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Welcome to The Caplener Group!

Proudly rooted in SE Portland, our team specializes in selling homes across the Portland Metro and surrounding areas. Our team members bring a wealth of knowledge and experience, with Jan earning his real estate license in 1983, Kevin in 2005, and Gina in 2020. Our extensive transaction history and collaborative approach to real estate makes us uniquely equipped to tackle any challenge with confidence. Our commitment is to guide you every step of the way, from pre-approval to possession. We are here to ensure your experience is seamless, successful, and, enjoyable.

Thank you for considering The Caplener Group. We value the opportunity to be a part of your story.

5015 SE Hawthorne Blvd.

Portland, OR 97215

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Who We Are


Jan Caplener

Portland is my home. I know the local schools, businesses, and neighborhoods - and even boast a collection of rare antique photographs from the area. Having lived in the Mt. Tabor area since 1955, I have seen the exciting evolution of our community.

For 15 years I coached little league and also taught seventh-grade history at Robert Gray Middle School. Simply put, I believe in teamwork. As a coach and a teacher, I learned that to achieve greatness, you must win respect and commitment of your team.

When my partners and I decided to form Realty Trust Group in 1997, we agreed that teamwork and client-focus would be guiding principles for the company. In building relationships and combining talents, we knew that we would have a far greater chance to ensure everyone’s success. As a result, all agents at Windermere Realty Trust are committed to making each transaction a win-win.

Sports are still a big part of my life. As a graduate of Oregon State University and a Beaver Football season ticket holder, I am no fair-weather fan. Golf is also one of my greatest passions. I am fortunate enough to have played at many of the top courses in the world, and count St. Andrews in Scotland, Royal County Downs in Ireland, and Pacific Dunes in Bandon, Oregon among my favorites.


Kevin Caplener

I entered the real estate scene in 2005, inspired by my father, Jan Caplener. I had the fortunate opportunity to join his team, with the goal of helping future buyers and sellers, and maintaining a client base that he has been nurturing since 1983. 

Born and raised in the Mt. Tabor neighborhood, my wife and I and two kids now live on same street that I grew up on. I now have the best commute ever, needing to head just down the street to our lovely office right on 50th and SE Hawthorne. 

Away from work, I love spending time in Mt. Tabor park with my kids, going on adventurous trips in our camper trailer, and occasionally hitting the golf links as well. 


Gina Hall

I moved to Portland, Oregon in 2017 from Northern California and immediately found my passion in real estate. I started my career working on the administrative side of the industry, and after three years decided to join The Caplener Group. While I still assist our team with some “behind the scenes” work, my real strength comes in working with first time home buyers. I take pride in my communication skills, my patience, my knowledge of all four quadrants of Portland, and I feel I am uniquely qualified to work with both native Portlanders and out of town clients.

I make a point to be ready and available for my clients, but when I am not working I can be found exploring the Portland food scene, cooking, or watching old movies with my fiancé.

Catherine and Jordan

Chelsie was lovely and went above and beyond to ensure a smooth buying process. We moved cross country and her expertise helped us find the right neighborhood. She worked with our travel schedule, even showing us houses via FaceTime when necessary. Chelsie was extremely trustworthy even checking up on the house in the weeks after closing before we were able to move. We are so grateful to have found her and would absolutely work with her again.

Dennis and Mindy

Jan and Windermere Realty Trust team, thank you for your tremendous job in selling our house. Your professional presentation featured our house at it’s best. Your negotiating skills got us a very good selling price. Patience, resolve and persistence got us through the challenges of extra inspections required for rural property. We are very happy to be former homeowners. Thank you for making it happen!

Lisa & Tim

Throughout the entire process, from last fall’s introduction through mid-winter Internet searching, through Portland visits and tours, through the recent purchase process, Kevin has been fantastic. He developed a keen sense of who we are as buyers, both likes and dislikes, and understood our unique needs as parents of a special needs son. He has been proactive, responsive, and helpful with every detail from explaining house features to steering us to vendors and providing on-site support. Doing this search and purchase from CT has not been easy; we have leaned on Kevin to be our eyes and ears and to use his good judgment to help us out in many ways. We are very grateful for his time and his support.


Kevin is my hero. He went way above and beyond the call of duty, preparing my property for sale. He was always right on top of the next need, getting things done well and at low cost. Kevin got the main brunt of difficult and fairly unique obstacles that arose to meeting my sale deadline. Kevin was ever-ready and ever clever. I’m no shill for Windermere Realty Trust—just a very grateful customer. It’s a fine company to work with; keeps you believing in humanity!


