$800,000
739 Roughbeard Road
Winter Park, FL 32792
Listing updated: May 16, 2026 at 5:06 PM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history12 days on market
- Status: ActiveMay 5, 2026
- Listed$800,000May 4, 2026
- Price increased$800,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 12
- Subdivision
- Winter Park Pines
- County
- Orange
- Year built
- 1968
- Living area
- 2,194 sq ft
- Price/sq ft
- $365
- Building area
- 2,784 sq ft (Public Records)
- Lot size
- 10,799 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12095C0260F)
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $6,179 (2025)
- Parcel #
- 09-22-30-9438-00-060
- Zoning
- R-1A
- MLS #
- O6404545
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Interior Details
- Bedrooms
- 5
- Full bathrooms
- 3
- Flooring
- Tile
- Appliances
- Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Interior features
- Built-in Features, Ceiling Fans(s), Crown Molding, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Thermostat, Walk-In Closet(s)
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- East
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Driveway, Garage Door Opener, On Street, Oversized, Workshop in Garage
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Buyer to verify.
- Approval process
- Buyer to verify.
Exterior & Construction
- Exterior features
- French Doors, Lighting, Sidewalk
- Construction materials
- Block, Concrete
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Asphalt, Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Bathroom 2 | First | 13x11 |
| Bathroom 3 | First | 11x11 |
| Bathroom 4 | First | 11x10 |
| Bedroom 5 | First | 12x10 |
| Primary Bedroom | First | 12x16 |
| Family Room | First | 21x14 |
| Dining Room | First | 14x12 |
| Kitchen | First | 13x11 |
| Living Room | First | 13x21 |
Listing Details
- Listing date
- 2026-05-04
- On market date
- 2026-05-04
- Original list price
- $800,000
- Occupant type
- Owner
- MLS area
- 32792 - Winter Park/Aloma
- Listing AOR
- Orlando Regional
- Status changed
- 2026-05-05
- Tax legal description
- WINTER PARK PINES UNIT FOURTEEN 2/59 LOT6
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From downtown Orlando, take FL-408 East to Exit 14 for FL-436/Semoran Blvd and head north. Continue on Semoran Blvd, then turn left onto Aloma Ave. Turn right onto Ranger Blvd into Winter Park Pines, then turn left onto Balfour Dr and follow to Roughbeard Dr; home will be on your right.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of May 16, 2026 at 5:06 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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