About Us

Our Mission

Windy City RE aims to generate the maximum amount of revenue for investors by adding value to property. We work at a fast pace while delivering exceptional quality.

We acquire apartment buildings that have upside potential for improvement & add-value.

We do this with:
- Unit Remodel/Modification
- Rent Increases/Increase Cash-Flow
- Restructuring of Existing Use
- Implementing More Cost Efficient Management

We grow equity quickly
-Acquire, Renovate, Sell/Refinance

We buy into larger buildings

Market Adaptation

The real estate market is constantly changing. Windy City RE has a history of success and adapts to changing conditions.

1999-2008 15-80 unit Apartment Buildings
2008 Single Family Homes / Existing & Additions
2010-2012 2-10 Unit Apartment Buildings

Recent Market Change:
Small Foreclosed Apartment Buildings
Larger Buildings 20 - 400 Unit Apartment Buildings
New Construction / Re-Development

What Makes Us Different?

Not A Fund
Investors choose which projects they want to invest in. We acquire first and add investors second.

In-House Crew

- General Contractor License and insurance
- Renovate quickly
- Lower construction costs
- Time and Materials Only
- Better Over-site
- No potential problems with sub-contractors
- No General Contractor Fees

Broker License

- Better ability to find and purchase a good deal
- Better knowledge of the market and comparable sales
- Better knowledge of contracts and negotiations
- Working for the investor - No conflict of interest
- Ability to forfeit commission to add advantage to win the bid


- Lower Overall Costs, Quicker Turnover and Rental Increases
- More Efficient and Aggressive at Renting Units
- More in Touch with Day to Day Activities
- No asset management fees

Investor Relations

Projects are entirely open book to investors in addition to quarterly reports and dividends.

Quarterly Reports

Current status of building at any time
Dividend checks and reports sent quarterly

8% preferred return

70/30 split on positive cash flow thereafter

70/30 split on profit from sale

70% to investor after 8% preferred return


Windy City RE has a team with in-depth understanding of the real estate market and financing sources.

Loan Types Include:
Short Term Local Bank Financing
Floating & Adjustable Rate Financing
Construction Financing
Bridge Financing / Hard Money Loans
Permanent Financing - Agency Financing
Mezzanine Financing


Joshua G. Rubenstein

Joshua Rubenstein invited Amy and Milan to Chicago to start working with him in 2010, signaling the formation of Windy City RE. Josh graduated from Indiana University and worked with Amy and Milan in Los Angeles in 2007. Joshua decided to open a real estate firm in Chicago in 2008. He is now a managing partner at the firm, and his focus is in acquisitions and construction management. Windy City RE LLC and Milan Properties Inc. combined currently own approximately 1000 apartment units in California and 400 apartment units in Chicago. The companies focus primarily on small and mid-sized apartment buildings ranging between 2-70 units. Most properties are bought, completely rehabbed, and re-tenanted within six months. Improvements to the buildings may include re-plumbing of the entire building, new electrical service, new roofing, new HVAC systems, new bathrooms and kitchens, hardwood floors, tiles, kitchens, appliances, painting exteriors and interiors, have had great success revitalizing the distressed properties of Chicago. Their finished products have been well received by quality tenants and potential buyers.

Amy M. Rubenstein

Amy M. Rubenstein is originally from Chicago and graduated from Brandeis University, Magna Cum Laude. She has been working in real estate for the past twelve years and holds a real estate broker license in the state of California and a Managing Broker’s license in the state of Illinois. She started out investing in small projects on her own, with attention on buying and selling properties quickly in order to build capital. After her first few properties, Amy began to acquire investors, quickly expanding her portfolio. After merging with Milan Properties Inc., Amy began centering her attention on increasing income and value of the Milan Properties’ portfolio. She specializes in the restructuring of building management and the revitalization of acquired buildings. Amy oversees the accounting, reorganization, and re-renting of the individual buildings and apartments, achieving maximum incomes. Most of the properties they have purchased in the last two years have required complete remodels, which instigated the formation of an entire construction crew in Chicago. Together, Amy, Joshua and Milan have created a formula for success with the combination of their past experiences, strong knowledge of the California and Illinois real estate markets, and superb staff.

Milan P. Rubenstein

Milan has been a leader in commercial real estate for the Greater Los Angeles community for the past fifteen years, and in 2010 he entered the Chicago market, focusing on the acquisitions of bank-owned, distressed and mismanaged apartment buildings. Milan is originally from Eastern Europe and holds a degree from UCLA. He started out as a broker at Remax Commercial where he was ranked top ten worldwide. His focus is on smaller apartment buildings on the North Side of Chicago, and larger complexes in the suburbs. He deals with acquisitions and dispositions, in-house construction crews, bank financing, and managing investor relations. In the last three years, Windy City RE LLC purchased approximately 900 apartment units and around 40,000 sqf. of prime retail, valued at over 100 million dollars.

Our Team

















Mariana Tomuta

Director of Accounting

Will Oney-Paige

Director of Operations

Anthony Pratola

Project Superintendent

Daniel Bernecker

Accounting Manager

Mark Kramer

Creative Director

Randy Eich

Sales Specialist