ASHLEY JEFFERY | REAL ESTATE BROKER

Lake of Bays & Baysville Real Estate — Local Knowledge. Honest Advice. Real Results.

Looking for a trusted Lake of Bays Realtor? I specialize in helping clients buy and sell waterfront homes, cottages, and year-round properties throughout the Lake of Bays area.

ASHLEY JEFFERY | REAL ESTATE BROKER

Your local guide to Muskoka and Lake of Bays real estate.

Whether buying or selling, I help you navigate cottages, homes, and waterfront properties with confidence. Relocating to Muskoka? I’ll make your transition seamless.

Your Muskoka dream awaits you.

Chestnut Team

 Let Ashley guide your next move.

Buying or selling in Muskoka or Lake of Bays? Ashley is a Real Estate Broker who brings a thoughtful, strategic approach to cottages, homes, waterfront properties, and vacant land. With nearly a decade in real estate and over 14 years of sales and marketing experience, she understands how to position properties, navigate negotiations, and deliver results in a constantly shifting market.

Known for her honest advice, calm approach, and genuine care for her clients, Ashley focuses on making the process feel clear and manageable from start to finish. She combines local market knowledge with a strong understanding of Muskoka’s unique communities—helping clients not just find a property, but the right fit for their lifestyle.

With a natural eye for design and potential, Ashley sees beyond what a property is today and helps clients recognize what it can become—whether it’s a turnkey cottage or a piece of land ready for your vision.

Ashley is a proud mom of three. When she’s not working with clients, you’ll find her at the lake or on the trails, enjoying everything that makes Muskoka and Lake of Bays such a special place to call home.

 

“And into the woods I go, to lose my mind and find my soul.”                                                                                                     - John Muir

 

Featured Communities

Testimonials

Denae profile picture
Denae
October 16, 2023
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Exceptional service to say the least! We were one of those buyers who were looking for something in particular and it took us many weekends and over a year to find the right one! (funny enough 2 doors down from the first house we looked at and originally met Ashley at). She understood our needs and only sent us listings she thought we would like, and also entertained us by showing the ones she knew we wouldn't but we insisted looking at lol. Ashley sacrificed her weekends to help our family find our northern home and we wouldn't have wanted anyone else to share the experience with! Personable, friendly, professional and knowledgeable! Thanks Ashley for all of your hard work!
Stephanie Ott profile picture
Stephanie Ott
October 12, 2023
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Ashley was our realtor when we decided to make the move to Huntsville. She was patient, knowledgeable about the properties we were seeing, and knew everything there was to know about the area! I cannot recommend her enough if you are buying or selling in the Muskoka region.
Rachel Vaughan profile picture
Rachel Vaughan
May 23, 2023
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Ashley is beyond amazing!! She goes out of her way to really listen to your needs and wants and make them a reality. Ashley helped me find my house a few years ago and she really helped me get exactly what I wanted. She is the highest professional and the kindest person. You won’t be sorry if you choose her. As far as I’m concerned, there is no other option!
Brad Laking profile picture
Brad Laking
May 7, 2023
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Ashley is an exceptional realtor. She goes above and beyond in every aspect of the sale, from the initial listing to the final closing. Ashley's attention to detail, prompt communication, and market knowledge make the entire process stress-free. I highly recommend Ashley to anyone in need of a top-notch realtor.
Cathy Chant profile picture
Cathy Chant
May 4, 2023
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Ashley Jeffery helped us find our forever home in Huntsville. She was so patient with us. She showed us properties all over Ontario for over a year, and her consistent mandate was to ensure that we were happy, that we had a wide variety of options, and that we were all in the home search journey together. Ashley continued to support us throughout the purchase process and beyond. She was full of enthusiastic decorating ideas, and resources for renovations, and she was committed to making sure we settled happily in the community with options for getting involved there as well. Ashley is the absolute best person to help with real estate decisions.
Shawna McDonald profile picture
Shawna McDonald
May 4, 2023
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Ashley is absolutely amazing to work with! I was actively searching for a home for over a year and she stuck with me the entire way. She was so patient, offer after offer and she always tried for the best deal. She went the extra mile to make sure I had all the information I wanted/needed, I work away from home so she was great for doing video walk throughs when I couldn’t be there for viewings. She is so kind and easy to work with, I would recommend her to anyone! I will definitely work with Ashley again in the future, I can’t thank her enough for everything she did during my home search.
Jennifer Koop profile picture
Jennifer Koop
May 4, 2023
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Ashley is Amazing. We choose Ashley to help us sell our home because she was highly recommended. She did not disappoint. She provided exception service and went above and beyond. She was professional and understood our needs. She gave us valuable insights into the local market, was on top of all matters pertaining to agreement negotiations and handled every stage of selling our home. If you are looking for a knowledgeable, trustworthy, professional Realtor call Ashley Jeffrey with Chestnut Park for an exceptional experience. Highly Recommend! Thank you, Ashley!
Danielle Hutt profile picture
Danielle Hutt
May 4, 2023
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Ashley is an amazing realtor! Very professional, helpful, always on time and easy to talk to. She is incredibly knowledgeable in her field and went out of her way to help us out. Thank you Ashley!
Danae Bean profile picture
Danae Bean
July 25, 2022
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What can I say about our amazing realtor Ashley?!? She was not only our realtor but now has become a close friend of ours. My husband and I had been looking for a house for 2 years! We had such a hard time and was slowly giving up hope in finding our very first home. We had looked at over 50 homes and put in 23 offers. Trying to find a house during Covid was not easy! Once we moved to Muskoka, we met Ashley and she instantly starting trying to help us look for our home. We told her want we wanted and where we wanted to be located and she ran with it. She gave us good advice about every property we went and saw. 2 years of looking, 3 other realtors that didn’t work out and 23 offers later, she was able to help us find the perfect house and FINALLY our offer was accepted! We couldn’t have done it without Ashley!!
Suzanne Villeneuve profile picture
Suzanne Villeneuve
July 23, 2022
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We recently engaged Ashley to sell our cottage on Lake of Bays, which is our year round home. We made the decision to list while the market was still quite active - spurred by Covid-related decisions by many to find a place outside of the city. But a few upgrades that had been planned for our property meant that we actually listed when the market had stalled a little, after several interest rate increases and talk of recession. Throughout the process Ashley supported us, helped us arrive at an asking price we were comfortable with, did a beautiful, sensitive job of staging and marketing our property, advised us and fully represented in the negotiation process once we had an offer in hand. We ended up selling with both timing and at a price point that fully met our aspirations. Can't say enough about Ashley's professionalism, attention to detail, commitment to her clients, lovely demeanor that is a real treat to work with. We would highly recommend Ashley for any property purchase/sale, but most especially in the Muskoka area where lakefront properties come with their own special needs/demands. You really can't find better!!!!