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Meet Trent Estabrook

Trent Estabrook Madison, WI Real Estate Agent Headshot

Trent Estabrook

Trent was born and raised in Northern Wisconsin. After graduating from the University of Wisconsin–Eau Claire in 2004, he moved to Madison, Wisconsin, where he began his full-time career in real estate. He specializes in new construction, existing residential homes, condominiums, lake properties, raw land, and investment real estate.
 
Recognized as one of Madison’s Top 40 Under 40, Trent is an Accredited Buyer Representative (ABR), a Certified Residential Specialist (CRS), and a Graduate of the REALTOR® Institute (GRI). His clients benefit from his in-depth market knowledge, attention to detail, and ability to confidently navigate even the most complex transactions.
 
Outside of real estate, Trent enjoys spending time with his wife, two children, their goldendoodle, Millie, and family and friends. An outdoor enthusiast, he can often be found hiking, boating, or golfing.

Contact Details

Email address [email protected]
Primary phone (608) 213-4282
Address 8201 Mayo Dr Madison WI, 53719
License #58196-94
See Why Our Clients Love Us

Testimonials

Read what our clients have to say about working with us.

"We can’t say enough good things about Mason! From day one, he’s been incredibly patient, supportive, and genuinely invested in helping us find the right home — not just any home. Our search took longer than expected, but he never rushed us or made us feel pressured. Instead, he offered thoughtful guidance, expert advice, and constant encouragement along the way. Highly recommend Mason to anyone looking for an agent who is patient, knowledgeable, and genuinely cares about their clients. We’re so grateful for all the time and effort he put into helping us find our perfect home. We truly couldn’t have asked for a better partner in this journey!"
"We can’t say enough good things about Mason! From day one, he’s been incredibly patient, supportive, and genuinely invested in helping us find the right home — not just any home. Our search took longer than expected, but he never rushed us or made us feel pressured. Instead, he offered thoughtful guidance, expert advice, and constant encouragement along the way. Highly recommend Mason to anyone looking for an agent who is patient, knowledgeable, and genuinely cares about their clients. We’re so grateful for all the time and effort he put into helping us find our perfect home. We truly couldn’t have asked for a better partner in this journey!"
Lauren B.
"Working with Sam was a pleasure. He actively listens to your wants and needs and asks all the pertinent questions to gain accurate understanding. Sam is knowledgeable, patient and solidly invested in meeting your needs. In today’s high pressure society, you’ll not be receiving any unwanted pressure from him. I highly recommend Sam for all your real estate needs."
"Working with Sam was a pleasure. He actively listens to your wants and needs and asks all the pertinent questions to gain accurate understanding. Sam is knowledgeable, patient and solidly invested in meeting your needs. In today’s high pressure society, you’ll not be receiving any unwanted pressure from him. I highly recommend Sam for all your real estate needs."
Dawn K.
"Sam was an outstanding agent for both my purchase and sale of a home in the Verona area. He knew the area, could find houses that matched my interests, and was always timely and diligent. I highly recommend him and the rest of the Pinnacle team to anyone looking to purchase or sell a home in the Madison area."
"Sam was an outstanding agent for both my purchase and sale of a home in the Verona area. He knew the area, could find houses that matched my interests, and was always timely and diligent. I highly recommend him and the rest of the Pinnacle team to anyone looking to purchase or sell a home in the Madison area."
Eugene M.
"We were first time home buyers and Pinnacle was a top class group to work with for our first time home buying experience. Jordan is our agent and his vast knowledge of real estate including the Madison/Middleton/Waunakee markets was incredibly helpful. We have since sold and purchased another home with help of Jordan and our experience was great as always. Great customer service, communication and overall experience. We always recommend without any hesitation Pinnacle Real Estate Group to anyone looking, planning, or thinking about selling or purchasing real estate."
"We were first time home buyers and Pinnacle was a top class group to work with for our first time home buying experience. Jordan is our agent and his vast knowledge of real estate including the Madison/Middleton/Waunakee markets was incredibly helpful. We have since sold and purchased another home with help of Jordan and our experience was great as always. Great customer service, communication and overall experience. We always recommend without any hesitation Pinnacle Real Estate Group to anyone looking, planning, or thinking about selling or purchasing real estate."
Mike P.
"First time I met Sam was in an open house. He was very nice and welcoming. At the end of our tour he asked if we need help finding a house and if it is ok if he checks on us and send some listings. Since then he kept following up very nicely and sending postings that exactly fit our needs. Sam was very helpful and supportive through out this long and sometime annoying journey. His advices, very fast and efective responses, diligence and above all his gentleness are the main reasons to be able to navigate through this long journey. In essence Sam is the main reason that we finally landed our first dream home. Thank you Sam, see you at the closing."
"First time I met Sam was in an open house. He was very nice and welcoming. At the end of our tour he asked if we need help finding a house and if it is ok if he checks on us and send some listings. Since then he kept following up very nicely and sending postings that exactly fit our needs. Sam was very helpful and supportive through out this long and sometime annoying journey. His advices, very fast and efective responses, diligence and above all his gentleness are the main reasons to be able to navigate through this long journey. In essence Sam is the main reason that we finally landed our first dream home. Thank you Sam, see you at the closing."
George B.
"Mason was great to work with from start to finish! He was patient with us as we searched for our new home, fought for us to get into a home that was looking to sell quick, and helped us put together the strongest offer possible for our situation. Very knowledgeable and always available. Thank you, Mason, for your great service!"
"Mason was great to work with from start to finish! He was patient with us as we searched for our new home, fought for us to get into a home that was looking to sell quick, and helped us put together the strongest offer possible for our situation. Very knowledgeable and always available. Thank you, Mason, for your great service!"
Brad C.
"This was my third home I’ve purchased and by far my best experience. Mainly due to my agent, Sam. He was simply amazing. Sam’s interest was always mine and what was best for me. His communication was with me exceptional, always answering his phone and providing updates as the process evolved. I moved here from out of state and Sam made the process stress free. If you are looking for representation, I highly recommend Sam and Pinnacle Real Estate."
"This was my third home I’ve purchased and by far my best experience. Mainly due to my agent, Sam. He was simply amazing. Sam’s interest was always mine and what was best for me. His communication was with me exceptional, always answering his phone and providing updates as the process evolved. I moved here from out of state and Sam made the process stress free. If you are looking for representation, I highly recommend Sam and Pinnacle Real Estate."
John K.
"I met Sam at an open house he was holding and was so impressed. I decided to work with him on my home search, which was like looking for a needle in a haystack. Sam was incredibly professional and patient. Pointed out the pluses and minuses of particular homes and consistently checked in with me on my priorities. I would work with him again in a minute."
"I met Sam at an open house he was holding and was so impressed. I decided to work with him on my home search, which was like looking for a needle in a haystack. Sam was incredibly professional and patient. Pointed out the pluses and minuses of particular homes and consistently checked in with me on my priorities. I would work with him again in a minute."
Sue
"We bought our house with Mason. He is really helpful and patient when speaking with us, taking the time to make sure we understand every detail. He is knowledgeable and is willing to find the right answer even after normal working hours. We appreciate all of his help and would definitely work with him on any housing endeavors in the future!"
"We bought our house with Mason. He is really helpful and patient when speaking with us, taking the time to make sure we understand every detail. He is knowledgeable and is willing to find the right answer even after normal working hours. We appreciate all of his help and would definitely work with him on any housing endeavors in the future!"
Yilin S.
"There are no words that can truly describe how happy I am to have chosen Sam Jessup to help with selling our home. He was very professional through the entire process. He explained things very well and always answered any questions that we had. He is knowledgeable in his work and it was easy to trust him for this reason. We all know how difficult it can be to purchase or sell a home and he made the entire process as painless as possible. Sam is a genuine person and you can tell he loves to help people. I will recommend Sam to any person who is in need of a realtor! If you pick Sam for any of your realtor needs- you will not be disappointed! 20/10!"
