Working at Windsor Communities | Glassdoor

Windsor Communities Overview

Boston, MA
501 to 1000 employees
Company - Private
Real Estate
$10 to $25 million (USD) per year

Windsor Communities – Why Work For Us?

undefinedPremium Living Experience

Our residents enjoy beautiful homes in excellent locations, with no home ownership hassles. Better yet, we offer superb customer service, resort-style amenities, and the reassurance of 24-hour emergency maintenance service.


Throughout its long history, Windsor Property Management has sustained a reputation for outstanding professional property management with an emphasis on service. The company has achieved a national presence through continued expansion.

A Tradition of Achievement

Windsor first entered the real estate arena in 1960, with the renovation of three apartment buildings in Cambridge, MA. Two years later, the company developed another property in Norwood, MA. Since then, Windsor has managed properties in 22 states in excess of 40,000 apartment homes. Today our portfolio extends from California to Massachusetts including over 80 residential communities in 16 states and the District of Columbia. These communities, which comprise more than 22,000 apartment homes, are currently located in the Northeast, Mid-Atlantic, West, Southeast, and Southwest regions of the country. Windsor maintains an attentive owner relationship with all of the properties to be able to immediately respond to the needs of its residents and invest in the communities’ continued excellence.

A privately held company, Windsor is based in Boston, MA. The company maintains its strong financial foundation through vigilant management and selective growth.

Windsor Communities are affiliated with The General Investment & Development Companies of Boston, Massachusetts.


Our mission reflects our long-held belief that we can enhance the lives of our residents through unparalleled service, by building a staff of well-qualified, friendly people who love what they do.

Upholding A Tradition

At Windsor, we pledge:

  • To dedicate ourselves to our residents and provide them with an exceptional living experience through high-quality service, personalized attention, and the very best management and maintenance of their communities.
  • To support, encourage, and inspire our employees in a work environment that values communication, teamwork, loyalty, training, and the recognition of personal achievements.

At Windsor Communities, it's all about people. Our residents depend on us to be observant, interested in their lives, and quick to respond to their needs. We enjoy working with them and with each other. Every day is different: demanding, rewarding, and fun.

Windsor is a growing company that fosters a professional attitude and a strong team spirit. We are committed to training our employees well, honoring their achievements, and promoting from within. The people who work here are outgoing, caring, and proud of what they do. If you're someone who welcomes responsibility and enjoys getting involved, you'll fit right in.

Windsor Communities Reviews

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Jeffrey A. Harris
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  • Featured Review

    Helpful (6)

    "One of the best in the industry and promising growth!"

    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Current Employee - Leasing Consultant in Edgewater, NJ
    Current Employee - Leasing Consultant in Edgewater, NJ
    Positive Outlook

    I have been working at Windsor Communities full-time (Less than a year)


    I had the opportunity to interview and be offered positions with multiple different property management companies before accepting my position at Windsor, and after being with the company for a few months now, I know I made the right choice. From the start, I was impressed with Windsor’s hiring process. It is evident that they take it very seriously (4-5 interviews for an “entry level” job). This is because they truly hire from within. I have witnessed multiple different promotions already, one being why the position I applied for was open. They really invest in their employees and their growth. The training I have received and constant on-going training have been FANTASTIC! I had the opportunity to go to Massachusetts for hands on training as well, and already planning to again soon. Not only that, but they send their experts in different categories (software, customer service, etc.) to your onsite location to train with you all day. The regional trainer flew out of Boston to train with me one on one for two whole days! They really know how to make you feel special. They also pair you up with a mentor for your first 6 months that you constantly meet with to make sure you are on track for success. Everyone I have met within the company is truly AWESOME. I have never been at a company where I have met some of the most genuine, fun, and caring people. The culture here is not overly bureaucratic and job titles really don’t mean much, your input and suggestions matter and are taken into consideration. Many employees here have been with the company for 10+ years which is unheard of in the property management industry where turnover is very high. This was a huge selling point for me and why I ultimately chose to accelerate my career in the industry with Windsor. The salary and benefits were also highly competitive. I plan to stay with the company for a very long time considering there is room for growth.


    Little to no cons that are outside of the industry standards. I wish Windsor had more properties in the metropolitan area/central jersey.

    Advice to Management

    Remain competitive and stay on top of the competition for your employees. I know a few employees who thought Windsor was the only company that offered the clothing allowance, however, this is not true. Competition is copying from the best and they just might take some of your employees if you don't stay vigilant. Management is excellent thus far, don't let constant growth change that.

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Windsor Communities Photos

Windsor Communities photo of: Windsor Communities Operations Conference 2015 - Wrigley Field
Windsor Communities photo of: Windsor at Oak Grove team photo!
Windsor Communities photo of: Maintenance Technician | Windsor at Oak Grove
Windsor Communities photo of: Windsor Maintenance Technician
Windsor Communities photo of: Leasing Office | Windsor at Oak Grove
Windsor Communities photo of: The 5550 staff packed bags with essentials (food, water, tooth brushes and baby wipes) for the homeless community on Wilshire Boulevard.
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Windsor Communities Interviews



Getting an Interview

Getting an Interview





    Leasing Consultant Interview

    Anonymous Employee in San Francisco, CA
    Accepted Offer
    Positive Experience
    Average Interview


    I applied online. I interviewed at Windsor Communities (San Francisco, CA) in April 2017.


    Asked the 3 basic questions. First there was a phone interview, then in person interview. There are often multiple properties hiring. Can ask your regional manager about each.

    Interview Questions

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Windsor Communities Awards & Accolades

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