101 Chestnut St #E, Boston, MA 02108
Property image
Property image
FOR SALE
NEW - 9 HRS AGO

$3,499,950

  • 2 Beds
  • 3 Baths
  • 2,500 sqft

101 Chestnut St #E, Boston, MA 02108

Beacon Hill
Est. Mortgage $23,928/mo*
Get Pre-Qualified
We estimate this home will sell faster than 82% nearby.

Home Highlights

Coop
Built in 1918
$1,400/sqft
HOA $3,610/mo

Local Information

  • Map ViewExplore the area around 101 Chestnut St #E.
  • Schools30 Preschool Schools31 Elementary Schools20 Middle Schools19 High Schools
  • Shop & Eat
-- mins to
Commute Destination

About this House

Set within one of Beacon Hill’s most distinguished buildings, 101 Chestnut Street is celebrated for its gracious architecture, elegant courtyard and exceptional service. Unit E offers approximately 2,500 sq. ft. of expansive single-floor living with 2 bedrooms plus a library/office/guest room and 3 full baths. At the heart of the residence is an impressive 22' × 22' living and dining room, offering exceptional scale for both entertaining and everyday living. Desirable corner exposure brings natural light throughout, while the south-facing primary suite features generous proportions, an en suite bath and exceptional closet space. A separate guest wing provides wonderful privacy with a second bedroom, full bath and flexible library/office/guest room with an additional bath. Courtyard views, a well-appointed kitchen, concierge service, beautifully landscaped common roof deck and private storage complete this gracious Beacon Hill residence.
Last check for updates: about 9 hours ago
Listing courtesy of Rebecca Davis Tulman and Leslie Singleton Adam, (617) 510-5050
Gibson Sotheby's International Realty, (857) 310-5632
Source: MLS PIN, MLS#73576624
Also Listed on MLS PIN.
We estimate this home will sell faster than 82% nearby.

Home Details for 101 Chestnut St #E

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Master Bathroom, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2500 Square Feet
Appliances & Utilities
Appliances: Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, DryerDishwasherDisposalDryerRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Number of Fireplaces: 3Fireplace: Living Room, Master BedroomHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Wood
Levels, Entrance, & Accessibility
Number of Stories: 1Entry Location: Unit Placement(Front)Floors: Wood
Security
Security: Concierge

Exterior Features

Exterior Home Features
Roof: Rubber OtherPatio / Porch: Deck - RoofExterior: Deck - Roof
Parking & Garage
No Garage
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2500

Days on Market

Days on Market: 1

Property Information

Year Built
Year Built: 1918
Property Type / Style
Property Type: ResidentialProperty Subtype: Stock CooperativeStructure Type: Mid-RiseArchitecture: Mid-Rise
Building
Construction Materials: Brick, See RemarksAttached To Another StructureDoes Not Include Home Warranty
Property Information
Not Included in Sale: Fireplace Mantel In Living Room Is Excluded.Parcel Number: 3353906

Price & Status

Price
List Price: $3,499,950Price Per Sqft: $1,400

Active Status

MLS Status: New

Location

Direction & Address
City: Boston

Agent Information

Listing Agent
Listing ID: 73576624

Building

Building Area
Building Area: 2500 Square Feet

Community

Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Bike Path, Highway Access, OtherNot Senior Community

HOA

HOA Fee Includes: Water, Sewer, Insurance, Maintenance Structure, Maintenance Grounds, Snow Removal, Trash, Reserve FundsHOA Fee: $3,610/Monthly

Miscellaneous

Mls Number: 73576624Above Grade Unfinished Area: 2500

Additional Information

HOA Amenities: Hot Water,Laundry,Elevator(s),Fitness Center,Storage,Garden Area

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Beacon Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Beacon Hill

At least 135 Trulia users voted on each feature.

