Market Report · 2nd Quarter 2026 · As of June 29, 2026

MLS data updated Jun 28, 2026

Oakland Park

Master-planned, green-certified living along Lake Apopka and the West Orange Trail

Winter Garden, FL

Oakland Park is a master-planned community on the Winter Garden/Town of Oakland border near Lake Apopka, known for oak-lined streets, front-porch homes, and FGBC green certification, with resort-style amenities and direct access to the 22-mile West Orange Trail.

9
For Sale
$1.3M
Avg. List Price
4
Under Contract
Median Sold (12 mo)
Homes Sold (12 mo)

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Ryan's Take on Oakland Park

Oakland Park draws the kind of buyer who wants a genuine neighborhood — not a gated compound — with a master-planned sense of place and a lifestyle built around the outdoors. Families with school-age children are the dominant profile here: the OCPS feeder pattern runs from Tildenville Elementary through Lakeview Middle to West Orange High, all within a short drive, and the community's scale and green-certified homes signal a long-term commitment to the area rather than a transitional stop.

The commute anchor is SR 408, which puts downtown Orlando roughly twenty minutes east — close enough for professionals in the central business district, the healthcare system, or the theme park corridor to make it work without feeling tethered to the interstate. The SR 429 interchange also opens the door to the Lake Mary and Heathrow employment corridors to the north.

What makes Oakland Park distinctive is the combination of serious lifestyle infrastructure and a lakeside setting that most comparably priced communities can't match. Direct access to the West Orange Trail is a genuine differentiator — residents walk, bike, and run from their front door onto one of Central Florida's premier paved trail networks, with Lake Apopka as the backdrop. The community's FGBC green certification and diverse builder roster — David Weekley, RockWell, RCB — produced a range of architectural styles that give the streets real character rather than the monotony common to large planned developments.

Buyers who cross-shop Oakland Park typically look at Hamlin to the south for a more retail-integrated lifestyle, or at Summerport in Windermere for a slightly more established lakefront address.

— Ryan Solberg, Broker/Owner, MaxLife Realty

Under Contract

4 homes pending in Oakland Park · Avg. $948K

Oakland Park pending
Pending
$766,000
4 bd4 ba2,831 sqft
Oakland Park pending
Pending
$1,050,000
4 bd4 ba2,667 sqft
Oakland Park pending
Pending
$1,025,000
5 bd3 ba2,999 sqft
Oakland Park pending
Pending
$949,000
4 bd4 ba2,667 sqft

Recent Sales Map

Recent sales activity in Oakland Park

No recent public sales records found for this area. Call Ryan for a detailed sold analysis.

Currently For Sale

9 active listings in Oakland Park

BedsBathsSq FtList Price$/Sq FtDOMPoolView
442,637$890,000$33819
654,104$1,674,999$40841
432,710$1,225,000$452122
331,642$649,000$39532
455,138$2,199,000$42834
442,667$1,175,000$4411
443,781$1,699,000$44995
332,252$865,000$3842
543,784$1,765,000$46672Water
All 9 active listings in Oakland Park · live Stellar MLS · no addresses published

Oakland Park Market — Common Questions

Is Oakland Park a buyer's or seller's market in 2026?+

Recent public-record sales volume in Oakland Park is currently too low to call the market definitively. There are 9 active listings right now. Contact Ryan Solberg at MaxLife Realty for a current read.

How many homes are for sale in Oakland Park?+

There are currently 9 active listings in Oakland Park.

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What Is Your Oakland Park Home Worth?

I analyze active competition, recent sales, and neighborhood trends to give you a precise estimate of what your home is worth right now — no automated Zestimate, a real analysis from a local expert.

Ryan Solberg, MaxLife Realty

Ryan Solberg

MaxLife Realty

321.373.3536

Report generated June 29, 2026 at 3:24 PM ET· Powered by Stellar MLS

MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.

Sold Data: Sales analysis is derived from Florida Department of Revenue public property records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Oakland Parkor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.

Based on information submitted to the MLS GRID as of June 28, 2026 at 7:06 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of June 28, 2026 at 7:06 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA