Meet a Dad: John Macaskill of Cross Roads Property Group! - Greenwich Moms

Tonight’s Meet a Dad, John Macaskill, is a Dad of two, and the founder of Crossroads Property Group. 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, and with his childhood love of construction, whether it was building his own tree house with a drawbridge for bikes or fixing those bikes after taking them off a jump that was too big, 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 shares with us his passion for building, favorite projects and everything he loves about Greenwich!

Please tell us a bit about your family and life in Greenwich (names/ages of kids, where you live, etc), what do you like to do as a family?
We moved to Greenwich during the summer of 2021 having bought an old house named “The Crossroads” which was built in 1894. We spent most of last summer renovating the house and have loved our time in Greenwich thus far. We love the proximity to Greenwich Country Day School where our two children, John (6) and Emma (3), go to school. When we are not running around between flag football, lacrosse, taekwondo, and ballet we enjoy sitting around the dinner table talking about our days and answering silly questions. We also love making dinners, our recent specialty is homemade pasta with steak and broccoli.

What do you love about Greenwich and your neighborhood?
The best part of our day is our walk to school, through the grass fields, sometimes we race, but we always walk along the stone wall (unless it’s really rainy, then we drive). As we have recently moved to Greenwich from New York City we LOVE the green spaces and have really enjoyed meeting so many new friends, either through school or around town.

For anyone who isn’t familiar, how would you describe Crossroads Property Group?
Crossroads is a full-service partner for homeowners. We manage properties for a number of snowbirds that fly south for the winter as well as full time Greenwich families who don’t want to spend all their free time taking care of their homes. Recently we’ve been doing more consulting with homeowners considering additions and renovations, helping them think through costs, timelines and functionality. There isn’t really one type of customer, we try to help everyone get a little more worry-free time back for themselves and their families.

Can you please share about your professional background and what led you to launch Crossroads Property Group?
From an early age I was always into construction, whether it was building my own tree house with a drawbridge for bikes or fixing those bikes after taking them off a jump that was too big. Professionally, I spent 16 years in finance, most recently buying and renovating hotels near iconic golf courses in the UK. Throughout my finance career I have always worked in real estate whether advising some of the largest real estate investors or renovating my own apartments. Problem solving both big and small issues with a home or property has always been interesting to me and how I like to spend my free time so the move to Property Management seemed inevitable. During the renovation of our home in Greenwich it became increasingly apparent that the area needed high quality property management and client consultation. I apply my financial background and real estate acumen to ensure customers get the very best.

What differentiates your company from other property management groups?
We’ve been in your shoes; we know the level of service you expect and we’re here to provide that. In addition to taking care of your house as if it were our own, we bring a creative approach to maximize the potential of your home and property, plus we have curated a collection of some of the best tradesmen in the area to ensure any work you do is done right the first time. I started a Property Management business because I’m passionate about a home being managed as efficiently and stress-free as possible so I wake up each morning excited to see what the day will bring.

What would you say are the biggest benefits from working with a property manager?
Most homes that use a property manager or owners rep generally save about 30% in the long run as issues are caught early before they become big problems. The familiarity that a property manager has with the systems within a house allow them to quickly notice and diagnose problems before they become costly. We’ve had several situations where we’ve caught small issues and know how to fix them quickly and efficiently, most of the time cheaper than when a homeowner tries to troubleshoot themselves.

Another is that a lot of families have ideas of what they would like to do to their house but assume they are cost prohibitive. One of the things I love about my job is that I can help scope, design and price projects that will hopefully make you realize that what you dream of can actually become a reality.

What is your favorite home project you have worked on and why?
Selfishly, my favorite project is our own home renovation. As mentioned our home was built in 1894, when we purchased it there were a number of “traditional” aspects that no longer fit in todays modern way of living. We converted a smoking room into the primary bathroom, opened up a traditional butler’s pantry to accommodate a larger open concept kitchen and family room. When my wife initially walked into our home she turned and ran the other way. But when I helped her see my vision and that it could all be done within our budget she was not only shocked, but excited to start building the house that we would raise our kids in.

Other fun projects have been re-imagining the interior of an old barn, strategizing a larger expansion for dressing rooms and upstairs laundry, and watching a new homeowner transform the house they bought into their home.

What is your favorite activity to do with your kids?
We are running around a lot with our kids’ activities, it is amazing to watch them improve and have fun. Sometimes I get to coach them, although they don’t always listen to Dad! I love playing golf with my son, being the tickle monster with my daughter and brushing her hair, which somehow is always a mess. My favorite activity with them, however, is reading them bedtime stories, one kid under each arm, which is almost a nightly activity, something which wasn’t possible before we moved to Greenwich. That is my true happy place.

What are you focusing on now?
Our family is very busy at the moment, aside from the start of the school year and lots of sports with the kids, my wife, Macy, has recently launched a financial consulting business, focused on advising startup companies that aren’t quite big enough to hire a full time CFO, which has kept her very busy. Plus, Crossroads is starting to bring on several new clients and I have been meeting with them.

Anything else you’d like to share?
I love people, projects and making things better. If you are considering getting a Property Manager, doing some work on your home or simply want a second opinion, please give me a call. I will be the first person to say if there is a better approach than hiring Crossroads. I look forward to meeting many of you.

We love to support local businesses. What are your fave places locally to:

Grab coffee: I don’t drink coffee, I was blessed with the ability to pop out of bed in the morning and get straight to it, but I am a sucker for a good sandwich, Rinaldi’s and Something Natural are my favorites at the moment.
Workout: I love building things and tinkering, I will generally do that if I can’t play golf or some racquet sports.
Go on a date night: I love pretty much anywhere we can get away just the two of us. I love the mood and food at Le Penguin and the energy of East End.
Go out for a girls night: I’m rarely invited!!
Go out to dinner as a family: We’ve done Abis recently and although the theatrics are amazing, Emma isn’t the biggest fan. Doppio is another family favorite.
Get your hair done: Glenn at East Putnam barbers
Get your nails done: I’ve never had my nails done, although I did take Emma to Posh, which was my first nail salon experience… she fell asleep mid painting, but loved the color.
Have fun as a family: Tod’s Point, Bowling or being outside with them anywhere.

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