739 ROUGHBEARD ROAD, Winter Park, FL 32792

• 5 beds |
• 3 baths |
• 2,194 sqft

Property Description

Welcome to Winter Park Pines, one of Winter Park’s most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood-plank tile flooring throughout most of the home. Inside, the formal living and dining rooms flow together and overlook the pool through French doors, while the large primary suite offers an en-suite bath, walk-in closet, and its own French doors to the huge covered, insulated patio. The light and bright kitchen includes a large breakfast bar, built-in pantry, and white cabinetry and appliances, and opens to the family room with a wood-burning fireplace and built-in desk. A separate bedroom wing provides four generous guest bedrooms and two full baths, including a Jack-and-Jill setup with walk-in closet, plus a true pool bath with access to the backyard and an inside utility/laundry room. Outdoor living is a highlight, with a fenced backyard, kidney-shaped pool, plenty of deck space, and ample yard beyond the pool so you’re not sacrificing green space. The large covered, insulated patio is ideal for year-round use. Major updates include a new roof (2022), new electric panel and updated outlets (2022), water lines re-piped to CPVC by a previous owner, new fence (2023), new dishwasher (2024), new water heater (2025), newer stove, washer, and dryer, new light fixtures throughout, and bathrooms updated with modern colors and fixtures. The exterior, garage, patio, and pool deck have all been freshly painted, giving the home a clean, move-in ready feel. This is a rare opportunity to own a well-maintained pool home in a prime Winter Park location—just steps from Cady Way Park and Trail and moments from Winter Park Pines Golf Course, with Winter Park High School and the nearby hospital campus within short distance and quick access to downtown Orlando, major highways, both airports, Disney, and Universal.

Listing Status:

Active

Date Added:

May 4, 2026

Data Last Updated:

May 7, 2026 at 9:23PM

Listing Office:

SERHANT : 786-296-8626

Listing Agent:

John Harbuck : 407-538-2841

MLS ID:

O6404545

Interior

• General: Built-in FeaturesCeiling Fans(s)Crown MoldingKitchen/Family Room ComboLiving Room/Dining Room ComboPrimary Bedroom Main FloorThermostatWalk-In Closet(s)
• Rooms: Family RoomInside Utility
• Appliances: DishwasherDryerMicrowaveRangeRefrigeratorWasher
• Laundry: InsideLaundry Room
• Flooring: Tile
• A/C: Central Air
• Heating: Central
• Fireplace: Living RoomWood BurningFireplace

Exterior

• General: French DoorsLightingSidewalk
• Other Structures: Front PorchPatioCovered
• Pool: In Ground
• Parking: DrivewayGarage Door OpenerOn StreetOversizedWorkshop in Garage

Construction

• Roofing: Shingle
• General: BlockConcreteOneSlab

Location

• Road/Access: AsphaltPaved
• HOA Amenities: ParkPlaygroundTrail(s)
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1AWINTER PARK PINES UNIT FOURTEEN 2/59 LOT609-22-30-9438-00-060
• Fencing: FencedWood

Utilities

• Utilities: Cable AvailableElectricity ConnectedNatural Gas ConnectedSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple