Your Bruce Peninsula REALTORS®

Get to know us!






Ashley Jackson

Broker, Team Leader

Growing up in Red Bay and returning to the area after post-secondary education, Ashley is familiar with what makes the Bruce Peninsula unique, and shows her passion for the area in her work. Hiking the Bruce Trail, visiting the many beaches, enjoying Lake Huron sunsets & cross-country skiing are some of her favorite things to do on the Bruce Peninsula. Summer or Winter there is lots to do!

Working as an administrative assistant with Darlene James for over two years, focusing in advertising, customer care and staff training, Ashley has established a deep understanding of the ins and outs of the real estate industry.

Her passion for the industry led her to pursue her real estate certification while attending Conestoga College, allowing her to move into her next role at RE/MAX Grey Bruce Realty Inc., as a Sales Representative.

Ashley received her Bachelors Degree in Interior Design, graduating with honours from Conestoga College. During this time, Ashley studied the Ontario Building Code, zoning by-laws and construction methods, and developed practical negotiating skills; knowledge which translates perfectly into the real estate industry. Ashley has received several awards for academic proficiency and skillful design solutions. During her spare time, she participated in design competitions and pursued several volunteer projects.

Interior design is all about listening to your clients and understanding what they need, then translating this need into a reality. This is what Ashley strives to do in real estate as well. Searching for a home or property is a journey, and Ashley cannot wait to help you embark on that journey!


  • 2017 Awarded RE/MAX 100% CLUB AWARD
  • 2017 Ashley is Now a Broker with the Team
  • 2017 Diamond Team Award
  • 2018 Diamond Team Award
  • 2019 RE/MAX Diamond Team Award
  • 2020 RE/MAX Diamond Team Award
  • 2021 RE/MAX Diamond Team Award

Ashley Barker, Broker MCNE, ASA, & Team Leader

  • 2018-2017 Diamond Team Member
  • Certified Negotiation Expert 2018
  • Certified Senior Designation 2017
  • Young Guns 2018 award

Darlene James

Broker, Team Consultant

Darlene James Broker is a dedicated, experienced enthusiastic Real Estate Broker with a proven celebrated record of accomplishments.

  • RE/MAX Club awards, Platinum Club, and Chairman’s Club! 2013, 2014, 2015, 2016 . 2017, 2018 Titan
  • 2017 – Amazing Year, RE/MAX TITAN Individual award, Diamond Team 2017
  • 2018 – Amazing Year, RE/MAX TITAN Individual award, Diamond Team 2018
  • 2019 RE/MAX Diamond Team Award
  • 2020 RE/MAX Diamond Team Award
  • 2021 RE/MAX Diamond Team Award

CLHMS Designation Awarded 2014 – Luxury Home Marketing: Awarded the Accredited Buyers Representation (ABR) Awarded The Certified Residential Specialist (CRS) is the professional designation offered by the Council of Residential Specialists.

Darlene has been the Number One Salesperson from 2010 onward for RE/MAX Grey Bruce Realty Inc., Brokerage. # 1 Team on the Bruce

Testimonial EXCEPTIONAL! Dave Craig

Approximately a year ago, I engaged Darlene James to sell my three waterfront properties on the Bruce Peninsula; two properties in Tobermory and one in Lion’s Head, and she got the job done, quickly and efficiently! I can sum up my experience dealing with Darlene and her team of professionals in one word – EXCEPTIONAL!1) EXCEPTIONAL MARKET KNOWLEDGE AND INTEGRITY! Darlene provided me with a detailed market analysis for each of my three properties, along with a scientifically determined pricing recommendation for each of the three properties, with reams of relevant historical data to back up her conclusions. In addition, several years ago I had Darlene appraise one of my properties and she came back with an honest appraised market value, which I didn’t much care for at the time (LOL!). However, she resisted the temptation to give me an inflated market value simply to get the listing (the old ‘bait and switch’), thus demonstrating her honesty and integrity. 2) EXCEPTIONAL MARKETING! Darlene actively promoted my properties on the MLS, her website, local publications, to her associate real estate brokers and her ongoing commitment to finding new qualified buying customers is tremendous. She provided me with regular market activity reports, detailing the number of online views of my properties and actual on-site buyer showings to keep me informed of her progress.3) EXCEPTIONAL CUSTOMER SERVICE!

Darlene’s customer service is second to none. She returned all of my telephone calls and replied to all of e-mail and text messages, more or less instantaneously 24/7; even while she was away on vacation! She made countless useful recommendations for maintenance and repairs (one example was her suggestion to trim trees at one of my properties to improve the lake view) and arranged to have local contractors visit my properties and take care of the required work prior to the closing date(s). Darlene also did on-site buyer showings during the winter months, many times under lousy weather conditions, arranged to have the private roads plowed to achieve access to the properties, and arranged to have water tests done, septic system inspections/final pump outs and sent me constant reminders to take care of necessary tasks on my end. Her assistant Tara MacAskill also did a fantastic job assisting Darlene when needed! 4) EXCEPTIONAL RESULTS! Darlene got the job done – she sold all three of my properties; quickly; efficiently and at prices that were very close to my asking price for each of the three properties. In one case the final selling price exceeded my asking price. Two of my properties were in the challenging north of $700k price territory; with a limited universe of qualified buyers; thus making her job that much more difficult! THANK YOU DARLENE!!

