A native of Hinsdale and a licensed real estate agent herself, Ashley Baird proudly serves as a liaison between her Florida community and fellow Midwesterners. In 2021, Ashley was awarded the title, "30 Under 30," an honor presented from Coldwell Banker for her achievements in sales, philanthropy and leadership.
Ashley has a strong background in marketing and management, as well as luxury real estate. She apprenticed with a top real estate agent in Lake Geneva, Wisconsin that closed over $300 million in total sales before serving as a sales manager for a luxury high-rise in Streeterville for two years. These experiences gave her a rich knowledge base from which to draw upon at the Dawn McKenna Group.
Described as a genuine “people person” who is “honest” and “puts her clients at ease,” Ashley always saw real estate as a career path. She believes that real estate gives her a chance to play a meaningful role in people’s lives. Purchasing a home is one of the most monumental decisions a person can make in a lifetime, so she aims to make the experience as enjoyable and stress-free as possible. Both buyers and sellers benefit from her strong Midwestern work ethic and determination to succeed. Energetic and tech-savvy, she makes herself accessible to clients 24-hours a day, seven days a week. All of these qualities help her make lasting connections with her clients.
Ashley is no stranger to the Florida lifestyle. Her roots in the Sunshine State date back more than 15 years, as her family often “wintered” in the Naples area. Prior to moving to Naples, she lived in Wellington - a premier winter equestrian destination. A five-time world champion horseback rider, she is well-versed in the horse world.
Whether it’s beachfront, golf course, or equestrian properties, Ashley is eager to share her knowledge and enthusiasm for real estate with all of her clients.
Ashley specializes in luxury residential, waterfront properties, relocation, Midwest-to-Naples relocation specialist (former Hinsdale resident), Park Shore, Pelican Bay, gated communities, and seasonal residents.
3200 Green Dolphin LN, NAPLES, FL 34102
Property description
One or more photo(s) has been virtually staged, AI generated or rendered. Set behind its own private gates, 3200 Green Dolphin Lane encompasses nearly one acre with coveted southwestern exposure, a...
23 6TH AVE N, NAPLES, FL 34102
Property description
Experience the pinnacle of beachfront luxury from this extraordinary Naples coastal estate, where timeless Bermuda-inspired architecture meets effortless modern elegance. Perfectly positioned along...
1990 7th ST S, NAPLES, FL 34102
Property description
Winner of the 2026 Sand Dollar Award for Product Design of the Year, this rare custom built new construction residence showcases timeless architecture and bespoke finishes in highly sought-after Aq...
1305 Marlin DR, NAPLES, FL 34102
Property description
NEW CONSTRUCTION in coveted Naples Bay featuring 121 feet of direct water frontage. A collaboration between Stofft Cooney Architects, Forge Construction, and KSA Design Group brings this exceptiona...
160 16th AVE S, NAPLES, FL 34102
Property description
Perfectly positioned on over half an acre in the prestigious community of Aqualane Shores, this extraordinary estate embodies the essence of refined coastal luxury. This timelessly updated residenc...
1640 Dolphin CT, NAPLES, FL 34102
Property description
Step into the pinnacle of luxury waterfront living with this one-of-a-kind masterpiece, built to the newest base flood elevation code. Crafted by the acclaimed team of C&E Builders and renowned des...
682 17th AVE S, NAPLES, FL 34102
Property description
This newly built waterfront home by Oakley Home Builders with direct Gulf access & smart home automation is a boater & car collector's dream! The 2-story design masterpiece exudes contemporary eleg...
660 21st AVE S, NAPLES, FL 34102
Property description
The only brand new construction being sold furnished on a south facing lot. Nothing better in Aqualane Shores! Experience this ultra-custom, ultra-luxurious home located in Aqualane Shores, one of ...
6897 Grenadier BLVD 1701, NAPLES, FL 34108
Property description
Welcome to 1701 Mystique, the crown jewel of Naples' most prestigious high-rise, where custom craftsmanship and coastal sophistication meet on a grand scale. More than 5,500 square feet of reimagin...
800 17th AVE S, NAPLES, FL 34102
Property description
Surround yourself with elegance and beauty in this classic waterfront home in prestigious Aqualane Shores. With a three-car garage and nearly 5,000 square feet of elegant yet comfortable living spa...
26564 Hickory BLVD, BONITA SPRINGS, FL 34134
Property description
Built in 2020 by award-winning Potter Homes, this magnificent 3-story beachfront home includes 5 bedrooms and den, 8 bathrooms with 5,560-square-feet of living space. There are dual master suites, ...
1019 Spyglass LN, NAPLES, FL 34102
Property description
Every buyer’s dream! Port Royal’s newest gated jewel is located on one of the most coveted streets and waterways in Naples. Remastered in a down-to-the-studs transformation by Oakley Home Builders....
4 Sabre LN, NAPLES, FL 34102
Property description
Nestled within the prestigious Port Royal enclave of Sabre Cay, discover an unparalleled opportunity to build your dream home. Set on a .48-acre lot with 156 feet of frontage, this exceptional prop...
186 North ST, NAPLES, FL 34108
Property description
A statement in modern luxury, this estate combines thoughtful design, exceptional craftsmanship, and resort level amenities rarely found in residential living, including one of the area's very few ...
470 17th AVE S, NAPLES, FL 34102
Property description
Home is high and dry and never had water - not even in the garage! Sold turnkey furnished - move in today and start enjoying all Aqualane Shores has to offer. Tucked along a direct Gulf-access cana...
2825 Leeward LN, NAPLES, FL 34103
Property description
Enjoy breathtaking, picture-perfect sunsets from this prime Moorings waterfront residence. Featuring 103 feet of deep-water frontage and direct, no-bridge access to the Gulf, this home provides an ...
2350 Windward WAY, NAPLES, FL 34103
Property description
Elevated turnkey coastal contemporary home on one of the nicest streets in Moorings, walking distance to the Moorings Beach Club! A grand entrance ushers you inside more than 5,000 square feet. Loc...
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