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101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
101 Chestnut Street E, Boston MA 02108
Massachusetts>Boston>Flat of the Hill

101 Chestnut Street EBoston, MA 02108

For Sale

$3,750,000

Smart Buyer Rebate $18,750

One of the most notable buildings in all of Boston, 101 Chestnut Street in Beacon Hill is known for its incredibly gracious architecture, intimate community. and impeccable service. The elegant entry courtyard w/ fountain is the perfect backdrop to this one of a kind residence that's both welcoming and distinguished. Unit E offers 2500 sqft of living space on one floor: 3 bedrooms, 3 bathrooms and a graceful living/dining room w/ front facing Chestnut Street views. The expansive space occupies a desirable corner exposure w/ courtyard views seen from the chef's kitchen & addt'l exposures throughout. The primary bedroom is generously proportioned & boasts South facing sun. A primary bathroom & oversized closet offer incredible storage. A separate bedroom wing w/ 2 add'tl bedrooms & 2 bathrooms is on the West side of the unit & offer privacy. 101 Chestnut features a concierge and a beautifully landscaped common roofdeck. A private storage closet completes this truly exceptional offering.

Listed by Rebecca Davis Tulman and Leslie Singleton Adam

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Gibson Sotheby's International Realty

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(617) 5105050

Last updated April 14, 2026

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Source: MLSPin #73499714

Listing Facts

  • TypeSingle-family
  • NeighborhoodFlat of the Hill
  • Bedrooms3
  • Bathrooms3
  • Days on Prevu21
  • HOA/Maint. Fees$3,610/month
  • Size2,500 sqft
  • Price per sqft$1,500

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Pets Allowed
  • Air Conditioning
  • Parking
  • Storage
  • Fitness Center

Location

Mortgage Calculator

Listing History

04/10/2026
Listed by Gibson Sotheby's International Realty
$3,750,000

Property Details for 101 Chestnut Street E

Association

Amenities

  • 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
  • Pets Allowed: Yes

Fees

  • Association Fee: $3,610.00 Monthly
  • Association Fee Includes: Water, Sewer, Insurance, Maintenance Structure, Maintenance Grounds, Snow Removal, Trash, Reserve Funds

Exterior

Construction

  • Number Of Units Total: 18
  • Property Attached: Yes
  • Roof: Rubber, Other
  • Stories: 1
  • Stories Total: 1
  • Structure Type: Mid-Rise
  • Year Built: 1918
  • Year Built Details: Approximate
  • Construction Materials: Brick, See Remarks
  • Entry Level: 2
  • Entry Location: Unit Placement(Front)
  • Exterior Features: Deck - Roof

Features

  • Patio And Porch Features: Deck - Roof

Measurements

  • Building Area Total: 2,500
  • Building Area Units: Square Feet
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 3353906
  • Tax Year: 2025

Interior

Features

  • Appliances: Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer
  • Fireplace Features: Living Room, Master Bedroom
  • Fireplace: Yes
  • Fireplaces Total: 3
  • Flooring: Wood

Measurements

  • Living Area: 2,500
  • Living Area Source: Other

Rooms

  • Basement: N
  • Bathrooms Full: 3
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 3
  • Rooms Total: 6

Other

General

  • Exclusions: Fireplace Mantel In Living Room Is Excluded.

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Central
  • Has Heating: Yes
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 3 bedrooms and 3 bathrooms in this single-family home at 101 Chestnut Street E.

How does 101 Chestnut Street E compare to other single-family homes in Flat of the Hill?

This single-family home is listed 57% below the average price for single-family homes in Flat of the Hill and has been on the market for 11 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 2,500 sqft.

101 Chestnut Street E is a 3-bedroom, 3-bath single-family home for sale in Boston MA 02108. Listed on Prevu for 21 days at $3,750,000. This property features 2,500 square feet of living space, located in Flat of the Hill. The median listing price for single-family homes in this area is $4,872,500. The home offers private outdoor space, dishwasher, pets allowed, air conditioning, storage, fitness center, parking, and washer/dryer. Explore more single-family home listings in Boston.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.