
Your Real Estate Team in Oakland, FL
Jared Jones Team, brokered by eXp Realty. 20+ years in Central Florida, roughly 4,000 homes sold, and deep local knowledge of the Town of Oakland, a small historic community on Lake Apopka just west of Winter Garden. The team relocation clients, nature lovers, and move-up buyers trust to price sharp, negotiate hard, and close clean in a market this small.
The Short Answer
The Jared Jones Team, brokered by eXp Realty, brings 20+ years of Central Florida experience and roughly 4,000 homes sold. The team helps buyers and sellers in the Town of Oakland, a small historic community on Lake Apopka just west of Winter Garden, from Longleaf and Oakland Park to Hull Island and the historic core, spanning both the 34760 and 34787 ZIP codes.
The Track Record
Numbers that hold up
Selling in Oakland
In a town this small, a well-priced home near the trail or downtown finds its buyer fast. Get a precise, data-backed valuation and marketing that reaches the relocation and lifestyle buyers specifically looking for Oakland.
Get Your Home ValueBuying in Oakland
Inventory here is thin and moves quickly. Work with a team that watches both the 34760 and 34787 sides of town, knows Longleaf, Oakland Park, and Hull Island, and helps you act with conviction when the right home appears.
Start Your Home SearchWho the Jared Jones Team is built for
Oakland is small, but it is not one market. Someone relocating for the small-town lifestyle, a buyer choosing a new build in Oakland Park, and an owner selling a historic or lakefront home are three different transactions. The team is organized around exactly those buyers and sellers.
Relocation & out-of-state buyers
The strongest specialty. Many clients find Jared through the Orlando Living videos months before they call, then arrive already understanding what makes Oakland different from the bigger towns around it. For anyone buying sight-unseen, that head start matters even more in a market with so few homes.
New construction & planned communities
From townhomes at Longleaf to the traditional-neighborhood design of Oakland Park and the lakeside homes of Hull Island, having your own agent, rather than relying on the builder's rep, protects your upgrades, your timeline, and your price.
Luxury, historic & lakefront
Custom homes in the historic core, estates at Briley Farm, and lakefront property on Lake Apopka call for discretion and accurate pricing. In a low-inventory market, pricing these correctly is both harder and more important.
Move-up buyers & downsizers
For buyers drawn to Oakland's trail-and-lake lifestyle, whether trading up for more space or right-sizing into a lower-maintenance home, the team matches the right community to how you actually plan to live.
The Community
Life in Oakland
The Town of Oakland is a small, historic community in West Orange County, set on the south shore of Lake Apopka just west of Winter Garden. With only a few thousand residents, canopy oak-lined streets, and a strong conservation ethic, it trades big-city bustle for trails, lake access, and a genuine small-town feel, while keeping downtown Winter Garden and the wider metro minutes away.
The West Orange TrailThe paved trail runs right through town, connecting Oakland to Winter Garden and Killarney for biking, running, and weekend rides.
Lake Apopka & Nature PreserveThe Oakland Nature Preserve on Lake Apopka offers boardwalks, an education center, and trails, and conservation is central to the town's identity.
Small-town characterA town of a few thousand residents, with historic homes and shaded, walkable streets.
Oakland Avenue Charter SchoolA free public charter elementary school (VPK and kindergarten through 5th grade) on E Oakland Avenue, owned and operated by the Town of Oakland. Older grades are served by Orange County Public Schools.
Communities & homesFrom Longleaf townhomes and the Oakland Park and Hull Island communities to custom homes in the historic core and Briley Farm.
Getting aroundMinutes from downtown Winter Garden, with quick SR-429 and Florida's Turnpike access to the rest of Orlando.
The Oakland market right now
Oakland is a very small, low-inventory market with a wide range, from Longleaf townhomes at the entry level to new construction and lakefront custom homes. Its newer communities carry Winter Garden's 34787 ZIP while the historic core sits in 34760, so the whole town is easy to miss in a standard search. Here is where it sits this month.
For 12-month Town of Oakland sales, lot sizes, property taxes and the drive to Plant Street, see our Oakland, FL Guide 2026.
Oakland market snapshot
Town of Oakland, 12 months ending Oct. 2, 2026.
Sources: Stellar MLS, 12 months ending Oct. 2, 2026, matched to Orange County Property Appraiser town-limits data (94 single-family and townhome sales; single-family median $681,500); lot size from Orange County Property Appraiser parcel data, accessed Oct. 6, 2026; analysis: Jared Jones Team. Oakland is a very small, low-inventory market and most of its homes, including newer communities such as Hull Island and Oakland Trails, use Winter Garden's 34787 ZIP, so a few sales can move these figures. For a valuation on your specific home, contact the Jared Jones Team.
Reviews
Oakland Google Reviews
Posted on Google![]()
Stephanie STrustindex verifies that the original source of the review is Google.
The team possesses extensive knowledge of the Orlando real estate market, which proved invaluable in helping us select the ideal home. I highly recommend their services to anyone seeking professional assistance.Posted on Google![]()
Gurj DTrustindex verifies that the original source of the review is Google.
We had such a great experience working with Connor and would absolutely recommend him. As we were buying a house in Florida while still living in Utah, we relied on Connor for so much throughout the process. He was always incredibly responsive and went out of his way to make things easier for us. When we couldn’t view houses ourselves, he would visit them and send us detailed video walkthroughs, which was a huge help when trying to make decisions from another state. He handled communication with the agents, put together our offers, arranged the inspection and, once we had the inspection results, gave us great advice on how to negotiate so we could get the best possible deal. What really stood out was how willing he was to help with things that went beyond simply buying the house. Because we were in Utah, Connor offered to go back to the property whenever something needed checking, helped arrange appointments such as getting an electrician out, and even offered to continue checking on the house and things like the lawn for us after closing until we’re able to be there. Throughout the whole process Connor was friendly, attentive, patient and extremely easy to work with. Buying a house from across the country could have been incredibly stressful, but having someone local who was so responsive and willing to help made the whole experience much easier. Thank you for everything, Connor! We couldn’t be happier with our new home and really appreciate everything you did for us.Posted on Google![]()
Jonathan TTrustindex verifies that the original source of the review is Google.
Jared Jones went above and beyond in every aspect of our home-buying experience. From the very beginning to closing, Jared was there for us every step of the way. Buying a new home can be overwhelming, with countless details, questions, decisions, and unexpected bumps along the road, but Jared made the entire process feel manageable because we always knew he had our back. What really stood out to us was how involved and proactive he was. He didn't just show up for the big moments — he was there throughout the entire process, staying on top of details, answering our questions, advocating for us, and making sure we understood what was happening. Whenever something came up, Jared was quick to jump in and help find a solution. We genuinely felt like he was looking out for our best interests from start to finish. He was incredibly responsive, knowledgeable, patient, and professional, but what we appreciated most was that he truly cared. We never felt like we were just another transaction or another set of clients. Jared treated the purchase of our home as if it were his own, and that made a huge difference. We honestly cannot say enough good things about Jared. He exceeded our expectations in every way and made what could have been a stressful experience so much easier. If you're looking for a realtor who will truly go to bat for you, be there when you need him, and genuinely care about getting you into the right home, we couldn't recommend Jared more highly. Five stars doesn't really feel like enough. Thank you, Jared, for everything you did for us!Posted on Google![]()
Geoffrey ZTrustindex verifies that the original source of the review is Google.
Jared Jones is an absolute main stay in the Orlando Real Estate world. I've now had the pleasure of working with him in Orlando as well as Las Vegas years ago, and while he shifted coasts, his skills, care, and diligence in this business have remained sharp and calculated. Jared knows his stuff. I would question whether anyone knew Orland Real Estate better than Jared and his team. Whether I'm working with him directly, or one of his hand picked, expertly trained team members, I know I'm getting the same level of sill and dedication to meet our very demanding needs. Thank you Jared, and your team, for being our absolute Go-To in Orlando Real Estate!Posted on Google![]()
Steven MTrustindex verifies that the original source of the review is Google.
⭐⭐⭐⭐⭐ When we found out we were moving across the country to the Orlando area, we started watching Jared Jones’ Orlando housing market videos on YouTube. His videos provided a ton of great information about the different communities, neighborhoods, and the Orlando housing market and really helped us get familiar with the area before making the move. As good as Jared’s videos are, his team is even better in person! We had the pleasure of working with Leonard O’Connor, and he was awesome from the very beginning. Communication was excellent throughout the entire process. Leonard took the time to show us several existing homes and really helped us narrow down exactly what we were looking for. Once we zeroed in on the right property, Leonard was there every step of the way. He helped us through the negotiations and, because we were still living across the country, went above and beyond to help with measurements and other things we needed taken care of before we could arrive in Orlando. Having someone local we could trust made a huge difference and took a lot of stress out of buying a home from thousands of miles away. The entire process went incredibly smoothly, and closing was a breeze. We couldn’t be happier with our experience. If you’re moving to the Orlando area—especially if you’re relocating from out of state—I highly recommend Jared Jones, Leonard O’Connor, and the eXp Realty team. Great communication, great service, and people who genuinely work hard for their clients. Five stars all the way!Posted on Google![]()
Peter MTrustindex verifies that the original source of the review is Google.
Jared and his team helped me and my family in purchasing a home in Orlando and I would highly recommend them to anyone. They are extremely knowledgeable about the greater Orlando area which was important to me moving from New Jersey. They kept us informed every step of the way and did a phenomenal job when it came time to present an offer and close the deal. This team is top notch!Posted on Google![]()
Dyan DTrustindex verifies that the original source of the review is Google.
