739 Roughbeard Rd, photo 1
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Overview

5 bd3 ba2,194 sqft2 car garageSingle Family
TypeSingle Family
HOANone listed
Built1968
Lot10,799 sqft
Living area2,194 sqft
Price / sqft$356
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Built-in FeaturesCeiling Fans(s)Crown MoldingKitchen/Family Room ComboLiving Room/Dining Room ComboPrimary Bedroom Main FloorThermostatWalk-in Closet(s)

739 Roughbeard Rd is a 1968-built home in Winter Park Pines, Winter Park. Inside you'll find 5 bedrooms, 3 bathrooms, and 2,194 square feet of living space. Listed at $780,000 (about $356/sqft), 17 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

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.

The essentials

Built
1968
Price / sqft
$356
On market
17 days
Annual tax
$6,179
Flood zone
X · Low risk
Lot
10,799 sqft
Type
Single Family Residence

At a glance

Single family
Built 1968
Private pool
In Ground
2 car garage
Driveway
0.25 acres
Lot size
2,194 sqft
Living area

Payment

Est. monthly payment
$4,973/mo
Down payment (20%)
$156,000
Property taxes
$515/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1968
Lot
10,799 sqft
Cooling
Central Air
Heating
Central
Parking
Driveway, Garage Door Opener, On Street, Oversized, Workshop in Garage
Pool
In Ground
Days on Market
17
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)
Lighting
Sidewalk
Golf Carts OK
Golf
Sidewalks
Dishwasher
Dryer
Microwave
Range
Refrigerator
Washer
Elementary
Aloma Elem
Middle
Glenridge Middle
High
Winter Park High

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone X
Annual Tax (2025)
$6,179
Parcel #
09-22-30-9438-00-060

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Winter Park Pines
County
Orange
MLS Area
32792 - Winter Park/Aloma
Lot Size
10,799 sqft
In CountyNear Golf CourseSidewalkPaved

Price history

Date
Event
Price
9/24/2026
Listed for sale
Source: Stellar MLS #O6444000
$780,000
$356/sqft

Neighborhood

739 Roughbeard Rd
Winter Park, FL, 32792 · 32792 - Winter Park/Aloma

Market insights

Offer Insights

Choose an offer strength

List price: $780,000
$775,000 – $780,000
99.5% – 100% of listTops out right at the list price
80% of listList price
103 of the last 199 home closings in 32792 landed at this number or higher (52%). The median one sat 19 days before it went under contract, and this one is on day 17.

Sample: 199 closed home sales in 32792 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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Calculator

Est. monthly payment
$4,973/mo
Principal & interest$4,068
Property taxes$515
Insurance$390
Down payment20% · $156,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$780,000

$356 per sq ft

Beds and baths

5 beds, 3 baths

Size

2,194 sq ft

Time on market

17 days

Year built

1968

Monthly payment

About $4,973/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $6,179 annual tax bill, insurance.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered bySERHANTListing agent: John HarbuckListing data from Stellar MLS, MLS# O6444000.

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