Episode 5: Leading in Luxury: A Conversation with Chris Lynch, Founder of Legacy Properties Sotheby’s International Realty

In this inspiring and insightful episode of Elegant Maine Living, Elise sits down with Chris Lynch, founder and owner of Legacy Properties Sotheby’s International Realty, to discuss the origins of Maine’s premier luxury real estate brokerage. Chris shares his personal journey from a demanding Wall Street career to a deliberate and life-changing move to Maine to focus on family, community, and a new kind of professional purpose.

Together, Elise and Chris reflect on the early days of building a real estate firm from the ground up—including founding during a market peak in 2006, navigating the crash of 2008, and leading through the unprecedented shifts of the 2020 pandemic. Chris also offers his perspective on what makes Maine’s real estate market so uniquely valuable and unrepeatable—and why savvy buyers know not to wait when a rare property speaks to them.

Key Moments:

• [01:30] Chris’s transition from Wall Street to Maine and the pivotal family moment that inspired the change
• [05:15] Why Portland stood out among global coastal cities as a lifestyle destination
• [07:00] How Legacy Properties Sotheby’s was born—and the early uphill climb
• [10:30] What it took to build a new real estate firm in a fragmented market
• [13:00] Reflections on the 2008 crash and the founding team that helped weather it
• [16:00] Leading through the COVID-19 pandemic: crisis management and communication
• [19:00] The power of the Sotheby’s global network and national peer collaboration
• [20:15] Chris’s favorite transaction: how a couple’s bold move in 2008 turned into a fivefold return
• [22:45] Why buying in Maine is about timing, not speculation
• [23:30] Elise and Chris on the accessible, authentic lifestyle that defines Maine living

Quotable Moments:

“You don’t find your dream property in Maine twice. When you see it, buy it. That’s how this market works.” — Chris Lynch
 “Maine offers access—to nature, to community, to opportunity—in a way that’s almost impossible to replicate elsewhere.” — Elise Kiely

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• Reach out directly at elise@elisekiely.com

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Please remember this podcast is for entertainment and educational purposes only and does not create an attorney client or real estate advisor client relationship. Please reach out to me directly if I can assist you in your real estate journey.

Transcript

Lynch, Chris Pt.1 4.21.25

Elise Kiely: [00:00:00] Welcome to Elegant Maine Living, where we explore the beauty, charm and sophistication of life in Maine. My name is Elise Kiely, your host, and a real estate advisor with Legacy Properties Sotheby's International Realty. On each episode, we dive into Maine's residential real estate market, sharing key trends, inventory, insights, and notable sales, while also highlighting the extraordinary lifestyle that makes Maine such a special place to live, work, and play.

Elise Kiely: Whether you're seeking a coastal retreat. A vibrant community or an escape into nature. Elegant main living is your guide to the home and experiences that defined our great state. Let's get started. This morning [00:01:00] I am delighted to welcome Chris Lynch, the founder and owner of Legacy Properties Sotheby's International Realty, and the leader in Maine's luxury residential real estate market.

Elise Kiely: Thank you. Good morning. 

Chris Lynch: Thank you. Congratulations on your podcast. 

Elise Kiely: Chris. Thank you. I really appreciate that. As I was sharing with you, I am having a lot of fun doing it. It is a learning and process for sure. Chris is going to share his journey in founding the company and leading through market shifts, both when it was a strong real estate market, maybe a more challenging real estate market, and of course the pandemic and hopefully getting his outlook for 2025.

Elise Kiely: Chris, why don't you start, if you would, with a little background of, 'cause you're not a Mainer like me, I don't think you were born and raised here, were you?

Chris Lynch: No. Still from away.  

Elise Kiely: Me too 

Chris Lynch: here for 23 years, but I'm still from away. 

Chris Lynch: So you we're getting there.

Elise Kiely: I'm about the same.. And how did you come to Maine?

Chris Lynch: I worked on Wall Street for 17 years, I think, and worked in [00:02:00] New York and London, was back in New York and. Had three children, that were basically growing up without me. I was away all the time. On a good day, I'd leave the house at 5, 5 30 in the morning, get home at 9, 9 30 at night, three hours of commuting.

