86 Chester Ave, Winthrop, MA 02152 - Photo 1

1/1

$1,060,000

Sold
Closed
Multi-Family
2 Units
6 Total Beds
0.1 Acres
2 Car Garage

1/1

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.

Full Property Details

Full Property Details for 86 Chester Ave

General

Sold For: $1,060,000
Taxes: $8,048 (2025)
Status: Closed
Type: Multi-Family
MLS ID: 73361929
Added to Site: 271 day(s) ago

Rooms

Bathrooms

Total Bathrooms: 3
Full Bathrooms: 2
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 6

Parking

Garage: Yes
Garage Spaces: 2
Parking Features: Paved Drive, Off Street, Tandem, Paved

Location

County: Suffolk

Structural Information

Basement: Yes
Stories/Levels: 3
Square Feet: 2,692
Year Built: 1900

Lot Features

Lot Size (Acres): 0.1

Financial Considerations

Tax Amount: $8,048
Tax Year: 2025

Disclosures and Reports

Exclusions: Personal Items.
Disclosures/Rstr.: Buyer and Buyer's Agent to verify all information and perform their own due diligence. Flood insurance is required on this home. One of the units has been rented for $3, 500, furnished, on Furnished Finder.
Property ID: M:037 L:066, 1422682

Listed by Redfin Corp., Kyle Macnichol
Sold by Compass, Karin O Connor

What's Your Home Worth?

* Indicates a required field

For a complimentary comparative market analysis, please contact us so we can discuss your home's value.

Your Property Information

Address optional

City *State *

Zip Code optional

Your Contact Information

First Name *Last Name *

Email Address *

Phone Number *

Comment *

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Submit, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

Listing agent

— 86 Chester Ave —

Kyle Macnichol

Redfin Corp.

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender

NMLS#: 1598647

Get Pre-Approved

Schools

Schools serving 86 Chester Ave

School District:Winthrop School District

Name	Grades	Distance
Arthur T. Cummings Elementary School 40 Hermon Street, Winthrop, MA 02152	3-5	0.3 mi
William P. Gorman/Fort Banks Elementary School 101 Kennedy Drive, Winthrop, MA 02152	PK-2	0.7 mi
Winthrop Middle School, Winthrop, MA 60 Payson Street, Winthrop, MA 02152	6-8	0.3 mi
Winthrop Sr High School 400 Main Street, Winthrop, MA 02152	9-12	0.3 mi

Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 86 Chester Ave

Date

Details

Price

Change

Source

8/15/2025

Sold

$1,060,000

-3.55%

MLS

4/21/2025

Listed

$1,099,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

891 N Shore Rd, Revere, MA 02151 - Photo 1

Just Listed

$10,500

891 N Shore Rd Revere, MA 02151

Commercial Lease
Active

35 Liberty Ave, Revere, MA 02151 - Photo 1

Just Listed

$1,189,000

Open House

35 Liberty Ave Revere, MA 02151

Multi-Family
Active
Updated 1 day ago

2
Units
6
Total Beds
0.09
Acres

100 Pitcairn, Revere, MA 02151 - Photo 1

Just Listed

$699,000

Open House

100 Pitcairn Revere, MA 02151

Single Family
Active
Updated 1 day ago

4
Beds
2
Total Baths
1,714
Sq. Ft.

4 Belle Isle Ave, Revere, MA 02151 - Photo 1

Just Listed

$599,000

Open House

4 Belle Isle Ave Revere, MA 02151

Single Family
Active
Updated 12 hours ago

3
Beds
1
Total Bath
1,562
Sq. Ft.

315 Park Ave, Revere, MA 02151 - Photo 1

Price Reduced

-$150 (-5.36%)

$2,650

315 Park Ave #2 Revere, MA 02151

Commercial Lease
Active

Listed by The Caceda Team (781) 334-5700

350 Revere Beach, Revere, MA 02151 - Photo 1

Price Reduced

-$20,000 (-3.13%)

$620,000

350 Revere Beach #P2-13I Revere, MA 02151

Condo
Active
Updated 1 day ago

2
Beds
2
Total Baths
1,184
Sq. Ft.

Price Reduced

-$24,999 (-8.33%)

$275,000

14 Beverly Revere, MA 02151

Land Residential
Active
Updated 2 days ago

0.24
Acres

753 Winthrop Ave, Revere, MA 02151 - Photo 1

Price Reduced

-$200 (-15.38%)

$1,100

753 Winthrop Ave Revere, MA 02151

Commercial Lease
Active

52 Washington Ave, Winthrop, MA 02152 - Photo 1

Sold

$1,100,000

52 Washington Ave Winthrop, MA 02152

Multi-Family
Closed

2
Units
5
Total Beds
0.15
Acres

339 Winthrop St, Winthrop, MA 02152 - Photo 1

Sold

$910,000

339 Winthrop St Winthrop, MA 02152

Multi-Family
Closed

2
Units
5
Total Beds
0.15
Acres

29 Dolphin Ave, Winthrop, MA 02152 - Photo 1

Sold

$1,050,000

29 Dolphin Ave Winthrop, MA 02152

Multi-Family
Closed

2
Units
6
Total Beds
0.11
Acres

40 Cottage Park Rd, Winthrop, MA 02152 - Photo 1

Sold

$950,000

40 Cottage Park Rd Winthrop, MA 02152

Multi-Family
Closed

2
Units
5
Total Beds
0.08
Acres

86 Chester Ave, Winthrop, MA 02152 (MLS# 73361929) is a Multi-Family property that was sold at $1,060,000 on August 15, 2025. Want to learn more about 86 Chester Ave? Do you have questions about finding other Multi-Family real estate for sale in Winthrop? You can browse all Winthrop real estate or contact a Coldwell Banker agent to request more information.

86 Chester Ave Winthrop, MA 02152