“Michelle was very responsive and provided us with all of the pertinent information concerning the purchase of our property, I would definitely recommend Michelle Olds to handle any real estate transactions.”
LPT Realty
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The best way to find top real estate agents in Oakland Hills, Rotonda, FL
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Compare top Oakland Hills real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for May 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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Oakland Hills real estate Market Report.
Information and statistics on the latest trends in the Oakland Hills real estate market, updated for May 2026. *
Homes in Oakland Hills are taking time to sell, with the median listing sitting on the market for 135 days in March 2026. That pace has actually sped up compared with the prior month, dropping almost 25 percent, even though properties still linger significantly longer than a year ago.
Prices are adjusting as the pace changes. The typical home value is about $275,000, down 1.43 percent from last year and 2.81 percent from the prior month. Median list price, however, is roughly $272,500 and has inched up nearly 2.9 percent month over month. Only about 13 percent of recent sales closed above the asking price, and homes are selling for about 94.6 percent of list on average.
Supply is limited but growing, with 36 homes on the market in March and inventory up more than 24 percent from the previous month, even as it is still down 18.18 percent from a year ago. New listings slipped to 23, a drop of about 20.69 percent year over year, while pending sales rose more than 14 percent, highlighting solid buyer interest. Oakland Hills is classified as a seller's market with a market gauge score of 23, and typical values remain lower than in Rotonda overall, where they stand near $400,000. Projections for April suggest inventory could rise to 39 listings and list prices may edge up to about $276,300, so both buyers and sellers can benefit from having Agent Pronto connect them with a knowledgeable local agent.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Oakland Hills has to offer.
Oakland Hills offers residents a peaceful, golf- and water-adjacent community with a friendly, tight-knit atmosphere, easy access to outdoor recreation, and convenient local amenities.
Oakland Hills in Rotonda offers a relaxed, practical rhythm of life. Mornings often start with a quiet walk or bike ride along the canal-lined streets, a round at the nearby Rotonda Golf & Country Club, or a quick drive to shopping and services in Rotonda West. Daily errands are simple, with grocery options, medical offices, and local dining clustered along South McCall Road in Englewood.
Water and outdoor time shape much of the lifestyle here. Residents are a short drive from the beaches and boat ramps of Englewood Beach, while fishing and kayak launches at Lemon Bay Park and Environmental Center and the trails of Cape Haze Pioneer Trail Park are close enough for frequent after‑work or weekend outings. Families pay attention to school options in the wider Charlotte County area, and enjoy nearby programs and events at Elsie Quirk Library.
Homes in Oakland Hills appeal to seasonal residents and year round homeowners who value easy maintenance, canal or golf course views, and a laid back coastal setting without giving up access to Port Charlotte and Punta Gorda. Because the neighborhood’s canals, deed restrictions, and golf frontage can affect value and lifestyle, working with a local Oakland Hills agent who knows the community block by block can make every decision more confident. Agent Pronto connects both buyers and sellers with that kind of trusted local expertise.
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“The level of service that Matt provided for us during our search for our home in Cape Coral Fl. was above and beyond. Matt showed us multiple homes and was very honest and thorough explaining the upsides as well as the downsides of each property. When we narrowed our search down Matt quickly set up second showings so we could be sure in our decision. There was never any pressure to make a decision or purchase. We thought we were going to have to compromise on some things but Matt found us a home that checked every box and then negotiated a price that worked for us. We would highly recommend Matt Bonson to be your realtor.”
Century 21 Selling Paradise
“Laurine is an excellent realtor with great knowledge and integrity. She is very easy to work with, and she was instrumental in our getting the home we always wanted. We appreciate her going the extra mile in getting us from viewing to closing.”
Century 21 Beggins Enterprises
“Jessica went above expectations in helping us locate this property. Her knowledge of the area and recommendations facilitated our decision to purchase.”
Century 21 Sunbelt Realty
“Sherry Bourque got my house up and sold so quick. We had a high volume of people coming through. The closing process was smooth.I would so recommend Sherry and her team anytime.”
Diamond Key Real Estate
“My experience with Agent Pronto was a very good one. The process was simple and effective. After talking to Shelby, I felt very comfortable selecting her as my Realtor. She answered all of my questions and a great professional! The whole experience was nice with is viewing several condos and villas. I would highly recommend Shelby Solley to anyone who wants an intelligent, experienced and diligent Realtor.”
Medway Realty
“Kevin was very kind, listened, responded to all my questions, and got my house listed with beautiful pictures to show the beauty of my house. All went as smooth as possible!”
Keller Williams South Shore
“Larry is by far the most AMAZING Realtor. He was always very responsive to my calls, texts, request, etc. We built up such a great relationship through this crazy process, that even after we closed on our new home, he reached out to check on us. He is always looking to get the best deal for his clients. He is like family now to us and will always have his own seat next to the firepit in our backyard. I would DEFINETLY recommend Larry to anyone and everyone looking to buy or sell. AMAZING.. Can't say enough Great things about Larry.”
Charles Rutenberg Realty Charles Rutenberg
“Please see the previous comments. Tiffany is the best and truly world class! Tiffany was so wonderful to work with. She knew everything we needed and led us through a very unusual market with results beyond our expectations! We would not have trusted anyone else and she was gracious and kind even when we may not have been. We have referred our friends to work with her, she is the best. Grateful to her and the team.”
eXp Realty, LLC
“Jonas was selected by the realty plus program for me. However, he did an excellent job! He knew exactly what we were looking for and made sure that we got it. I don’t think any other realtor could’ve taken care of us like he did. Jonas was not involved in the closing process but that was not his fault. He fought for us every step of the way and did everything he could to ensure our satisfaction. Jonas was the face of the company and represented it well.”
Century 21 Sunbelt
“Phill is very accommodating, responsive to our needs, prompt and pleasure to deal with. Phillip Bishop made our purchase easy since we didn’t know Florida laws and process. I would certainly highly recommend Phillip Bishop. Al and Branka Neuman”
LPT Realty LPT
“The Davies were everything in a real estate agency we hoped for. They treated us with respect and gave us helpful information from the beginning. Their expertise was evident. Five days after the online listing, our property was sold—for the price listed. The closing process was efficient. We would recommend them to everyone. Thank you. ”
Dalton Wade Real Estate Group
Frequently Asked Questions
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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 Oakland Hills. 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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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Oakland Hills Realtor® or real estate agent today.
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