About Kathleen

Kathleen Usherwood

Kathleen Usherwood

Licensed Real Estate Salesperson NY/CT

Get to Know Me

After years in real estate, Kathleen Usherwood joined Compass in the fall of 2021. She was drawn to their luxury marketing skills, their use of client-friendly technology, and their commitment to a high bar of personal excellence provided to buyers and sellers. She and her husband, plus their two daughters, have been residents of Pound Ridge for over 24 years. She has been an active volunteer in the local schools, including Pound Ridge Elementary and The Harvey School where her daughters attended. Kathleen and her family have been active fosters for over 14 different rescue dogs. They are now the proud owners of two small dogs, a sweet Yorkie, and a feisty Chi. As a Parsons School of Design alumnus and former fashion designer,

Kathleen brings an experienced eye for design to everything she does, along with a passion for matching buyers to sellers and sellers to buyers. When representing a seller, she uses her style experience and marketing skills to prepare a house to achieve the most attention from qualified buyers. When representing a buyer, she takes a creative, personalized approach to find a perfect property and winning the bid. Kathleen is the curator/creator of Housetalks, featuring local design events featuring local design professionals. Along with Housewalks, a monthly blog, and newsletter featuring local design and unique properties in the counties of Westchester NY, and Fairfield CT. Kathleen is licensed in CT and NY, with a focus on Westchester County and Fairfield County, providing buyers and sellers with an intimate knowledge of both areas.

“You’re not buying a house, you’re buying a lifestyle.”


We cannot recommend Kathleen highly enough for your home sale and purchase. She was a true partner in the process, down to the landscaping and staging, which helped ...

Vanessa and Reinis V.

Kathleen was so knowledgeable and instantly knew what we wanted in a dream home. She is kind, easily accessible, and fun! We met Kathleen coincidentally at an open h...

Amy R and Dylan C.

Kathleen is a highly resourceful and well-connected agent, who is a pleasure to work with. She was always available, highly responsive, and very effective-helping us...

Greg and Tara C.

I met Kathleen online in May when I was looking for a summer rental in Connecticut or upstate NY. After just one or two conversations, she got my requirements, my st...

Poojitha R.

I had the good fortune to be referred to Kathleen when my condo became available to rent or sell. She is the most dedicated and hard working agent a lessor could hav...

Robin B.

Kathleen not only brokered the purchase of my dream home, a goal that seemed unattainable just 12 months ago...her business acumen, market knowledge, humor, and tena...

Hazel L.

We cannot recommend Kathleen highly enough for your home sale and purchase. She was a true partner in the process, down to the landscaping and staging, which helped ...

Vanessa & Reinis V.

Kathleen clearly knew the market and positioned the property for what buyers are looking for today. Most importantly, she took a true interest in our family and supp...

Mike D.

In such a tough buyers market with limited inventory available, Kathleen was able to find and help us quickly lock down our dream home.

Tom R. & Megan H.

After just a couple of conversations, Kathleen got my requirements, my style, and my budget. We found the perfect house within a week.

Poojitha R.

Kathleen held my hand through the entire buying process and enlisted an army of professionals to get me across the finish line.

Hazel L.

Kathleen is enormously helpful and skilled at navigating the challenges that come with buying, selling, renting, and moving.

Mitchell K.

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Work With Kathleen

Get assistance in determining the current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Contact me today.

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