NOT LISTED FOR SALE

86 Chester Ave Winthrop, MA 02152

Downtown Winthrop Neighborhood

Estimated Value: $946,000 - $1,077,000

6 Beds
2.5 Baths
2,692 Sq Ft
$378/Sq Ft Est. Value

Sale Details

Date Sold: August 15, 2025

Last sale price $1,060,000 $394 Per Sq Ft

Est. 4% decrease in value since last sale

Current estimated payment $6,170 / mo

36 Days on Market

Highlights

  • Marina
  • On Golf Course
  • Deck
  • William P. Gorman/Fort Banks Elementary School Rated A-
  • Open Floorplan
  • Property is near golf course, public transit, and schools

About This Home

As of August 2025

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.

Last Agent to Sell the Property

Kyle MacNichol

Redfin Corp. Listed on: 04/21/2025

Redfin Corp.

Last Buyer's Agent

Karin O Connor

Compass

Compass

Property Details

Home Type

  • Multi-Family

Est. Annual Taxes

  • $8,048

Year Built

  • Built in 1900

Lot Details

  • 4,378 Sq Ft Lot
  • On Golf Course
  • Fenced
  • Corner Lot

Parking

  • 2 Car Garage
  • Tandem Parking
  • Driveway
  • Open Parking
  • Off-Street Parking

Home Design

  • Block Foundation

Interior Spaces

  • 2,692 Sq Ft Home
  • Property has 1 Level
  • Open Floorplan
  • Crown Molding
  • Ceiling Fan
  • Family Room
  • Living Room
  • Dining Room
  • Sun or Florida Room
  • Basement Fills Entire Space Under The House
  • Washer and Dryer

Kitchen

  • Range
  • Microwave
  • Dishwasher
  • Solid Surface Countertops
  • Disposal

Flooring

  • Wood
  • Tile

Bedrooms and Bathrooms

  • 6 Bedrooms

Additional Features

  • Deck
  • Property is near golf course, public transit, and schools

Listing and Financial Details

  • Assessor Parcel Number M:037 L:066,1422682

Community Details

Recreation

  • Marina
  • Tennis Courts
  • Park
  • Jogging Path
  • Bike Trail

Additional Features

  • 2 Units
  • Shops

Property Details

Home Type

Multi-Family

Est. Annual Taxes

$8,048

Year Built

Built in 1900

Lot Details

4,378 Sq Ft Lot

Parking

2

Listing Details

  • Property Type: Residential Income
  • Property Sub Type: Multi Family
  • Year Built: 1900
  • Levels: 3
  • Year Built Details: Actual
  • APOD AVAILABLE: No
  • Special Features: VirtualTour
  • Stories: 3

Interior Features

  • Flooring: Wood, Tile, Hardwood
  • Interior Amenities: Ceiling Fan(s), Pantry, Crown Molding, Stone/Granite/Solid Counters, Upgraded Cabinets, Upgraded Countertops, Open Floorplan, Remodeled, Living Room, Dining Room, Kitchen, Family Room, Laundry Room, Sunroom
  • Fireplace YN: No
  • Appliances: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Washer/Dryer
  • Total Bedrooms: 6
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Total Bathrooms: 3
  • Basement: Full
  • Above Grade Finished Sq Ft: 2692
  • Living Area: 2692
  • Spa YN: No
  • Stories Total: 3
  • Window Features: Picture Window
  • MAIN LO: NB3534
  • MAIN SO: AN2383

Exterior Features

  • Fencing: Fenced
  • Foundation Details: Block
  • Frontage Type: Golf Course
  • Home Warranty YN: No
  • Patio And Porch Features: Deck
  • Road Frontage Type: Public
  • Road Surface Type: Paved
  • Waterfront Features: 1/2 to 1 Mile To Beach, Beach Ownership(Public)
  • Waterfront YN: No
  • Waterview Flag: No

Garage/Parking

  • Garage Spaces: 2
  • Covered Parking Spaces: 2
  • Garage YN: Yes
  • Open Parking YN: Yes
  • Parking Features: Paved Drive, Off Street, Tandem, Paved
  • Total Parking Spaces: 7

Utilities

  • Sewer: Public Sewer
  • Utilities: for Gas Range
  • Water Source: Public

Condo/Co-op/Association

  • Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Bike Path, Highway Access, House of Worship, Marina, Public School, T-Station
  • Senior Community YN: No

Lot Info

  • Parcel Number: M:037 L:066,1422682
  • Zoning: RAS
  • Farm Land Area Units: Square Feet
  • Lot Features: Corner Lot
  • Lot Size Acres: 0.1
  • Lot Size Sq Ft: 4378
  • Lot Size Units: Acres

