About 739 Roughbeard Road
Set on a quarter-acre lot on a tree-lined street in Winter Park Pines, this 5-bedroom, 3-bath pool home offers 2,194 sq ft of single-story living with room for everyone. The split floor plan places a spacious primary suite on its own side of the home, with a walk-in closet and French doors that open directly to the covered patio. The four guest bedrooms are generously sized, and one pair shares a Jack-and-Jill bath. The kitchen has a breakfast bar, a pantry, and views of the pool. It opens to a family room anchored by a wood-burning fireplace and a built-in desk. The formal living and dining rooms, crown molding, and three sets of French doors bring in natural light and a connection to the outdoors. Outside, the large covered, insulated patio overlooks a sparkling pool and a fenced backyard with real yard space. There is no mandatory HOA, and the oversized 2-car garage includes workshop space. You're minutes from Winter Park Pines Golf Club, Aloma Ave shopping, and Park Avenue. Zoned for Winter Park High.
Features of 739 Roughbeard Road
| MLS® # | O6444000 |
|---|---|
| Price | $780,000 |
| Bedrooms | 5 |
| Bathrooms | 3.00 |
| Full Baths | 3 |
| Square Footage | 2,194 |
| Acres | 0.25 |
| Year Built | 1968 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 739 Roughbeard Road |
|---|---|
| Area | Winter Park/Aloma |
| Subdivision | WINTER PARK PINES |
| City | WINTER PARK |
| County | Orange |
| State | FL |
| Zip Code | 32792-4518 |
Amenities
| Amenities | Park, Playground, Trail(s) |
|---|---|
| Parking | Driveway, Garage Door Opener, On Street, Oversized, Workshop in Garage |
| # of Garages | 2 |
| Is Waterfront | No |
| Has Pool | Yes |
Interior
| Interior Features | Built-in Features, Ceiling Fan(s), Crown Molding, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Thermostat, Walk-In Closet(s) |
|---|---|
| Appliances | Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer |
| Heating | Central |
| Cooling | Central Air |
| Fireplace | Yes |
| Fireplaces | Living Room, Wood Burning |
Exterior
| Exterior Features | French Doors, Lighting, Sidewalk |
|---|---|
| Lot Description | In County, Near Golf Course, Sidewalk |
| Roof | Shingle |
| Foundation | Slab |
School Information
| Elementary | Aloma Elem |
|---|---|
| Middle | Glenridge Middle |
| High | Winter Park High |
Additional Information
| Date Listed | September 24th, 2026 |
|---|---|
| Days on Market | 3 |
| Zoning | R-1A |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | SERHANT |
|---|