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Meet Ashley Baird Fenttiman

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Agent Details

Meet Ashley

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.

Testimonials

What Our Clients Say

Ashley was absolutely amazing, along with her teammate Wendy. From the beginning and our first meeting, we were beaming with confidence that our condo listing would get everything it would need to be correctly marketed and prepared for sale. And that is exactly what happened. Our condo was among 19 other listings in the same complex and had stiff competition. But that wasn't a problem for the Ashley and Wendy team. They suggested we lower our price at exactly the right time and at the right amount to get a sale. Brilliant! The A&W team kept us abreast of every showing, open house, new competition, and more. Do you want to sell your home with the right agents? Your first interview should be with Ashley and Wendy, and DMG!
Ashley was absolutely amazing, along with her teammate Wendy. From the beginning and our first meeting, we were beaming with confidence that our condo listing would get everything it would need to be correctly marketed and prepared for sale. And that is exactly what happened. Our condo was among 19 other listings in the same complex and had stiff competition. But that wasn't a problem for the Ashley and Wendy team. They suggested we lower our price at exactly the right time and at the right amount to get a sale. Brilliant! The A&W team kept us abreast of every showing, open house, new competition, and more. Do you want to sell your home with the right agents? Your first interview should be with Ashley and Wendy, and DMG!
Mike S.
Ashley is an outstanding real estate agent. She is extremely professional, knowledgeable, easily accessible, and willing to answer all questions. As out-of-town buyers, we relied on Ashley every step of the way. She went to countless properties for us and provided immediate, honest feedback via FaceTime or phone. She does not pressure and will continue to search for the right property for you. We purchased an off-market property that is perfect for us. We never would have found it if not for Ashley's dedication to her clients and her professional relationships and resources. We highly recommend Ashley and will not hesitate to work with her again in the future.
Ashley is an outstanding real estate agent. She is extremely professional, knowledgeable, easily accessible, and willing to answer all questions. As out-of-town buyers, we relied on Ashley every step of the way. She went to countless properties for us and provided immediate, honest feedback via FaceTime or phone. She does not pressure and will continue to search for the right property for you. We purchased an off-market property that is perfect for us. We never would have found it if not for Ashley's dedication to her clients and her professional relationships and resources. We highly recommend Ashley and will not hesitate to work with her again in the future.
Buyer
My family and I have worked with Ashley Baird on two home purchases in Naples, Florida. Ashley has been wonderful to work with on both home transactions. She continues to go above and beyond for her clients.
My family and I have worked with Ashley Baird on two home purchases in Naples, Florida. Ashley has been wonderful to work with on both home transactions. She continues to go above and beyond for her clients.
Ryan V.
We are so impressed with Ashley! She is knowledgeable, professional, and patient. Her ability to work quickly in scheduling showings and putting together offers was instrumental in helping us purchase our home in a very competitive real estate market. Ashley responded to our calls right away and was happy to answer the many questions that we had. Ashley showed us everything we wanted to see, so we felt sure of our final decision. We are so happy with our new home!
We are so impressed with Ashley! She is knowledgeable, professional, and patient. Her ability to work quickly in scheduling showings and putting together offers was instrumental in helping us purchase our home in a very competitive real estate market. Ashley responded to our calls right away and was happy to answer the many questions that we had. Ashley showed us everything we wanted to see, so we felt sure of our final decision. We are so happy with our new home!
Shirley
Ashley with the Dawn McKenna Group helped me with the purchase of a property in Naples, FL. The idea was to find a solid investment. When Dawn and Ashley brought up Naples instead of some of the other areas we were considering, I thought it would be too much for us. Ashley honed in on an area called Naples Park in northern Naples. Fast forward time, the place has appreciated rapidly and turned out to be an excellent investment. Cannot recommend Ashley Baird with DMG enough. Thank you again!
Ashley with the Dawn McKenna Group helped me with the purchase of a property in Naples, FL. The idea was to find a solid investment. When Dawn and Ashley brought up Naples instead of some of the other areas we were considering, I thought it would be too much for us. Ashley honed in on an area called Naples Park in northern Naples. Fast forward time, the place has appreciated rapidly and turned out to be an excellent investment. Cannot recommend Ashley Baird with DMG enough. Thank you again!
Jeff D.
Ashley was wonderful to work with. She made the process of looking for places as seamless as can be and showed us a wide variety of options that fit all of our criteria. She helped us find our home very quickly with her extensive knowledge, hard work, and constant availability. She made us her priority from start to finish cannot say enough great things. She is a dear friend and we will always go to her!
Ashley was wonderful to work with. She made the process of looking for places as seamless as can be and showed us a wide variety of options that fit all of our criteria. She helped us find our home very quickly with her extensive knowledge, hard work, and constant availability. She made us her priority from start to finish cannot say enough great things. She is a dear friend and we will always go to her!
Emily C.
We can't say enough good things about Ashley. She sold our house in The Moorings for much more than we had hoped we would get. She also showed us numerous off-market listings that weren't readily available to all agents. We feel her combination of professionalism and social connections makes all the difference. Five stars cross the board!
We can't say enough good things about Ashley. She sold our house in The Moorings for much more than we had hoped we would get. She also showed us numerous off-market listings that weren't readily available to all agents. We feel her combination of professionalism and social connections makes all the difference. Five stars cross the board!
Genevieve B.
A couple of months ago, a friend & neighbor at my community, Kalea Bay, introduced me to the Dawn McKenna Group to discuss marketing my penthouse condo. From my first contact with DMG professionals, Ashley & Ardel, right through to the very fast (and fruitful) closing, I was ecstatic with the process! The communication and each detail were well thought out and perfectly executed. Not to mention a record sales price!
A couple of months ago, a friend & neighbor at my community, Kalea Bay, introduced me to the Dawn McKenna Group to discuss marketing my penthouse condo. From my first contact with DMG professionals, Ashley & Ardel, right through to the very fast (and fruitful) closing, I was ecstatic with the process! The communication and each detail were well thought out and perfectly executed. Not to mention a record sales price!
Julie D.
Ashley was a complete pleasure to work with! As we began our search for a condo, we met with Ashley, and she quickly understood what we liked and what we wanted to stay away from. After our initial meeting, we gave her the daunting task of finding the perfect place while being long-distance. She was up to the task! Her motivation, knowledge of the housing market, professional approach, and most of all, patience made the process painless. She always made us feel we were a priority and no request was too much to ask. We totally recommend Ashley Baird and know you will too!
Ashley was a complete pleasure to work with! As we began our search for a condo, we met with Ashley, and she quickly understood what we liked and what we wanted to stay away from. After our initial meeting, we gave her the daunting task of finding the perfect place while being long-distance. She was up to the task! Her motivation, knowledge of the housing market, professional approach, and most of all, patience made the process painless. She always made us feel we were a priority and no request was too much to ask. We totally recommend Ashley Baird and know you will too!
Javois K.
It was such a pleasure to work with Ashley Baird during our search in Naples. She understood our wants and needs and worked very well with us while visiting Naples as well as long distance. She was knowledgeable, professional, and such a pleasure to work with. Highly recommend!
It was such a pleasure to work with Ashley Baird during our search in Naples. She understood our wants and needs and worked very well with us while visiting Naples as well as long distance. She was knowledgeable, professional, and such a pleasure to work with. Highly recommend!
Buyer