Leonard O’Connor, with Jared Jones Realty team, did a fantastic job helping us find our new home in Clermont, Florida. He was very accommodating, often squeezing last minute home viewing into his schedule and doing virtual walkthroughs with us from Michigan. His communication throughout the process was exemplary and his vast experience shown through in his advice and negotiating skills. Leonard and the whole team at Jared Jones Realty worked together seamlessly to assist us every step of the way through the home buying process. We couldn’t be happier!Posted on Google![]()
Dan HTrustindex verifies that the original source of the review is Google.
Heidi was incredibly helpful and kind during the entire process. She negotiated effectively for us and was always reachable whenever we had a question and now we live in our dream home!Posted on Google![]()
Paul HTrustindex verifies that the original source of the review is Google.
Selling a home from overseas could have been stressful, but Jared and his team made the whole process feel incredibly straightforward. From the very beginning we felt we were in safe hands. Jared was always approachable, responsive and happy to answer any questions we had. His communication was excellent throughout, keeping us updated every step of the way, and his advice was always honest and reassuring. The professional photography and video marketing were first class and really showed our Davenport home at its very best. What impressed us most was how much Jared genuinely cared about achieving the best possible outcome for us. Even when unexpected issues arose during the sale, he remained calm, proactive and worked hard to keep everything moving towards a successful closing. We couldn’t have asked for a better Realtor and would wholeheartedly recommend Jared Jones and his team to anyone buying or selling a home in the Davenport and Central Florida area. Thank you, Jared, for all your hard work, professionalism and support—it has been a pleasure working with you.Posted on Google![]()
David RTrustindex verifies that the original source of the review is Google.
My wife and I purchased a home in Kissimmee, Florida and it was by far the best home buying experience we have ever had. This is our 7th home we have purchased. Stephany Cornelius was our Realtor from Jared Jones Real Estate Team and we couldn't have been more pleased. She made the process so easy, less stressful and guided us through every aspect including a very quick closing. I highly recommend Stephany if you're trying to navigate the home buying experience here in Florida.Verified by TrustindexTrustindex verified badge is the Universal Symbol of Trust. Only the greatest companies can get the verified badge who has a review score above 4.5, based on customer reviews over the past 12 months. Read more
Homes for Sale
Oakland Listings
Oakland, FL real estate FAQ
Who can help me buy or sell a home in Oakland, FL?
The Jared Jones Team, brokered by eXp Realty, has 20+ years of local experience and roughly 4,000 homes sold. The team knows the Town of Oakland well, from Longleaf and Oakland Park to Hull Island and the historic core, and is known for relocation expertise, a large Orlando Living video library, and precise pricing across the 34760 and 34787 markets.
How do I search for homes in Oakland, FL?
Search by the town name or draw a map boundary along Lake Apopka rather than filtering by a single ZIP. Oakland's newer communities, including Hull Island and Oakland Trails, carry Winter Garden's 34787 ZIP, while the historic core sits in 34760, so a 34760-only search misses most of the town and a Winter Garden search buries it. The Jared Jones Team watches both sides and sets alerts so you do not miss a rare listing.
What is the Oakland, FL housing market like right now?
In the 12 months ending Oct. 2, 2026, the Town of Oakland had 94 single-family and townhome sales at a median price of $656,500, according to Stellar MLS matched to Orange County Property Appraiser town-limits data. Homes built before 2025 sold for a median $600,000, and 17 homes built in 2025 or 2026 sold for a median $2,417,730. Most Oakland homes use a Winter Garden 34787 mailing address. It is a very small market, so a few sales can move these numbers. For a valuation on your specific home, contact the Jared Jones Team.
What is it like to live in the Town of Oakland?
Oakland is a small historic town of a few thousand on Lake Apopka, west of Winter Garden. It is known for the West Orange Trail running through town, the Oakland Nature Preserve, canopy oak-lined streets, and Oakland Avenue Charter School, a public charter elementary school (VPK through 5th grade) run by the town. It offers trails, lake access and nature preserves, with quick access to Winter Garden and the rest of the metro.
How do I contact the Jared Jones Team?
Call or text 407-706-5000, email info@jaredjones.com, or visit jaredjones.com. The office is at 504 W Plant Street, 1st and 2nd Floors, Winter Garden, FL 34787, minutes from Oakland. Tell the team whether you are buying, selling, or both, and share your timeline for clear next steps.
Ready to make your Oakland move?
Whether you are relocating for the small-town lifestyle, buying a new build, or selling a historic or lakefront home, talk with a team that works this small market.
Jared Jones Team · Brokered by eXp Realty
Jared Jones is a Realtor with the Jared Jones Team, brokered by eXp Realty, serving the Town of Oakland, Winter Garden, and the greater Orlando / Central Florida area. 20+ years, roughly 4,000 homes sold. Specialties: relocation and out-of-state buyers, new construction and planned communities, luxury, historic and lakefront homes, and move-up buyers and downsizers. Office: 504 W Plant Street, 1st and 2nd Floors, Winter Garden, FL 34787 · 407-706-5000 · info@jaredjones.com · jaredjones.com




















