INNOVATE
Real Estate
No photos available for this listing

$2,699,000

27 Chestnut Street, Boston MA 02108
Boston, MA 02108
Listed by Rebecca Davis Tulman and Leslie Singleton Adam
Bedrooms
3
Bathrooms
2
Living area
2,180 sqft
Year built
1913

About this home

This spectacular 3+ bedroom, 2 bath duplex w/ 18ft ceilings combines Beacon Hill elegance w/ contemporary style! With a unique double height living room, the spaces are extraordinary, creating an architectural masterpiece all within one of the most notable South Slope buildings. Oversized windows add to the appeal of this incredible condo. Polished concrete flooring along w/ industrial elements including a metal staircase & steel beam accents, create a space that is both visually appealing, as well as open, inviting & dramatic. A private entry is located off the building's enclosed courtyard-a hidden oasis. An inviting sitting room, bdrm & bath are located on the upper floor that overlooks the expansive lower floor where the living room & den have access to a charming enclosed patio. Two addt'l bdrms & a bath are located on one side of the unit, and the opposite side offers a large dining room & fantastic oversized kitchen. Common courtyard, common deck w/sweeping views, live-in super.

Property details

MLS #
73504892
Property type
Condominium
Subdivision
N/A
Status
Active
Days on market
N/A
On market date
N/A
Stories
2
Garage spaces
N/A
Lot size
N/A

Location

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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Josiah Quincy
0.69 mi away · Grades -1-5
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
711
Student:teacher ratio
10.9:1
District
Boston
Middle
Cambridge Street Upper School
1.57 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
279
Student:teacher ratio
7.5:1
District
Cambridge
High
Boston Adult Academy
0.62 mi away · Grades 11-12
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
120
Student:teacher ratio
6.7:1
District
Boston

Mortgage calculator

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Est. monthly payment
$16,404/mo
$539,800 down
$2,159,200 loan
Principal & interest$14,005
Property tax (est.)$2,249
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated April 25, 2026.

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.