Chris Lynch: Best case, long days. International travel and the few days I was home, which was usually just Saturdays, I was sleeping most of the day because I was exhausted. Yeah. And I was enjoying it. It was fantastic. It was really invigorating. I loved every day. It wasn't hard to get up and go to work.

Chris Lynch: But my kids watching my kids start to grow up without me. It was a, there, there were lots of. Sort of aha moments. I came home one day and, one of my kids looked at me and said, you having a sleepover tonight, dad? I was like, no, I live here. Yeah. So that was a wake up call and a month after my 38th birthday said to my wife, let's do something different.

Chris Lynch: I'm willing to give up this job to raise our family and the first thing she said is, I want to have another child, who just graduated from college. 

Chris Lynch: Congratulations. 

Yeah. So we had three kids and then now four, it was about four and a half years between the third and the [00:03:00] fourth.

Chris Lynch: And it was the first time for me that I was actually. Home with a young child growing up, it was a fantastic experience. 

Elise Kiely: How wonderful to take a time out in your life. A lot of us will have the inertia of keeping going work and work, and it takes sometimes an event or a comment.

Elise Kiely: From a child to say, I think let's re-look at what we're doing. Yeah. And why Maine? 

Chris Lynch: Maine was a concept really. If I think about it, we were living in New Canaan, Connecticut. We had lived in London. We talked about going back to London. We didn't really have a specific spot.

Chris Lynch: It was more of a concept. I went to Australia, looked in Sydney and Melbourne, and, ultimately we thought that was too far away concepts if you would be like Marblehead, Massachusetts. Annapolis, Maryland. We were looking for sort of a ocean front coastal community summer lifestyle where there was infrastructure for a young family.

Chris Lynch: Connectivity, the rest of the world. Infrastructure parks, playground schools, travel. Airports. And turns out, [00:04:00] Portland, Maine, has all those things and a whole bunch of other things that we didn't actually really know. We were su we've been surprised for 23 years on the upside.

Elise Kiely: And you had act, you'd gone to college here? 

Chris Lynch: I went to Bates, yep. To Bates College here. 

Elise Kiely: So you had some experience. I had some experience here. 

Chris Lynch: My wife had really not spent much timein Maine. 

Elise Kiely: That's a bold move.

Chris Lynch: It was a bold move. Yeah.

Elise Kiely: and exciting. I had a, similar story of how I came to Maine.

Completely unexpected. I was supposed to be here for one year and that was 1996, almost 30 years ago. So it's it does capture you when you arrive. And then what year did you start the company? 

Chris Lynch: I started working on it in 2005. And it was a, it took a lot more work than I thought, because I wasn't a real estate person by background.

Chris Lynch: I didn't have a real estate company. I didn't have a real estate license. I hadn't practiced real estate. I only bought one house that wasn't a corporate relocation, which is my house in Maine. And so it was one that, Sotheby's International Realty wasn't keen to have someone who didn't know what they were doing, quote unquote running a Sotheby's business in what was a very important [00:05:00] state to them.

Elise Kiely: And did you set out with the intent of redefining luxury real estate in Maine? 

Chris Lynch: I did. Funny enough, I wasn't sure I was going to be be successful but you know, when I got to Maine first thing that struck me was just how undervalued it seemed. I'd look at a property and I know I was coming from New Canan, Connecticut, which is obviously, a more expensive town, but it just, every house I would look just seemed like incredible value.

Chris Lynch: And I thought it seems like it's under marketed. I. It seems like it was a very fragmented market in that there were, multiple small real estate companies all over the state. Who didn't, who and meant most all of whom were owner operators, they were brokers, and they were also managers and they were founders.

Chris Lynch: And they were trying to grow a business, run a business, and also pursue their own business interests at the same time. That just seemed like a very difficult model and a lot of those companies are still out there. 

Elise Kiely: And was Sotheby's the only. Franchise corporate office that you looked at for starting the company?

