Hillsborough Realtor Reviews: Jenn Gilson

Jenn is a "machine" who delivers. Understandably, no one wants to move out and have their home staged when they have nowhere to put furniture and live. We had already contracted for a new home. But we trusted Jenn and moved everything into storage. Jenn put her crew to work and within a week or so from our commitment, our house was staged and the yard brightened-up. She had 5 quiet showings over the weekend and we had 2 offers. One was a hair over our asking, cash, no contingencies, and a 10 day close. Perfection.

Selling my mother’s home was one of the most emotional and difficult things I’ve ever had to do, and I truly cannot imagine going through that process without Jenn. From day one, she was incredibly communicative, organized, and compassionate. I was told from the start that there was no one else who could close like her — and she absolutely delivered. She kept me informed every step of the way, helped manage all the details that come with selling a home, and never once made the process feel overwhelming. I truly trusted her throughout the entire journey.

What meant the most to me was how genuinely supportive she was while navigating such a personal loss. Jenn and her entire team were incredible to work with — even her husband stepped in to help when needed. Anytime I came to them with a problem or question, they made me feel completely at ease and confident that everything would be handled.

Beyond her professionalism, market knowledge, and attention to detail, Jenn brought so much kindness and calm to a situation that could have easily felt heavy and stressful. I am forever grateful to her and would recommend her without hesitation to anyone looking for not just a great realtor, but a truly exceptional human.

Jenn Gilson

My husband Richard and I are new to California and it's challenging real estate market. We were lucky to find Jennifer Gilson. Jenn is delightful, very professional, organized and responsive. First and foremost, she worked to achieve the best price for us, which was under asking. When there were obstacles, Jenn and her great team addressed them, even when it meant bringing in her own contractor. She is a closer. A great experience all around. Thank you, Jenn!

The Gilson Team is an exceptional and highly professional real estate group—they really know their business! We bought a new home before selling our current one, and Jenn, Danny, and the entire team were incredibly supportive throughout the entire process. As first-time sellers, we truly appreciated their thoughtful suggestions for improving our home before listing. They skillfully negotiated strong deals on both the purchase of our new home and the sale of our old one. On a personal level, they were respectful and mindful of our budget, never pressuring us to exceed our comfort zone. It was clear they always had our best interests at heart.

Jenn Gilson and her team assisted me on sourcing a fixer-upper which we did a full remodel on and then put it back on the market as a resale. It was a great experience working with Jenn. She is highly professional possesses a vast level of experience in the industry. In addition, she is quite friendly. She also dispenses alot of good advice which was beneficial. I can't recommend her highly enough. I would not hesitate to work with her again and look forward to continued business with her.

First and foremost, Jennifer's knowledge of the Bay Area Peninsula is truly impressive. She possesses an intimate understanding of the neighborhoods, market trends, and property values, which proved invaluable throughout the buying/selling process. Whether I had questions about school districts, commuting options, or local amenities, Jennifer provided comprehensive and insightful answers, ensuring that I felt confident and informed every step of the way.

We started our process almost a year ago. We interviewed Jenn and two other very capable brokers and chose Jenn because of her connections not just in the real estate community but with banking and construction as well. It was a very concierge, one stop shopping experience which made the process easier for us. We were downsizing, we needed to purchase our new place, move out of the place to sell, clear it out, paint and stage it, etc etc. She has connections that assisted with all phases of our transition. I don’t know when she sleeps! She was literally available to us 24/7.

Jenn did an amazing job. Not only did she help us buy a rather difficult house in 2017 (over 30 something offers and 12 serious offers), she also helped us sell it quickly when we received an unexpected opportunity. She has an amazing team of contractors and professionals who were not only able to do updates to the house, but staging and conducting the required inspections quickly, doing paperwork while we were across the country, and on our rather weird timeline. (Trying to schedule everything between school years, moving two jobs, and an unexpected death.) She was a lifesaver during the entire process!

Jenn did an excellent job and it was not an easy job. We were selling our parents home after they had passed away and I had seven siblings who all wanted to add their concerns to what we expected. On top of that we asked her to work with my brothers wife who is a real estate saleswoman in southern California. She hung in there and was able to give us competent advice throughout the process including updating the house. We were all satisfied with the selling price. And I was very impressed with Jenn's patience with my family. I highly recommend her!!!

