# 100 MATHER SMITH Drive, Oakland, FL 34760 > **TL;DR:** 3bd/2ba single family, $600,000 ($382/sqft), built 1997, 1,571 sqft. > A/C, 2-car garage. Est. $3,209/mo. Listed 15 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $600,000 | | Price/sqft | $382 | | Bedrooms | 3 | | Bathrooms | 2 full | | Square Feet | 1,571 | | Year Built | 1997 | | Lot Size | 12,197 sqft (0.28 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 15 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $3,034 | | Estimated Insurance | $175 | | **Total** | **$3,209** | ## Nearby Schools - **Elementary:** Tildenville Elem - **Middle:** Lakeview Middle - **High:** West Orange High ## Key Amenities - A/C - 2-car garage ## Property Highlights - Built in 1997 - 0.28 acre lot ## Description ### Agent Description 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. ## Location - **Address:** 100 MATHER SMITH Drive, Oakland, FL 34760 - **County:** Orange - **Neighborhood:** OAKLAND SHORES - **Coordinates:** 28.557758, -81.62661 - **Google Maps:** https://www.google.com/maps?q=28.557758,-81.62661 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/stellar/O6443938 ## Listing Agent - **Name:** Christopher Bessette - **Brokerage:** Keller Williams Classic Realty - **Phone:** 4072925400 - **Broker Phone:** (407) 445-7002 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/100-Mather-Smith-Dr_Oakland_FL_34760_M52297-59919?f=listhub&s=MFRMLSFL&m=O6443938&c=propsimple) ## Photos ![100 MATHER SMITH Drive - Photo 1](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f1729145472r.jpg) ![100 MATHER SMITH Drive - Photo 2](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f1515410843r.jpg) ![100 MATHER SMITH Drive - Photo 3](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f1225684120r.jpg) ![100 MATHER SMITH Drive - Photo 4](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f306627104r.jpg) ![100 MATHER SMITH Drive - Photo 5](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f3184999162r.jpg) ![100 MATHER SMITH Drive - Photo 6](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f512862616r.jpg) ![100 MATHER SMITH Drive - Photo 7](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f2068656640r.jpg) ![100 MATHER SMITH Drive - Photo 8](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f4288634753r.jpg) ![100 MATHER SMITH Drive - Photo 9](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f2367246543r.jpg) ![100 MATHER SMITH Drive - Photo 10](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f3624466672r.jpg) ![100 MATHER SMITH Drive - Photo 11](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f1140934062r.jpg) ![100 MATHER SMITH Drive - Photo 12](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f472139494r.jpg) ![100 MATHER SMITH Drive - Photo 13](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f935397520r.jpg) ![100 MATHER SMITH Drive - Photo 14](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f106406648r.jpg) ![100 MATHER SMITH Drive - Photo 15](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f2479336844r.jpg) ![100 MATHER SMITH Drive - Photo 16](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f3461235473r.jpg) ![100 MATHER SMITH Drive - Photo 17](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f41820168r.jpg) ![100 MATHER SMITH Drive - Photo 18](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f711440280r.jpg) ![100 MATHER SMITH Drive - Photo 19](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f2373873377r.jpg) ![100 MATHER SMITH Drive - Photo 20](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f2714465808r.jpg) ![100 MATHER SMITH Drive - Photo 21](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f3667135591r.jpg) ![100 MATHER SMITH Drive - Photo 22](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f537653889r.jpg) ![100 MATHER SMITH Drive - Photo 23](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f1145462428r.jpg) ![100 MATHER SMITH Drive - Photo 24](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f4218133157r.jpg) ![100 MATHER SMITH Drive - Photo 25](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f2872619325r.jpg) ![100 MATHER SMITH Drive - Photo 26](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f470421746r.jpg) ![100 MATHER SMITH Drive - Photo 27](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f2608174302r.jpg) ![100 MATHER SMITH Drive - Photo 28](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f820455760r.jpg) ![100 MATHER SMITH Drive - Photo 29](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f363161228r.jpg) ![100 MATHER SMITH Drive - Photo 30](http://lh.rdcpix.com/90de9ba637e95a99b14b89b2b19a8cecl-f820955542r.jpg) --- **MLS#:** O6443938 | **Updated:** 2026-10-06 **Source:** listhub *Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/100-mather-smith-drive-oakland-fl-34760-o6443938) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/100-mather-smith-drive-oakland-fl-34760-o6443938#listing", "url": "https://www.propertysimple.ai/listing/100-mather-smith-drive-oakland-fl-34760-o6443938", "name": "100 MATHER SMITH Drive, Oakland, FL 34760", "description": "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. 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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. 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