Chris Lynch: Sotheby's was the only reason I got [00:06:00] into real estate, so I didn't, I came to Maine in, 2002 and really three years later in 2005, and I've been thinking about what I was going to do next, and I was dabbling in different things over those couple of years, spending a lot of time with my family, travel and coaching and really enjoying life. It was the Sotheby's brand and knowing that the Sotheby's brand was going to be available in Maine, and I'm thinking to myself, you have this incredible lifestyle destination, right? Maine Coastal Communities, Maine Interior, Maine, Northern Maine, Southern Maine, it's fantastic.

Chris Lynch: And Sotheby's, international Realty is this global lifestyle brand. And so the idea was just take the lifestyle, take the brand, put them together. And it seemed to me it would be hard to fail. Yeah. It turns out it was harder to succeed than I thought it was going to be, but it was. But as I said, it took some time.

Elise Kiely: You entered the market at a really interesting time in the real estate market. Yeah. 2006 was a really booming time in the real estate, and then things shifted very [00:07:00] quickly. 

Chris Lynch: We started in January, 2006. I think the world calls that peak August of 2006. So I had eight, eight good months before the market started going down.

Chris Lynch: And so 2007 wasn't terrible, but we were in growth mode. So in, in the first two years, I opened four offices and grew to about 50 agents having started on day one with one office and six agents. Yeah. 

Elise Kiely: You had, several agents from another agency Yes. Came over as soon as you started the company.

Chris Lynch: Yes. That was the quid pro quo with Sotheby's is Chris, if you don't know what you're doing, you have to find agents to do. And so I did, and these agents were fantastic. They were some of the best. I said, if there was a real estate hall of fame, they would be in it. They'd in, they'd all be in it.

Chris Lynch: Yeah. 

Elise Kiely: And I agree. I know some of those agents, they're very good agents. They're great. Yeah. And you had a, you're the real estate broker that advised you in buying your house in Maine, ended up coming over and helping you. Bob Stevens.

Chris Lynch: Bob Stevens. 

Elise Kiely: So Bob, great guy. 

Chris Lynch: Bob was actually, so because I moved to Maine.

Chris Lynch: I thought there was value. I went and first thing I did was I bought an [00:08:00] investment property just to see what it was like to own buy and sell. And actually Bob was representing the buyer on the property that I was selling. And it was kind of a complicated transaction and there was a lot of communication back and forth between my agent, the buyer's agent, which was Bob Stevens.

Chris Lynch: And I was so impressed with Bob's communication skills and the way he handled the transaction. And it was the transaction closed and I called Bob afterward and I said, Bob, would you be my broker? I'd love to have you as an agent. I thought you did a terrific job. So I hired Bob to start looking for more things and it was actually Bob that told me that his company was, had the Sotheby's International Realty brand, but didn't really do anything with it, and they were getting rid of it.

Chris Lynch: And I said, not for nothing. I didn't know you had it, number one and number two, if you actually did something with it. I think it could be incredibly successful here in Maine. And Bob was me like, you know, I think you're right. And so one conversation led to another.

Chris Lynch: And about a year later, we teamed up to start the company. 

Elise Kiely: Wow.. And was it continual [00:09:00] growth mode? The 

Chris Lynch: once we started, yes. No, it was bumpy. Yeah, it was a bumpy time. It was really bumpy. It was a bumpy time. I mean, the expenses continued to grow. Yeah. But the revenues didn't continue to grow, and then we had the, obviously the market crash in 2008, nine. And really 10. And even into the beginning of 11, we were still feeling it. 

Elise Kiely: And then we felt like we were slowly getting out of it. And then we had some normalcy until things shifted quite a bit. In 2020. Yes, they did. Yeah. Five, almost five years ago.

Elise Kiely: So, how did running a company and at that time, in March of 2020, how many agents did you have? 

Chris Lynch: At the time, we probably had 80 agents. Yeah. So we had 80 agents, five offices and things were going really well. 2019 was a fit. When your kids are young, you say, at this age, and they're all great ages, I'd love to freeze my child at seven years old.

Chris Lynch: It's, if I could. Frozen the world at 2019, so that was pretty good. Yeah. Everything was in balance, right? We had plenty of inventory, we had plenty of buyers. 

