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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

$3,499,950

Smart Buyer Rebate $17,500

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 updated September 14, 2026

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Source: MLSPin #73576624

Listing Facts

  • TypeSingle-family
  • NeighborhoodFlat of the Hill
  • Bedrooms2
  • Bathrooms3
  • Days on Prevu1
  • HOA/Maint. Fees$3,610/month
  • Size2,500 sqft
  • Price per sqft$1,400

Amenities

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

Location

Mortgage Calculator

Listing History

09/15/2026
Price Increased
$3,499,950
09/14/2026
Listed by
$3,499,000
  1. 09/15/2026$3,499,950
    Price Increased
  2. 09/14/2026$3,499,000
    Listed by

Property Details for 101 Chestnut Street E

Association

Amenities

  • Association Amenities: Hot Water, Laundry, Elevator(s), Fitness Center, Storage
  • Community Features: Tennis Court(s), Park, Other
  • Pets Allowed: Yes

Fees

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

Exterior

Construction

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

Features

  • Patio And Porch Features: Deck

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

  • Bathrooms Full: 3
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 2
  • 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 2 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 45% below the average price for single-family homes in Flat of the Hill and has been on the market for 87 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 2-bedroom, 3-bath single-family home for sale in Boston MA 02108. Listed on Prevu for 1 days at $3,499,950. This includes a recent price increase of $950. 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 $4,795,000. Additional amenities include private outdoor space, dishwasher, pets allowed, air conditioning, storage, fitness center, and washer/dryer. Browse 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.