Nellie From


Twenty-four years ago, in search of a lifestyle change, Nellie, her husband Chris and their three children moved to their 90 acres of paradise on the Bruce Peninsula. Since then, they have been enthusiastic tour guides for friends and family showing off the sights spectacular beaches and participating in local events and festivals. Nellie sums it up this way: Twenty plus years on and we’re still discovering the beauty of our surroundings.

After careers in Administrative roles; as an accomplished interior painting entrepreneur; landscape designer/installer (and a Member of the Rural Gardens of Grey and Bruce Counties), Administrative Assistant to Ashley Barker, Broker at RE/MAX Grey Bruce; and a personal journey with cancer; Nellie has successfully realized her personal goal of achieving her real estate certification and has enjoyed a successful career in real estate the last number of years. She loves working with both Buyers and Sellers, helping people find their own piece of paradise on the Peninsula or helping Sellers transition and move on to new adventures.

  • 2018 Diamond Team Award
  • 2019 RE/MAX Diamond Team Award
  • 2020 RE/MAX Diamond Team Award
  • 2021 RE/MAX Diamond Team Award

100% Club, MCNE

Client Review
Professional Help & Guidance
Tiffiny Laidlaw-Heo

Nellie From was an amazing realtor to work with. She spent so much time with us taking us from place to place and answering all our questions. She really knows the area and the ideal places for specific family needs. We really were not even sure where to start but with her help we managed to find a perfect location for our family. She made sure to tell us about lots in many different areas and showed us the perfect lot for our family as soon as it became available and we were able to buy it. We are so thankful for her professional help and guidance and for taking time to help us and either answer the questions we had or send us to the people who did know the answers. We cannot thank Nellie enough for all her work on our behalf and for finding the perfect lot for our family’s needs.

Chris Mawdsley


 The Bruce Peninsula has been near and dear to Chris for almost 50 years.  Since coming here as a teenager on a family vacation, he has always considered this area special.  When he first met his wife, Angela, he brought her here on vacation, and ‘warned’ her that he would very much like to live here one day.  That day came within two weeks of their nest being empty.  They moved in November 2009 and are completely at home here, enjoying the attractions, activities and the marvellous sense of community afforded by life in a rural area.

Prior to entering real estate in 2013, Chris had a long and successful career as a server IT guru,  IT service delivery manager and program manager for IBM Canada.  He worked in the tech sector from 1980 until taking early retirement from IBM.

Chris has been a church pianist; community theatre actor, director, and musical director; he has been a tourist railway conductor, rules instructor and board member; SCUBA diver; photographer and entrepreneur.  His interest in trains and railway history led him start a model railway in a purpose-built basement at his home at Miller Lake.  This is an on-going project that will keep him going for a long time to come.

Currently, Chris holds a national snooker referee’s certificate.  He refereed and acted as assistant tournament director for the 2021 Pan American championship in Toronto, a tournament which saw the champion earn a two-year exemption to the World Snooker Tour.  Chris is looking forward to the return of the Canadian Championships which have been on hold during the COVID-19 pandemic.

Chris is an active member of the Royal Canadian Legion Branch 202 in Lion’s Head, and is membership chair for the branch.

Chris and Angela will soon celebrate their 25th Anniversary.  They have raised five children and have three grandchildren to spoil!

Chris has received awards for customer service and sales from IBM, RE/MAX and Keller Williams, and looks forward to bringing you personal service and a commitment to your success in all your real estate needs.

Client Review
Above & Beyond

Chris went above and beyond to help us find the perfect spot to call home.  He helped us find a beautiful lot for a house to be built. He helped us fit into our new community. He truly cares about people and is willing to help.  If you are looking to buy or sell, I would say Chris is who you want to represent you.  

Dylan Dolson

Sales Representative

Dylan’s deep-seated roots started on the family farm just outside of Owen Sound. Dylan has also had a second home here on the tip of the Bruce Peninsula for nearly two decades! This connection to the land in both Grey and Bruce gave him an appreciation of everything there is to offer. The Bruce Peninsula is where Dylan worked his summer job for many years at the National Parks, eventually managing a business in the area, and now lives full time in Tobermory. He is truly in love with the area and wonderful local community!

For many years prior to entering into the world of real estate, Dylan managed a number of vacation cottage rentals. For him, he always took pleasure in welcoming families arriving for their week on the beautiful Bruce Peninsula and guiding them on their stay. Dylan also enjoyed renovating the cottages. This gave him a good understating of the building code and local bylaws as well as a great connection with local contractors and construction crews.

Dylan has a true passion in aviation and enjoys being in the air whenever possible! Starting as a childhood dream while on a school trip with his class, Dylan visited the home of WW1 Flying Ace Billy Bishop in Owen Sound. A fitting start to his passion as he later took all his aviation courses at the Billy Bishop Airport. Dylan took to the skies solo for the first time more than 6 years ago and has loved every minute since! He says seeing the cliffs and turquoise waters from above is truly breathtaking and further grows his appreciation for living here on the Bruce! 

  • 2021 RE/MAX Diamond Team Award