: 2
  • Total Half Baths: 1
  • Amenities: Bike Path, Golf Course, Highway Access, House of Worship, Marina, Park, Public School, Public Transportation, Shopping, Tennis Court, T-Station, Walk/Jog Trails
  • Basement Features: Full
  • Common Rooms: Dining Room, Family Room, Kitchen, Living Room, Sunroom
  • Common Interior Features: Ceiling Fans, Crown Molding, Pantry, Stone/Granite/Solid Counters, Tile Floor, Upgraded Cabinets, Upgraded Countertops
  • Common Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer, Washer / Dryer Combo

Financial

  • APOD Available: No
  • Gross Operating Income: 27600

Utilities

  • Utility Connections: for Gas Range
  • Water: City/Town Water, Private
  • Sewer: City/Town Sewer, Private

Unit 1 Description

  • Under Lease: No
  • Floors: 1
  • Levels: 1

Unit 2 Description

  • Under Lease: No
  • Floors: 2
  • Levels: 2

Construction

  • Year Built: 1900
  • Foundation Info: Concrete Block
  • Flooring Type: Hardwood, Tile, Wood
  • Lead Paint: Unknown
  • Warranty: No

Other Information

  • MLS ID# 73361929
  • Last Updated: 05/31/25

Property History click or tap to expand

Date Event Price Price/Sq Ft Source
05/31/2025Contingent$1,099,000$408MLSPIN
04/25/2025Active$1,099,000$408MLSPIN
04/21/2025New$1,099,000$408MLSPIN

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View Breakdown

Map & Resources

Winthrop Middle School

Public Middle School, Grades: 6-8

0.33mi

Saint Johns School

School

0.33mi

Arthur T. Cummings Elementary School

Public Elementary School, Grades: 3-5

0.34mi

Winthrop High School

Public Secondary School, Grades: 9-12

0.34mi

Winthrop Fire Department

Fire Station

0.29mi

Winthrop Fire Department

Fire Station

0.42mi

Winthrop Police Department

Local Police

0.25mi

Winthrop Public Library and Museum

Museum

0.27mi

Miller Field

Sports Centre. Sports: American Football, Soccer

0.31mi

Thornton Park

Park

0.12mi

Metcalf Square

Municipal Park

0.24mi

Metcalf Square

Park

0.25mi

Norman F. Daw Playground

Municipal Park

0.35mi

Ingleside Park

Municipal Park

0.39mi

Winthrop Golf Club

Golf Course

0.02mi

Winthrop Public Library

Library

0.26mi

Center Nails Spa

Nails, Eyelash, Waxing

0.37mi

Washington Ave @ Winthrop St

713

0.23mi

Washington Ave @ Willow Ave

713

0.23mi

Washington Ave opp Willow Ave

713

0.24mi

Pleasant St @ Winthrop St

713

0.24mi

Pleasant St @ Vine Ave

713

0.25mi

Pleasant St @ Seaview Ave

713

0.27mi

Veterans Rd opp Seafoam Ave

712

0.28mi

Washington Ave opp Lewis Ave

713

0.28mi

Seller's Representative: Kyle Macnichol, Redfin Corp.
MLS ID#: 73361929

© 2025 MLS Property Information Network, Inc.. All rights reserved.

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.

MLS PIN data last updated at 2025-05-31 08:44:00

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