  • 95 % Say it's dog friendly

  • 93 % Say it's walkable to restaurants

  • 91 % Say it's walkable to grocery stores

  • 91 % Say there are sidewalks

  • 84 % Say streets are well-lit

  • 80 % Say people would walk alone at night

  • 72 % Say there's holiday spirit

  • 53 % Say kids play outside

  • 48 % Say it's quiet

  • 48 % Say neighbors are friendly

  • 40 % Say they plan to stay for at least 5 years

  • 36 % Say there are community events

  • 31 % Say there's wildlife

  • 27 % Say parking is easy

  • 24 % Say yards are well-kept

  • 17 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Evan Canney
    "Plenty of parks and clean places to let them off leash within just 5 minutes of any side of beacon hill"
    0
    Flag
  • Ms. Barr
    "Historic, friendly neighbors, clean neighborhood, lots of restaurants, nearby parks and playgrounds."
    0
    Flag
  • Nthzbvgbmq
    "Great location close to Downtown and back bay and nice pubs and restaurants. Feels safe at night. Very close to public transport. Parking is impossible "
    0
    Flag
  • Ms. Barr
    "Dog friendly neighborhood. Just respect residents and shop owners property. Pick up after you dog. Overall, a very good area for dogs to walk and play at the local dog friendly parks. "
    0
    Flag
  • Ms. Barr
    "Very dog friendly neighborhood with access to two main public parks and more beyond the neighborhood. The Boston Commons have a dog community area for their human owners. Most shops on Charles street put out dog treats and dog water bowls during the warmer months. Beacon Hill appreciate well behaved and trained dogs. Don't forget to pick after your dog poo 'cause the neighbors do their part to keep the neighborhood clean for locals and tourists. We frown upon bad dog owners. "
    0
    Flag
  • Trulia User
    "The Back Bay is a central neighborhood with historic homes, shopping, parks, and public transportation. "
    1
    Flag
  • Trulia User
    "By train. Commuting everyday by train is awful because train delays and fullness during peak times. But such is life without a car and very little parking spaces on the streets. Time to move to the country…"
    1
    Flag
  • KRH
    "Great parks, walkable, friendly, easy access to T if needed. Great shops so you can grab most of what you need locally if you so choose. Feels very safe, quiet for being an urban setting. "
    2
    Flag
  • Joshuaaleffler
    "Beacon Hill Is a great place to live. It is friendly, safe, and central. There is access to public transportation, parks, shopping, restaurants and cafes, grocery stores, etc. "
    1
    Flag
  • Joshuaaleffler
    "There's nothing not to like. The neighborhood is very dog friendly and there are man dog related resources in Beacon Hill. "
    2
    Flag
  • Artie B.
    "Great access to public transportation, the Red Line, and downtown is only a 10-15 minute walk. It’s lovely. "
    1
    Flag
  • Andrew V. .
    "There is limited parking even with a parking pass. There is a nice preschool on joy st. The one way traffic keep the traffic low in beacon hill"
    0
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  • Jenna M.
    "It’s the best and most central place to live in Boston!! I have lived here for over 10 years, easy to walk to grocery store, parks, gym etc."
    1
    Flag
  • Wes Q.
    "I walk to downtown from my apartment. It only about a 12-15 minute walk and I am on the further end of beacon hill from the financial district"
    0
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  • Megan F.
    "There are many families in this neighborhood and parks and community events designed for children. There are also a couple of preschools. "
    0
    Flag
  • Christine K. .
    "People don’t pick up after their dogs so every patch of grass is fenced so there is no where for the dogs to go unless you leave the neighborhood "
    1
    Flag
  • Christina V.
    "Seems like a dog friendly neighborhood - I see many dog owners waking their dogs every day on my commute to work! "
    1
    Flag
  • Donaldmerisier
    "schools and crime plus transportation must have shopping centers close by and services needs. people can't say too much about, because I trust no one so that's out the window long time ago."
    2
    Flag
  • Kristin n.
    "Very friendly people and picturesque streets with people walking dogs regularly. Lovely people and amazing atmosphere ! "
    4
    Flag
  • Lulu L.
    "There are a lot of beautiful parks."
    0
    Flag
  • Karan M.
    "There's a lot of character and charm."
    0
    Flag
  • Lulu L.
    "Beacon Hill is a beautiful place with lots of trees and flowers."
    1
    Flag
  • Julia S.
    "There isn't a lot of backyard space for dog owners. But there are parks that are close."
    1
    Flag
  • Julia S.
    "Beacon Hill is in the middle of everything."
    0
    Flag
  • Julia S.
    "One train or bus gets me anywhere I need to go. The commute is easy to learn."
    0
    Flag
  • Kelsey R.
    "There's a lot of history and charm. The cobblestone streets, gas lamps, and overall preservation of history is beautiful and makes living here even more special."
    0
    Flag
  • Kelsey R.
    "The commute is super easy. Beautiful. Quick and pretty straightforward. Beacon Hill is perfectly centrally located."
    0
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  • Kelsey R.
    "It is very safe, and a great place for kids. Lots of schools and daycare options."
    0
    Flag
  • Shannon S.
    "The houses are all very quaint."
    0
    Flag
  • Shannon S.
    "It is a safe place, and there are a lot of kids. There are great playgrounds on the Esplanade and on Myrtle Street. There are several schools too."
    0
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  • Courtney S.
    "It's very historic and pretty. There are a lot of old buildings with brick. On the flip side, it's also very expensive and full of traffic."
    0
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  • Re B.
    "Beacon Hill is a very ethnically diverse environment."
    0
    Flag
  • William S.
    "It is quiet and clean. It is on a steep hill, but the streets are very attractive and lined with stores."
    0
    Flag
  • William S.
    "There are many students, and the neighbors are very kind."
    0
    Flag
  • Merrily
    "It feels like a small town within a city. Charles Street is like a mini Main Street. People know each other. It’s a great neighborhood!"
    3
    Flag
  • Robert C.
    "Beacon Hill is a historic neighborhood of Boston, Massachusetts. Today, Beacon Hill is regarded as one of the most desirable neighborhoods in Boston. It is predominantly residential, known for old Federal style brick row houses with beautiful doors, decorative iron work, brick sidewalks, narrow streets, and gas lamps. This cozy enclave, filled with nearly 10,000 people, is more like a village than an anonymous city. It has a rich community life, with neighbors knowing neighbors and everyone meeting on the Hill's commercial streets and at its myriad activities. Restaurants, antique shops and grocery stores are located on Charles Street and Cambridge St. "
    2
    Flag
  • Robert C.
    "Beacon Hill is a historic neighborhood of Boston, Massachusetts. Today, Beacon Hill is regarded as one of the most desirable neighborhoods in Boston. It is predominantly residential, known for old Federal style brick row houses with beautiful doors, decorative iron work, brick sidewalks, narrow streets, and gas lamps. This cozy enclave, filled with nearly 10,000 people, is more like a village than an anonymous city. It has a rich community life, with neighbors knowing neighbors and everyone meeting on the Hill's commercial streets and at its myriad activities. Restaurants, antique shops and grocery stores are located on Charles Street and Cambridge St. "
    0
    Flag
  • FM
    "Walk to public transporation: Green, Red and Orange subway lines. Walk to Whole Foods, CVS, restaurants, night life and various shops. Walk to MGH (Massachusetts General Hospital), medical & dental offices. Walk to: the Boston Commons & Gardens, Downtown Crossing, the North End, Back Bay, Lowe's theater and the Theatre District. Quiet neighborhood. Many one way steets so no much through traffic. "
    0
    Flag

