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27 Chestnut Street, Boston MA 02108

Boston, MA 02108 • Beacon Hill
$2,699,000
Est. $16,407/month
3
Beds
2
Baths
2,180
Sq Ft
$1,238
Price/Sq Ft
1913
Year Built
90
Days on Market
Active Listed Apr 21, 2026 • MLS# 73504892 Copied! • Updated Jul 20, 2026

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.

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Recently Sold Nearby

Property History

Market Insights

46.3%
Price Range
2
Previous Sales

Property Timeline

🏠
Listed for Sale
Apr 21, 2026
$2,699,000
Original listing
Agent: Rebecca Davis Tulman and Leslie Singleton Adam Office: Gibson Sotheby's International Realty
Previous Transaction - MLS #72732235
Full transaction history available when tracking began
🏷️
Previously Sold
Jan 15, 2021
$1,880,000
MLS #72732235
Previous Transaction - MLS #72624900
Full transaction history available when tracking began
🏷️
Previously Sold
Apr 24, 2020
$1,450,000
MLS #72624900

Tax History

Year Taxes Assessment
2026 $15,918 $1,623,100

Financial Details

Annual Property Tax
$15,918
Tax Year 2026
HOA Fee
$1,233
Monthly
Assessed Value
$1,623,100

Facts & Features

Central AC

Home Facts

Type Residential
Style Condominium
Year Built 1913
Living Area 2,180 sq ft
Bedrooms 3
Full Baths 2
Total Rooms 7

Interior

Heating Forced Air, Natural Gas
Cooling Central Air
Flooring Concrete, Other
Appliances Range, Dishwasher, Refrigerator, Freezer, Washer, Dryer
Fireplace None
Basement N
Laundry In Unit, Electric Dryer Hookup
Features None

Exterior

Construction See Remarks
Architecture Other (see Remarks)
Roof Other
Features Deck - Roof, Patio, Patio - Enclosed
Pool None
Spa None
Fencing None
Patio/Porch Deck - Roof, Patio, Patio - Enclosed
Features On Street
Electric None
Water Public
Sewer Public Sewer
Gas None
Other For Electric Range, For Electric Oven, For Electric Dryer
Annual Tax $15,918
Assessed Value $1,623,100

HOA & Community

HOA Fee $1,233 Monthly
Fee Includes Heat, Water, Sewer, Insurance, Maintenance Structure, Maintenance Grounds, Snow Removal, Trash, Air Conditioning, Reserve Funds
Amenities Hot Water, Elevator(s), Fitness Center, Storage, Garden Area
Optional Fee Includes None
Owner-Occupied Units 29
Pets Yes
Seller Disclosures Phenomenal Common Roofdeck, One Of The Highest In The City, With Incredible River And City Views. Fee Also Includes Live-in Superintendent.
Possession None
Accepted Financing None
Structure Type ["High-Rise"]
Unit/Building GA
Sq Ft Source Master Deed
Documents None
County Suffolk
Total market time (incl. prior listings) 90 days

Property Overview

Property Type
Condominium
Listing Type
For Sale
Year Built
1913
Bedrooms
3
Full Bathrooms
2
Living Area
2,180 sq ft
Total Rooms
7
Stories
2
Entry Level
1

Room Details

Other Floor

Bathroom1
Bedroom5
Bedroom4
Bedroom3
11 x 14
Dining Room
9 x 18
Kitchen
10 x 22
Bathroom2
Bedroom2
12 x 13
Living Room
11 x 33
Bathroom3
Master Bedroom
12 x 14
Office
Family Room
Master Bathroom

Interior Features

Flooring: Concrete, Other
Appliances: Range, Dishwasher, Refrigerator, Freezer, Washer, Dryer
Interior Features:
Windows:
Basement: N
Laundry: In Unit, Electric Dryer Hookup
Security: Intercom, Other

Construction & Materials

Style: Other (See Remarks)
Year Built: 1913
Structure Type: High-Rise
Exterior Materials: See Remarks
Roof: Other
Foundation:
Stories: 2

Heating, Cooling & Utilities

Heating: Forced Air, Natural Gas
Heating Zones: 2
Cooling: Central Air
Cooling Zones: 2
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Deck - Roof, Patio, Patio - Enclosed
Patio & Porch: Deck - Roof, Patio, Patio - Enclosed
Fencing:
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Parking Features: On Street

Nearby Schools

School information not available for this location.

Monthly Payment Calculator

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Loan Amount
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After down payment
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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 $1,327
Homeowners Insurance $200
HOA Fee $1,233/mo
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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$0/mo
Save $0/mo
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.

Location

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Neighborhood

Beacon Hill

27 Chestnut Street, Boston MA 02108

Boston, MA 02108

Listing Information

Listing Agent Rebecca Davis Tulman and Leslie Singleton Adam
Listing Office Gibson Sotheby's International Realty
Office Phone 857-310-5632
Agent MLS ID TM348767
Office MLS ID AN7429
Listing Data Updated Jul 20, 2026 2:13 PM EDT
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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