15722 E OAKLAND AVENUE, Winter Garden, FL 34787

• 3 beds |
• 2 baths |
• 3,340 sqft

Property Description

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!

Listing Status:

Pending

Date Added:

February 20, 2026

Data Last Updated:

March 12, 2026 at 7:24AM

Listing Office:

RE/MAX PRIME PROPERTIES : 407-347-4512

Listing Agent:

Matt Erickson : 407-432-8498

MLS ID:

O6383983

Interior

• General: Built-in FeaturesCeiling Fans(s)Crown MoldingEat-in KitchenHigh CeilingsL DiningPrimary Bedroom Main FloorSplit BedroomWalk-In Closet(s)Window Treatments
• Appliances: DishwasherRangeRange HoodRefrigeratorWasher
• Laundry: InsideLaundry Room
• Flooring: Wood
• A/C: Central Air
• Heating: Central
• Fireplace: Wood BurningFireplace

Exterior

• General: Courtyard

Construction

• Roofing: Shingle
• General: BlockOneCrawlspace

Location

• Road/Access: Asphalt
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1ABEG 372.77 FT W OF NE COR OF SE1/4 OF SW1/4 RUN S 340 FT W 273 FT N 340 FT E 273FT TO POB (LESS N 30 FT FOR RD R/W) & (LESS W 100 FT) IN SEC 21-22-2721-22-27-0000-00-081

Utilities

• Utilities: BB/HS Internet AvailableCable ConnectedElectricity Connected
• Water: Well
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple