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86-88 Pearl Street, Boston MA 02129

Boston, MA 02129 • Charlestown
$1,600,000
Est. $9,754/month
7
Beds
2
Baths
2,690
Sq Ft
$595
Price/Sq Ft
0.08
Acres
1930
Year Built
18
Days on Market
Pending Listed Jan 22, 2026 • MLS# 73470882 Copied!

About this home

A rare development / investment opportunity in Charlestown available for the first time. The combined 3,500± sq ft lot features 50'+ of street frontage which includes an existing curb cut with off-street parking for 3 or more vehicles—an exceptional advantage in this neighborhood. Zoned 3F-2000, the property offers meaningful flexibility for future redevelopment or renovation. Currently configured as a side by side two-family, it provides income potential while allowing a buyer to evaluate long-term value creation. The wide frontage and generous lot open highest-and-best-use scenarios aligned with zoning. The property would also be an incredible single-family project where an owner would enjoy beautiful yard space and plenty of room to grow. Ideally located just off Bunker Hill St, the property is close to shops, parks, restaurants, MBTA & other neighborhood amenities. One of the few remaining multi-family offerings in Charlestown that combines parking, potential and scale.

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Property Overview

Property Type
Multi Family
Listing Type
For Sale
Year Built
1930
Bedrooms
7
Full Bathrooms
2
Living Area
2,690 sq ft
Total Rooms
11
Stories
4
Levels
4

Facts & Features

Home Facts

Type Residential Income
Style Multi Family
Year Built 1930
Living Area 2,690 sq ft
Lot Size 0.08 acres
Bedrooms 7
Full Baths 2
Total Rooms 11

Interior

Heating None
Cooling None
Flooring None
Appliances None
Fireplace None
Basement Unfinished
Laundry None
Features None

Exterior

Construction None
Architecture None
Roof None
Features None
Pool None
Spa None
Fencing None
Patio/Porch None

Parking

Features Paved Drive, Off Street, Paved
Total Spaces 3

Utilities

Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $17,557
Assessed Value $1,415,900

Interior Features

Flooring:
Appliances:
Interior Features:
Windows:
Basement: Unfinished
Laundry:
Security:

Construction & Materials

Year Built: 1930
Structure Type:
Exterior Materials:
Roof:
Foundation: Stone
Stories: 4

Heating, Cooling & Utilities

Heating:
Cooling:
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Total Parking Spaces: 3
Parking Features: Paved Drive, Off Street, Paved

Location

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Neighborhood

Charlestown

86-88 Pearl Street, Boston MA 02129

Boston, MA 02129

Walkability

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Nearby Schools

School District
Boston School District local
C-
🎓 Where Graduates Go Class of 2021
52% attend college
38% 4-Year 14% 2-Year 7% Out of State 7% Working
School Safety 2024-25
3.7% Above Average
3.2% Suspensions 0.3% In-School 0.5% Emergency
1.8% below state avg
E

Elementary Schools

10 schools
A-
Warren-Prescott K-8 School
0.2 mi | #85 of 352 | Score: 51.3
Improved 4 spots from last year
-7 below state avg
507 students Diverse
Grades PK-08
D
Horace Mann School for the Deaf Hard of Hearing
0.2 mi | #374 of 346 | Score: 33.9
Same rank as last year
73 students Diverse
Diverse Student Body
Grades PK-12
C
Harvard-Kent Elementary School
0.4 mi | #589 of 824 | Score: 41.5
Dropped 181 spots from last year
-16.7 below state avg
334 students Very Diverse
Diverse Student Body
Grades PK-06
C+
Mario Umana Academy
1.1 mi | #11 of 16 | Score: 26.9
Improved 333 spots from last year
-31.3 below state avg
634 students Less Diverse
Rising School
Grades PK-08
A
Eliot K-8 Innovation School
1.1 mi | #48 of 352 | Score: 57.2
Improved 2 spots from last year
-1.1 below state avg
784 students Diverse
Strong Attendance
Grades PK-08
St. John Elementary School
1.3 mi
Grades PK-08
D
O'Donnell Elementary School
1.3 mi | #777 of 824 | Score: 30.7
Dropped 52 spots from last year
-27.5 below state avg
256 students Less Diverse
Grades PK-06
East Boston Central Catholic School
1.3 mi
Grades PK-08
C-
Kennedy Patrick J Elementary School
1.4 mi | #670 of 824 | Score: 37.5
Improved 47 spots from last year
-20.7 below state avg
279 students Less Diverse
Rising School
Grades PK-06
B+
Alighieri Dante Montessori School
1.4 mi | #5 of 12 | Score: 45.3
Improved 124 spots from last year
-12.9 below state avg
109 students Diverse
Rising School
Grades PK-06
M

