739 Roughbeard Rd

Winter Park, FL 32792

$800,000
Price
5
Beds
2,194 Sq. Ft.
$365 / Sq. Ft.
2,194
Sq. Ft.
$365
per Sq. Ft.
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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...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.

Property Details for 739 Roughbeard Road

Subdivision Name
WINTER PARK PINES
Township
22
Garage Spaces
2
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 05/16/2026 05:10 PM

Property Details for 739 Roughbeard Road

StatusActive
MLS #O6404545
Days on Market15
Taxes$6,179 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1968
Lot Size0.25 AC / 10,799 SF
CountyOrange County
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Location

Listing Courtesy of SERHANT, John Harbuck
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Building Information for 739 Roughbeard Road

Stories-Year Built1968Building Size-Lot Size0.25 AC / 10,799 SF

Payment Calculator

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$4,501 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,986

Property Taxes

$515

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 739 Roughbeard Road

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 2784.0
  • Building Area Units: Square Feet
  • Community Features: Golf Carts OK, Golf, Sidewalks
  • Direction Faces: East
  • 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.
  • Elementary School: Aloma Elem
  • Middle Or Junior School: Glenridge Middle
  • High School: Winter Park High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 739
  • Street Name: ROUGHBEARD
  • Street Suffix: ROAD
  • State: FL
  • City: WINTER PARK
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Driveway, Garage Door Opener, On Street, Oversized, Workshop in Garage
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Requirement: None
  • Association: No
  • CDD: No
  • Pet Restrictions: Buyer to verify.
  • Tax Block: 0
  • Tax Book Number: 2-59
  • Tax Legal Description: WINTER PARK PINES UNIT FOURTEEN 2/59 LOT6
  • Tax Lot: 6
  • Tax Year: 2025
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: In County, Near Golf Course, Sidewalk
  • Parcel Number: 092230943800060
  • Total Acreage: 1/4 to less than 1/2
  • Water Access: No
  • Water Extras: No
  • Zoning: R-1A
  • Living Area: 2194
Property and Assessments
  • Year Built Numeric: 1968
  • Amenities Additional Fees: Cady way pool and Winter Pine's golf club have memberships available for additional fees, if interested.
  • Association Amenities: Park, Playground, Trail(s)
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0260F
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 30
  • Public Survey Section: 09
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Concrete
  • Exterior Features: French Doors, Lighting, Sidewalk
  • Fencing: Fenced, Wood
  • Foundation Details: Slab
  • Levels: One
  • Patio And Porch Features: Covered, Front Porch, Patio
  • Pool Features: In Ground
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shingle
  • Vegetation: Mature Landscaping
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 3
  • Additional Rooms: Family Room, Inside Utility
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace Features: Living Room, Wood Burning
  • Fireplace: Yes
  • Flooring: Tile
  • Heating: Central
  • 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)
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 9.0
  • Water View: No
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 739 Roughbeard Road

DateEvent & SourcePriceAppreciation
May 4, 2026

Listed (Active)

MFRMLS #O6404545

$800,000—
Oct 28, 2021

Sold (Public Record)

Public Record #1476345734

$495,000

+3.9% / yr

Oct 28, 2021

Sold

MFRMLS #O5970079

$495,000—
DateEvent & SourcePrice
05/04/2026

Listed (Active)

MFRMLS #O6404545

$800,000
10/28/2021

Sold (Public Record)

Public Record #1476345734

$495,000

+3.9% / yr

10/28/2021

Sold

MFRMLS #O5970079

$495,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 739 Roughbeard Road

Taxable ValueLand-Additions-Total-
Tax Record2024$6,355 ($530 / month)
Home Facts
Beds5Total Finished SqFt2,194 SqFtAbove Grade Finished SqFt2,194 SqFtStories1Lot Size10,799 SqFtStyleSingle Family ResidenceYear Built1968Year Renovated1973ZoningR-1ACountyORANGEAPN09-22-30-9438-00-060Fireplace TypeHas Fireplace

Schools near 739 Roughbeard Road

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Aloma Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Glenridge Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Aloma Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Glenridge Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 739 Roughbeard Road, Winter Park, FL 32792

739 Roughbeard Road is a single family home for sale in Winter Park, FL 32792. This property was listed for sale on May 4, 2026 by SERHANT, it's currently listed at $800,000. It has been on the market for a total of 15 days and was last sold on October 28, 2021. This listing's school district is Orange County Public Schools. Nearby schools include Aloma Elementary School, Cornerstone Academy Charter and Glenridge Middle School. 739 Roughbeard Road is a 5-bed, 3-bath, 2,194 sqft single family home built in 1968.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of SERHANT, John Harbuck

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 05/16/2026 05:10 PM