$3,499,950
101 Chestnut Street
Boston, MA, 02108
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.
Property Details
Price:
$3,499,950
MLS #:
73576624
Status:
Active
Beds:
2
Baths:
3
Type:
Single Family
Subtype:
Stock Cooperative
Neighborhood:
beaconhill
Listed Date:
Sep 14, 2026
Finished Sq Ft:
2,500
Total Sq Ft:
2,500
Year Built:
1918
Schools
Interior
Above Grade Finished Area
2500
Appliances
Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Fireplaces Total
3
Flooring
Wood
Heating
Central
Interior Features
Study
Exterior
Association Amenities
Hot Water, Laundry, Elevator(s), Fitness Center, Storage, Garden Area
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Bike Path, Highway Access, Other
Construction Materials
Brick, See Remarks
Exterior Features
Deck – Roof
Patio And Porch Features
Deck – Roof
Roof
Rubber, Other
Security Features
Concierge
Stories
1
Financial
HOA Fee
$3,610
HOA Fee Frequency
Monthly
HOA Includes
Water, Sewer, Insurance, Maintenance Structure, Maintenance Grounds, Snow Removal, Trash, Reserve Funds
Tax Year
2025
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Boston as of Sep 21, 2026
367
Single Family Listed
121
Avg DOM
647
Avg $ / SqFt
$1,834,846
Avg List Price
Community
- Address101 Chestnut Street Boston MA
- CityBoston
- CountySuffolk
- Zip Code02108
Subdivisions in Boston
- Adams Village
- Allston
- Ashmont Hill / Carruth Area
- Bellevue Hill
- Bellevue Hill/ Roxbury Latin
- Boston
- Brighton
- Brighton-Oak Square
- Carruth’s Hill
- Charlestown
- Dorchester
- Fairmount Hill
- Farlow Hill
- Fort Hill Highland Park
- Harbor View-Orient Heights
- Harborview
- Hyde Park
- Jamaica Plain Moss Hill
- Lower Mills
- Lowermills
- Mattapan
- Melville Park
- Mission Hill – Longwood Medical
- Moss Hill
- Moss Hill, across from Emerald Necklace & Jamaica Pond
- Moss Hill, Jamaica Plain
- Orient Heights
- Peak Hill Neighborhood
- Pondside/Monument Square Historic District
- Readville
- Roslindale Village
- ROXBURY
- South End
- St Botolph
- Stonybrook Village
- Thomas Park / Dorchester Heights
- Thompson Square
- Tommy’s Rock
- Well Respected Hyde Park Neighborhood Area of Boston.
- West Roxbury
- West Roxbury’s Bellevue Hill
- West Side
- Woodbourne Historic District
- Woodbourne in JP/Roslindale
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Property Summary
- 101 Chestnut Street Boston MA is a Single Family for sale in Boston, MA, 02108. It is listed for $3,499,950 and features 2 beds, 3 baths, and has approximately 2,500 square feet of living space, and was originally constructed in 1918. The current price per square foot is $1,400. The average price per square foot for Single Family listings in Boston is $647. The average listing price for Single Family in Boston is $1,834,846. To schedule a showing of MLS#73576624 at 101 Chestnut Street in Boston, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Gibson Sotheby’s International Realty. 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.
101 Chestnut Street
Boston, MA