Middle Schools

10 schools
Middle School Academy
3.3 mi
F
Higginson/Lewis K-8 School
4.3 mi | #349 of 352 | Score: 23.6
Improved 3 spots from last year
-34.6 below state avg
213 students Diverse
Grades 03-08
Nativity Prep School
4.5 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
4.8 mi | #4 of 16 | Score: 41.9
Improved 187 spots from last year
-16.3 below state avg
1,126 students Diverse
Rising School College Ready Curriculum
Grades 05-08
Dearborn Middle School
5.1 mi
Mother Caroline Academy
5.2 mi
Grades 05-08
Epiphany School
6.1 mi
Grades 05-08
C
Ohrenberger School
9.3 mi | #265 of 352 | Score: 34.9
Improved 20 spots from last year
-23.3 below state avg
477 students Diverse
Rising School Diverse Student Body
Grades 03-08
Edwards Middle
0.2 mi
UP Academy
3.3 mi
H

High Schools

10 schools
D
Charlestown High School
0.1 mi | #322 of 346 | Score: 31.0
Improved 49 spots from last year
-27.2 below state avg
754 students Diverse
11 sports • 488 athletes
Early College Program Rising School
Grades 07-12
C-
East Boston High School
1.4 mi | #305 of 346 | Score: 37.3
Improved 31 spots from last year
-20.9 below state avg
1,252 students Less Diverse
14 sports • 584 athletes
Early College Program Rising School
Grades 07-12
Newman School
2.2 mi
Grades 07-12
C
Quincy Upper School
2.3 mi | #268 of 346 | Score: 44.6
Improved 4 spots from last year
-13.6 below state avg
557 students Very Diverse
12 sports • 208 athletes
High Graduation Rate Diverse Student Body
Grades 06-12
Cathedral High School
2.7 mi
9 sports • 430 athletes
Grades 07-12
A+
Boston Latin School
3.5 mi | #19 of 346 | Score: 73.3
Improved 61 spots from last year
+15.1 above state avg
2,424 students Very Diverse
18 sports • 2,006 athletes
Strong AP Program High Graduation Rate Rising School Strong Athletics
Grades 07-12
A-
O'Bryant School of Math & Science
3.7 mi | #90 of 346 | Score: 61.1
Improved 94 spots from last year
+2.9 above state avg
1,509 students Very Diverse
High Graduation Rate Rising School College Ready Curriculum Diverse Student Body
Grades 07-12
B
Dearborn STEM Academy
3.8 mi | #13 of 25 | Score: 31.7
Improved 356 spots from last year
-26.6 below state avg
565 students Diverse
10 sports • 242 athletes
Early College Program Rising School
Grades 07-12
C
Ruth Batson Academy
4.5 mi | #19 of 25 | Score: 27.6
Improved 346 spots from last year
-30.6 below state avg
604 students Diverse
8 sports • 128 athletes
Early College Program Rising School
Grades 07-12
A+
Boston Latin Academy
4.6 mi | #2 of 25 | Score: 63.9
Improved 214 spots from last year
+5.7 above state avg
1,693 students Very Diverse
17 sports • 1,298 athletes
High Graduation Rate Rising School Strong Athletics Diverse Student Body
Grades 07-12
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Monthly Payment Calculator

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Over life of loan
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Including down payment
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Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,463
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

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Current Rate
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+0.5% Rate
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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Market Insights

Property Timeline

Pending Sale
Feb 10, 2026
Offer accepted, sale pending
🏠
Listed for Sale
Jan 22, 2026
$1,600,000
Original listing
Agent: Jesse MacDonald Office: Gibson Sotheby's International Realty

Price & Status History

Date Event Price Change
Jan 22, 2026 New Listing Added $1,600,000

Market Statistics

Days on Market
18 days
Price per Sq Ft
$595

Tax History

Year Taxes Assessment
2026 $17,557 $1,415,900

Financial Details

Annual Property Tax
$17,557
Tax Year 2026
Assessed Value
$1,415,900

Listing Information

Listing Agent Jesse MacDonald
Listing Office Gibson Sotheby's International Realty
Agent MLS ID BB700098
Office MLS ID BB9059
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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Steven Novak

Steven Novak

BMN Boston Real Estate

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