Market trends in Boston

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$830K
$6.67KMoM
Sale-to-List Price
99.3%
0.3%MoM
Price per sq ft
$759
$20MoM
Available listings
1905
310MoM

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
16 Harcourt St #4C, Boston, MA
0.79
Coop
$1,200,000
07/20/26
2
2
1,100
16 Harcourt St #3D, Boston, MA
0.79
Coop
$1,175,000
07/01/26
2
2
1,100
249 66 #A, Boston, MA
1.29
Coop
$848,500
02/19/26
2
1
1,599
249 A St, Boston, MA
1.29
Coop
$845,577
05/06/26
1
1
1,609
46 Lewis St #10, Boston, MA
1.14
Coop
$395,000
06/08/26
1
1
391
566 Commonwealth Ave #1110, Boston, MA
1.46
Coop
$525,000
12/16/25
1
1
890
566 Commonwealth Ave #710, Boston, MA
1.46
Coop
$510,000
01/06/26
1
1
890
566 Commonwealth Ave #1207, Boston, MA
1.46
Coop
$450,000
07/31/26
1
1
845
566 Commonwealth Ave #308, Boston, MA
1.46
Coop
$360,000
10/28/25
2
1
890
21 Moon St #2, Boston, MA
1.15
Coop
$480,000
12/17/25
1
383