"There are no words that can truly describe how happy I am to have chosen Sam Jessup to help with selling our home. He was very professional through the entire process. He explained things very well and always answered any questions that we had. He is knowledgeable in his work and it was easy to trust him for this reason. We all know how difficult it can be to purchase or sell a home and he made the entire process as painless as possible. Sam is a genuine person and you can tell he loves to help people. I will recommend Sam to any person who is in need of a realtor! If you pick Sam for any of your realtor needs- you will not be disappointed! 20/10!"
Kathryn G.
"I’ve purchased and sold multiple properties with Jordan. The team at Pinnacle has a family first atmosphere. The team is relationship first and focuses on what's best for buyers and sellers."
"I’ve purchased and sold multiple properties with Jordan. The team at Pinnacle has a family first atmosphere. The team is relationship first and focuses on what's best for buyers and sellers."
Dan S.
"I am currently working with Joe Armentrout at Pinnacle Real Estate Group on purchasing a new lot and the sale of my current home. This will be the third house where I've worked with Joe. He is an excellent realtor. His attentiveness to our needs is unparalleled. He is always quick to respond to any inquiries and his knowledge of the market is incredible. Whenever I learn of a friend looking to sell or buy, I always recommend Joe as I don't believe there is a better agent in the area. I highly recommend Pinnacle Real Estate Group for either buying a new property, selling your current property, or both."
"I am currently working with Joe Armentrout at Pinnacle Real Estate Group on purchasing a new lot and the sale of my current home. This will be the third house where I've worked with Joe. He is an excellent realtor. His attentiveness to our needs is unparalleled. He is always quick to respond to any inquiries and his knowledge of the market is incredible. Whenever I learn of a friend looking to sell or buy, I always recommend Joe as I don't believe there is a better agent in the area. I highly recommend Pinnacle Real Estate Group for either buying a new property, selling your current property, or both."
Marc G.
"Staff was professional and helpful. Sold my house quickly and answered questions promptly. Jordan went above and beyond finding me a builder as well after he sold me a lot. I would highly recommend these folks."
"Staff was professional and helpful. Sold my house quickly and answered questions promptly. Jordan went above and beyond finding me a builder as well after he sold me a lot. I would highly recommend these folks."
Laurie B.
"Jordan and Pinnacle Real Estate Group are top class. Jordan made purchasing a home a wonderful experience. His top class communication and knowledge of the Madison market made the process a breeze. I will be using him again in my future!"
"Jordan and Pinnacle Real Estate Group are top class. Jordan made purchasing a home a wonderful experience. His top class communication and knowledge of the Madison market made the process a breeze. I will be using him again in my future!"
Cale C.
"Amazing company to work with. I have bought and sold several homes over the years and worked with many realtors but Joe is by far the best. His client-oriented approach and attention to detail is second to none. I highly recommend this company for your real estate needs."
"Amazing company to work with. I have bought and sold several homes over the years and worked with many realtors but Joe is by far the best. His client-oriented approach and attention to detail is second to none. I highly recommend this company for your real estate needs."
Dave O.
"Trent was great to work with. He was very knowledgeable of the Madison area which was so helpful in narrowing our search. Trent was very responsive and was there through the entire process. We would highly recommend him to anyone looking for a property on the Madison area."
"Trent was great to work with. He was very knowledgeable of the Madison area which was so helpful in narrowing our search. Trent was very responsive and was there through the entire process. We would highly recommend him to anyone looking for a property on the Madison area."
Heather K.
"Trent and Jordan are top notch people to work with! They have integrity in what they do and treat you like family from the get go! It feels good to have a local real estate agency that I can trust.. I highly recommend them!"
"Trent and Jordan are top notch people to work with! They have integrity in what they do and treat you like family from the get go! It feels good to have a local real estate agency that I can trust.. I highly recommend them!"
Sally A.
"Bought our home through Trent and will again - he's a great realtor, great person, and found us a perfect home. Thank you!"
"Bought our home through Trent and will again - he's a great realtor, great person, and found us a perfect home. Thank you!"
Scott J.
"We purchased two houses and sold one with Trent Estebrook. He was a great agent. I would highly recommend Trent and Pinnacle to anyone looking to buy or sell a house."
"We purchased two houses and sold one with Trent Estebrook. He was a great agent. I would highly recommend Trent and Pinnacle to anyone looking to buy or sell a house."
Matthew H.
