100 MATHER SMITH DRIVE, OAKLAND, FL, 34760
Active19 days on marketListed Sep 24, 2026MLS #O6443938
About this home
100 MATHER SMITH DRIVE
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.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,571
Sqft
0.28 ac
Lot size
2
Garage
1997
Year built
One
Levels
$382
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$3,923 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$3,923/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+36.9%
$/sqft vs Oakland actives
$382 vs $259
Days on market
19 vs 43 typical
Where $382/sqft sits among the 31 Oakland actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Oakland
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Oakland. See the full Oakland guide →
OAKLAND 34760 — neighborhood snapshot
Population
778
Median age
49.8
Median income
$136,042
Median home value
$401,200
Avg household
3.3
Households w/ children
69%
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Oakland market
$605K → $697K
Oakland median sold, yr/yr
98.1%
Sale-to-list ratio (12 mo)
12 of 31
Oakland actives have cut their price
Median sold price, Oakland, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 47% below the OAKLAND 34760 median. See the full Oakland market guide →
Paper trail
This home's history
Reality check
What actually sold near 100 MATHER SMITH DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$395,000
637 MAGNOLIA DRIVE · same community
3 bd · 2 ba · 1,851 sqft · $213/sqft · 84 DOM
Sold · Mar ’26$345,000
633 MAGNOLIA DRIVE · same community
3 bd · 2 ba · 1,285 sqft · $268/sqft · 31 DOM
Sold · Dec ’25$379,000
518 OAK LANE · same community
3 bd · 3 ba · 1,999 sqft · $190/sqft · 21 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Shawn Headley
Realtor · CENTURY 21 Edge
Tours, negotiation, and every question about 100 MATHER SMITH DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 100 MATHER SMITH DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Shawn's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
100 MATHER SMITH DRIVE FAQs
What would the monthly payment be for 100 MATHER SMITH DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $3,923/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 100 MATHER SMITH DRIVE?+
The most recent tax bill on record (2025) was $3,603. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 100 MATHER SMITH DRIVE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Oakland?+
At $600,000, this home is listed about 25% below the Oakland median of $796,000. The market section on this page shows how the area is trending.
Which schools are assigned to 100 MATHER SMITH DRIVE?+
Tildenville Elementary (elementary), Lakeview Middle (middle), West Orange High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS CLASSIC · Christopher Bessette. MLS #O6443938.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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