Jennifer and her capable associates delivered a wonderful sale through 1031 of house in Atherton of 40 years. She managed a 1-year rental at reasonable rate. Then sold into a difficult and declining market in fall of 2023. She had a strategy of private listing for a couple of weeks to get the price right. We had 2 open houses and one cash bid at asking price -- so we really believe we got the best price!

There were difficult decisions on staging, fixing the landscaping, preparing house for sale. We spent $50k. Jennifer was always cognizant of cost/benefit. Her right-hand-man Dan (husband) was terrific with helping fix-ups and meeting prospective purchasers. Jose was a wonderful contractor who took care of the challenging updating of items in an older house. Highest recommendation and you may contact me directly by asking Jennifer for my contact information.

Jennifer is the kind of professional that listens, gets the job done, and has the background to give her clients every advantage possible. After she was recommended to us by a close friend, I contacted her and knew after the first phone call she was going to be the right person to help sell our house. I told her I was busy and to just keep me updated but to do whatever was necessary for the best sale. She kept in touch, messaged me about any changes, and responded immediately whenever I had a question. We had a number of offers after a week of listing, including a couple that we were very happy with. I highly recommend her.

My wife and I had an incredible experience with Sophia and the Gilson Team. Before we decided to both sell our home in Oakland and purchase in Alamo, we were lost as to who we should use as an agent.

Sophia connected us with 2 amazing agents and throughout the entire process with both of our transactions, Sophia constantly guided my wife and I. Her insight and knowledge is unparalleled. Even given the fact she was not formally part of either transaction (or compensated), she treated us like clients. And that meant responses within the hour, unbelievable insight and advise, and always a professional demeanor.

If we ever decide to make a move across the Bay, there is zero doubt Sophia and the Gilson Team are who we will use. They are technical experts who know how to get deals done, but, have a human side, as well. I can't thank them enough for being so thoughtful and helpful to our family.

We absolutely loved working with Jennifer and Sophia - we'd recommend them to anyone (and in fact, we already have!). They are so knowledgeable about the north Peninsula market and are very plugged in. We also appreciated that they're not pushy at all and were really thoughtful in helping us decide which part of the north Peninsula would be right for our family. What we also loved about Sophia and Jennifer is that they were great with helping us brainstorm things we could do/change to properties that we saw - they both have great vision!

Jennifer has helped us rent and manage our home twice now. She was able to quickly find renters and made the whole process very easy. Jennifer truly goes above and beyond by setting up movers, gardener, handyman, etc and making sure everything went smoothly and was ready for our tenants to move in. We would not hesitate to work with her again for anything we needed with selling / renting our home or buying. Thanks Jennifer and Gilson Team for all your help!!

I cannot recommend The Gilson Team enough. My fiance and I were buying our first home together and both Sophia and Jennifer were the perfect team to help us through the process. Their knowledge and relationships in the Peninsula market are unparalleled....they literally got us into a home while it was in the middle of a renovation and their coaching to move quickly helped us get to an agreement before the house even hit the market. Sophia was very strategic throughout the process, giving us great advice on a deal and home we felt really good about. They work around the clock, have the utmost integrity, have trusted relationships with other agents and vendors...and above all, they are fun and amazing to work with. You can be absolutely confident in working with the Gilson team that you are getting professionals that are at the peak of their game. Thanks for everything Sophia and Jennifer!

I represent a nonprofit conservation organization that inherited real property from one of our supporters, and we wanted to sell it right away. Jennifer Gilson was recommended to us not only from her real estate credentials and reputation in San Mateo County but also because of her commitment to charitable work. From the start, we were in excellent hands: Jennifer guided us firmly through the process, her team was in constant touch with our staff, and they maximized outreach and showings during the pandemic lockdown, ably advised us on next steps, were transparent and open, were immediately responsive when an obstacle or challenge presented itself, and allowed me to be worry-free from the time the property was put on the market until escrow closed. Even after that, the team continued to check in to make sure that all loose ends were tied up. They made us feel like we were their most important client. I definitely would engage them again.

