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 specializes in the leasing and management of a nationwide portfolio of luxury properties. Founded in 1960, Windsor seeks to provide residents with exceptionally well-managed apartment homes. Going above and beyond its unwavering commitment to outstanding ... Read more

Mission: We take pride in our management expertise, our dedication to our residents, and our commitment to our company.

Company Updates

  • Windsor is thrilled to announce the addition of EIGHT beautiful new properties in Washington, Oregon, California, Colorado, and Florida! We are so happy to welcome over 50 new members to the Windsor family, and a huge thank you to everyone involved who worked tirelessly to make this takeover a great success! Windsor Communities is a fast growing company with exciting properties and positions all over the country, over 100 people have been hired in the last two months alone! Check out all our current open positions so you can work at Windsor too!

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Windsor Communities – Why Work For Us?

Premium 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 100 residential communities in 16 states and the District of Columbia. These communities, which comprise more than 29,000 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.

Windsor’s commitment to valuing people means that it takes care of its employees, as well as its residents. 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, the best and brightest of the property management industry. Check out the videos below to learn more about our positions and why our employees love working at Windsor.

Our sales and customer service positions offer exciting, rewarding work. Our employees understand that for our residents, it’s not just an apartment, it’s their home. They are committed to creating unique experiences for our residents and love creating a community to be called home.

Our maintenance positions provide opportunities to work in a team to create exceptional living accommodations through a commitment to customer service and luxury apartment expertise.

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.

One of the best perks of working at Windsor is the array of training and educational opportunities for employees. Whether it's learning the best practices to be an effective manager or taking a class to develop a new technical skill, Windsor really helps its employees grow and succeed in their roles. No matter which location employees work at, the overall Windsor culture recognizes success as a team effort—and makes sure to celebrate team wins.

Windsor Communities Reviews

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Recommend to a friend
Approve of CEO
Windsor Communities President Jeffrey A. Harris
Jeffrey A. Harris
3 Ratings
  • "Excellent company focused on growing its employees"

    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Current Employee - Anonymous Employee in Boston, MA
    Current Employee - Anonymous Employee in Boston, MA
    Approves of CEO

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


    Windsor cares a lot about its employees. There is an emphasis on training employees, recognizing accomplishments, and pushing toward goals. There are many employees with long tenure who feel like Windsor is their work family.


    There are opportunities to update systems and streamline processes. I can see the company is working on that. Some changes take longer than expected.

    Advice to Management

    Keep listening to your employees and investing in training and developing them.

See All 123 Reviews

Windsor Communities Photos

Windsor Communities photo of: Windsor Communities Operations Conference 2015 - Wrigley Field
Windsor Communities photo of: Leasing Office
Windsor Communities photo of: 1000 Grand by Windsor
Windsor Communities photo of: Maintenance Technicians preparing an apartment for move-in
Windsor Communities photo of: Our residents love our pet friendly apartments!
Windsor Communities photo of: The Sovereign at Regent Square
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Windsor Communities Interviews



Getting an Interview

Getting an Interview





    Marketing Representative Interview

    Anonymous Employee in Washington, DC
    Accepted Offer
    Positive Experience
    Average Interview


    The process took 3 days. I interviewed at Windsor Communities (Washington, DC) in December 2011.


    First I had a phone interview with one of the recruiters in Boston. I guess she liked what she heard and sent my information to regional in Arlington. The called me to schedule and interview. I went up three times to meet with different property managers--all were very upbeat and generally seemed like the cared! They asked me to join their team pending background and drug test.

    A week later I was hired! I have been working here for a year and the company treats you well!

    Interview Questions

    • How Would I react to a certain situations   1 Answer
    • What are some past experiences I've had where I had to deal with a difficult customer, and how did I deal with it   1 Answer



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Windsor Communities Awards & Accolades

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