About Us

Crossroads Property Group

A year into the pandemic our Founder was at a Crossroads, knowing that buying a home and moving his family would be life changing. Deciding whether his family remain in New York City or make a big transition to the suburbs. When they ultimately made the decision to move out of the city, his family settled on a property in Greenwich, CT built in 1894. The home, aptly named Crossroads, needed a lot of work and a lot of upkeep. Embarking on this huge project proved to be incredibly life-altering, both personally and professionally. It made him realize that his interest and experience in building relationships, construction and efficient property management could turn into a fulfilling career.

Throughout the renovation process John became increasingly aware of the time, effort, skill-set and hidden costs required to both renovate a home and also manage one, too. In speaking to many local homeowners and recent city transplants he saw a pattern. Many homeowners at their own crossroads either weren’t equipped or simply didn’t have the time or interest to take on the huge mental and physical load of envisioning, executing, and maintaining their dream home. There was a hole in the local market to support this need and Crossroads Property Group was created to fill it.

Meet The Founder

About John Macaskill

John spent 15 years in finance focused on real estate and infrastructure before moving on to real estate development and hospitality private equity, building and renovating hotels in Scotland. 

Having completed personal renovation projects in NYC and CT over the past two decades, he began to consult and oversee projects for other homeowners. Realizing the need for high-level representation and guidance in home ownership he founded Crossroads Property Group in 2022.

John lives in Greenwich, CT with his wife and two children. He is active in the community and looks forward to working with you. 

Get in Touch

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