The Gilson Team did an amazing job with the sale and purchase of our new home. The whole team was amazing but Sophia was our main contact. She was easy to work with, extremely knowledgeable, available when we needed and new exactly what to do with every step. We did not have the easiest selling and buying process but she got the job done with a quick close on selling our 1st home and buying our forever home. I can’t say enough wonderful things. Should we ever do another real-estate transaction we will use Gilson team again!

I could not be more grateful to the Gilson team. We had been working with previous agents before switching to Sophia, and the experience was vastly different. Right away (from the very first phone call!) we could tell Sophia was passionate and driven about finding us a home. She was proactive about finding us properties, helped us in thinking through what we wanted and what our options were, gave great advice about the financials and what we needed to do to be competitive, and truly felt like our partner in the process. Sophia and Jennifer were very responsive, personable, knowledgeable, and had great connections with the local listing agents - which helped us stand out from the crowd. And to top it all of, within a few weeks of working with them, we got the most amazing home we never thought possible for us to get! I would recommend them without hesitation to anyone.

Sophia Waldman (and the Gilson team) is everything I had hoped for in a partner to help us find our dream home and SO MUCH more! We had been looking around the Bay Area for years, working with a variety of brokers who just didn’t quite understand us as a couple or how to help us find what we were looking for (we were “green”, and in such, highly skeptical/critical of listings and indecisive). We started to just manage and attend viewings ourselves since prior brokers were not helping or moving our search forward at all. We were introduced to Sophia to help us with a listing we had found on the peninsula in a very high demand area — and we loved her instantly.

She is sweet, personable, honest, and professional with just enough persistence where she will always get you the information you’re looking for and/or negotiate a deal to your favor. In the case of our home, we ended up winning the deal even though we weren’t the highest bid — and it was because we did everything Sophia advised us to do.

She is also highly connected to the broker network and always knows the selling broker (more often than not, on a deeper level well beyond just business relations). This is the case with her clients as well, where she takes the time to get to know them, understands what they want in a home, the elements that matter most to them, and then will curate listings to us (2x per week, but we weren’t aggressively looking). Any listings we found, she would give us her honest opinion on it immediately: either she had seen the home already and felt it wasn’t for us (quality, style, neighborhood, etc.) or if she hadn’t seen it, she would make time within the day to see it in person before we did, or she would arrange a viewing within 3 days for us if she thought it was worth our time. She made things so easy for us, and helped us make progress on our hunt and not waste time on listings.

She is also incredibly responsive, and always replied to any question or concern within the hour, always offering her time to chat.

She has deep expertise and knowledge of the real estate market and broker dynamics. (She will be upfront with you if she’s less familiar with an area but her connections always gets us to inside information). On the first listing we worked with her on, we knew the property was underpriced for the neighborhood but Sophia knew it was misleading + the “types” of interested parties, and that it would go well over (to the point where it’d be well out of our range). Long story short, she was spot on for what the property went for and the affiliated deal dynamics. On other listings we prepared bids for, she knew when to underbid, overbid, or add favorable terms to the bid, given her knowledge of the market, relationship to the selling broker, and knowledge of interest in those homes. She knew us well enough too, to advise when not to move forward in a counter bidding process (given how the home lacked in what we were looking for).

She has someone for everything. This was my favorite part! While she knows almost every broker working in the Bay Area on familiar terms, she also is highly connected to the development industry where anytime I needed a last minute inspection or expert, she had a guy! This was so helpful, especially in the closing process and beyond.

She continues to be so helpful to us and goes above and beyond what a typical broker would give you. She gives you her time, energy, thoughtfulness, help, empathy, professionalism, and so much more. We now consider her a good friend, given how wonderful she’s been to us and continues to be.

My fiancé and I worked with Sophia mostly, with some conversations with Jennifer as well. Sophia was a pleasure to work with - very responsive and always offered to make a call or reach out to get us an answer to any questions we had! As first time home buyers, we were quite unfamiliar with the escrow process so we would have loved a little more insight into that prior to starting, but we know we should have done that research beforehand. Overall, we really enjoyed working with Sophia! Both her and Jennifer were very eager to help in any way they could. And Sophia even went out of her way to help us find a tenant for our ADU, which was above and beyond!

