1. Massachusetts
  2. Winthrop
  3. 45 Highland Ave
$1,400,000

45 Highland Ave, Winthrop, MA 02152

  • 10 beds |
  • 4 baths |
  • 4,671 sqft
  • Property Icon Triplex
  • Property Year Built Icon Built in 1900
  • Property Lot Size Icon5,663sqft lot
  • Property Parking Icon —— car garage
  • Property Price Per Square Feet Icon $300/sqft
  • Property List Date Icon Listed 1 month ago

Property Description

Incredible investment opportunity in the heart of the Highlands! This oversized 3-family property is has been generating strong income with potential for more. One unit is available for an owner occupant or savvy investor looking to maximize cashflow. Walk-out ground level 2-bedroom apartment. First-floor 2-bedroom unit with an additional office, living room, and dining room. Owner’s unit, spanning the 2nd and 3rd floors, this enormous 5-bedroom, 2-bathroom unit can be delivered vacant for owner occupancy or new tenants. Enjoy a paved driveway with ample off-street parking. The property directly abuts Crest Ave Park, offering green space right next door. Commuter-friendly location with easy access to Boston and points North/South via major routes. Public transit is a breeze. Don't miss this massive 3-family gem

Listing Status:
Active
Date Added:
June 25, 2025 at 05:00AM
Listing Office:
Legacy Realty Advisors LLC : 216-973-3072
Listing Agent:
Jonathan Mathews : 781-853-1765
MLS ID:
73396488
  • General: Laundry RoomLiving RoomKitchenDining RoomOffice/DenFamily Room
  • Appliances: RangeDishwasherDisposalRefrigerator
  • Basement: Partial
  • Flooring: WoodCarpetHardwood
  • Heating: Natural Gas
  • Fireplace: Fireplaces: 0

This listing courtesy of Jonathan Mathews, Legacy Realty Advisors LLC

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

Ready to Start a VA Loan?

Get Started Veterans United Home LoansNMLS #1907  †
Get Prequalified »
Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

Location

Schools Nearby

W

William P. Gorman/Fort Banks Elementary School

101 Kennedy Rd, Winthrop, MA, 02152

Grades PK-2

0.33 miles away

W

Winthrop Middle School

60 Payson St, Winthrop, MA, 02152

Grades 6-8

0.48 miles away

W

Winthrop High School

400 Main St, Winthrop, MA, 02152

Grades 9-12

0.50 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.