Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
1989 to 2002Years built
1,500 to 2,600 sq ftHome size
3 to 4 bedroomsBedrooms
Lake Apopka Shore & the PreserveArea
Why people move here

An established lakeside street on Oakland's north side.

Oakland Shores is about 25 homes built from 1989 to 2002, on homesites of about a third of an acre near the Lake Apopka shore. It is a settled street where most owners have been in place for years.
The preserve, the trail and the town center are all close. When a home here lists, it usually needs a buyer who is ready to act.
Downsizers and buyers who want an established home close to the lake and the preserve.

Oakland Shores at a glance

Location: The Millholland Street area near the Lake Apopka shore

Builder: Custom and individual builders

Built: 1989 to 2002

Homes: About 25 homes

Home types: Single-family homes

Size: About 1,500 to 2,600 sq ft

Bedrooms: 3 to 4 bedrooms

Area: Lake Apopka Shore & the Preserve

Life here

What Oakland Shores has

🏡Third-acre homesites
🌊Near the Lake Apopka shore
🌳Close to the Oakland Nature Preserve
Proximity

What is close to Oakland Shores

  • Oakland Nature Preserve ~0.5 mi
  • West Orange Trail ~0.5 mi
  • Historic Downtown Winter Garden ~3.5 mi
  • Florida's Turnpike at SR 50 ~3 mi

Approximate distances from the community entrance. Walt Disney World is roughly 25 to 30 minutes away off-peak. SR 50 and the Turnpike interchange back up at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Oakland Avenue Charter School (K to 5, enrollment rules apply)

🏫 Tildenville Elementary

🏫 Lakeview Middle

🏫 West Orange High

Orange County Public Schools. Zoning changes, so verify every address.

OCPS school locator
The numbers

Oakland Shores market snapshot

Oakland Shores had no closed sales in the last 12 months. That is too few for a median that means anything, so I price homes here one at a time.

Get the real numbers for Oakland Shores

Call or text me at 407.502.4719 and I will send every recent closed sale in and around Oakland Shores, straight from Stellar MLS, with what each one tells us about value.

Request a custom report

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 15, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Oakland Shores homes for sale right now

Straight from Stellar MLS. Save the search and get new Oakland Shores listings the day they hit.

Start of list of properties

Active, 100 MATHER SMITH DRIVE, , ,press enter for more details, To favorite this property press control+s.
$600,000
$382
Active
100 MATHER SMITH DRIVE
Oakland, FL 34760
3
Beds
,
2
Baths
,
1,571
square feet,
A vaulted central living space carries the eye from the front dining room through an island kitchen to glass doors opening onto a garden-framed patio, giving this single-story Oakland home a natural indoor-outdoor rhythm. The kitchen serves as the everyday hub, with an expansive island, breakfast-bar seating, abundant cabinetry and clear sightlines that keep meal preparation connected to the main gathering area. Just beyond the living room, the open-air patio is arranged beneath pergola-style shade and surrounded by planted beds, creating an inviting place for morning coffee, outdoor meals or a quiet evening beneath the trees. The split-bedroom plan adds practical separation, positioning the primary suite apart from two secondary bedrooms and a full hall bath. Multiple windows and a tray ceiling shape the primary bedroom, while its en suite bath includes dual sinks, a separate tub and shower and a walk-in closet. Ceramic tile extends through the main living areas, kitchen and bathrooms, with carpet in the bedrooms and an interior laundry area supporting an easy daily routine. Set on a 0.28-acre corner lot with no HOA, the property combines open lawn, mature landscaping and room to enjoy the outdoors, while an attached two-car garage and broad driveway add useful parking and storage. Located in a golf cart-friendly community, you’ll enjoy easy access to downtown Winter Garden’s shops, restaurants and local events, along with the nearby West Orange Trail for walking and biking. This Oakland location offers a relaxed residential setting with convenient access to everything that makes the Winter Garden area so enjoyable.
Residential
MLS# O6443938 Keller Williams Classic
More Details
See all Oakland Shores homes for sale
Free guides

Buying or selling in Oakland Shores?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Oakland Shores works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Oakland Shores FAQ

Where is Oakland Shores in Oakland?

Oakland Shores is in north and west Oakland near the Lake Apopka shore and the Oakland Nature Preserve, at The Millholland Street area near the Lake Apopka shore.

How far is Oakland Shores from Walt Disney World?

Roughly 25 to 30 minutes off-peak from this part of Oakland. I will map the exact drive from the entrance before you choose.

When were homes in Oakland Shores built?

1989 to 2002. Most homes were built by individual or custom builders.

What amenities does Oakland Shores have?

Third-acre homesites, Near the Lake Apopka shore, Close to the Oakland Nature Preserve.

Is Oakland Shores a gated community?

Oakland Shores is not listed as gated. Ask me about gated options nearby.

What schools serve Oakland Shores?

Schools commonly listed for this community: Oakland Avenue Charter School (K to 5, enrollment rules apply), Tildenville Elementary, Lakeview Middle, West Orange High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Oakland Shores in the Town of Oakland?

Oakland Shores is inside the Town of Oakland, its own incorporated town since 1887 with its own government and police department. Many Oakland homes carry a Winter Garden 34787 mailing address, and a few nearby streets are in Winter Garden city limits or unincorporated Orange County, so I confirm the jurisdiction for every address.

What do homes in Oakland Shores sell for?

Too few homes sold in Oakland Shores in the last 12 months for a reliable median. Call or text me at 407.502.4719 and I will send recent closed sales in and around Oakland Shores from Stellar MLS.

Your next step

Thinking about Oakland Shores?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Oakland Shores, straight from Stellar MLS
  • Town of Oakland or Winter Garden, HOA, well and septic for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719
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Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify Town of Oakland, city or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.