Sophia is an excellent agent. We were referred to her through an agent in SF, and could not have had a better experience. She brought us to a house in Pacifica that was on our wish list, but originally priced out of our range. She took us it to see as the price had dropped that day. It was perfect for us! Within 12 hours of seeing the home, Sophia helped us put in an extremely competitive offer. By day's end, we had gotten our adorable beach chalet below the original asking price! Sophia's responsiveness, savvy advice, and strong negotiation skills impressed us. Highly recommended! Can't say enough good things about our experience with Sophia.

I recently sold my house after 15 years of ownership in the heart of San Mateo Park. This was not an easy decision on my part and I will admit I shed many tears as I navigated the steps needed to finding the right realtors to list my home. Jennifer and Sophia took all of my needs into consideration, they listened and then executed a seamless plan to prep and list. Their advice on prepping to list was invaluable and my small investment was paid back to me ten fold at the close of escrow. Due to the Gilson Team's local contacts and connections they found the perfect buyers, who love and appreciate their new home. I can not share enough appreciation for their professionalism, negotiation skills and heart throughout the entire process. I highly recommend that you sit down with Jennifer and Sophia if you plan to sell your home.

My husband and I worked with Sophia Waldman and the Gilson Team to purchase our first home. I can't say enough about how wonderful Sophia is! She helped us find homes that matched our preferences and budget, and was incredibly knowledgable about the market in the peninsula. She guided us in interpreting disclosure reports. She coached us on making offers that were reasonable and competitive. She answered the millions of questions we posed to her about homes, financing, paperwork, etc. She is responsive, kind, and helpful, and we were lucky to work with her! I am sure that we had a smooth and successful home buying experience because of her, and I highly recommend her to others!

My husband and I worked with Sophia to purchase our first home and we couldn't have asked for a better agent to help us through the whole process that seemed scary to us (as first time buyers).

She went above and beyond to make sure that we had all our questions answered, helped us out getting things moving forward with different partners (bank, escrow, inspections...) and continues to be super helpful even beyond the closing, connecting us with handymen, cleaning services, etc.

My wife and I had a great experience buying our first home. Jennifer and her team did a fantastic job of making the sometimes tedious process personal and the advice and knowledge they gave us ended up being invaluable. Their contacts with the other various parties in the process was extremely helpful. Our offer was accepted and we’re happily moved into our new home. We would highly recommend them to others that are looking!

Using the Gilson team is the best decision we made. While it was a long process for us to find a place we were comfortable putting an offer in on, Jennifer and her team (we worked with Sophia specifically) were with us every step of the way, which we greatly appreciate and forever grateful for. Local knowledge of the area and the market at any given time are so important, and having the right team by your side makes all the difference. Jennifer even went above and beyond in working to set us up with the best homeowners insurance policy with a great and reliable contact of hers. I would highly recommend Jennifer and her wonderful team, we are so glad that they were able to help us get into our first place in such a challenging market!

The Gilson team was incredible! They made the overwhelming process of selling a home so easy! They know what they are doing, so I felt like I was in the best hands and could fully trust them. From the initial meeting to the preparation, staging, and marketing of our home, everything went smoothly. I believe we got such an amazing offer because of the Gilson's team expertise. I would recommend them to anyone buying or selling a home.

It was a pleasure working with Jennifer and the entire Gilson team! They made the process so easy from prep to close. Jennifer's knowledge of the San Mateo market and her outstanding marketing expertise helped us get dozens of people seeing the house, multiple offers in less than a week, and a final sale more than $300K over the asking price. We appreciated her responsiveness and willingness to carefully address our questions and concerns. The team has a great sense of style and the staging of what was a very simple house really made it shine. They knew how to show it off to its best potential. I'd be very happy to work with Jennifer again in the future.

