Gretchen Almy
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From selling distinctive properties on Beacon Hill to waterfront gems on the South Shore, Gretchen has a passion for helping her clients realize their real estate goals. Gretchen prides herself on her integrity, problem-solving capabilities, and attention to detail while bringing her professional, yet personal common-sense approach to every transaction.
Gretchen grew up in Fairfield County and spent her summers on the family farm in Westport, MA where she discovered her passion for horses. She was fortunate enough to hone her riding skills at one of the top hunter jumper facilities in North Salem, NY. She continued her love of riding and competed in equestrian sports through college in Virginia. After college, she ventured west to pursue a childhood dream of being a wrangler on a ranch in Wyoming before moving back east to manage foxhunting and dressage farms in Kentucky and Rhode Island.
Gretchen turned her love of horses, animals, and nature into an ongoing 25-year career as an accomplished artist. Her works in oils and pencil capture the essence and mood of her subject, whether it’s a landscape, equestrian commission, or a colorful abstract painting. Some of the most elite equestrian facilities spanning the east coast from Myopia to Wellington, have featured her art of Olympic showjumpers and dressage competitors for their event program covers. Gretchen maintains studios in Plymouth and Westport, MA, and is a member of the South Coast Artist Association.
Gretchen is on the Ashley Place Board of Trustees and volunteers her time with various rescues helping horses and dogs. Since her horse, Skye, passed, Gretchen now spends her free time painting and enjoying the outdoors mountain biking, hiking and playing with her rescue shepherd mix, Tallulah.
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Testimonials
Gretchen was a pleasure to work with! As first time buyers, we were nervous going into the process. She was attentive to our needs, honest with expectations and on the ball with the multitude of paperwork that goes along with it. Should we ever need to do this all again, I couldn't dream of doing [...]
As you know we have invested a ton of time (and mileage!) around New England in search for the best place and you’ve been an impressive ambassador for Plymouth and all it offers. We have really enjoyed our time with you and your profound insights into the Plymouth social, artistic, food and [...]
From the moment I contacted Gretchen about a property I was interested in, and asked if she would be willing to help me, she immediately jumped in to action. Within hours, I had detailed information on the property; a scheduled appointment to do a private walkthrough; and market research & [...]
As we entered the real estate buying game we realized we needed guidance, it’s a complex detailed process and was intimidating after living in the same place for 30 years. Enter Gretchen who not only guided us to our dream home but became a friend in the process. She’s a strong negotiator and has [...]
Gretchen Almy has been absolutely wonderful in representing me in the sale of my home. This has been a difficult situation for me in terms of the emotions involved, Gretchen has been exceptionally supportive in dealing with my issues while at the same time being consistently professional and [...]
Gretchen was approachable, responsive and dependable in all areas large and small. She helped with everything and was an excellent listener and coach! We were very fortunate to work with her. Thank you very, very much Gretchen!!!
Gretchen was the right choice to help us sell this property. Her responsiveness, flexibility and knowledge of the market got a complicated transaction completed as quicky as possible. I would be happy to work with Gretchen and LandVest again in the future.
In 1997, we purchased an abandoned 1905 landmark building originally built for the Plymouth town water department. We spent years on this extensive adaptive reuse—rehabbing every inch, restoring its character, and transforming it into a home for Shields Design Studio and a community of talented [...]
Gretchen was an over the top excellent realtor for us. She listened carefully to what we were looking for, took us to many available options, and pointed out all of the pros and cons of the properties we looked at. She was friendly, and easy to talk to, and provided us with so much support all [...]





