June 2017

A Legacy of Signature Service: Courtney Woodward May Waterfront Real Estate

Author: Kitty Bartell | Photographer: M.Kat Photography

“I can say everything in my life has had a purpose, especially my years watching my mom just juggle it all and carry it off gracefully,”said Courtney Woodward May, Hilton Head Island Realtor and nearly-native daughter of the Lowcountry. Moving to the island in 1979 with her mother and sister, five-year-old Courtney’s roots became as intertwined with her mother’s clients as the Liberty Oak is with Harbour Town. “I grew up with a mom in real estate. Back then, when the island seemed so little, Mom was her clients’ concierge to the whole island, and I was their children’s playmate. We’d spend days at the beach and would get to know them so well that I would sometimes spend the night. They became our friends.”

It was her mother, Lottie Woodward, and those early years on Hilton Head Island, that gave May both the wings and the footing on which to establish her own real estate course. Attending Sea Pines Academy through sixth grade, May went to boarding school in New York and Tennessee, attended college in Charleston, worked as a snowboard instructor in Colorado and New Zealand, and in 2002 returned to Hilton Head Island, married fellow area native Jeremy May the next year, and somewhat unwittingly began preparing for the career she now believes her mother knew all along would be her future.

Having worked in mortgage lending, residential building, rental management, and retail operations, May joined her mother’s real estate business in 2012. “I believe your life kind of prepares you for the next thing,” she said. “I truly have lived that, because I had the mortgage experience, and then I had the custom home building, and I was all the time in a little bit of sales, a little bit of marketing, a little bit of people.”

When her mother passed away in 2016, May saw the next chapter of her own life through the lens of her mom. “I would have sworn to you that I wouldn’t be doing this. I think if you asked my mom, she would say yes, she saw me doing this. I’m a very faithful person, and I think this is part of the plan. I was so fortunate to have gotten those years with my mom at the end.”

From the lovely, coastal-modern offices of Courtney Woodward May Waterfront Realty in the shops at Sea Pines Center, a part of Sea Pines Real Estate’s Cottage Group, May has created a space that meets the changing needs of her clients, while staying true to her mission: a mission endowed by her mother’s legacy. “It is all, ultimately a people business. My mom said that from the very beginning. I love people—the whole process of getting to know them. I keep asking questions; I keep getting to know.”

Finding a real estate home where her professional partners are as supportive as Woodward was as a mother and guidepost, May embraces connecting, personally and in her business. “I am so fortunate. I cannot say enough about The Cottage Group as a company. We sometimes have meetings here or host our Cottage Group brown bag lunches,” she said. “On farmers’ market Tuesdays, I open my door and invite my clients to come in, have some water, have some coffee, plug your phone in, check your e-mail—whatever you need to do. My goal is to do some seminars here—make this a hub of real estate activity.” With large format screens for viewing properties, comfortable spaces to work and relax, and an inspiration center with décor samples selected to help clients visualize their staging and renovation possibilities, May said, “I wanted to create a space that gave people a reason to still connect.

“There is nothing that can replace personal experience, and having grown up with a mom who was this encyclopedia of knowledge (she has sold some houses two and three times), it’s fun to speak from that experience.” Blending an inheritance of personal service with her own defined approach, May said, “I want it to feel familiar, but still offer that additional advantage of technology. I say, let’s blend both the nostalgia of knowing and having lived it, and the osmosis of knowing, having watched my mom do it for 35 years, and yet embrace the future.”

This is all a part of May’s Signature Service approach to real estate. “Signature Service was something she [Mom] and I talked about. I had to embrace what was different about us. I want to stay personal without limiting myself—do what I do best. I know my market, and that’s Hilton Head. If I can’t serve you well, I’m going to send you to who can. When it’s a good fit, the sky’s the limit. If it’s not a fit, it’s not a fit. I just want to stay effective and really on top of what I know—stay true to myself.”

May recently worked with a client on their twelfth real estate transaction on Hilton Head Island; all 12 with either Woodward and/or May. “I’ve known them since I was a child,” May said. And there are clients who began their real estate relationship with Hilton Head Island, buying a condominium, who have gradually moved their way closer and closer to the shoreline. “First it would be a condo, then fifth row, then third row, then oceanfront. This is full-flavored Hilton Head Island real estate. This is not watered down.”

Woodward was a pioneer in Hilton Head Island real estate and a mother who led by example. “I had no idea how hard she worked,” May said. May and her husband are raising son, Thompson, and daughter, Alden, students at the Hilton Head School for the Creative Arts. “To pull off what she did so seemingly effortlessly…. She made lunches; she was the best cook. She put her touch on everything she did, whether it was her children, or her work, or her friends. She was very much her own person, and she did it her way. I like to think I’ve taken that and made it my own.”

May is making good use of both her wings and her roots, taking the best of her mother’s legacy, putting her own Signature Service stamp on every real estate relationship and transaction. “I’ve learned from everything I’ve done. I’m not filling any shoes,” she said.

Courtney Woodward May is navigating a familiar path, but a path she’s making all her own—rather gracefully. 
Courtney Woodward May Waterfront Real Estate is located at 71 Lighthouse Road, #612, Hilton Head Island. For more information, please visit welcomehhome.com or call (843) 816-0706.

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