I found the entire team of Jan, Kevin, and Caroline amazingly competent, knowledgeable, and responsive during the entire process of buying my first rental property. These are good people with whom to work. I highly recommend them.

Maureen & Dave

I was a first time homebuyer and very intimidated by the Inner Eastside market. Luckily, I had Jan and Kevin on my side to help me every step of the way. They found me an incredible house at a great price, helped negotiate repairs that were very beneficial for me, and most importantly, they made me feel safe with my investment. I would highly recommend Jan and Kevin to anyone looking to buy a house in Portland!

Eric & Amber

First, we wanted to thank Kevin for being so helpful, honest and most of all patient with us during our transaction, we know we can be difficult to deal with. My wife and I could not be happier and are your clients for probably forever. We could not ask for anything more!

Teresa & Grant

Caroline was wonderful to work with! She helped us navigate our first investment property hunt and purchase with ease and was always available for questions and quick with answers from start to finish. We wouldn’t hesitate to use Caroline and the Caplener Group again.

Tom and Janet

Chelsie was a god send for my wife and I. We spent some time with her and she asked great questions and quickly knew just what we were looking for in our new home. We saw the house that day that perfectly matched our wishes. But that’s when Chelsie really showed her professionalism. She oversaw all aspects of the process from the inspection to the closing.
It could not have gone better. If you want great customer service when looking for a home, look no further than Chelsie. She is the best!

Forrest & Nan

Our experience couldn’t have been better. Both Caroline and Kevin were immediately responsive to our every request and need, in addition to being ever patient and friendly. I don’t know what more to say. God forbid we should ever have to repeat the experience of buying and selling a house, but should we have to we would use The Caplener Group as our agent.


Caroline was fabulous to work with. She was extremely responsive any time we contacted her for information, for access to the new home or with numerous questions. I thought that Caroline was proactive in anticipating our needs and next steps in the home buying process. I whole-heartedly would recommend Caroline to anyone who is searching for a home.


I had the pleasure of working with Kevin, who contributed a consistently positive and confident approach to the home-search process, with its numerous imperfect matches and rejected offers! I wanted to give up a few times, but ended up with a house I love. Also, he fought for me when it was necessary, both during the inspection period and through the closing. He managed to obtain a few key concessions from the seller that I never expected us to get and never would have gotten on my own.

Dennis and Lisa

We worked with Chelsie to buy one home and sell another home in SW Portland. Finding the right home was a fairly lengthy process and Chelsie was very helpful and patient throughout. Once our bid was accepted she was great during the entire process including our being on an already planned vacation during the inspection process. Chelsie was incredibly helpful during the sale of our other house and helped us get the whole thing done during our kids summer break.


It has been fabulous to work with you all on the preparation and sale of my Aunt’s house. You have more than accomplished this task with professional, courteous and forward looking assistance. I could not have asked for anything beyond what you have given me. I thank you from the bottom of my heart in making this potentially difficult process so successful.

Dave and Joan

My wife and I have lived in our Mt. Tabor home for close to 30 years, a home purchased with the support and services of The Caplener Group. The Caplener Group provided more than just the buy/sell transaction support, they worked at a personal level to ensure that both parties interests and concerns were addressed and we were kept informed through every step of the way. We have tremendous confidence in their knowledge of the market and have used their services in other real estate transactions.

Vyasa & Emma

My wife and I are thrilled about our new home and it’s thanks to Kevin that we were able to get exactly what we wanted. Kevin stayed patient while we searched for over a year for our ideal home in a very inhospitable real estate market. We never felt pressured to settle for something that didn’t fit our needs and there were numerous times when he provided much needed advice. It felt great to know that he was in our corner and had our best interests in mind.


After almost 60 years, my grandmother moved out of her South Tabor home and put it up for sale. From our first meeting with The Caplener Group, my family was impressed with their knowledge, experience, and specific suggestions on how best to price and market the house. They were very hands-on with every aspect of the transaction, and my grandmother received a great price that gave her financial peace of mind as she enters the next phase of her life.

Jeffrey and Margaret

We received stellar representation from Caroline Easton when we purchased our home in Portland, so when we found a beach house in Rockaway Beach we again called Caroline for help. Despite the fact that she does not typically work on the coast, she provided all the assistance we needed in our purchase. She tracked down an excellent inspector and plumber, drove the distance to attend our inspection, and did all the leg work to make our transaction smooth. If we ever have another real estate transaction in the area, we’ll use Caroline Easton again in a heart beat.

Sean and Kate

Kevin helped us a great deal. He secured a good price for our new home, responded quickly to our needs, and coordinated effectively with every other party. We felt safe with Kevin. We totally trust him and would recommend him to anyone else who’s looking for a new home.


