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 to live in the "owner's unit" and keep a tenant in 1st floor unit; or buyers looking to convert into a spectacular single family home; or a developer/investor to convert into two high-end condos. 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/fireplace 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. An unfinished basement offers future expansion capabilities, and a lush garden patio completes this special offering.
For sale
$2,500,000
51 Chestnut St, Boston, MA 02129
4beds
3,593sqft
Single Family Residence
Built in 1865
2,136 Square Feet Lot
$2,415,500 Zestimate®
$696/sqft
$-- HOA
What's special
Gas-lit streetMarble spa bathAmple closet spaceGrand entranceLush garden patioPeriod moldingsSweeping staircase
- 2 days
- 573
- 36
Zillow last checked:
Listing updated:
Listed by:
Nancy Roth 617-429-6396,
Gibson Sotheby's International Realty 617-242-4222,
Colin Boylan 603-325-3016
Source: MLS PIN,MLS#: 73573036
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bedrooms: 2
Primary bedroom
- Features: Bathroom - Full, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Tray Ceiling(s)
- Level: Third
- Area: 257.31
- Dimensions: 13.08 x 19.67
Bedroom 2
- Features: Closet/Cabinets - Custom Built, Flooring - Wood, French Doors, Recessed Lighting, Lighting - Overhead, Decorative Molding
- Level: Main,First
- Area: 228.02
- Dimensions: 13.75 x 16.58
Bedroom 3
- Features: Flooring - Wall to Wall Carpet, Lighting - Pendant, Decorative Molding
- Level: Main,First
- Area: 217.53
- Dimensions: 13.67 x 15.92
Bedroom 4
- Features: Ceiling Fan(s), Closet, Flooring - Wood, Lighting - Overhead
- Level: Third
- Area: 140.13
- Dimensions: 9.83 x 14.25
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Sconce, Lighting - Pendant
- Level: First
- Area: 42.88
- Dimensions: 5.25 x 8.17
Bathroom 2
- Features: Bathroom - Half, Flooring - Stone/Ceramic Tile, Lighting - Sconce, Lighting - Overhead, Pedestal Sink
- Level: Second
Bathroom 3
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower, Bathroom - With Shower Stall, Skylight, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Marble, Countertops - Stone/Granite/Solid, Recessed Lighting, Lighting - Pendant
- Level: Third
- Area: 250.52
- Dimensions: 15.42 x 16.25
Dining room
- Features: Flooring - Wood, Chair Rail, Recessed Lighting, Lighting - Pendant, Pocket Door, Tray Ceiling(s)
- Level: Second
- Area: 233.94
- Dimensions: 14.25 x 16.42
Family room
- Features: Ceiling Fan(s), Closet, Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Lighting - Overhead
- Level: Second
- Area: 287.84
- Dimensions: 15.08 x 19.08
Kitchen
- Features: Flooring - Wood, Countertops - Stone/Granite/Solid, Kitchen Island, Recessed Lighting, Stainless Steel Appliances, Peninsula, Lighting - Pendant
- Level: Second
- Area: 181
- Dimensions: 15.08 x 12
Living room
- Features: Flooring - Wood, Recessed Lighting, Lighting - Overhead, Archway
- Level: Second
- Area: 426.71
- Dimensions: 24.5 x 17.42
Heating
- Forced Air, Baseboard, Natural Gas
Cooling
- Central Air
Appliances
- Included: Gas Water Heater, Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Stainless Steel Appliance(s), Gas Cooktop
- 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
- Flooring: Wood, Tile, Carpet, Marble, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wood, Flooring - Hardwood
- Basement: Full,Interior Entry,Unfinished
- Number of fireplaces: 4
- Fireplace features: Family Room, Living Room, Master Bedroom
Interior area
- Total structure area: 3,593
- Total interior livable area: 3,593 sqft
- Finished area above ground: 3,593
- Finished area below ground: 1,230
Property
Parking
- Total spaces: 1
- Parking features: Detached, Leased
- Garage spaces: 1
Features
- Patio & porch: Deck - Roof, Patio
- Exterior features: Deck - Roof, Patio, Garden
- Has view: Yes
- View description: Water, Harbor
- Has water view: Yes
- Water view: Harbor,Water
Lot
- Size: 2,136 Square Feet
- Features: Other
Details
- Parcel number: 0203412000,3356557
- Zoning: Multi-Fam
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Italianate
- Property subtype: Single Family Residence
- Attached to another structure: Yes
Materials
- Conventional (2x4-2x6)
- Foundation: Granite
- Roof: Rubber
Condition
- Year built: 1865
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: for Gas Range
Community & HOA
Community
- Features: 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
- Subdivision: Charlestown
HOA
- Has HOA: No
Location
- Region: Boston
Financial & listing details
- Price per square foot: $696/sqft
- Tax assessed value: $2,454,500
- Annual tax amount: $30,727
- Date on market: 9/8/2026
- Exclusions: 2nd Floor Dining Room Brass Uplight.
Estimated market value
$2,415,500
$2.29M - $2.54M
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 9/8/2026 | Listed for sale | $2,500,000+19%$696/sqft |
Source: MLS PIN #73573036 Report a problem | ||
| 7/11/2016 | Sold | $2,100,000+56.4%$584/sqft |
Source: Public Record Report a problem | ||
| 6/11/2013 | Sold | $1,342,500-3.8%$374/sqft |
Source: LINK #139684 Report a problem | ||
| 5/11/2013 | Pending sale | $1,395,000$388/sqft |
Source: Gibson Sotheby's International Realty #71438517 Report a problem | ||
| 4/13/2013 | Price change | $1,395,000-6.7%$388/sqft |
Source: Gibson Sotheby's International Realty #71438517 Report a problem | ||
| 9/22/2012 | Listed for sale | $1,495,000$416/sqft |
Source: Gibson Sotheby's International Realty #71438517 Report a problem | ||
| 7/25/2012 | Listing removed | $1,495,000$416/sqft |
Source: Gibson Sotheby's International Realty #71395956 Report a problem | ||
| 6/14/2012 | Listed for sale | $1,495,000+464.2%$416/sqft |
Source: Gibson Sotheby's International Realty #71397029 Report a problem | ||
| 12/21/1995 | Sold | $265,000$74/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $27,866 +19.7% | $2,406,400 +12.6% |
| 2024 | $23,287 +1.5% | $2,136,400 |
| 2023 | $22,945 +1.7% | $2,136,400 +3% |
| 2022 | $22,567 +2% | $2,074,200 |
| 2021 | $22,132 +2.6% | $2,074,200 +1.6% |
| 2020 | $21,567 +10.4% | $2,042,300 +10.2% |
| 2019 | $19,533 +11.9% | $1,853,200 +11.3% |
| 2018 | $17,451 +392.2% | $1,665,200 +6.2% |
| 2017 | $3,546 -78% | $1,567,900 +6.8% |
| 2016 | $16,145 +18.3% | $1,467,700 +30.2% |
| 2015 | $13,648 +11.4% | $1,127,000 +20.9% |
| 2013 | $12,249 +2.7% | $932,200 +1.9% |
| 2012 | $11,930 +1.9% | $914,900 |
| 2011 | $11,702 +6.6% | $914,900 -1% |
| 2010 | $10,979 +4.3% | $924,200 -6.7% |
| 2009 | $10,528 -9.7% | $990,440 -6.8% |
| 2008 | $11,659 -0.3% | $1,062,820 -0.1% |
| 2007 | $11,689 | $1,063,590 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: Charlestown
Nearby schools
Schools provided by the listing agent
- Elementary: Bps
- Middle: Bps
- High: Bps
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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