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
2 photos

$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. (Some photos virtually enhanced for visualization purposes.)

Property details

MLS #
73583097
Property type
2 Family - 2 Units Up/Down
Subdivision
N/A
Status
Active
Days on market
1
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 · public school directory data (NCES)

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: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 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
Nearby-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 1 days -- 115 fewer days than Boston's current average of 116 days.
For reference, the median list price across 8,098 active listings in Boston right now is $9,500.

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 7 hr 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.