501 HENKEL CIRCLE, Winter Park, FL 32789

• 5 beds |
• 5 baths |
• 3,746 sqft

Property Description

Walk to Park Avenue from this stylish and impeccably maintained Winter Park home, tucked along a charming brick street just minutes from the shops, dining, and vibrant energy of downtown Winter Park. Designed for both effortless living and entertaining, the main residence offers 3,410 SF with 4 bedrooms and 3.5 baths, while a detached studio apartment sits above the two-car garage, adding 300+ SF of living space. Complete with a full bath, separate AC unit, and oversized storage room, this flexible space is perfect for in-laws or guests, a gym, art studio, game room, or the home office of your dreams. Truly turnkey, this home comes with an impressive list of recent improvements... And when we say NEW, we mean BRAND NEW! Major updates include a NEW gas tankless water heater (2026), THREE NEW HVAC systems - 2 in the main home (2026) & 1 in the studio apartment (2025) - and a NEW roof (2025). Additional recent improvements include a freshly painted interior (2026), new light fixtures (even in the closets) and NEW LED ceiling lighting throughout (2026), a newly re-screened rear patio (2026), dishwasher (2025), garage door motor (2025), and a whole-home Reverse Osmosis water purification system. The exterior was painted in 2018, and a beautiful saltwater pool with a sun shelf and waterfall feature was built in 2017. The ideal floor plan centers around the kitchen, featuring a gas cooktop, stainless steel appliances, and walk-in pantry. The kitchen flows effortlessly into the spacious family room, highlighted by vaulted ceilings and a gas fireplace, then around to the bright sunroom lined with windows and charming built-in window benches that create the perfect space to relax or gather. A bar/butler’s area connects the kitchen to the front-facing dining room, while a 2nd living/sitting room, with a second gas fireplace, sits just across the foyer. The downstairs primary suite offers a peaceful retreat with 2 walk-in closets, a vaulted wood-plank ceiling, and a large picture window overlooking the resort-style pool and backyard. Upstairs are 3 generously sized bedrooms with large walk-in closets, and 2 full bathrooms. Outdoor living is just as inviting, with a newly screened, brick patio that spans over 500 square feet for covered dining or lounging, including a dedicated grilling station that is ready for your grill and beverage refrigerator. Just outside the screens, an open courtyard leads to the saltwater pool with a sun shelf and soothing waterfall feature, all surrounded by a spacious backyard with gated access and room to discreetly store a boat trailer. A rare combination of prime location, thoughtful design, and extensive upgrades, this charming and fresh Winter Park home is the perfect blend of elevated entertaining and everyday comfort…all just a short stroll to Park Avenue.

Listing Status:

Pending

Date Added:

March 12, 2026

Data Last Updated:

March 27, 2026 at 6:22PM

Listing Office:

FANNIE HILLMAN & ASSOCIATES : 407-644-1234

Listing Agent:

MaryStuart Day : 407-620-8683

MLS ID:

O6389996

Interior

• General: Built-in FeaturesCeiling Fans(s)Dry BarHigh CeilingsKitchen/Family Room ComboPrimary Bedroom Main FloorVaulted Ceiling(s)Walk-In Closet(s)
• Rooms: Florida RoomFormal Dining Room SeparateFormal Living Room SeparateGarage ApartmentInside Utility
• Appliances: Built-In OvenCooktopDishwasherDisposalExhaust FanGas Water HeaterMicrowaveRefrigeratorTankless Water HeaterWater Filtration SystemWater PurifierWater SoftenerWine Refrigerator
• Laundry: Electric Dryer HookupInsideLaundry RoomWasher Hookup
• Flooring: CarpetSlateTileWood
• A/C: Central Air
• Heating: Central
• Fireplace: Family RoomGasLiving RoomMasonryFireplace

Exterior

• General: French DoorsRain Gutters
• Style: Traditional
• Other Structures: Front PorchRear PorchScreenedCovered
• Pool: GuniteIn GroundLightingSalt Water
• Parking: Circular DrivewayDrivewayGarage Faces RearGarage Faces SideOversized

Construction

• Roofing: Shingle
• Windows: Aluminum FramesDouble Pane WindowsShades
• General: BlockHardiPlank TypeFrameTwoSlab

Location

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

Lot

• Zoning: R-1AATHOMAS M HENKELS ADDITION F/61 LOT 2208-22-30-3488-00-220
• Fencing: FencedWood

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedNatural Gas ConnectedPublicSewer ConnectedUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple