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Only two owners since 1952 have called this Oakland mansion home, will you be the third? Set on over an acre, surrounded by majestic oaks, and multi-million dollar homes this elegant home is time capsule of yesteryear. The long paver driveway, with ample parking for all, eventually leads to the oversized two car garage. A spacious front porch is perfect for languishing about over coffee in the morning, or beverages in the evening. Enter through the original front door and prepare to be wowed! Gleaming original hardwood floors adorn the grand reception foyer, extending nearly to the back of the home. To your right you will appreciate the quality of old world construction, complete with built-in book case, WOOD BURNING fire place, and hardwood floors. To the back of the house you will note the spacious and graceful dining room, just waiting for new memories to be made. The kitchen features a breathtaking 6 burner gas range with hood, sub zero refrigerator, a walk-in pantry, original glass front cabinets, and an eat in area. A massive laundry room leads to the oversized garage that is already plumbed to add a pool bath in the future. Adjacent to the kitchen is a stunning wood paneled office that actually served as a citrus moguls office, complete with a private entrance. Returning to the front of the home, is a bright Florida room/family room. The enormous primary bedroom has an original en-suite bath, walk in closet, and second closet. The other two bedrooms are very large by today's standards, and the original hall bath recalls to a simpler time, when things were built to last. As if that isn't enough, there is an upstairs bonus room which could serve as a multitude of options. A rear courtyard styled patio is perfect for grilling out with family and friends. The entire home is bathed in tons of natural lighting. Outback you will see a very large shed, capable of housing another car, she shed, man cave, workshop etc. There simply is nothing else like this home, anywhere with-in such great proximity to the year-round events happening in Downtown Winter Garden, and Oakland. You can even drive your golf cart through Oakland, and into Downtown Winter Garden!
| DAYS ON MARKET | 22 | LAST UPDATED | 2/24/2026 |
|---|---|---|---|
| TRACT | OAKLAND | YEAR BUILT | 1952 |
| COMMUNITY | 34787 - Winter Garden/Oakland | GARAGE SPACES | 2.0 |
| COUNTY | Orange | STATUS | Pending |
| PROPERTY TYPE(S) | Single Family |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Range, Range Hood, Refrigerator, Washer |
| AREA | 34787 - Winter Garden/Oakland |
| BASEMENT | Crawl Space |
| CONSTRUCTION | Block |
| EXTERIOR | Courtyard |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central |
| INTERIOR | Built-in Features, Crown Molding, Eat-in Kitchen, High Ceilings, Walk-In Closet(s) |
| LOT | 1.23 acre(s) |
| PARKING | Attached |
| SEWER | Septic Tank |
| STORIES | 1 |
| SUBDIVISION | OAKLAND |
| TAXES | 2752.58 |
| UTILITIES | Cable Available, Cable Connected, Electricity Connected |
| WATER | Private, Well |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Matt Erickson, RE/MAX PRIME PROPERTIES, 407-347-4512
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 3/12/26 6:34 PM PDT.
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