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45 Highland Ave, Winthrop MA 02152 – 10 bed 4 bath For Sale – 73396488

$ 1,400,000
45 Highland Ave, Winthrop MA 02152,

Overview

  • Updated On:
  • July 29, 2025
  • listingid
  • 73396488
  • 10 Bedrooms
  • 4 Bathrooms
  • 0 Garage Spaces
  • 4 Non-Garage Parking Spaces
  • 1900

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

This property is listed by Jonathan Mathews from Legacy Realty Advisors LLC

Property Listing Details

Overview

MLS Status
Price $ 1,400,000
Living Area 4,671.00 ft2
Bedrooms 10
Total Rooms 18
Listing MLS ID 73396488
Days on Market 33
Bathrooms 4

Unit Information

Bedrooms 10
Full Bathrooms 4
Half Bathrooms 0
Cooling
Heating Natural Gas
Uncovered Parking 4
Garage Parking 0
Water View Yes
Unit Level
Common Walls
Laundry Features
Lead Paint Certified Treated
Outdoor Space Available
Living Area Includes Basement Partial
Patio And Porch Features Porch
Parking Features Paved Drive,Off Street
Waterview Features Bay,Ocean,Walk to
Flooring Wood,Carpet,Hardwood

Building Information

Building Name
Units in Building 3
Pets Allowed
Association Amenities
Pool Features
Waterfront Features Ocean,0 to 1/10 Mile To Beach,Beach Ownership(Public)
Association Fee Includes
Construction Materials
Year Built 1900
Security Features
Sewer Public Sewer
Spa Features
Structure Type
Water Source Public
Basement Partial
Roof

Additional Details

Community Features Public Transportation,Shopping,Park,Walk/Jog Trails,Golf,Medical Facility,Laundromat,Bike Path,Conservation Area,Highway Access,House of Worship,Marina,Public School
Disclosures ***Unit 3 is vacant. Rent is projected to be $3900,the same rent amount that is was last listed at this year***
Last Updated July 28, 2025 at 11:41pm
Building Area Source Public Records
MLS PIN Page
Parcel Number 1424984
Original List Price 1400000
Listing Office legacy realty advisors llc
Tax Annual Amount 8476
Tax Assessed Value 821300
Tax Book Number 39771
Tax Year 2025
Year Built Details Actual
Year Built Source Public Records
Zoning R
Listing Agent jonathan mathews

Property Address

Address: 45 Highland Ave, Winthrop MA 02152
City:
State/County:
Zip: 02152
Country: US

Amenities and Features

Other Features
Dining Room
Dishwasher
Disposal
Family Room
Has Heating System
Kitchen
Laundry Room
Living Room
Office/Den
Open Parking
Range
Refrigerator

Payment Calculator

$ 8,021.63
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
$ 6,714.97

Map

Transport
Supermarkets
Schools
Restaurants
Pharmacies
Hospitals

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45 Highland Ave, Winthrop MA 02152 | © 2024 DOUGLAS ELLIMAN REAL ESTATE. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS ARE DEEMED RELIABLE, BUT SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT OR ZONING EXPERT. THE NUMBER OF BEDROOMS LISTED ABOVE IS NOT A LEGAL CONCLUSION. EACH PERSON SHOULD CONSULT WITH HIS/HER OWN ATTORNEY, ARCHITECT OR ZONING EXPERT TO MAKE A DETERMINATION AS TO THE NUMBER OF ROOMS IN THE UNIT THAT MAY BE LEGALLY USED AS A BEDROOM. EQUAL HOUSING OPPORTUNITY.

Property Details

45 Highland Ave, Winthrop MA 02152 – 10 bed 4 bath For Sale – 73396488

$ 1,400,000

Status:

45 Highland Ave, Winthrop MA 02152, , , 02152

Country: US

Property Overview

MLS #: 73396488

Type: /

Action:

Year Built: 1900 (Actual, Source: Public Records, Effective: )

Living Area: 4,671.00 ft2 (Total: 4671 Square Feet, Source: Public Records)

Lot Size: 0.13 ft2 (Area: 0.13 Acres, SqFt: 5710)

Total Rooms: 18

Condition:

Availability:

Building Name:

Interior Features

Bedrooms: 10 (Main Level: )

Bathrooms: Total: 4 (Full: 4, Half: 0, Decimal: 4, Main Level: )

Basement: Partial

Fireplaces: 0 ()

Flooring: Wood,Carpet,Hardwood

Laundry:

Window Features:

Door Features:

Accessibility:

Entry: Level , Location:

Other Equipment:

Construction & Design

Style:

Materials:

Foundation: Other (Area: )

Roof:

Stories: 4 (4)

Common Walls:

Body Type:

Utilities & Green Features

Heating: Natural Gas

Cooling:

Water Source: Public

Sewer: Public Sewer ()

Utilities:

Electric: Circuit Breakers,Individually Metered (Expense: )

Gas:

Energy Certificate:

Green Energy Efficient:

Green Energy Generation:

Green Indoor Air Quality:

Green Water Conservation:

Insulation:

Exterior & Lot Features

Garage Spaces: 0

Covered Spaces: 0

Parking Total: 4

Parking Features: Paved Drive,Off Street

Pool:

Spa:

Patio/Porch: Porch

Fencing:

Lot Features:

View: (Bay,Ocean,Walk to, Waterview Y/N: Yes)

Waterfront: Ocean,0 to 1/10 Mile To Beach,Beach Ownership(Public)

Road Frontage: Public ()

Road Surface:

Road Responsibility:

Other Structures:

Horse Amenities:

Wooded Area:

Pasture Area:

Cultivated Area:

Additional Parcels: (Number: )

Outdoor Space:

Community & Association

Community Features: Public Transportation,Shopping,Park,Walk/Jog Trails,Golf,Medical Facility,Laundromat,Bike Path,Conservation Area,Highway Access,House of Worship,Marina,Public School

Association Fee: ()

Fee Includes:

Association Amenities:

Pets Allowed:

Schools: E: , M: , H:

Zoning: R ()

MLS Area: Major: , Minor:

Management:

Optional Fee: (Includes: )

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

Room Details

Living Room (): x ( sqft) - Features:

Dining Room (): x ( sqft) - Features:

Kitchen (): x ( sqft) - Features:

Master Bedroom (): x ( sqft) - Features:

Master Bathroom: Features:

Laundry Dimensions:

Multi-Unit Information (if applicable)

Total Units: 3

Units Owner Occupied:

Unit 1: Beds: 2, Full Baths: 1, Half Baths: 0, Levels: 1, Rent: 0, Lease: N

Unit 2: Beds: 3, Full Baths: 1, Half Baths: 0, Levels: 1, Rent: 0, Lease: Y

Unit 3: Beds: 5, Full Baths: 2, Half Baths: , Levels: 2, Rent: 3900, Lease: N

Unit 4: Beds: , Full Baths: , Half Baths: , Levels: , Rent: , Lease:

Complex Complete:

Unit Building:

Financial & Lease Information

Tax Annual Amount: 8476 (Year: 2025)

Tax Assessed Value: 821300

Tax Block/Lot/Book/Map: / / 39771 /

Parcel Number: 1424984

Special Licenses:

Current Financing:

Gross Income: 106356 (Scheduled: )

Net Operating Income: 106356

Operating Expense: (Water/Sewer: , Insurance: )

Financial Data Source:

APOD Available: No

Tenant Pays:

Rent Includes:

Total Actual Rent: 0

Lease Term: (Existing Type: )

Deposit Required: (Security: , First Month: , Last Month: )

Insurance Required:

References Required:

Listing & Agent Information

Listing Agent: Jonathan Mathews (MLS ID: CT001073) / Team:

Listing Office: Legacy Realty Advisors LLC (MLS ID: AN9036)

Agent (Property): 369593

Buyer Agent MLS ID:

Buyer Office MLS ID:

Listing Agreement: Exclusive Right To Sell

Listing Contract Date: 2025-06-25

Expiration Date: 1900-01-01

Original List Price: 1400000

Price Per SqFt (List): 299.72

Market Time (Property): 33 (Broker: 33, Prev Broker: 0, Prev Property: 0)

MLS Status: Active

Possession:

Directions: Revere St to Highland Ave. Highland Ave runs parallel with Crest Ave.

Disclosures: ***Unit 3 is vacant. Rent is projected to be $3900,the same rent amount that is was last listed at this year***, N

Lead Paint: Certified Treated

Title 5:

Exclusions:

Contingency:

Special Listing Conditions:

Lender Owned:

Short Sale Lender Approval Required:

Home Warranty Y/N:

Documents Available: (Count: )

Showings Deferral Date:

Open House Flag: 1

Listing Alert: No

Square Feet Disclosures: (Incl. Base: No, Other: )

Master Book/Page: / (Page: 320)

Sale Information (if applicable)

Close Date:

Close Price:

Price Per SqFt (Sold):

Anticipated Sold Date:

Concessions Amount:

Purchase Contract Date:

Sold vs Rent:

System Information

Property ID: 2257453

Modification Timestamp: July 28, 2025 at 11:41pm

Bridge Modification Timestamp: July 28, 2025 at 11:40pm

Original Entry Timestamp: June 25, 2025 at 06:41pm

Status Change Timestamp: June 25, 2025 at 06:41pm

Off Market Date:

Development Status:

Business Type:

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