My husband and I had the pleasure of working with Jennifer and Sophia for our house shopping process. Compared to other agents we had worked with before, we received a lot more personalized and proactive attention from them, which made our process so much more enjoyable. This team is well-connected in the Bay Area with other agents, which always helps during the touring and bidding process. They helped us find our home fast, and were candid and helpful throughout the bidding strategy process. I'd love to work with them again in the future.

I contacted the Jennifer Gilson team along with my fiancee to buy a single-family house in the San Francisco Bay Area peninsula in January 2018. This is a notoriously competitive and expensive area to buy a home in and we came into the process fearing the worst.

Jennifer and Sophia took excellent care of us during this home buying process. We initially looked at a number of houses during the months of December and January, typically the slowest time of the year, with the intention to reduce competition against other buyers. We didn't find any houses we liked after several weeks of touring mostly due to the low inventory during this time. Jennifer and Sophia kept in touch with us throughout, sending us notifications of new listings and offering to go to open houses with us.

In mid January we found the house we wanted to buy and asked the team to make an offer on it. We were on vacation at this time, but Jennifer and Sophia helped us establish a strategy over the phone and prepare a strong offer to submit to the seller. The house was not staged and did not have a description prepared for the listing, which may have helped reduce the number of competitive offers. We ended up getting our offer accepted, and proceeded to order additional home inspections under an inspection contingency according to strategy.

The extra inspections ended up finding an additional issue with the house that we did not expect, requiring an extra repair to fix. We found ourselves unable to close the deal with the original offer price in addition to this unexpected repair, but the team initiated a price reduction counteroffer (still under contingency) and the sellers accepted! This price reduction allowed us to close the deal and get into the home we really wanted, and even though we have some repair to arrange over the next year or so, we are confident in our financial readiness for this step in the presence of some careful planning and budgeting on our part.

We want to express how responsive and knowledgable the team was during this entire process. We ended up closing the offer and the whole home buying process took about two months from start to finish in one of the most competitive and expensive single-family home markets in the U.S. I've heard stories from my co-workers in this area taking 6-12 months or longer to close a house and losing many offers during this process, but thanks to the Gilson team's expertise, we were able to finish the process and find a great house (with some minor updates to take care of) in a relatively short time. We are definitely happy with the outcome and would recommend the Gilson team to others in the future for home buying needs.

Jennifer and her team were very responsive and had great attention to every detail from staging to Marketing. We were selling from out of the area so we relied on Jennifer’s team to be on site for the entire process and they did a wonderful job of keeping us informed.

Jennifer and her team attained a sales price for our parent’s home, far beyond our expectations. We are thrilled with her team and the outcome. We highly recommend them.

The G-Team is the best!!! After looking for more than two years in San Francisco, and honestly with very little interest in relocating down the Peninsula, Jennifer, a close family friend, took a chance in showing me a listing in San Mateo that she knew (better than I) would knock my socks off. She was right! We wrote one offer, and just like that, as serendipity would have it, we closed seamlessly. I don’t know how they do it – but boy, oh boy DO THEY DO IT!!!!! I would recommend highly to even the most discerning and difficult client!

Wife and I had a very good experience with Sophia and Jennifer in purchasing our first home. We were able to find a home that fit our needs and budget. And since we were first time home buyers, we certainly needed and appreciated the extra guidance, which they graciously provided. They were knowledgeable and patient every step of the way. Additionally, they worked very well with our lender to get an offer in very timely manner. They made our first home purchase as smooth as possible.

My family and I had the good fortune to have Jennifer Gilson as our realtor for both selling and buying.

After a demoralizing experience with a previous realtor in the past in an attempt to sell our house, my mom had lost all her confidence and trust in realtors and felt our house will never be able to be sold.

Jennifer, with her professionalism, expertise, and kind heart, provided my mom with hope and comfort.

Upon our first meeting with Jennifer, her presentation was well-prepared, knowledgeable about the market for our area, and informative of the sale process.

After going through a few interviews with other realtors to get our business prior to meeting with Jennifer, the attribute that set Jennifer above all of other realtors is the way she treats you like family. She cares.

My mom knew Jennifer was her realtor immediately after her first meeting. My mom was not looking for the most skilled and absolutely best realtor (which Jennifer is) but she was looking for someone she can truly trust and respect.

