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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  • Helpful (4)

    "Great Company, Needs More Growth Opportunities"

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    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Former Employee - Leasing Consultant in San Francisco, CA
    Former Employee - Leasing Consultant in San Francisco, CA
    Positive Outlook
    Approves of CEO

    I worked at Windsor Communities full-time (More than a year)


    Expectations are clear and the training is there for you, just sign up! The properties, even if older, are very well maintained, making it an easy sell. I always felt valued as an employee. The commission structure and hourly pay is better than most other companies. The benefits are better too, $1000 a year to buy new clothes! Yes, working weekends is a must, but most properties have shorter hours which is nice. They offer more paid holidays than most companies. I always felt like the employee & the customer were most valued with Windsor, more than the dollar.


    Smaller company, means not a lot of room for promotions. Properties are few and not too close to each other, which is hard if you want to work at one property and live at another. There is some favoritism, but also opportunities for those who work hard. They don't fire people. This is also a good aspect, but if you have a bad employee in your team it takes a long time to get rid of them, if you ever do.

    Advice to Management

    Build more communities and watch out for favoritism.

See All 71 Reviews

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 Pleasanton, CA
    Accepted Offer
    Positive Experience
    Easy Interview


    I applied online. I interviewed at Windsor Communities (Pleasanton, CA) in September 2015.


    Applied online and took a personality test to assess best fit for the job. Over the phone contacted by Boston HR, panel of three people. District and Property managers relevant to hire.

    Interview Questions

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Windsor Communities Awards & Accolades

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