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108-116 Winthrop RdBrookline, MA 02445

For Sale

$16,000,000

Smart Buyer Rebate $80,000

We are pleased to present the opportunity to acquire 108-116 Winthrop Road, a boutique 18-unit, 100% market rate apartment building located in the heart of Brookline, Massachusetts. The property is situated in one of the most sought after streets in the coveted Washington Square neighborhood. The building features charming common area spaces, attractively landscaped grounds, 14 on-site parking spaces, five (5) 3-bedroom units, ten (10) 3-bedroom units with dens and three (3) 3-bedrooms with two bathrooms units. All the apartment units offer large floor plans with oversized bedrooms, high ceilings, hardwood floors, large closets, and abundant natural light. Units have been updated with renovated kitchens and bathrooms. With these upgrades, and significantly below market rents, a new owner could significantly increase rents. The building is located a short walk from the MBTA Green line and a variety of bus routes. Group showings 7/8 & 7/10

Listed by Adam Aroesty

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Hammond Residential Real Estate

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617-571-9843

Listed by Marika Feuerstein

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Hammond Residential Real Estate

Listed by Marika and Adam Real Estate Group

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Hammond Residential Real Estate

Last updated September 01, 2025

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Source: MLSPin #73400447

Listing Facts

  • TypeMulti-family
  • NeighborhoodAspinwall Hill
  • Bedrooms54
  • Bathrooms21
  • Days on Prevu63
  • Taxes$105,273/year
  • Size34,849 sqft
  • Price per sqft$459

Amenities

  • Dishwasher
  • Parking

Location

Mortgage Calculator

Listing History

07/07/2025
Listed by Hammond Residential Real Estate
$16,000,000

Property Details for 108-116 Winthrop Rd

Exterior

Construction

  • Number Of Units Total: 18
  • Roof: Rubber
  • Stories: 3
  • Stories Total: 3
  • Year Built: 1910
  • Year Built Details: Actual
  • Construction Materials: Brick

Features

  • Road Frontage Type: Public
  • View: City View(s)

Measurements

  • Building Area Total: 34,849
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.20
  • Lot Size Area: 0
  • Lot Size Square Feet: 8,726
  • Lot Size Units: Acres

Financial

Residential Income

  • Gross Income: $149,820.00

Taxes

  • Parcel Number: 37322
  • Tax Annual Amount: $105,273.00
  • Tax Assessed Value: $1,066,600.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Range, Dishwasher, Disposal, Refrigerator, Freezer
  • Flooring: Wood
  • Interior Features: Ceiling Fan(s), Kitchen, Living RM/Dining RM Combo, Office/Den

Measurements

  • Living Area: 34,849
  • Living Area Source: Public Record

Rooms

  • Basement: Full, Concrete
  • Bathrooms Full: 21
  • Bathrooms Total Integer: 21
  • Bedrooms Total: 54
  • Rooms Total: 99

Other

General

  • Exclusions: Tenants Personal Property

Parking

Parking

  • Parking Features: Off Street
  • Parking Total: 14

Utilities

Equipment

  • Sewer: Public Sewer
  • Water Source: Public

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.