"Austin was incredibly responsive and knowledgeable throughout our first home-buying experience. He went out of his way to ensure we secured our dream home, and we couldn’t have asked for a better realtor. I highly recommend Austin to anyone looking for someone they can truly rely on."
"Austin was incredibly responsive and knowledgeable throughout our first home-buying experience. He went out of his way to ensure we secured our dream home, and we couldn’t have asked for a better realtor. I highly recommend Austin to anyone looking for someone they can truly rely on."
Trevor K.
"Austin was fantastic to work with on the sale of our home. He has a stellar sense of the housing market and explains them in a digestible manner, creating a great sense of cohesion in the selling process. In addition he was incredibly approachable, kind, respectful and most importantly patient with us as first time sellers. We can’t recommend Austin enough!"
"Austin was fantastic to work with on the sale of our home. He has a stellar sense of the housing market and explains them in a digestible manner, creating a great sense of cohesion in the selling process. In addition he was incredibly approachable, kind, respectful and most importantly patient with us as first time sellers. We can’t recommend Austin enough!"
Adam S.
"We had an incredible experience working with Austin as our realtor! As first-time home buyers, we had a lot to learn, and Austin made the entire process feel fun, smooth, and completely painless. He took the time to explain everything clearly, answered all our questions with patience, and always brought such positive energy to every interaction. His schedule was super flexible, which made it easy to work around our busy work lives. We couldn’t have asked for a better person to guide us through this journey. We highly recommend working with Austin and will absolutely be using him again for any future purchases!"
"We had an incredible experience working with Austin as our realtor! As first-time home buyers, we had a lot to learn, and Austin made the entire process feel fun, smooth, and completely painless. He took the time to explain everything clearly, answered all our questions with patience, and always brought such positive energy to every interaction. His schedule was super flexible, which made it easy to work around our busy work lives. We couldn’t have asked for a better person to guide us through this journey. We highly recommend working with Austin and will absolutely be using him again for any future purchases!"
Hallie R.
"Austin made house hunting fun and helped our young kids feel included in the house search process. He was flexible with his schedule, provided valuable insights, was collaborative and creative with decision-making and offers, was optimistic and positive, and through the process of working with him he became a friend we looked forward to seeing houses with. I would recommend Austin to anyone and everyone. We are so thankful that he was referred to us."
"Austin made house hunting fun and helped our young kids feel included in the house search process. He was flexible with his schedule, provided valuable insights, was collaborative and creative with decision-making and offers, was optimistic and positive, and through the process of working with him he became a friend we looked forward to seeing houses with. I would recommend Austin to anyone and everyone. We are so thankful that he was referred to us."
Jack P.
"Austin is a great realtor and at this point, a trusted friend - someone you can count on in what can be a very stressful process. Austin has now helped me buy a condo, sell a condo, and also a purchase a house with my partner. He is detail-oriented, attentive, and knows the City of Madison exceedingly well. I wouldn't hesitate to recommend Austin to anyone looking for a home."
"Austin is a great realtor and at this point, a trusted friend - someone you can count on in what can be a very stressful process. Austin has now helped me buy a condo, sell a condo, and also a purchase a house with my partner. He is detail-oriented, attentive, and knows the City of Madison exceedingly well. I wouldn't hesitate to recommend Austin to anyone looking for a home."
Bryce H.
"Austin provided exceptional service and knowledge throughout the process of selling our home and purchasing a new one. He is a highly effective communicator, listens to the needs & wants of his customers and works FAST! He is also helpful with many of the concerns that buyers and sellers have, that aren't strictly a part of his job, and is always willing to help and find the answers for you even if he doesn't know them himself."
"Austin provided exceptional service and knowledge throughout the process of selling our home and purchasing a new one. He is a highly effective communicator, listens to the needs & wants of his customers and works FAST! He is also helpful with many of the concerns that buyers and sellers have, that aren't strictly a part of his job, and is always willing to help and find the answers for you even if he doesn't know them himself."
Morgan C.

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