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51 Chestnut Street, Boston MA 02129

Boston, MA 02129 • Charlestown
$2,700,000
Est. $16,413/month
4
Beds
3.5
Baths
3,593
Sq Ft
$751
Price/Sq Ft
0.05
Acres
1865
Year Built
Single Family Residence
Type
20
Days on Market
Active Listed Jun 9, 2026 • MLS# 73532468 Copied!

About this home

Located on a gas-lit street near Monument Square, this rarely available, 4BR/3.5BA, two-family home offers 3,593+sf and an extraordinary opportunity for an owner occupant, investor/developer, or buyer looking to convert into a spectacular single family home. The grand entrance is defined by soaring ceilings, period moldings, and a sweeping staircase that leads to an impressive formal living room. An elegant dining room flows into a chef’s kitchen with luxury finishes and top-tier appliances. A charming family room w/wet bar and gas FP provides an inviting hub for daily living. A spacious primary suite w/FP has ample closet space and marble spa bath. An addt’l bedroom and full bath complete this level. The separate entrance, 1BR rental unit in the rear of the first floor is well maintained. The crown jewel is an expansive 480sf private roof deck, w/head house, wet bar, and panoramic views of the harbor, Monument, and Boston skyline. A lush garden patio completes this special offering.

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Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1865
Bedrooms
4
Full Bathrooms
3
Half Bathrooms
1
Living Area
3,593 sq ft
Total Rooms
10
Main Level Bedrooms
2

Facts & Features

1 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1865
Living Area 3,593 sq ft
Lot Size 0.05 acres
Bedrooms 4
Full Baths 3
Half Baths 1
Total Rooms 10

Interior

Heating Forced Air, Baseboard, Natural Gas
Cooling Central Air
Flooring Wood, Tile, Carpet, Marble, Hardwood, Flooring - Stone/ceramic Tile, Flooring - Wood, Flooring - Hardwood
Appliances Gas Water Heater, Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Stainless Steel Appliance(s), Gas Cooktop
Fireplace Family Room, Living Room, Master Bedroom
Fireplaces 4
Basement Full, Interior Entry, Unfinished
Laundry Third Floor
Features Bathroom - Full, Bathroom - Tiled With Shower Stall, Lighting - Overhead, Dining Area, Beadboard, Lighting - Pendant, Archway, Vestibule, Chair Rail, Bathroom, Kitchen, Foyer, Living/dining Rm Combo

Exterior

Construction Conventional (2x4-2x6)
Architecture Italianate
Roof Rubber
Features Deck - Roof, Patio, Garden
Pool None
Spa None
Fencing None
Patio/Porch Deck - Roof, Patio

Parking

Garage Spaces 1
Has Garage Yes
Features Detached, Leased
Total Spaces 1

Utilities

Electric None
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range

Financial

Annual Tax $30,728
Assessed Value $2,454,500

Interior Features

Flooring: Wood, Tile, Carpet, Marble, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wood, Flooring - Hardwood
Appliances: Gas Water Heater, Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Stainless Steel Appliance(s), Gas Cooktop
Interior Features: Bathroom - Full, Bathroom - Tiled With Shower Stall, Lighting - Overhead, Dining Area, Beadboard, Lighting - Pendant, Archway, Vestibule, Chair Rail, Bathroom, Kitchen, Foyer, Living/Dining Rm Combo
Windows:
Basement: Full, Interior Entry, Unfinished
Laundry: Third Floor
Security:

Construction & Materials

Style: Italianate
Year Built: 1865
Structure Type:
Exterior Materials: Conventional (2x4-2x6)
Roof: Rubber
Foundation: Granite

Heating, Cooling & Utilities

Heating: Forced Air, Baseboard, Natural Gas
Heating Zones: 4
Cooling: Central Air
Cooling Zones: 2
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

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

Parking & Garage

Garage Spaces: 1
Total Parking Spaces: 1
Parking Features: Detached, Leased

Special Features

Fireplaces: 4
Fireplace Type: Family Room, Living Room, Master Bedroom
Community Amenities: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Private School, Public School, T-Station, University

Location

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Neighborhood

Charlestown

51 Chestnut Street, Boston MA 02129

Boston, MA 02129

Walkability

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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
C
Harvard-Kent Elementary School
0.1 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
A-
Warren-Prescott K-8 School
0.3 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
0.5 mi | #374 of 346 | Score: 33.9
Same rank as last year
73 students Diverse
Diverse Student Body
Grades PK-12
A
Eliot K-8 Innovation School
0.7 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
0.9 mi
Grades PK-08
C+
Mario Umana Academy
0.9 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
East Boston Central Catholic School
1.0 mi
Grades PK-08
D
O'Donnell Elementary School
1.1 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
B+
Alighieri Dante Montessori School
1.1 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
C-
Kennedy Patrick J Elementary School
1.2 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
M

Middle Schools

10 schools
Middle School Academy
2.9 mi
F
Higginson/Lewis K-8 School
4.0 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
4.3 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
4.5 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
4.8 mi
Mother Caroline Academy
4.9 mi
Grades 05-08
Epiphany School
5.7 mi
Grades 05-08
C
Ohrenberger School
9.1 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
0.5 mi
UP Academy
2.9 mi
H

High Schools

10 schools
D
Charlestown High School
0.3 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
1.3 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
C
Quincy Upper School
2.0 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
Newman School
2.0 mi
Grades 07-12
Cathedral High School
2.4 mi
9 sports • 430 athletes
Grades 07-12
A+
Boston Latin School
3.4 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
3.5 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
3.6 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
4.1 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
4.3 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
Learn about these ratings
School data provided by BMN Schools

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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $2,561
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
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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

•
Back On Market
Jun 19, 2026
Active
📋
Status: Active under contract
Jun 12, 2026
Active → Active Under Contract
🏠
Listed for Sale
Jun 9, 2026
$2,700,000
Original listing
Agent: Nancy Roth Office: Gibson Sotheby's International Realty

Price & Status History

Date Event Price Change
Jun 23, 2026 Sold $2,700,000 —
Jun 12, 2026 Status: Active under contract $0 —
Jun 9, 2026 New Listing Added $2,700,000 —

Market Statistics

Days on Market
20 days
Price per Sq Ft
$751

Tax History

Year Taxes Assessment
2026 $30,728 $2,454,500

Financial Details

Annual Property Tax
$30,728
Tax Year 2026
Assessed Value
$2,454,500

Listing Information

Listing Agent Nancy Roth
Listing Office Gibson Sotheby's International Realty
Agent MLS ID H8000088
Office MLS ID BB9059
Listing Data Updated Jun 23, 2026 3:05 AM 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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BMN Boston Real Estate

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