Windy City RE

Windy City RE


Windy City RE is a leader in Chicago real estate investment with expertise in buying, renovating, and selling apartment buildings. Windy City RE recently acquired approximately 1000 apartment units and around 40,000 square feet of prime retail in Chicagoland, valued at over $200 million.

The team at Windy City RE always strives to find the best opportunities to grow and has proven success since its start in 1998.

Management Team

Milan P. Rubenstein - Managing Partner
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 200 million dollars.

Joshua G. Rubenstein - Partner
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 - Partner
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.

More Information

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 and 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

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