Elise Kiely: It seemed equal. 

Chris Lynch: Prices seemed equal. Prices were going up, [00:10:00] negotiations were fair.

Chris Lynch: Everybody, you know what I love about Maine Real estate? Is it generally speaking and specifically speaking. It is you have buyers who are committed to buy and sellers who are committed to sell and they act in good faith. And whenever there's a problem and there's always a problem in every transaction, there's something that comes up.

Chris Lynch: that good faith commitment to closing has always in 2019 was like everything was really good. We had a lot of people involved in the market and that good faith commitment to closingwas fantastic. It really felt good. 

Elise Kiely: So share with us a little bit as we look back, five years ago, March, there was so much change, so quickly, there were orders of not going into offices.

Elise Kiely: All around the country. All around the world. People were staying home and people were scared. People were very scared to go to the grocery store. They're very scared to go out in their community. Churches were shut down. Schools obviously were shut down. When did you start noticing the phone ringing, the emails coming in [00:11:00] from buyers looking to Maine as a lifeboat or a safe haven?

Chris Lynch: I would say it was probably beginning of April. There was a two week period where I think everybody was just shell-shocked. And again, when they started the shutdowns with the schools like, we're just going to close down for a couple weeks. And so you, you didn't really, at the time, at the beginning, there was this light that was very close by, and it wasn't a very long tunnel that we thought were gonna be there in a couple of weeks, maybe a month. But really once I think it became very clear to people that this wasn't going away quickly, our phone started ringing off the hook.

Chris Lynch: And initially it was for long-term rentals. Everybody wanted a rental. And we don't have a lot of rentals in Maine. And talk about a fragmented market. There's no central clearing house for rentals in Maine, and we just don't have a lot of rentals to begin with.

Chris Lynch: We don't have a lot of people, but we don't have a lot of rentals. And I remember big families looking for big property where they could all be together, multi-generational and all. A lot of island properties they wanted to be, so the, [00:12:00] some of the islands actually shut down their ferries closed to outs.

Chris Lynch: Even people who owned homes there couldn't get there, couldn't get there. Yeah. And so it was such a disrupted time. I mean, looking back on it, navigating those waters at the time was really tricky. 

Elise Kiely: And what were some of the things you did to stay in touch with and manage?

Elise Kiely: The advisors who work with legacy properties. 

Chris Lynch: So when I look back on, in, when I was on Wall Street, I started in the investment banking world and I ended up in the sales and trading world. I worked on a bond trading floor for about 14 years. And I look back and what was that all about?

Chris Lynch: It was really about crisis management. And so now we had a big crisis and crisis management is all about communication. It's all about finding out what everybody's worried about and really trying to make sure we're doing everything we can to make people feel comfortable.

Chris Lynch: I was very concerned having, and again, keep in mind, 2008, nine, and 10 from a. Business perspective was a disaster if you werein the real estate business. It was and so I started to think, oh my goodness, we're going to go [00:13:00] back into that sort of crisis, economic crisis where the real estate market might not exist for some period of time.

Chris Lynch: And my son Andy, who's our chief financial officer's, been with the company for about six years, the oldest of the four, he and I immediately connected. Portland was shut down. You weren't allowed actually to be in the city unless you lived there. And then you weren't really allowed to go out for a couple weeks, maybe three weeks.

Chris Lynch: He and I were in every morning. First thing in the morning, 7:00 AM pulled the shades and just started going through every single, expense that we had. We were doing daily Zoom calls, which you were part of. With all the agents, an hour or two, sometimes at a clip, making sure that, we were keeping real time.

Chris Lynch: And the agents were picking up all this information and each city and town had different rules and regulations. Certain counties had regulations. So we're trying to keep up with all of that. Our geographic reach is super broad. We do business about 12 counties.

Chris Lynch: A hundred, probably a hundred cities and towns. speak of geographic reach. I remember during that time being on Zoom calls [00:14:00] with other Sotheby's, international Realty agents around the country and including Canada and a lot of those calls of friends in Toronto, and hearing about experiences that were happening in California and Chicago and Florida.