Tax Info

  • Tax Year: 2025
  • Tax Annual Amount: 8048

Multi Family

  • Number Of Units Total: 2
  • LEVELS 1: 1
  • Basement Included Sq Ft: No
  • LEASE 2: N
  • LEASE 1: N

Ownership History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Name Owned For Owner Type

Purchase Details

Listed on
Apr 21, 2025
Closed on
Aug 15, 2025
Sold by
Bought by
Seller's Agent
Kyle MacNichol
Redfin Corp.
Buyer's Agent
Karin O Connor
Compass
List Price
$1,099,000
Sold Price
$1,060,000
Premium/Discount to List
-$39,000
-3.55%
Views
34
Current Estimated Value
$1,018,231

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
-$41,769
Avg. Annual Appreciation
-4.62%
Original Mortgage
$890,400
Outstanding Balance
$884,857
Interest Rate
6.67%
Mortgage Type
New Conventional
Estimated Equity
$133,374

Purchase Details

Closed on
Aug 16, 2022
Sold by
Bought by

Purchase Details

Listed on
Aug 28, 2012
Closed on
Dec 17, 2012
Sold by
Bought by
Seller's Agent
Mary Ann Cash
Charlesgate Realty Group, llc
Buyer's Agent
Susan Tallent
Coldwell Banker Residential Brokerage - Winthrop
List Price
$299,900
Sold Price
$290,000
Premium/Discount to List
-$9,900
-3.3%

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
9.68%
Original Mortgage
$210,000
Interest Rate
3.39%
Mortgage Type
New Conventional

Purchase Details

Listed on
Aug 28, 2012
Closed on
Nov 19, 2012
Sold by
Bought by
Seller's Agent
Mary Ann Cash
Charlesgate Realty Group, llc
Buyer's Agent
Susan Tallent
Coldwell Banker Residential Brokerage - Winthrop
List Price
$299,900
Sold Price
$290,000
Premium/Discount to List
-$9,900
-3.3%

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$210,000
Interest Rate
3.39%
Mortgage Type
New Conventional
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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Average Value
Not Available
List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Buyer Sale Price Title Company
$1,060,000 --
$1,060,000 --
-- None Available
-- None Available
-- --
-- --
-- --
$290,000 --
$290,000 --
$290,000 --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Borrower Loan Amount
Open $890,400
Closed $890,400
Previous Owner $210,000
Previous Owner $10,000
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft Prior Sale
08/15/2025 08/15/25 Sold $1,060,000 -3.5% $394 / Sq Ft
05/27/2025 05/27/25 Pending -- -- --
04/21/2025 04/21/25 For Sale $1,099,000 +279.0% $408 / Sq Ft
11/19/2012 11/19/12 Sold $290,000 -3.3% $119 / Sq Ft View Prior Sale
10/20/2012 10/20/12 Pending -- -- --
08/28/2012 08/28/12 For Sale $299,900 -- $123 / Sq Ft
Source: MLS Property Information Network (MLS PIN)

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $8,048 $779,800 $331,400 $448,400
2024 $7,471 $717,000 $318,500 $398,500
2023 $7,863 $734,900 $291,500 $443,400
2022 $7,742 $658,300 $260,400 $397,900
2021 $7,576 $597,500 $232,500 $365,000
2020 $7,381 $584,900 $232,500 $352,400
2019 $7,269 $551,500 $214,300 $337,200
2018 $6,573 $464,200 $184,000 $280,200
2017 $5,964 $413,900 $162,900 $251,000
2016 $5,655 $367,900 $141,700 $226,200
2015 $5,012 $349,500 $137,600 $211,900
2014 $4,528 $290,600 $127,900 $162,700
Source: Public Records

Agents Affiliated with this Home

  • Karin O Connor

    Buyer's Agent in 2025

    Karin O Connor

    Compass

    (617) 448-5003

    1 in this area

    36 Total Sales

    Karin O Connor
    Section Image

  • M

    Seller's Agent in 2012

    Mary Ann Cash

    Charlesgate Realty Group, llc

    (617) 846-1234

    13 in this area

    42 Total Sales

    Mary Ann Cash
    Section Image

  • S

    Buyer's Agent in 2012

    Susan Tallent

    Coldwell Banker Residential Brokerage - Winthrop

    Section Image
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Map

Source: MLS Property Information Network (MLS PIN)

MLS Number: 73361929

MLS Property Information Network (MLS PIN)

APN: WINT-000037-000000-000066

Massachusetts Suffolk County Winthrop 02152 Downtown Winthrop

86 Chester Ave, Winthrop, MA

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MLS Property Information Network (MLS PIN) The property listing data and information, or the Images, 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, and the Images, 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, or as to the accuracy of any of the Images, set forth herein.

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