The Best 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 relocating families, 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. A family 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 a family moving 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 tight-knit town of a few thousand, with historic homes, shaded streets, and a walkable, neighborly pace.
Oakland Avenue Charter SchoolA sought-after K-8 charter school that draws many families to the town, with Orange County high schools nearby.
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.
Oakland market snapshot
A quick read on the Town of Oakland market as of August 2026.
Snapshot as of August 2026. Sources: Zillow Home Value Index for ZIP 34760 (~$522K typical value, up ~2.4% year over year, June 2026); Redfin new-construction median ~$750K (May 2026); newer-community resales in the mid $500,000s this spring; and historic-core and Lake Apopka lakefront sales up to ~$3.8M. Oakland is a very small, low-inventory market and its newer communities (Hull Island, Oakland Trails) use Winter Garden's 34787 ZIP, so figures vary widely and move week to week. For a valuation on your specific home, contact the Jared Jones Team.
Oakland, FL real estate FAQ
Who is the best real estate agent in Oakland, FL?
The Jared Jones Team, brokered by eXp Realty, is one of West Orange County's top-producing teams, with 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?
As of August 2026, the typical home value in ZIP 34760 is roughly $522,000, up about 2.4% year over year. New construction has listed around a $750,000 median, newer-community resales have closed in the mid $500,000s, and historic-core and Lake Apopka lakefront homes have sold as high as $3.8 million. It is a very small, low-inventory market, so a well-priced home can sell fast. 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 the sought-after Oakland Avenue Charter School. Buyers choose it for a quiet, nature-focused lifestyle 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, start with the team that knows this small market best.