2 Family - 2 Units Up/Down at 66 Pleasant, Boston MA 02125, Boston
2 Family - 2 Units Up/Down at 66 Pleasant, Boston MA 02125, Boston, photo 2 of 2
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$1,100,000

66 Pleasant, Boston MA 02125
Boston, MA 02125
Listed by Danielle Canty
Bedrooms
9
Bathrooms
2
Living area
3,204 sqft
Year built
1928

About this home

Rarely available and cherished by the same family for over 30 years, this classic Dorchester two-family home presents an incredible opportunity on the edge of the highly sought-after Savin Hill area. Boasting over 3,200 square feet of multi-level living space, this robust property is perfect for savvy investors looking to add a premier asset to their portfolio, or owner-occupants ready to start their real estate journey off strong with built-in rental income. The building offers grand-scale proportions, highlighted by a massive, unfinished basement featuring impressive 6-foot ceilings that offer immense potential for future expansion (basement square footage is not included in the official total). Situated a short distance from the Savin Hill and JFK/UMass T-stations, local beaches, and vibrant neighborhood favorites like McKenna's Cafe, this is a true urban oasis. Bring your vision to this longtime family gem and anchor yourself in one of Boston's most dynamic markets.

Property details

MLS #
73583097
Property type
2 Family - 2 Units Up/Down
Subdivision
N/A
Status
Active
Days on market
2
On market date
September 27, 2026
Stories
3
Total bathrooms
2
Garage spaces
N/A
Parking spaces
2
Lot size
0.1 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Edward Everett
0.04 mi away · Grades -1-6
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
270
Student:teacher ratio
12.3:1
District
Boston
MiddleCharter
Helen Y. Davis Leadership Academy Charter Public School
0.87 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
138
Student:teacher ratio
6.9:1
District
Helen Y. Davis Leadership Academy Charter Public (District)
HighCharter
Boston Collegiate Charter School
0.54 mi away · Grades 5-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
702
Student:teacher ratio
9.4:1
District
Boston Collegiate Charter (District)

Walkability

Blended score for Boston's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

92
Highly walkable
out of 100
EPA National Walkability Index
17.2 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores20
Parks20
Schools20
Transit stops20
Pharmacies9

Market position

How this listing compares to current activity in Boston, from live MLS data.

On the market 2 days -- 114 fewer days than Boston's current average of 116 days.
For reference, the median list price across 8,146 active listings in Boston right now is $9,634.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$6,774/mo
$220,000 down
$880,000 loan
Principal & interest$5,708
Property tax (est.)$917
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 1 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.