The little gestures that Jennifer did for my mom in the first meeting: greeting and treating her who does not speak the same language with respect and dignity, providing a gentle smile, and hugging her to give comfort and assurance that this will be a great experience and to look forward to it.

Jennifer truly went above and beyond for my family and provided us a VIP experience throughout the entire process of selling and buying. She handled everything and anything that came up and connected us with some of the best people to work with.

Once the house was on market, the house was sold in a week and we were on our way to looking for our next home. For our new house, Jennifer consistently took the time to help us find the perfect home and got us a great price.

Our experience with Jennifer and her team have been nothing short of extraordinary. For my family, it truly has been life changing and Jennifer have earned a lifetime customer.

Special thanks to Jennifer, Sarah, Sophia, and Quinn. God Bless Jennifer and the Gilson Team!

She was the realtor we used to sell our 1 bd/1.5 bath in Burlingame. She was very professional and took care of everything, since we live in Souther California now. Highly recommend her. She was able to get us the highest $/sqft for a 1 bedroom townhouse in the history of Burlingame. Wouldnt hesistate to use her again. She even helped us understand and go through all of the logisitics of our first 1031 exchange. Thank you Jennifer!! A++++++

Sophia (who's part of Jennifer's team) is very friendly and helpful (my husband and I have encountered some very arrogant real estate agents in SV before Jennifer's team).

Sophia took the initiatives to make sure we got the information we needed. I'm thankful that my husband and I end up in exactly the kind of place we want. Love, love, love both our new home and our neighborhood.

Would recommend to family and friends.

Jennifer was a delight to work with. From our first discussion, to her detailed market analysis and property assessment, and ultimately her marketing strategy and execution she was a pro. Furthermore, she delivered all this with an exceptional team that worked together in a coordinated fashion. Jennifer and her team truly thought of nearly every detail so that execution was crisp with no surprises.

I highly recommend Jennifer.

If selling your home, packing, moving, gives you headache then leave the selling to Jennifer. We listed, closed and were in our new place in Hawaii in 21 days. Yep, I said 21 days: now that's remarkable! (and was with multiple offers over asking). It's also evidence of her knowledge of the market, marketing skills, and her network of connections.

Now, if you are a first time buyer/seller and need to be held by the hand and coddled, I sense she could do that and put you at ease. In my case though I am no nonsense and she adjusted to my abrupt personal style without blinking.

Then before I blinked I was at home in the islands.

Mahalo plenty and a hui hou,

Jennifer is a spectacularly good real estate agent.

We near-simultaneously bought and sold homes in the $1-2M range with Jennifer in a fairly complex situation in ultra-competitive markets. We have previously got to escrow or bought homes 3 different times with 3 different real estate agents within the past 5 years, so we have some experience to draw from on this.

Jennifer is incredible. She was the only real estate agent I've ever had who was genuinely looking after our interests. She is an absolute bulldog negotiator, incredibly prompt, available day and night, and handles the mountain of paperwork, home showings, touch-ups, arrangements with various contractors brilliantly. She was also very good in the initial phase, helping us identify promising neighborhoods for our needs and lifestyle. Jennifer was also respectful of our financial constraints and has a great support staff to handle things on the very rare occasions she is unavailable and for routine paperwork and such.

Lastly, we got great deals on both sides and love our new house in the neighborhood she suggested.

I strongly recommend Jennifer for any real estate transaction, buy side or sell side.

My husband & I really liked working with Jennifer. She puts her client's needs and worries ahead of everything else; and, does go above & beyond to help them as much as possible to make house shopping & purchase a good & successful experience. We highly recommend her for relocation as well as local purchasing in Silicon Valley's Peninsula. She knows a great network of other real-estate professionals as well as contractors that can help you in every aspect of a house purchase. Thanks Jennifer! LJ & FT

Jennifer has made the buying process so much easier for me. She is very passionate about her work. Her endless hours of work and guidance have put me at ease. I've referred her to my friends and family and they've all been delighted with her service and compassion! Whether buying or selling a home, I know she will be dedicated to making all go seamlessly and an enjoyable process. Her resources on the Peninsula have also been a tremendous help!