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Real estate in St. Petersburg’s Highland Oaks neighborhood.

Compare top Highland Oaks real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 2026.*


*Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.

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Learn more about what Highland Oaks has to offer.

Highland Oaks offers residents a welcoming, family-friendly community with tree-lined streets, convenient access to parks and local amenities, and a strong sense of neighborhood connection.

Real estate in St. Petersburg’s Highland Oaks neighborhood.

Highland Oaks tends to attract buyers who want a quieter pocket of St. Petersburg with easy access to daily conveniences and major routes. Residents who value one-story homes, manageable yards, and proximity to shopping along 34th Street N often find it a good fit. The neighborhood’s streets see mostly local traffic, which appeals to homeowners looking for a calmer setting close to the city’s core.

Housing in Highland Oaks ranges from mid-century ranch homes to updated properties that appeal to first-time buyers, downsizers, and investors seeking solid rental demand. Nearby destinations like Downtown St. Petersburg and the waterfront at North Shore Park are within a straightforward drive, adding cultural and recreational options without feeling tourist heavy. Everyday needs are covered by nearby grocers, local eateries, and quick access to Tyrone Square, while larger regional outings are simple via US-19 and I-275.

Families often look closely at local schools through resources like Pinellas County Schools, and enjoy weekend outings to Walter Fuller Park or the St. Petersburg Main Library. Because Highland Oaks sits within a patchwork of distinct neighborhoods across Pinellas County, values and micro-trends can shift from one street to the next. Connecting with an Agent Pronto recommended real estate agent who understands those neighborhood-level details helps both buyers and sellers align their goals with the right property decisions in Highland Oaks.

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“⭐⭐⭐⭐⭐ ¡Una experiencia maravillosa con Valentina! Quiero expresar nuestro más sincero agradecimiento a Valentina por habernos acompañado en uno de los momentos más importantes y especiales de nuestras vidas: ¡la compra de nuestra casa! Desde el primer día, Valentina estuvo siempre pendiente de nosotros, escuchando nuestras necesidades, tomando en cuenta lo que realmente buscábamos y ayudándonos a encontrar la mejor opción para nuestra familia. Tuvo muchísima paciencia con todas nuestras preguntas, siempre estuvo dispuesta a orientarnos y se aseguró de que nos sintiéramos acompañados y apoyados durante todo el proceso. Algo que valoramos muchísimo fue que no solo nos ayudó con la búsqueda y compra de nuestra casa, sino que también nos conectó con las personas adecuadas para ayudarnos en las diferentes etapas del proceso. Su compromiso, dedicación y atención a cada detalle fueron realmente excepcionales. ¡Estuvo con nosotros hasta el mismo día del cierre, siempre atenta y dispuesta a”

Liliana Sossa · Tampa, FL

Photo of Valentina Moreno
Century 21 Circle
“Sarah went above and beyond helping me sell my property. She was always available and answered all of my questions. I would recommend Sarah to anyone who is looking to sell or buy property. It was a pleasure working with her!”

sparkyele75 ·

Photo of Matt Brookens
Real Living Real Estate Real Living Casa Fina Realty
“Jacqueline & her team made our out-of-state home buying process seamless. They went above and beyond with their services, and they treated us with such care and kindness that our move (with a toddler and a dog!) felt manageable instead of overwhelming. They were responsive, patient, and honest from our first conversation to closing day, and no question was too small. Their knowledge of the area helped us find the right neighborhood from afar, and their negotiation got us a great deal on our home. We love our new home and couldn’t have done it without them. Highly recommend!”

Amanda Krauth ·

Photo of The Toledo Team
Keller Williams Tampa Properties
“Dan was extremely professional throughout the entire process. He provided a continuous line of communication and was very knowledgeable about the entire buying process. He was always respectful and listened to our thoughts and concerns. Another advantage I found with Dan was that he works with a network of people who are outstanding. Of course he never pressures you to use his referrals but we found that his inspector, insurance, and mortgage broker connections were the most informed and affordable. This made buying even better because everyone around us was an expert in their craft, explained everything well, and looked out for our best interest.”

A SW ·

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Keller Williams Realty Portfolio Collection
“We worked with Robby to purchase and sell our first home. We looked at a good amount of homes back in 2025 and eventually found the one we wanted. Robby walked us through the process and made it feel very easy! Due to work reasons, we had to sell the house less than 2 years later. In a very interesting 2026 market, Robby managed to sell our house very quickly! My favorite part about working with Robby is that you don't need to worry if anything will slip through the cracks. He is professional, organized and keeps you posted on anything you need to know. If you're looking to buy or sell, do yourself a favor and give Robby a call!”

wpkammerman ·

Photo of Robby King
Bianchi Realty & Property Management Inc.
“Carly was awesome throughout our home purchase experience. Very knowledgeable, helpful, and available! Extremely responsive and has a genuine care for her clients! Really appreciate all she did for us!”

grantspaul ·

Photo of ROOTS HOME GROUP
KELLER WILLIAMS TAMPA CENTRAL
“My husband and I used Christian to sell our condo. Christian worked extremely efficiently in getting us listed and conducted two open houses in a short period of time. Market conditions were not the best, but throughout the process, Christian kept us informed of any progress and was very quick to respond to the questions we had along the way. Christian assisted us in negotiating a fair price for our property and his hard work also provided us with a quick and painless closing. I highly recommend Christian and will absolutely use him again for any of our future real estate transactions.”

Jennifer Weis ·

Photo of Christian Tateo
Horizons By the Sea, Inc.
“Duc is not only my Realtor but also a great friend. He helped us find an amazing investment property in downtown Orlando at an unbeatable price. He answered all our questions upfront and guided us confidently throughout the entire process. We had such a great experience that we’re already working with him to purchase another property!”

Isabele · Orlando, FL

Photo of Duc Thang Nguyen
Alliance Real Estate Group
“First of all, we want to thank her for her patience throughout the entire process. She showed us so many homes, always making sure they were within our budget and aligned with what we were looking for. What we really appreciated was her knowledge and professionalism. She knew the area very well and guided us through every step of the process, from inspections and loan requirements to evaluating the property and the land, reviewing documentation, and negotiating on our behalf. She always made sure we understood what we were getting into and helped us make informed decisions. Buying a home is a big investment, and having someone who knows the process, pays attention to the details, and truly looks out for your best interests makes all the difference. We are incredibly grateful for her dedication, patience, and support. We highly recommend her to anyone looking to buy a home. Thank you for helping us find our home!”

Kenneth ·

Photo of Alicia Rinehart
LPT Realty
“Taylor was great through the whole process. Helped us identify our options and what made sense in the current market. Even helped us move into the new house!!”

Joshua Green ·

Photo of Taylor VanBeek
VanBeek Realty
“Maryann did such an amazing job finding my forever home. She was so helpful, knowledgeable and available when I needed questions answered. I would always recommend her for any realtor needs. She made the it so easy to purchase a home. I am very impressed on how much knowledge she has concerning the entire process. Thank you”

aokumura69 ·

Photo of Maryann Spearman
Viewpoint Realty International
“Andre was great! As out of towners, Andre provided local market knowledge and enabled us to understand the current trends in the area. He was patient as we worked through the process of home selection and advised us on the final purchase and inspections. He was thorough with closing tasks and we are happily in the home now. Highly recommended!”

mikkelsonbiz ·

Photo of The Tamburello Group
Keller Williams South Shore
“He is very professional and a great negotiator. He got me a great deal on my house and was a pleasure to work with, his lender included. Highly recommend to anyone in SWFL.”

Sebastian Hernandez ·

Photo of Kevin Bartlett
Knowledge Base Real Estate
“Nik was amazing throughout the process of buying our first home. We immediately loved his calm & confident personality and felt like he truly wanted us to take our time and make the right purchase, no matter how long it took. During the buying process he went above and beyond to help us make the deal happen, even when he was out of town. I would recommend Nik to anyone in the Tampa Bay Area, he really cares about his clients and is knowledgeable and super responsive!”

Jaelyn Anderson ·

Photo of Nikola Slavik
RE/MAX Champions
“Christina and Chris were truly amazing!! They were so invested in helping us find the perfect home, no matter how long it took. They are both extremely knowledgeable about the market and houses in general, making them the perfect team. They always made us feel comfortable and were super transparent, so there were never any surprises. They were also super responsive! Couldn’t recommend them enough!”

kellyrh79 ·

Photo of Team Richardson
Realty One Group Sunshine
“There’s not enough stars to give Kevin! Kevin is amazing! He went above and beyond to help us find our perfect home and quick! There was no time wasted! It was such a pleasure working with Kevin and we just knew we were in great hands with this whole process from very start to finish! Kevin is definitely who you want!”

Kierstyn Levin ·

Photo of David Lovitch
Keller Williams South Shore
“Alice, we appreciate everything you did for us. You seem to go above and beyond we appreciate everything you have done for us.”

Mike Purner · Homosassa, FL

Photo of Alice Prahm
Epique Realty
“I bought a condo with the help of Greg in downtown St. Pete. I am a business owner and don’t have a lot of free time, Greg was able to help me in every way possible and made the process about as stress free as buying a home can be. Thank you for all your hard work Greg!”

BartKnowles ·

Photo of Greg Bozek
LPT Realty
“Joey was knowledgeable, responsive, thoughtful and helped us sell our home with a quick turnaround! Through the entire process, from considering listing, pricing, seller renovations, listing, marketing, negotiating offers, closing and moving, Joey was supportive and helpful every step of the way.”

Whitney Gervais ·

Photo of Joe Torres
Stofel & Associates Realty
“First time home buyer here. From day one Michelle ensured I was taken care of. She took the time to walk me through all the processes and gave valuable input that helped me find my beautiful new home! Grateful for the time and energy she and her team put in to make the process easy and smooth. 10/10! I will be recommended all my my friends and family looking to purchase property out this way to work with Michelle.”

Jason Villarreal · Sarasota, FL

Photo of Michelle Olds
LPT Realty

Frequently Asked Questions

There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Highland Oaks. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.


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