Exquisite Penthouse Duplex at 101 Chestnut Street, a premier doorman/elevator building on the Flat of the Hill. Completely renovated to the highest standards, this 3,000 sq. ft. home has fantastic views from every room. The gracious living room features a fireplace and French doors opening to a balcony overlooking the courtyard. The grand eat-in chef’s kitchen, with custom cabinetry and a fireplace, has an adjacent butler’s pantry/wet bar. Both rooms are framed by oversized windows with spectacular views of Beacon Hill rooftops, the State House dome, and the Downtown skyline. 4 spacious bedrooms, all with ensuite baths • Library, Den, Home Office, and Butler’s Pantry • 4 full & 2 half bathrooms • Generous foyer entries on both levels • Exceptional craftsmanship throughout: built-ins, millwork, and custom finishes • Abundant storage and closet space • Rental parking transferable at Brimmer St. Garage • Spectacular common roof deck with panoramic city views • Fitness & storage rooms
Condo (co-op)Property Type
1918Year Built
$2,280Est. Price/Sq.Ft.
Listed by John Ranco• Gibson Sotheby's International Realty
Bought with Rebecca Davis Tulman and Leslie Singleton Adam• Gibson Sotheby's International Realty
Claim this home to receive a free report every month with insights on the changing estimate.
Earn from this home
Sell
$303,970
Est. take-home
List your home with Redfin and save $34,205
Rent
$4,931/mo
Redfin rental estimate
List your home for rent
Market trends in Flat of the Hill, MA
Last updated July 2026
Buyer's Market
Seller's Market
Seller's market
Sale-to-List Price
93.2%
0.0% MoM
Median sale price
$1.3M
$0 MoM
Avg. days on market
46d
0 days MoM
Recently sold homes
6
0 MoM
Provided by Redfin
Sale history for 101 Chestnut St Unit R
Date
Event
Price
MLS PIN #73357969
Jul 22, 2025
Sold
$7,900,000
$2,633/sq ft
Apr 13, 2025
Contingent
—
Apr 10, 2025
Listed
$7,900,000
$2,633/sq ft
MLS PIN #72893873
Dec 8, 2021
Sold
$6,825,000
$2,275/sq ft
Oct 29, 2021
Contingent
—
Sep 13, 2021
Listed
$7,250,000
$2,417/sq ft
+26
Reminiscent of a classic Venetian or Florentine palazzo, 101 Chestnut is a prized doorman building on the Flat of Beacon Hill featuring a stunning brick courtyard surrounded by an open colonnade with lush plantings, trees and central fountain. Residence R is a one-of-a-kind, newly renovated penthouse duplex with 4 beds, 4 full and 2 half baths and 3,000 SQFT. Take the elevator to the fifth floor and enter the main foyer. Just ahead is the sun-drenched living room offering high ceilings, fireplace and a Juliet balcony with French doors overlooking the courtyard. Sensational kitchen/dining area with mesmerizing views of Beacon Hill and the golden dome of the State House. There is also a library, home office, butler’s pantry, and a potting room or wet bar. All bedrooms feature en suites and ample closet space. Amenities include storage room, fitness room, common roof deck and 1 Brimmer garage rental space. Steps from Charles Street, Public Garden, Boston Common and the Esplanade.
MLS PIN #72324773
Oct 23, 2018
Sold
$4,400,000
$1,467/sq ft
Sep 10, 2018
Pending
—
Sep 8, 2018
Price Changed
$4,500,000
$1,500/sq ft
Sep 8, 2018
Relisted
—
Jun 11, 2018
Listing Removed
—
May 10, 2018
Listed
$5,100,000
$1,700/sq ft
+10
One of Beacon Hill's most prized doorman buildings,101 Chestnut Street is an Italian-Renaissance style building with a distinctive bricked courtyard with fountain surrounded by an open colonnade. Stunning penthouse duplex...elegant foyer leads to gracious formal living room, featuring fireplace, high ceilings, deep crown moldings and Juliet balcony. An exquisite formal dining room with fireplace, wainscoting, built-in china cabinets affords spectacular views of Chestnut Street to the golden dome of the State House. Cozy library features custom built-ins, fireplace and powder room. The unique kitchen has casual dining area, pantry, ample storage and Beacon Hill vistas. Spacious master suite includes fireplace, dressing room, his and hers baths. A large guest suite with full bath and versatile third bedroom/office with full bath complete this distinctive offering. Amenities include roof deck, Brimmer garage rental, storage room....One of the most beautifully appointed homes on the Hill.
As the MLS and public records start to fill up, we'll list the details here.