Chris Lynch: And Atlanta and New York and the different experiences people were having, and more importantly, the different tactics that advisors were using to help their clients. Because remember, we were in the middle of some transactions. And we had inspections that maybe. We're scheduled to happen, and that was complicated.

Chris Lynch: How do you inspect a property if nobody can be in the property? And would registry of deeds stay open so you could record deeds? Would title companies stay open? And there were different tactics that people shared all around the country, which is a huge benefit to a company like Sotheby's because of the sharing of information.

Chris Lynch: So we tie into those resources still every day. That it's not. Visible to the world, but the connectivity between the Sotheby's, [00:15:00] international realty companies all over the world and particularly in our feeder markets like Boston and New York and Washington DC West coast of Florida, the west coast of the United States.

Chris Lynch: Dallas. Houston is daily. And California.Yeah. And we share a ton of information, lots of buyers and sellers back and forth.. We work with them super closely. So Chris, looking back on the last. So call it five or even 10 years pre Covid, I, what are some memorable stories that you have about unique transactions and there's probably a tension or a struggle or a dispute that is in at the heart of some of them.

Chris Lynch: Yeah, so that's, it's a great question. I would say there's lots of memorable ones. they're memorable in, so many good ways. But probably one of the most memorable though, actually goes back to the, crash in 2008. One of my agents was working with a buyer, and the buyer had this interesting concept is they're both lawyers, both from New York, super interesting people.

Chris Lynch: And my agent said, can you know, can you meet with these folks? And so they [00:16:00] came into the office and we sat down and they spent a half hour going back and forth between the two of them. I remember, It was August of 2008 and their theory was that the economic world was coming to an end.

Chris Lynch: And that there was going to be a global financial crisis and meltdown, and the dollar was going to collapse and the economy was going to collapse and credit was going to collapse, and bankruptcies were going to be personal bankruptcies, all these things. And almost to the day ultimately that they actually happened.

Chris Lynch: And so they went on for about a half hour and just back and forth and back and forth and this. And finally, they get to the conclusion. And their conclusion is, so the reason we're here is we want to look at all these properties. They looked at 25, 30 properties.

Chris Lynch: So that when we hit rock bottom, which we think will be sometime 12 to 18 months, we can actually figure out how much we've saved by waiting for a year to two years to buy a property in Maine. What a great concept. So anyway, they get to the end, and I didn't say anything. I [00:17:00] was just listening intently and I was like, I agreed with everything.

Chris Lynch: It was hard, hard not to at the time, but they're, they were so spot on. It was pretty unbelievable. So they get to the conclusion, I said, the only thing I don't agree with is your conclusion. I said that is just not the way Maine real estate works. I said the way Maine real estate works is every house, every location is pretty unique, and when you find the one that you really love, you should figure out on that day what it's worth and you should buy it.

Chris Lynch: That's crazy. They said why would we do that? I said and again if it's a specific spot, specific house, it's just something you're looking for that's really special. You may never see another one. Or it may be five years or 10 years. It's not like we, I mean, we have, we're blessed with an incredible coastline and beautiful communities all over the state, but sometimes it's just, there's that special property.

Chris Lynch: So anyway, they thought it was crazy. Why would I even say that ? They were looking for a commodity. They were looking for a commodity, right? And again, there's no commodity properties here, super hard to value. No two properties [00:18:00] really are the same. We have very few subdivision type properties. So anyway, they walk out thinking I'm crazy. And, three weeks later, the husband calls me from New York, you're not going to believe it. We just put property under contract. What you said is so true. 

You said? It's so true. And, , he said, my wife is so mad at me because that's not the plan.  The plan was, we're going to, we're going wait for 18 months. And they bought this incredible property in, in Cape Elizabeth. And, and funny enough, that was in 2008 and, and they're closing on selling it tomorrow. Wow. Funny enough, 

Elise Kiely: I [00:21:00] imagine the appreciation has been significant, 

Chris Lynch: almost fivefold. 

Elise Kiely: Five x. Yeah.