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5 Otis Pl, Boston, MA 02108
0.02
$8,048,800
6
7.5
5,232
Off Market
50 Brimmer St, Boston, MA 02108
0.04
$3,965,500
3
3.5
3,177
Off Market
54 Brimmer St, Boston, MA 02108
0.04
$3,995,000
5
5
3,228
For Sale
8 Otis Pl, Boston, MA 02108
0.01
$7,500,000
4
6
4,896
For Sale
160 Mount Vernon St, Boston, MA 02108
0.05
$6,258,400
5
6.5
4,151
Off Market
36 Lime St, Boston, MA 02108
0.05
$9,509,100
5
6
5,875
Off Market
101 Chestnut St #R, Boston, MA 02108
0.00
$7,903,300
4
5
3,000
Off Market
28 Mount Vernon St #1, Boston, MA 02108
0.04
-
3
2.5
2,234
Off Market
107-109 Chestnut St #PH, Boston, MA 02108
0.01
$10,600,000
4
4.5
3,863
Recently Sold
107-109 Chestnut St #PENTHOUSE, Boston, MA 02108
0.01
$10,600,000
4
4.5
3,863
Recently Sold
140 Mount Vernon St #1, Boston, MA 02108
0.08
$1,601,700
2
2
1,174
Off Market

Price and Tax history

DateEventPrice
Sep 14, 2026
Source: MLS PIN #73576624
Listed For Sale
$3,499,950
Jun 26, 2026
Source: MLS PIN #73499714
ListingRemoved
$3,595,000
May 9, 2026
Source: MLS PIN #73499714
PriceChange
$3,595,000
Price decreased by 4%
Apr 10, 2026
Source: MLS PIN #73499714
Listed For Sale
$3,750,000
Dec 1, 2025
Source: MLS PIN #73363206
ListingRemoved
$3,999,999

LGBTQ Local Legal Protections

Rebecca Davis Tulman and Leslie Singleton Adam, Gibson Sotheby's International Realty, (857) 310-5632
Agent Phone: (617) 510-5050
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

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Frequently asked questions about 101 Chestnut St #E

  • What is the estimated monthly payment for 101 Chestnut St #E?
    Based on a $3,499,950 list price with 20% down at today's rates, the estimated monthly payment for 101 Chestnut St #E in Boston, MA is approximately $21,007 (about $19,036 principal & interest, $1,896 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 101 Chestnut St #E compare to homes in Boston?
    101 Chestnut St #E in Boston, MA is listed at $3,499,950, about 322% above the $830K median sale price in Boston.
  • What do residents say about the Beacon Hill neighborhood?
    Residents describe the Beacon Hill neighborhood in Boston, MA as dog-friendly, walkable to restaurants, and walkable to grocery stores. See homes for sale in Beacon Hill, Boston.
  • What are the closest schools to 101 Chestnut St #E?
    The closest schools to 101 Chestnut St #E in Boston, MA are Albert D Holland School of Technology (Middle/High, rated 2/10), Baldwin Early Learning Center (Pre-K/Elementary), Blackstone Elementary School (Pre-K, rated 3/10).
  • Does 101 Chestnut St #E have air conditioning?
    Yes, 101 Chestnut St #E in Boston, MA has air conditioning.
  • Does 101 Chestnut St #E have laundry facilities?
    Yes, 101 Chestnut St #E in Boston, MA has in-unit laundry.
101 Chestnut St #E, Boston, MA 02108 is a 2 bedroom, 3 bathroom, 2,500 sqft coop built in 1918. 101 Chestnut St #E is located in Beacon Hill, Boston. This property is currently available for sale and was listed by MLS PIN on Sep 14, 2026. The MLS # for this home is MLS# 73576624.