Thanks to Kevin Caplener’s expertise at Windermere Realty Trust we outbid four other parties and I still got instant equity after purchase!

Lou and Kelly

Listing our home for sale with The Caplener Group was the best decision we could have made. Kevin Caplener handled all aspects of the sale in a thoroughly professional manner. He was always available, attentive, and performed tasks reliably and quickly. Kevin met the usual bumps in the road that occur in a sale with a positive attitude, making us feel sure we were in good hands, and we were! We appreciate our good fortune in having Kevin and his team represent us.

Joe and Gia

We would like to extend our sincere thanks to Caroline Easton and the rest of the fantastic staff at Windermere Realty Trust. After receiving notification that my husband’s job was relocating our family from Hawaii to Portland, Oregon, we were excited, but also very overwhelmed. We were beginning a search for a home, while living in another state, in a city that we had only visited once while on vacation. Did I mention too that this was going to be our first home purchase and that our children (at that time) were 9-years old and 6-months old? Caroline did a tremendous job managing the emotions of first-time homebuyers and educating us (from afar) about our neighborhood options. In advance of our brief trip to Portland to find a home, we had sent Caroline a list of homes that we wanted to see in addition to the list that she had pulled together. When we met, she explained why she believed many of the houses on our list might not be a good fit for us, but genuinely expressed her willingness to show us all of the homes on our list in addition to the list that she had pulled. Although we had spoken to Caroline several times before over the phone to communicate our needs and desires, my husband and I were dubious that we could rely on the judgement of this (charming) stranger to cross homes off of our list. The hunt began – and by the second home on each of our lists, we realized that we could without question place our trust in Caroline’s judgement. Our list went out the window and we put ourselves in her very capable hands.

When we did finally find a home that we wanted to place an offer on, Caroline proved to be a diplomatic, yet firm, negotiator. As first time buyers, we were very grateful for her willingness to guide us through the purchasing process and her willingness to answer questions and function as a liaison at times between the lender and ourselves. As we were completing the purchase from out of state, this saved our sanity! During this time, Caroline had a previously arranged vacation, but she still made herself available to us should the need arise. Happily, her associates at Windermere Realty Trust provided us with stellar assistance while she was gone, although she still touched-base with us to ensure that we were satisfied.

Thanks to Caroline, we are now happy first-time homeowners in a house and neighborhood that perfectly suits the needs of our family! Caroline has an innate ability to quickly assess and understand the needs of a buyer, a willingness and desire to find a good fit, and a detailed understanding of the various areas of Portland. Added to this, Caroline’s calm and friendly demeanor alleviated much of the anxiety we felt as first-time buyers.

If you are in the market for a home, we highly recommend Caroline and Windermere Realty Trust. In our experience, these professionals were knowledgeable, responsive, and kind. What more could you ask for?


Caroline Easton recently found me a house in Portland. She is an exemplary realtor, and I will recommend her to any friend looking for a realtor in Portland (in fact, I have already given her name to a serious buyer). She is responsive, thoughtful, and respectful of her clients wishes. She quickly and thoroughly understood what I was looking for, and she showed me only those properties in my price range and those fitting my stated requirements. I especially appreciate that she did not pressure me in any way, but allowed me appropriate time and space to make decisions, offering advice only when I asked or apparently needed her opinion.

Abby and Jeremy

As first-time home buyers, my husband and I were intimidated by the home buying process. Kevin helped us feeling comfortable and excited about the prospect of purchasing a home. He was incredibly knowledgeable about the market, various neighborhoods in Portland, and things to look for when buying. But most importantly he was a great listener. My husband and I both felt heard by Kevin, we felt supported by Kevin, and we trusted Kevin. He beautifully balanced the art of letting us make our own decisions and giving his advice. Kevin was responsive to our every need, from phone calls, emails, drop-ins, and problem-solving. He communicated the process to us in a way in which we could understand and made us feel comfortable asking our questions. He was in constant contact with us regarding the schedule of events (signings, inspections, closings, etc.) and was there to give us a great big hug when it was all done. Kevin provides a professional and personal service to his clients and we will be singing his praises to anyone interested in buying/selling a home.

Maciej & Michelle

We worked with Caroline on selling our last house and buying our new house too. With the house we were selling we got great input from Caroline and Kevin on the updates that we could finish in a month that would provide the best return on investment. She was very helpful in the negotiation process by providing guidance through the process as well as providing advice. In purchasing the new house she was incredibly diligent managing the schedule and the dialog with the builder so we could get the dream house we wanted on time.


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