Chris Lynch: Four plus x. Wow. Yeah. Wow. So, uh, but, but anyway, the, the reason I tell that story is so that that holiday season, I get a package from Zurich, Switzerland, and, and it's a box of Monte Christo, number two Cuban cigars. And it was just, thank you. It was a thank you from the buyer saying, you know, we probably wouldn't have done that.

Chris Lynch: Without having that conversation with you, and I thought that was really special. Yeah, 

Elise Kiely: I, I'd say that's elegant. That was, yeah. 

Chris Lynch: Yeah, it was interesting that that's, I, 

Elise Kiely: I love that story, uh, for so many reasons. One, people coming in with a certain expectation of real estate in Maine being just like real estate in Manhattan or.

Elise Kiely: Connecticut or Florida or one of our other wonderful feeder markets, and it's not, it's so special. It's so specialized, and you use that phrase all the time [00:22:00] that if you see a property that speaks to you, really consider strongly putting an offer on it because you may not see it in a generation. And we have so many properties that are handed down to generations in this state because people realize.

Elise Kiely: If they let it go, they're not going to get it back.

Chris Lynch: It's not unusual that we'll bring a property on the market and someone will say, I've been waiting for that property for 30 years. Mm-hmm. To come on the market. It's my dream property. 

Elise Kiely: Well, if you think about it, in Maine, real estate, everything is a low commitment.

Elise Kiely: Whatever you want to do outside, if you want to be a boater. Go to town hall, get a permit for a mooring and buy a boat and you're a boater. And it's a pretty low commitment. It's, yeah, to do the things that people really wanna do on the outside from hiking to cross country, skiing, surfing, whatever your passion is.

Elise Kiely: Um, golf and tennis, it's very easy to do those things. And for your family to do those things. 

Elise Kiely: Yeah. Access. To just about anything you love to do. [00:23:00] It's so much easier here. 

Chris Lynch: I, I couldn't agree more. I'm not picking on Greenwich, Connecticut, but to get a mooring in the harbor in Greenwich is probably a lifetime.

Chris Lynch: Yeah, it's probably a lifetime there. You can have it tomorrow. 

Elise Kiely: I always say in Maine you could ski. At a downhill ski mountain, one of the ones that are within two hours and surf in the ocean the same day. You'd need a thick wetsuit and then you could go down and have a fabulous dinner in a great Portland restaurant.

Chris Lynch: Yeah, no, you're so right with, with fish that came in that morning off the boat. I mean, how do you beat that for, for a lifestyle? 

Elise Kiely: No, it's pretty good. You're so right. Chris, I always appreciate sitting down with you and talking real estate. I could talk to you for hours on these subjects. I think we'll close out this first half of our conversation at this point, and we can recap and regroup into your second part of our conversation, um, airing on the next episode.

Chris, I always appreciate sitting down with you and talking real estate. I could talk to you for hours on these subjects.

Chris Lynch: I think we'll close out this first half of our conversation at this point, and we can recap and regroup into your second part of our conversation, airing on the next episode. Chris, thank you so much for coming in and look forward to continuing the conversation. Thank you for joining us on Elegant Maine Living.

Chris Lynch: And remember, if you are dreaming of a lifestyle in Maine or already living it, this podcast is for you. Be sure to subscribe so you don't miss an episode. And I invite you to take this journey with me. Please share it with your friends, family, neighbors, and [00:19:00] coworkers. I would love a review and welcome feedback and encourage you to reach out with questions or topics you would like to hear about.

Chris Lynch: You can find me on Instagram, Facebook, and LinkedIn, or simply an email to elise@elisekylie.com, and all of those links will be in the show notes. And remember, this podcast is for entertainment and informational purposes only and does not create an attorney-client or real estate advisory relationship. I am happy to engage.

Chris Lynch: If you have any questions or if I can help in your real estate journey, simply click on the links in the show notes to contact me through social media or email. I'm always happy to help in any way that I can, and we welcome you to come and explore Maine. Thank you for listening to Elegant Maine Living where elegance isn't just an aesthetic, it's a way of life.

Chris Lynch: Until next time, keep living with [00:20:00] elegance.