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For Sale 3200 Green Dolphin LN

3200 Green Dolphin LN, NAPLES, FL 34102

$29,999,000

5 Beds
8 Baths
14,000 Sq.Ft.

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...

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For Sale 23 6TH AVE N

23 6TH AVE N, NAPLES, FL 34102

$27,900,000

6 Beds
6 Baths
5,945 Sq.Ft.

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...

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For Sale Open House: 10/28/2026, 10:00 AM - 12:00 PM 1990 7th ST S

1990 7th ST S, NAPLES, FL 34102

$19,995,000

6 Beds
7 Baths
6,550 Sq.Ft.

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...

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For Sale 1305 Marlin DR

1305 Marlin DR, NAPLES, FL 34102

$11,900,000

5 Beds
7 Baths
4,571 Sq.Ft.

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...

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For Sale 160 16th AVE S

160 16th AVE S, NAPLES, FL 34102

$10,995,000

5 Beds
7 Baths
5,442 Sq.Ft.

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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...

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Sold 1640 Dolphin CT

1640 Dolphin CT, NAPLES, FL 34102

$15,150,000

5 Beds
7 Baths
6,500 Sq.Ft.

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...

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Sold 682 17th AVE S

682 17th AVE S, NAPLES, FL 34102

$15,000,000

5 Beds
9 Baths
5,878 Sq.Ft.

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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...

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Sold 660 21st AVE S

660 21st AVE S, NAPLES, FL 34102

$13,000,000

5 Beds
6 Baths
5,483 Sq.Ft.

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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 ...

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Sold 6897 Grenadier BLVD # 1701

6897 Grenadier BLVD 1701, NAPLES, FL 34108

$12,850,000

5 Beds
5 Baths
5,280 Sq.Ft.

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...

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Sold 800 17th AVE S

800 17th AVE S, NAPLES, FL 34102

$12,100,000

5 Beds
6 Baths
4,781 Sq.Ft.

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...

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Sold 26564 Hickory BLVD

26564 Hickory BLVD, BONITA SPRINGS, FL 34134

$11,600,000

5 Beds
8 Baths
5,560 Sq.Ft.

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, ...

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Sold 1019 Spyglass Ln

1019 Spyglass LN, NAPLES, FL 34102

$11,000,000

4 Beds
5 Baths
4,801 Sq.Ft.

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....

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Sold 4 Sabre LN

4 Sabre LN, NAPLES, FL 34102

$9,995,000

3 Beds
3 Baths
2,544 Sq.Ft.

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...

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Sold 186 North ST

186 North ST, NAPLES, FL 34108

$9,500,000

5 Beds
8 Baths
7,766 Sq.Ft.

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 ...

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Sold 470 17th AVE S

470 17th AVE S, NAPLES, FL 34102

$7,450,000

4 Beds
5 Baths
4,718 Sq.Ft.

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...

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Sold 2825 Leeward LN

2825 Leeward LN, NAPLES, FL 34103

$6,600,000

4 Beds
5 Baths
3,694 Sq.Ft.

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 ...

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Sold 2350 Windward WAY

2350 Windward WAY, NAPLES, FL 34103

$6,500,000

4 Beds
4.5 Baths
5,057 Sq.Ft.

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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